3 places to visit in chicago

Chicago   Travel Guide

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28 Fun Things to Do in Chicago

Chicago shines for its world-class museums, various shopping districts, vibrant neighborhoods and lively nightlife venues. Explore the city's innovative roots at the Museum of Science and Industry, where you can walk inside the U-505 submarine.

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Millennium Park and Cloud Gate Millennium Park and Cloud Gate free

U.S. News Insider Tip: Construction around the Cloud Gate sculpture will limit the public's access to this top tourist attraction until spring 2024. While you might not be able to snag a selfie with "The Bean," many other attractions are available within the park. – Cortney Fries

A first-time visit to Chicago isn't complete without a stop at Millennium Park. Situated in the Loop just north of the Art Institute of Chicago , this 25-acre space is used to showcase cutting-edge art, architecture and landscaping; it also acts as a backdrop for concerts and festivals. Most visitors come to Millennium Park to see the Crown Fountain and Cloud Gate, better known as "The Bean." Designed by Spanish artist Jaume Plensa, the Crown Fountain features two 50-foot towers that face each other at opposite ends of a shallow reflecting pool. The towers' LED screens project the faces of 1,000 different Chicago residents, which are perfectly aligned with spouts so that it appears they are spitting water on passersby. The water flows mid-spring through mid-fall, while the faces are projected year-round. Cloud Gate – created by British-Indian artist Anish Kapoor – is a 110-ton bean-shaped sculpture forged from stainless steel. The Bean's elliptical shape reflects the Chicago skyline. A quintessential Chicago souvenir is a photo of your reflection in The Bean.

Grant Park and Buckingham Fountain Grant Park and Buckingham Fountain free

U.S. News Insider Tip: If you're visiting Chicago Sept. 8 through 10, head to Grant Park early – around 11 a.m. to avoid the lines – for the Taste of Chicago. Enjoy the park and eat the best cuisine the city has to offer. Admission is free. – Sarah Estime

Often referred to as "Chicago's front yard," Grant Park is an approximately 313-acre swath of green space that starts at the eastern edge of the Loop and stretches down to the northern fringes of the Near South Side. First-time visitors should plan on spending a fair amount of time in Grant Park: This is where you'll find several of Chicago's most popular things to do, including The Field Museum , the Art Institute of Chicago and Shedd Aquarium . ( Millennium Park also rubs elbows with the northwest corner of Grant Park.) Baseball diamonds, flower gardens, walking paths and wide-open grassy terrain are available as well.

Art Institute of Chicago Art Institute of Chicago

Home to one of the country's most impressive collections of impressionist and post-impressionist art (plus works from numerous other genres), the expansive Art Institute of Chicago features nearly 300,000 works from all over the world in its permanent collection. You'll find pieces created in the Byzantine era, as well as paintings completed just a few decades ago. Highlights include Jacob Lawrence's "The Wedding," Georgia O'Keeffe's "Sky above Clouds IV" and Grant Wood's "American Gothic." The Art Institute's exhibits also include all sorts of intriguing artifacts, from European armor to the Thorne Miniature Rooms, which showcase interior design and furnishings in Europe and America from the late 13th to early 20th centuries. In addition to the permanent collection, the Art Institute hosts traveling exhibitions covering a variety of subjects and showcasing a diverse array of artists and genres.

The Art Institute of Chicago earns high praise from recent visitors, thanks in part to its impressive collection. Art enthusiasts particularly commend the museum's impressionist collection, which features pieces from famous artists like van Gogh, Monet and Renoir.

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The Magnificent Mile The Magnificent Mile free

U.S. News Insider Tip: The Magnificent Mile, known for its world-class shopping, also has plenty to offer architecture buffs. Book a walking tour with the Chicago Architecture Center and hear the untold stories of North Michigan Avenue's architectural icons. Tours start at $30. – Sarah Estime

For shopping at more than 450 retailers within walking distance in downtown Chicago, make your way to The Magnificent Mile. This portion of Michigan Avenue – which stretches between Lake Shore Drive and the Chicago River – beckons to shopaholics with department stores and luxury retailers like Bloomingdale's, Marcus, Macy's, Tory Burch and Nordstrom. Additionally, The Magnificent Mile is home to several top-notch eateries and luxury hotels, including The Drake , the Sofitel Chicago Magnificent Mile and the InterContinental Chicago Magnificent Mile .

Navy Pier Navy Pier free

Extending out onto Lake Michigan, Navy Pier offers plenty in the way of family-friendly entertainment. The first thing you'll spot once you set foot on the pier is the towering Ferris wheel (which stands 196 feet tall); you'll also find a drop tower and a carousel. Once the kids have had their fill of thrill rides, you can spend some time cruising the Chicago River on a sightseeing or speedboat tour or spend a few hours exploring the Chicago Children's Museum , with hands-on exhibits ranging from treehouses to fire trucks.

But you don't have to be a kid to enjoy a visit to Navy Pier. Grown-ups can catch a show at the Chicago Shakespeare Theater, flex some credit card muscle at a variety of shops or grab a drink at the Navy Pier Beer Garden. And be sure to check Navy Pier's website for a list of events: Concerts are often held here, and from Memorial Day to Labor Day (as well as New Year's Eve), impressive fireworks displays light up the skies on Wednesday and Saturday nights. Many of the city's top Segway tours offer special summer evening tours to the pier to catch the semiweekly fireworks show.

Lincoln Park Zoo Lincoln Park Zoo free

U.S. News Insider Tip: North Avenue Beach is a short walk over the North Avenue Bridge when you park at the southern end of the Lincoln Park Zoo lot. Explore the zoo, then stroll over to the beach for an afternoon in the sand. – Cortney Fries

Located 2 miles north of the Loop in the North Side neighborhood of Lincoln Park, the Lincoln Park Zoo is home to nearly 200 species, such as zebras, sloths and hippos. Visitors can view the zoo's furry (or scaly) friends in their natural habitats: Check out the gorillas in the sprawling, award-winning Regenstein Center for African Apes, or head to the Kovler Seal Pool to get up close and personal with harbor seals. Seal training and feeding occurs daily at 11:30 a.m. and 2 p.m.

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360 CHICAGO Observation Deck 360 CHICAGO Observation Deck

One of Chicago's most notable attractions is its skyline, and one of the best places to experience it is at the 360 CHICAGO Observation Deck. Formerly known as the John Hancock Observatory, 360 CHICAGO towers 1,000 feet over The Magnificent Mile from its location on the 94th floor of the John Hancock Center (or 875 North Michigan Avenue as its more formally known). Encased by floor-to-ceiling windows, 360 CHICAGO boasts expansive views of the city; on a clear day, you can see four states. Meanwhile, the interactive screens will help you identify different landmarks that appear in your panorama.

For a different point of view (and an adrenaline rush), test out 360 CHICAGO's TILT. In this mechanized room, visitors hold on to handlebars as the top of the room's windows extend outward, tilting you toward bustling North Michigan Avenue down below. For another memorable way to immerse yourself in the views, try ClouldWalk, a 3D art experience introduced in 2022. Mural artist Nate Baranowski created an optical illusion on the observation deck that makes visitors feel as though they are standing on a crane platform in the clouds.  Should you prefer to experience the view without feeling your heart skip a beat, grab a cup of coffee, a glass of wine or a snack at the cafe and bar, or look for souvenirs in the gift shop.

The Field Museum The Field Museum

U.S. News Insider Tip: After hours of museum hopping, grab a kid-approved lunch at Kim & Carlo's Hot Dog Cart. The no-frills stand offers everything from vegan dogs to the traditional Chicago hotdog. Enjoy your lunch on the water. – Sarah Estime

This extensive natural history museum occupies half an acre of Grant Park 's Museum Campus and houses exhibits that showcase artifacts from multiple eras and destinations, making it a must-see for kids (as well as any fans of the "Indiana Jones" movies). Some of the most popular parts of the museum include the "Inside Ancient Egypt" exhibit, which features a reconstruction of a three-story replica of an Egyptian tomb, one of the largest collections of mummies in the United States and interactive representations of life on the Nile. There's also the Restoring Earth area in the Abbott Hall of Conservation, where visitors can learn more about sustainability through hands-on activities. But no visit to The Field Museum would be complete without some quality time with SUE, the facility's T. rex who just happens to be the largest, most complete T. rex ever discovered. SUE is 40 feet long from nose to tail and boasts 55 terrifying teeth.

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Chicago Architecture River Cruise Chicago Architecture River Cruise

A visit to 360 CHICAGO or Skydeck Chicago will give you a good overview of the city's layout. But if you want to learn more about Chicago's sky-high buildings, tag along on an architecture river cruise. During a river cruise, you'll gain great views and historical insight about well-known structures like the Wrigley Building, the Leo Burnett Building and the Fulton House.

Though several companies, including Wendella Sightseeing Co. and Chicago Line Cruises, offer architecture river cruises, most travelers recommend climbing aboard a Chicago's First Lady Cruises boat with a Chicago Architecture Center docent. You'll learn tons of information about the area's architecture, plus catch superb skyline photo-ops.

Maggie Daley Park Maggie Daley Park free

U.S. News Insider Tip: There are many restaurant options around the park, but Wildberry Pancakes & Café is a satisfying brunch spot. Choose from creative pancake options, a variety of omelets, crepes, sandwiches and salads. Go hungry and leave happy. – Cortney Fries

Opened in 2014, Maggie Daley Park is an expansive property located just east of Millennium Park in downtown Chicago. The 20-acre green space offers numerous activities for both kids and adults alike, including a climbing wall, a mini-golf course, a 3-acre playground, a public garden, an ice-skating skating "ribbon" during the winter and scooter and rollerblade rentals in the summer, not to mention a tennis facility. Whatever you choose to do, you'll get to enjoy fantastic views of the Chicago skyline. Recent visitors loved that the park is free to access, and they noted that the attraction is excellent for family fun.

Museum of Science and Industry Museum of Science and Industry

U.S. News Insider Tip: Mid-November through the first week of January, experience the annual "Christmas Around the World" and "Holidays of Light" exhibits. Volunteers decorate more than 50 trees in celebration of holiday traditions from around the globe. – Cortney Fries

Chicago's extensive Museum of Science and Industry is the Western Hemisphere's largest science museum, showcasing more than 35,000 artifacts and a variety of hands-on exhibits meant to inspire creativity. The museum resides in the 14-acre former Palace of Fine Arts, which hosted the famous World's Columbian Exposition in 1893. The fair brought together some of the world's greatest scientific minds, including Thomas Edison and Nikola Tesla, who at the time were competing to prove which type of electricity – direct current or alternating current – was more effective. 

Wrigley Field Wrigley Field

U.S. News Insider Tip: If you're visiting during the holiday season, don't miss Winterland at Gallagher Way for family-friendly rides and games inside and around the ballpark. Christkindlmarket Wrigleyville is free to enter. Enjoy festive shopping and international food and beverage selections. – Cortney Fries

Chicagoans take their love of sports very seriously. So, for a real taste of Chicago culture, head north of the Loop to Wrigley Field to watch the Chicago Cubs play ball at the Friendly Confines. History buffs will also appreciate this sports treasure, which first opened in 1914 and holds the honor of being the second-oldest Major League Baseball stadium in the country (after Fenway Park in Boston ).

Shedd Aquarium Shedd Aquarium

U.S. News Insider Tip: If you're visiting in the summer (June through August), check out Jazzin' at the Shedd. You can enjoy jazz music and drinks with incredible views from the terrace. Plus, the lights dim in the aquarium for a unique experience. – Elizabeth Von Tersch, Senior Editor

Shedd Aquarium is one of the world's largest indoor aquariums, housing around 32,000 creatures. While you're here, you can feel stingrays float beneath your fingers, listen to sea lions bark and learn all about a variety of turtles. A visit to Shedd Aquarium will lead you through a cornucopia of habitats, where you'll find additional animals like penguins, piranhas, sharks and beluga whales. Or, for an additional fee, you can participate in specialty experiences like animal encounters, feeding experiences and virtual reality.

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The Chicago Riverwalk The Chicago Riverwalk free

U.S. News Insider Tip: During the summer, there is nothing better than watching the boats go by as you relax at City Winery Riverwalk Wine Garden. Rent a retro boat from Chicago Electric Boat Company and cruise the river yourself. – Cortney Fries

When the weather warms up in Chicago, there are few better places to enjoy the outdoors than the Chicago Riverwalk. The 1.25-mile pedestrian walkway on the south bank of the Chicago River is the perfect place to take a stroll and observe the city skyline. Plus, there are numerous activity options to enjoy directly on the water, such as a boat or kayak tour . If you prefer to explore on your own two feet, visit the public gardens and art displays, or grab a meal at a popular restaurant or bar overlooking the Chicago River. And if you want to learn more about the river's unique history, check out the McCormick Bridgehouse & Chicago River Museum, which celebrates the city's famous movable bridges. What's more, Art on theMART – a massive digital art projection on the facade of theMART (formerly The Merchandise Mart) – is best viewed from the Riverwalk.

Skydeck Chicago at the Willis Tower Skydeck Chicago at the Willis Tower

More than 1.7 million people make their way to Willis Tower's Skydeck Chicago each year, and it's easy to see why. Occupying the 103rd floor – that's nine floors higher than 360 CHICAGO – of the 110-story Willis Tower (the third-tallest building in North America after One World Trade Center and Central Park Tower), Skydeck Chicago boasts breathtaking views of the city. Visit on a sunny day and you may be able to see far beyond Chicago's borders to Indiana, Michigan, Wisconsin and other parts of Illinois.

The highlight for most visitors is the Ledge. Extending 4.3 feet beyond the building's exterior, this platform is made entirely of glass – even the floor. Travelers also liked the video screens that show what it would be like to stand 103 floors above other Chicago attractions, including Wrigley Field and Millennium Park . However, long lines quickly form for Skydeck Chicago, so plan on arriving early or purchasing a Chicago CityPASS, which covers expedited admission into the attraction. Or, simply pay extra for expedited entry, which features an express line to the elevators. For the best views, it's advised that you visit just after opening or after sunset. If you'd like to enjoy the sunset from the tower, plan on arriving 30 to 45 minutes before sunset to ensure you have enough time to get through the elevator line and up to the top.

North Avenue Beach North Avenue Beach free

Located in Lincoln Park directly on Lake Michigan, North Avenue Beach is one of the most popular swimming spots in Chicago. The sandy beach has volleyball courts, plenty of space for visitors to stretch out and multiple things to do near nearby. Plus, it offers spectacular views of the city skyline. Beachgoers can also find restaurants, sports rental companies, restrooms and more inside a 22,000-square-foot beach house adjacent to the shore.

Recent visitors said the beach is a nice spot that is perfect for relaxing, biking and running, but they warned that it can get busy on warm summer days.

The Second City The Second City

If you've seen a sketch comedy show or hilarious movie in the last 40 years, it's likely that someone from The Second City appeared in it. The Second City is one of the world's most iconic improvisational comedy theaters, and it has helped launch the careers of numerous famous comedians, including Bill Murray, Tina Fey, Keegan-Michael Key, Steve Carell and Stephen Colbert. If you're in the mood for a laugh, check out a live show on any night of the week at any number of The Second City's seven stages (which are all housed in its facility at the northwest corner of North Avenue and Wells Street in Old Town). 

Recent reviewers said that everyone in their group could not stop laughing during the shows, which typically last 90 minutes to two hours. Ticket prices vary by the show and date, but run anywhere from $30 to $100.

The Chicago Theatre The Chicago Theatre

Aside from Cloud Gate and Buckingham Fountain , The Chicago Theatre's red and yellow marquee is perhaps one of the city's most recognizable landmarks. Illuminating North State Street at the northern edge of the Loop, The Chicago Theatre first opened its doors in 1921 as an extravagant movie theater and performance venue. Throughout its history, the theater has hosted such big names as Duke Ellington, Diana Ross and Prince, in addition to screening blockbuster flicks. Though the theater fell into disuse in the 1970s, new management and a full renovation in the 1980s helped return the venue to its former glory. Today, the theater is still used for a variety of comedic, theatrical and musical performances.

According to past patrons, the theater's historic appearance enhances the overall experience of catching an event here. Just remember, cameras and video cameras, including those on cell phones, cannot be used during tours or performances. If you're not in town for a show, consider signing up for one of the venue's guided tours. Tour tickets cost $20 for adults and $15 for kids ages 12 and younger. Tours are available Monday and Tuesday at noon and 2 p.m. and last about an hour.

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Chicago Children's Museum Chicago Children's Museum

Located at Navy Pier , the Chicago Children's Museum offers temporary and permanent play-based exhibits for babies, toddlers and kids ages 4 and older. Founded in 1982 by the Junior League of Chicago as a response to cuts in arts programming, the museum was originally housed in two hallways of what is now called the Chicago Cultural Center . Today, children can dig for "teeth" and "bones" in "Dinosaur Expedition," climb through tunnels of "Cloud Buster," test their STEAM (Science, Technology, Engineering, Art and Math) skills in the Tinkering Lab and paint, draw or sew in the art studio.

Recent visitors appreciated the interactive, hands-on exhibits, which they recommend for young children.

American Writers Museum American Writers Museum

U.S. News Insider Tip: Across the street from the museum, you will find the first Nutella Café, where you can savor French and Italian dishes featuring the heavenly hazelnut spread. The gelato is roll-your-eyes-to-the-back-of-your-head good. – Cortney Fries

The first museum in the United States dedicated to celebrating the diverse voices and influence of American authors, the American Writers Museum is an interactive journey through more than five centuries of written and spoken word. This relatively small museum, which opened in 2017, features thoughtful and reflective exhibits that you can touch, smell, hear and see. 

DuSable Black History Museum and Education Center DuSable Black History Museum and Education Center

U.S. News Insider Tip: If driving in Chicago isn’t your thing, consider taking the No. 55 bus to the museum. The bus drops you off within just a five-minute walk of the museum. – Sarah Estime

The DuSable Black History Museum and Education Center, named for Jean Baptiste Pointe DuSable, the entrepreneur who is credited with founding Chicago, is a must-visit for anyone looking to learn more about African American history in the city of Chicago and America. It celebrates its 62nd anniversary in 2023, and is full of thought-provoking exhibits, including those that showcase fine art created by influential African American artists and historical materials. Note that visitors hoping to enjoy “The March” exhibit, an immersive experience depicting the historic March on Washington and Martin Luther King Jr.'s "I Have A Dream" speech, can go in groups of no more than four at a time.

Adler Planetarium Adler Planetarium

The first planetarium in the Western Hemisphere, the Adler offers unrivaled insights into our solar system. Indeed, "Our Solar System" is one of its permanent exhibits, along with "Mission Moon," "The Universe: A Walk Through Space and Time," "Telescopes: Through the Looking Glass" and "Astronomy in Culture," among others. Its facilities include the Doane Observatory, which has the largest telescope available to the public in the Chicago area, through which visitors can glimpse celestial objects trillions of miles away. The Adler also has three full-size theaters – the 3D Universe Theater, the Definiti Space Theater and the Grainger Sky Theater – in which it screens programs like "Destination Solar System," "Planet Nine" and "One World, One Sky: Big Bird's Adventure."

Space enthusiasts invariably find the Adler's presentations both informative and entertaining, if somewhat pricey. Most visitors suggest setting aside a few hours to explore the various exhibits and shows. Travelers recommend maximizing your parking expenses by also visiting the Shedd Aquarium or The Field Museum , which also sit on the Museum Campus. Reviewers also appreciated the Lake Michigan and skyline views as seen from the planetarium.

Offbeat Street Art Tour Offbeat Street Art Tour

U.S. News Insider Tip: If you’re looking for unique souvenirs from your Chicago trip, consider The Goddess & Grocer for its gift baskets. – Sarah Estime

In Chicago, you can find eye-catching street art nearly everywhere. As you sightsee, you’ll be greeted with unique, thought-provoking art on the sides of buildings and underneath bridges. If you’re looking for an experience that walks you through the history and cultural significance of Chicago's street art scene, look no further than the Offbeat Street Art Tour. On this two-hour tour, you’ll discover new artists and learn the inspiration behind their colorful works, along with some interesting neighborhood history. You’ll also be able to take great photos along the way.

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The Green Mill The Green Mill

U.S. News Insider Tip: For visitors looking for a bite to eat after a night of jazz music, head across the street to Damera for an authentic Ethiopian meal, or down the block to the Fat Cat for a burger. – Sarah Estime

Best known for serving gangsters during its speakeasy days, the Green Mill invites travelers to step back in time. The long bar that runs along the club's left side sits in front of smokey mirrors and is peppered with decor reminiscent of the Prohibition era. The entire place is cast in a warm reddish glow while old-time jazz plays from the jukebox. The bar – one of Al Capone’s favorites – has no set menu; order whatever cocktails you like (though the chocolate martinis are delicious). There is also a selection of beer and wine.

Garfield Park Conservatory Garfield Park Conservatory free

One of the biggest botanical conservatories in the United States, the Garfield Park Conservatory houses thousands of plant species in eight indoor gardens, as well as 10 acres of outdoor gardens.

Each indoor space has a distinct focus. The Aroid House features varieties of its namesake, which are among the most popular houseplants; it also features sculptures by the world-renowned glass artist Dale Chihuly made specifically for the Aroid House. As its name suggests, the Desert House boasts cacti and succulents, while the Fern Room arranges ferns around an indoor lagoon. The Palm House, the conservatory's largest structure, recreates a tropical landscape complete with more than 70 palm trees. Meanwhile, the Elizabeth Morse Genius Children's Garden aims to educate little ones about plants. Horticulture Hall displays a range of flowers and plants and also has tables where visitors can take a seat and have a rest.

The Richard H. Driehaus Museum The Richard H. Driehaus Museum

Occupying a restored mansion built in 1883, the Richard H. Driehaus Museum presents exhibitions relating to architecture, art and design from the 19th century to the present day.

The Nickerson Mansion containing the museum boasts an entrance hall made with so much marble that the building was nicknamed "the Marble Palace." (The museum takes its current name from the philanthropist who founded it in 2003.) Its reception room features intricate woodwork as well as items from the museum's permanent collection, such as a Tiffany Studios lamp that dates back to the early 1900s. Meanwhile, the front parlor displays Renaissance Revival furniture original to the Nickerson Mansion. The dining room, fitted with elaborately carved oak, houses a silver punch bowl first exhibited at the 1893 World's Columbian Exposition. Other highlights from the permanent collection include a gem-encrusted inkstand, a ceramic clock, multiple chandeliers, paintings, sculptures and an array of decorative items.

Chicago Cultural Center Chicago Cultural Center free

The "People’s Palace," a popular destination occupying a full city block in the downtown Loop neighborhood, is a stunning architectural marvel as well as a venue for a great deal of cultural programming, including art exhibits and concerts. Among its features are one of the largest Tiffany stained-glass domes in the world (made with around 30,000 individual pieces of glass) and a marble lobby adorned with mosaics made of gold, glass and precious stones.

Visitors invariably rave about the impressive structure and its elaborate decorations, saying it’s worth it to pop in for free to see the ornate ceiling.

University of Chicago University of Chicago free

Founded in 1890 by John D. Rockefeller, the University of Chicago is an urban research university in the city's Hyde Park neighborhood close to Lake Michigan. Currently, it has more than 7,000 undergraduate students and more than 10,000 graduate, professional or other students as well as nearly 2,400 full-time faculty members.

Impressive as those statistics may be, they aren't reasons to visit. But the university's 217-acre campus, which was designated a botanic garden in 1997, and its mixture of English Gothic and modern architecture are. Some of the newer structures were designed by celebrated architects like Ludwig Mies van der Rohe and Eero Saarinen, while some of the older ones are adorned with gargoyles that date back to the 1893 World Columbian Exposition. The university welcomes visitors to explore its campus, and provides information about its architecture on its website. Those who've visited before routinely call the buildings diverse and beautiful, and many recommend stopping by in the spring when flowers bloom across campus, or fall when amber leaves transform the grounds.

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18 Top-Rated Tourist Attractions in Chicago

Written by Lana Law and Lura Seavey Updated Mar 18, 2024

Chicago, the "Windy City" as it is often called, lies along the shores of Lake Michigan. Known for its vibrant arts scene, numerous cultural attractions, excellent shopping, and interesting architecture, this city attracts visitors from the US and around the globe.

Chicago enjoys a worldwide reputation as a focal point of 20th-century architecture and art, with architects such as Louis Sullivan and Frank Lloyd Wright, and artists like Picasso, Mirõ, Dubuffet, and Chagall leaving their mark.

The city also has much to offer in the sporting sphere, too, with the Chicago Bears in American football, the Chicago White Sox and Cubs in baseball, and the Chicago Bulls in basketball.

Last, but not least, are the beautiful beaches that stretch along the waterfront, attracting throngs of sun seekers in the summer.

Deciding when to visit Chicago may depend on your interests, particularly if you are coming for sports or cultural events, but spring until fall is the best time for weather.

For a complete look at places to visit, see our list of the top attractions and things to do in Chicago.

1. Visit the Art Institute of Chicago

2. walk through millennium park, 3. stroll around navy pier, 4. reach for the stars at adler planetarium, 5. museum of science and industry, 6. see the view from the willis tower skydeck, 7. watch the water show at buckingham fountain, 8. 360 chicago, 9. field museum of natural history, 10. michigan avenue and the magnificent mile, 11. take a tour or see a game at wrigley field, 12. lincoln park, 13. shedd aquarium, 14. lincoln park zoo, 15. chicago riverwalk and lakefront trail, 16. oriental institute museum, 17. the rookery building, 18. enjoy a show in style at the chicago theater, where to stay in chicago for sightseeing, map of tourist attractions in chicago, best time of year to visit chicago.

The Art Institute of Chicago is a world class museum with hundreds of thousands of artworks. The diverse collection spans thousands of years and includes pieces from a variety of media including painting, prints, photography, sculpture, decorative arts, textiles, architectural drawings and more.

The Institute is known for its collection of impressionist and post-Impressionist paintings including Georges Seurat's 1884 A Sunday Afternoon on La Grande Jatte , Renoir's 1879 Acrobats at the Cirque Fernando, and numerous paintings by Claude Monet.

The main building, designed by Shepley, Rutan, and Coolidge in beaux-arts style, was built for the 1893 World's Columbian Exposition. Several other buildings have been added on over the years and today the complex measures 400,000 square feet.

Address: 111 South Michigan Avenue, Chicago, Illinois

Official site: http://www.artic.edu/

Millennium Park is part of the larger Grant Park , located in downtown Chicago bordered by Michigan Avenue to the west, Columbus Drive to the east, Randolph Street to the north, and Monroe Street to the south. Its centerpiece is a 110-ton sculpture name Cloud Gate , which has a polished, mirror-like stainless steel surface that was inspired by liquid mercury. It reflects the surroundings, including buildings, the sky, and the tourists who walk through its central arch.

Another top attraction in Millennium Park is Crown Fountain , a fascinating modern interpretation of the ancient gargoyle that gives the appearance of water flowing from the mouths of projected images of Chicago citizens. Other popular things to do here include seeing a performance at the Jay Pritzker Pavilion , an outdoor concert venue, and visiting Lurie Garden , which is open to the public at no cost year-round.

Located close to many of the major attractions, as well as great shopping, this area of the city is a convenient place to base yourself.

Address: 201 East Randolph Street, Chicago, Illinois

Official site: http://www.cityofchicago.org/city/en/depts/dca/supp_info/millennium_park.html

The Navy Pier originally opened in 1916 as an amusement area and shipping facility but is now one of Chicago's most popular tourist attractions. Today, the Navy Pier is made up of 50 acres of gardens, attractions, shops, restaurants, concert venues, and parks. There is a 150-foot Ferris wheel and an historic carousel in Navy Pier Park.

Visitors can also watch a film at the 3D Imax Theater, watch actors perform the classics at the Chicago Shakespeare Theater, or visit Crystal Gardens, a one-acre, six-story, indoor botanical garden. Also located here is the Chicago Children's Museum. The Pier hosts year-round festivities, including the Chicago Festival in August. Cruise ships leave from here on various sightseeing excursions.

Address: 600 East Grand Avenue, Chicago, Illinois

Official site: www.navypier.org

The Adler Planetarium is leaps and bounds beyond the ones most kids get to visit on school trips, and all ages will appreciate the shows and comprehensive exhibits it has to offer. The Adler prides itself in being the first planetarium in the Western Hemisphere, built in 1930 on the shore of Lake Michigan.

The planetarium is home to two dome theaters, which offer a variety of shows, including exploration of Chicago's night sky, the solar system, and the moon. There is also an extensive array of exhibits that explore topics including life on other worlds, meteors and meteorites, space exploration, the history of the scientific discipline, and even the history of astrology.

There are also several exhibits dedicated to the accomplishments of marginalized groups including female, Latinx, and LGBTQ+ astronomers. Of note is an excellent exhibit that looks at the importance of Islamic astronomers' contributions and how their studies affected the faith and the world. In addition, there are collections of artifacts from astronomers past, including many antique and ancient sundials, as well as telescopes.

While visiting, be sure to leave enough time for the Skyline Walk along the perimeter, the best place to get photos of the city skyline short of a boat cruise.

Address: 1300 S. DuSable Lake Shore Drive, Chicago, Illinois

Official site: www.adlerplanetarium.org

At the north end of Jackson Park is the Museum of Science and Industry, founded in 1933, and arguably the most impressive museum in Chicago. It is devoted to the application of natural laws in technological and industrial development.

The museum is thought to be the first in the U.S. to incorporate the idea of "hands-on" exhibits. Visitors are encouraged to interact with hundreds of exhibits. The MSI features permanent and changing exhibits, as well as an OMNIMAX theater.

Address: 5700 South Lake Shore Drive, Chicago, Illinois

Official site: http://www.msichicago.org/

Until 1996, when the Petronas Towers were built in Kuala Lumpur, the 110 story Sears Tower, now Willis Tower, was the world's tallest office block. While there are now several taller buildings, the view from here is incredible. On a clear day you can see 40 to 50 miles over four states, and gain a bird's eye view of Chicago's impressive architecture.

The Willis Tower took three years to build and was opened to the public in 1974. The building is 1,453 feet tall with an observation area, called the SkyDeck, on the 103rd floor, 1,353 feet above the ground. A glass box with a glass floor, known as the Ledge, juts out from the SkyDeck, where visitors can stand and look directly down at the city below.

Address: 233 South Wacker Drive, Chicago, Illinois

Official site: https://theskydeck.com/

Built in 1927 as a donation from the family, the Clarence Buckingham Memorial Fountain is one of the largest in the world. Designed in the period's iconic Art Deco style, the central fountain is surrounded by four seahorses that represent Lake Michigan's four bordering states. From 8am to 11pm, the fountain bursts to life hourly, shooting 15,000 gallons of water through nearly 200 nozzles each minute to create an impressive display.

After dusk, the water show is accompanied by lights, a must-see if you are in the neighborhood in the evening. The fountain is the central focal point of Grant Park , Chicago's expansive public space that contains many attractions and smaller parks like Millennium Park , comparable to Central Park, one of the top attractions in New York City .

One of the park's main tourist sites is Museum Campus , home to The Field Museum of Natural History , the Art Institute of Chicago , the Adler Planetarium , and Shedd Aquarium . Grant Park is also home to several gardens and recreational facilities, and hosts events, including music and food festivals.

Located in the John Hancock Center office building, 360 Chicago is an observation deck on the 94th floor of the John Hancock Building, easy to recognize by its dark metallic looking exterior and cross-braced steel design, which runs up the outside of the building. The large glass-walled observation deck has views that look out over Chicago's skyline and beyond.

More adventurous tourists will love the deck's newest feature, "Tilt," which gives visitors a unique view from more than 1,000 feet above the Magnificent Mile as they are tipped outward at an angle to look straight down from the glass enclosure.

The rest of the building contains a variety of shops, offices, and apartments, as well as a multimedia exhibit located on the first floor that includes information about the city of Chicago and the construction of the John Hancock Building.

Address: 875 North Michigan Avenue, Chicago, Illinois

Official site: http://www.360chicago.com/

Originally called the Columbian Museum of Chicago, the Field Museum of Natural History was founded in 1893 to showcase the biological and anthropological collections gathered for the World Columbian Exposition. The name changed in 1905 to honor Marshall Field, the department store owner, art patron, and major benefactor of the museum.

The permanent collection features approximately 20 million artifacts and specimens covering a variety of disciplines including geology, botany, zoology and anthropology. Of special note are the permanent displays on Ancient Egypt and the cultures of North, Central and South America and "Sue," the world's largest, most complete Tyrannosaurus rex skeleton. Special rotating exhibits take place on a regular basis throughout the year.

Address: 1400 South Lake Shore Drive, Chicago, Illinois

Official site: http://fieldmuseum.org/

Michigan Avenue is probably one of the most attractive boulevards in America. The city's famous Magnificent Mile is a section of Michigan Avenue north of the Chicago River, with numerous galleries, boutiques, and luxury shops.

Some of the attractions along here include the John Hancock Center, the Wrigley Building, and the Tribune Tower. Michigan Avenue splits between North and South designations at Madison Street. This district is also known for its theaters, which host touring plays, musicals, and comedy acts.

Official site: http://www.themagnificentmile.com/

Wrigley Field, home to the Chicago Cubs, was built in 1914 and is the second-oldest Major League Baseball park in the US, second only to Fenway Park in Boston. The park has seen some legendary moments in baseball history, including the 1917 no-hitter pitching duel between the Cubs' Jim Vaughn and the Reds' Fred Toney, and Babe Ruth's "called shot" during game three of the 1932 World Series.

Ballpark tours are conducted in-season, when you can visit the press box and field, as well as the dugouts if there is no game that day.

Official site: http://chicago.cubs.mlb.com/chc/ballpark/

Lincoln Park is a six-mile stretch of green space along the edge of Lake Michigan, and Chicago's biggest park. This popular park is home to the lovely Lincoln Park Conservatory and the Lincoln Park Zoo , one of the oldest zoos in the country. Also located here are the Peggy Notebaert Nature Museum , and the Chicago History Museum .

For those who simply want to enjoy the outdoor space there are playing fields, bike trails, jogging paths, and beaches. Visitors can see a number of significant statues and pieces of public art within the park grounds including Augustus Saint Gaudens' Standing Statue of Lincoln (1887).

If Lake Michigan has you wondering what sort of aquatic life exists just offshore from downtown Chicago, swing by the Shedd Aquarium. Inside are exhibits that cover aquatic regions of the world, from the Arctic to the Caribbean.

If you are visiting with young children, one of the must do's is the Polar Play Zone. Here, children can slip into their favorite animal costume, take a make-believe trip in a submarine, and touch sea stars. Another popular place for children of all ages is the Stingray touch tank. This massive tank is full of curious stingrays who love to be petted and touched.

Address: 1200 S DuSable Lake Shore Drive, Chicago, Illinois

Official site: www.sheddaquarium.org

Another fun thing for families to do in Chicago is a trip to the Lincoln Park Zoo. The zoo is home to over 200 species from around the world. Sixteen different exhibits showcase the wonderful animals that we share this world with. Some of the most entertaining animals include penguins, otters, and seals. For a truly fascinating experience, stop by the Regenstein Center for African Apes.

The zoo is not just about animals, in fact it's one of the best places in Chicago to see amazing floral displays. Each year, the gardening crew tends to over 2,000 individual plants across 1,200 species.

Address: 2001 N Clark Street, Chicago. Illinois

Official site: www.lpzoo.org

The Chicago River runs through the heart of the city, parallel to the lakeshore, and is known for its large number of movable bridges. In just two miles, there are 18 bridges, each with the ability to allow large boats to pass.

The McCormick Bridgehouse & Chicago River Museum treats tourists to an up-close look at the mechanisms of one of the city's most famous bridges, where you can actually watch the gears work as it moves.

The Riverwalk is home to many dining options and hosts special events throughout the year, and you can also find several river tours and cruises that depart from the Riverwalk.

The fully-paved Lakefront Trail offers beautiful views of the city skyline and Lake Michigan, stretching 18 miles from 71st Street on the South Side to Ardmore Street on the North Side. It is open to pedestrians and people-powered wheels, and is lined by parks, gardens, and recreation areas, as well as beaches. Many of the city's top attractions are located along the trail, including Navy Pier , Lincoln Park , and Soldier Field .

Official site: www.chicagoriverwalk.us

The Oriental Institute Museum, located on the University of Chicago campus, is dedicated to the archeology and art of the Near East, including antiquities from excavations in Egypt, Sudan, Nubia, Iraq, Turkey, Israel, and the ancient site of Megiddo.

Among the permanent exhibits are the Mesopotamian Gallery, which features objects from between 100,000 BC and the 7th century AD, and two Egyptian Galleries, which include artifacts that range from everyday objects to mummification relics.

Address: 1155 East 58th Street, Chicago, Illinois

Official site: http://oi.uchicago.edu/museum-exhibits

The Rookery Building was designed by architects Daniel Burnham and John Root in 1888, but the interior lobby and patio were remodeled by Frank Lloyd Wright in 1907. This 12-story building has a Roman Revival and Queen Anne-style façade, but it is the central light court and the ornamental ironwork of the elegant staircases that are the true gem of the building.

The Rookery, named for the large number of pigeons that frequented the building, is listed on the Register of National Historic Places. The Frank Lloyd Wright Trust conducts tours of the building, as well as other sites, like the Robie House in Hyde Park and the Bach House.

Address: 209 South LaSalle Street, Chicago, Illinois

Official site: http://therookerybuilding.com/

Between the theater's unmistakable sign and its stunning façade, it's impossible to miss this stunning Chicago landmark. Built in 1921, the front of the building was designed after the Arc de Triomphe in Paris, featuring stained glass and an ornate neon sign.

The interior features French Baroque architecture inspired by the palace at Versailles . Visitors will find a grand lobby with ornate details and a sweeping staircase before entering the immense theater that is seven stories high. Even if you don't have time to check out a show, be sure to pop in or schedule a tour to get a closer look.

The theater now hosts a variety of stage performances by major entertainers, from comedians to musicians. If you prefer a more intimate venue, check out The Second City on North Wells Street for nightly live comedy shows. This stage has seen many famous comedy performances, from the early careers of Tina Fey, Bill Murray, Steve Carrell, and many others.

Address: 175 N. State Street, Chicago, Illinois

Official site: www.msg.com/the-chicago-theatre

The best sightseeing, shopping, and dining and the most interesting architecture are found in Chicago's city center, and this is where most visitors will want to stay. The city center encompasses the famous Magnificent Mile and areas of the waterfront, which are particularly popular in summer.

The best time of the year to visit Chicago is between April and October during the shoulder season and the high-tourist summer season, when the selection of things to do is the most abundant.

During the busy summer tourist season , Chicago can be quite warm, especially in the concrete jungle of downtown. June, July, and August have the most festivals and convention activity, and that is when the Navy Pier is buzzing.

The summer crowds are big, so you may experience wait times on the observation decks at the Willis Tower and TILT, which tips you over the Magnificent Mile at 1,000 feet in the air. Be aware that the high tourist season also comes with higher prices at Chicago's most popular hotels.

The shoulder seasons of April and May are great times to visit, too, in the small window between spring and summer. September and October are also good times to go to Chicago, as temperatures become milder. The weather is still pleasantly warm, and many of the outdoor activities are still in full swing.

These are the best times to visit for moderate temperatures, especially for activities like strolling through downtown to the stores along the Magnificent Mile and snapping a selfie at the Bean in Millennium Park, one of the top tourist attractions in Illinois . The bonus to a shoulder season visit is that hotel rooms will be less expensive than in the summer months.

Spring : Spring is a beautiful time to visit Chicago , when the flowers and gardens are in full bloom and the city is awakening after the cold winter. Activity at the parks and lakefront is picking up, with walkers and bicyclists. Spring weather in Chicago is mild , with low humidity and comfortable daytime temperatures, from in the 50s Fahrenheit in March to the 70s by late May. These are perfect temperatures for walking around downtown and enjoying outdoor activities.

While springtime weather in Chicago is comfortable, it is also unpredictable—rain showers are likely, so pack a poncho or umbrella. The spring months have fewer crowds and lower prices , with the exception of mid-March when spring break tourists and St. Patrick's Day revelers flock to the city.

Summer : Summertime in Chicago is busy, and it is one of the most exciting times to visit . It is also hot and humid in Chicago in the summer. That is easy to remedy with an iced tea at one of the many open-patio restaurants and rooftop terraces. Summer temperatures range from the high 70s to the mid-90s Fahrenheit and feel even warmer with the humidity. You can also get storms in the summer, with June being the wettest month in Chicago .

Summer is the most popular time to visit Chicago , so expect large crowds everywhere, high prices for hotels, and long lines and wait times at restaurants. If you like being where the action is, summer is the best time to go to experience the festivals, outdoor music, and events . Some things, like the free fireworks at Navy Pier twice a week, you can only enjoy during the summer months. Availability is tough to come by in peak season, so it is best to book your Chicago resort or hotel far in advance if you plan on a summer getaway.

Fall : If your vacation goal is comfort and being able to maximize your time then the fall is the best time to go . The city is still active, and attractions and outdoor activities are still buzzing, but the temperatures start to drop, making it nice to walk around or sit in the stands at a Chicago White Sox baseball game. Daytime temperatures in the fall average in the 60s and 70s Fahrenheit. Restaurant patios are still open this time of year but with fewer crowds and without the summer vacationers competing for space.

Some attractions, like Lincoln Park Zoo and Navy Pier, may have reduced hours later in the fall season, but you can still enjoy the outdoor venues, city parks, and the lakefront. This is also a great time of year to experience the many cultural activities in Chicago with live theater and comedy performances and special exhibits at places like the Art Institute of Chicago .

Winter : While winters in Chicago can be brutal there are unique experiences during the colder months that can make for a fun vacation, especially around the holidays. Chicago winter weather usually means lake-effect snow up to 37 inches and average daytime temperatures below freezing. If you do not mind the cold weather then a few layers of winter clothing and a heavy coat will have you prepared to explore Chicago easily.

Winter in Chicago means indoor museums, theater, and shopping. The holiday displays in the store windows and festive lighting throughout the city creates a nice ambience that you can only experience during the winter. Since this is the low tourist season, you will find cheaper hotel rates and airfares . Keep in mind that the weather frequently causes flight delays in and out of Chicago in the winter, so it is best to pad your agenda with extra travel time.

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23 Best Things to Do in Chicago

By Nicole Schnitzler

Home to 77 neighborhoods, a robust lineup of festivals, a sprawling waterfront, and charming parks and walkways throughout, Chicago packs in something for every one of its locals. Add to that list award-winning theaters, iconic architecture, and a dynamic dining scene, and you’re looking at a world-class destination, too—smack dab in America’s heartland. The city’s draws only continue to grow, thanks to arrivals in everything from music venues to Michelin-starred restaurants—and the town’s hospitality remains strong, invested in helping others to enjoy those experiences across the board. From an education in the arts to an entirely outdoors itinerary (and plenty of easy-to-elegant noshes along the way), here are some of the best things to do in Chicago now.

Read our complete Chicago travel guide here.

This gallery has been updated with new information since its original publish date.

Garfield Park Conservatory Arrow

Step into the humid, glass-enclosed domes of Garfield Park where the air is clean thanks to thousands of jewel-toned plant specimens filtering toxins throughout. The space is fashionably untamed across its verdant showcase of flora from wet and dry environments, and those between. Spread across twelve acres, there's abundance year-round, from the colorful spring flower show to permanent indoor exhibits and holiday displays. Plant and garden enthusiasts should make the conservatory—easily accessed by Green Line—one of their stops.

Pizza City USA Arrow

In writing his book Pizza City USA , James Beard Award-winning food reporter Steve Dolinsky had organized the city into 10 different styles of pizza, quickly understanding Chicago’s wide array of pie styles. That research led him to start a tour showcasing that range, offering him and a team of “doughcents” a chance to tout Chicago’s diverse pizza scene to visitors and locals alike. There are four different kinds of tours, each exploring 3-4 styles of pizza. A walking tour Friday nights (downtown), a bus tour (various neighborhoods), and a walking tour (West Loop) on Saturdays, and a walking tour on Sundays (Bucktown/Wicker Park). Though the venues vary by tour, you can expect stops at favorites like Labriola (deep pan), My Pi (deep-dish), Robert’s (artisan), Paulie Gee’s Logan Square (Detroit-style), Eataly, and Bar Cargo (Roman). Get ready to grow your pizza IQ—in addition to discussing the range of pie styles, the team shares plenty of ‘za terminology and local history.

Urban Kayaks Arrow

Kayaking on the Chicago River or lake front is one way to shake up your perspective while visiting. Urban Kayaks offers tours along either. Move through the pulsing heart of the city on the river or travel Lake Michigan and circle Museum Campus (featuring the Field Museum , Adler Planetarium , Shedd Aquarium and Soldier Field). A night tour on the river boasts views of the glowing Merchandise Mart, which is showered in rotating, digital art displays projected onto the building. A one and a half hour skyline paddle in Lake Michigan gives you all the tourist sites without the foot traffic and crowds, showing you Grant Park and Navy Pier on a route few tourists trek.

The Salt Shed Arrow

The team responsible for some of Chicago’s best restaurants and concert halls is behind this hugely popular newcomer, housed within the iconic Morton Salt building on the North Branch of the Chicago River. The indoor-outdoor space made a soft debut last summer and continues those rollouts this year, with indoor shows this past winter and a full lineup this summer (including acts like First Aid Kit, Pretty Lights, Caamp, and Tash Sultana). Multi-level ticketing tiers help guests in selecting their vantage point for shows. Even if you don’t have prime sightlines every time (now considered the largest independent concert venue in Chicago, the space has a capacity of 5,000 for outdoor shows and 3,500 for indoors), you’re still in luck: They feature a state-of-the-art sound system by L-Acoustics. The venue also features a solid lineup of local food options, including Pizza Friendly Pizza and Café Tola. Find them in the outdoor Fairgrounds space (perfect for grabbing a bite pre-show).

Sarah Enelow-Snyder

Juliana Shallcross

Boutayna Chokrane

Sarah James

The Morton Arboretum Arrow

Located about 30 minutes west of downtown Chicago, the Morton Arboretum feels like a world away. It's a pastoral escape that feeds the mind and heart. Art installations on site are rotated seasonally, several of them are dedicated to the natural sciences, such as the living exhibit dedicated to tree growth. 'Human+Nature' is the current installation here, showcasing the work of acclaimed sculptor Daniel Popper. Five pieces are currently on display in various locations across the arboretum's 1,700 acres, making this Popper's largest exhibition to date anywhere in the world. Open from 7:00 a.m. to sunset, daily—it's a relative bargain at $16 a ticket. With a maze garden and over 16 miles of hiking trail, this is the ideal urban getaway for outdoorsy sorts looking to decompress.

Wrigley Field Arrow

Iconic Wrigley Field is arguably one of Chicago's most storied landmarks, with millions of baseball fans flocking to the stadium just to get a photo in front of the iconic Wrigley Field Marquee (whether they’re rooting for the Cubs or not). The stadium anchors the Wrigleyville neighborhood, which has experienced a boon in development. A new outdoor plaza, luxury hotels, and an influx of restaurants/bars have boosted the area's cultural cachet, so it's worth hanging around before or after your stop at the stadium.

Museum of Contemporary Art, Chicago Arrow

The MCA is one of the city’s museums that’s in a near constant state of transition. With its relatively small permanent collection, it relies on special shows—from large scale installations to video, fashion, music, photography, and more—that showcase just as many rising local talents and underground, avant-garde renegades as recognizable names. Past exhibits include David Bowie Is, Takashi Murakami: The Octopus Eats Its Own Leg, and Virgil Abloh: Figures of Speech.   It also has one of the best gift shops (ever) and is home to Marisol, where chef Jason Hammel puts forth thoughtful, seasonal cuisine. Come summer, visit for their “Tuesday on the Terrace” music series, along with 21 Minus, an annual festival celebrating the next generation of artists.

Midway Plaisance Arrow

Known simply as the Midway, this mile-long natural stretch on the South Side connects the east end's Washington Park to Jackson Park on the west. Once the site of amusements during the 1893 Columbian World's Exposition (AKA World's Fair), the Midway is flanked by Hyde Park's noted gothic architecture, particularly the University of Chicago campus, and tree-lined boulevards, as well as outfitted with an ice skating rink and other facilities to keep folks visiting year-round.

Lincoln Park Zoo Arrow

Located in the heart of Chicago's Lincoln Park, this zoo offers free, family-friendly entertainment year-round including the festive Zoolights around the holidays (reservations are required for all visits though). The sprawling grounds are seamlessly woven into the park’s landscape, balancing open, natural spaces and numerous animal exhibits. If you skip the pricey concessions (but maybe spring for a paddle boat ride), Lincoln Park Zoo is a great option to keep all ages occupied while staying on a budget. Visit the animals, take a spin on the AT&T Endangered Species Carousel or the Lionel Train Adventure, and enjoy family-friendly dining options, such as Bird’s Eye Bar & Grill or the Patio at Café Brauer. 

Art Institute of Chicago Arrow

If you're coming to Chicago for culture, you're hitting the Art Institute first. It is the city's grandest museum, a Beaux Arts gem flanked by two bronze lions that are as much a symbol of the city as the Willis Tower and it has as fine an impressionist collection as you'll find anywhere. While you're there, plan to take a stroll through Millennium Park next door.

Bloomingdale Trail (The 606) Arrow

Chicago's answer to New York's High Line , the Bloomingdale Trail—a.k.a. The 606—is a nearly three-mile, elevated greenway running west and east on the city’s North Side. Unlike its NYC counterpart, the trails are wide enough to accommodate active patrons running, walking and cycling without running off more casual strollers, the formerly abandoned rail line is also lined with public art installations and gardens. During fairer weather, the trail also hosts various free events for families with young children.

3 Arts Club Cafe Arrow

Today there are more than 15 RH restaurants across the nation, but Chicago’s 3 Arts Club Café, which opened in 2015, was the first. Guests will discover it within Restoration Hardware’s 70,000-square-foot design gallery, which formerly functioned as the Three Arts Club, a residence built in 1914 for young women studying music, drama and the visual arts. Today, that space has been royally reimagined in the hands of RH, turning the six-story building into a lavishly outfitted labyrinth featuring its myriad décor whimsies (from the brand’s Design Atelier line to its children’s collections). Come here with friends or a special plus one, and arrive early—you'll want to factor in time for grabbing a coupe and perusing the historic property as you await your table.

Humboldt Park Arrow

One of Chicago's prettiest parks, this nearly 200-acre green space is located within the larger neighborhood of Humboldt Park (both are named for German naturalist Alexander von Humboldt). It's home to several statues—including one of its namesake, and two bison that were placed there during the 1893 World's Fair—as well as the National Museum of Puerto Rican Arts & Culture, located in the park's former stables. It's easy to drop in if you're headed down the 606 trail, but the park is big enough that it could take more than half a day to do all of it, so it's best if you're not in a rush.

The Second City Arrow

Tina Fey, Bill Murray, and Chris Farley all grew out of the scene at Second City and it continues to nurture some of the country's best comedy talent. Over three stages and four intimate studio theaters, there's plenty to see. The Mainstage show, featuring that season's top billed act, features long-form improv sketch, and is often packed on marquee nights. The same can be said for the e.t.c. Theater, which showcases up-and-comers, and the Up Comedy Club, for stand-up comic acts. The shows tend to be full, and ticketed for general admission, so come early to snag a prime seat. (Pro-tip: Avoid front row if you don't want to crane your neck all night.)

Chicago Lakefront Trail Arrow

The 18-mile long trail hugs the coast of Lake Michigan, offering almost all manner of activity along the shore. From sandy beaches and sprawling parks, to some of the best views of the Chicago skyline, the Lakefront Path is one of the city's great public treasures, enjoyed by visitors and locals alike. Runners and cyclists love the width and ease of use of the trail, while intramural type teams make use of the many open spaces found up and down the path. If you don't want to run around, there’s plenty of room to just sit and people watch, as well as check out a number of art installations that pop up throughout the year.

Chicago Electric Boat Company Arrow

Auditorium Theatre Arrow

Inspired to build a theater that would benefit the city and serve as the world’s largest and most ornate building, Chicago businessman Ferdinand Wythe Peck began plans for the Auditorium Theatre and debuted the venue in 1889. Since then, the theater has been the site of major historical events and performances and earned impressive titles along the way (including a National Historic Landmark designation). Keep an eye on this season's calendar for events with Tom Hanks, The National, and Loreena McKennitt, among others. Anyone seeking a dose of the arts in elevated, historic environs will do well by a visit here. Gather friends for a speaker event or concert, or make it a date night.

Green Mill Arrow

Do not come here expecting fancy drinks—or anything fancy, really. This is living, breathing history. And it's a rocking good time. The Green Mill is a warm and inviting throwback to a bygone era. There’s live jazz, cheap drinks, and loads of local history (Al Capone used to have a booth reserved here during Prohibition); what's not to love? Bar eats are not on the menu here. Bring your own potato chips if you think you'll need a snack (no one will judge you). The craft beer list has expanded commendably over the past few years. So grab yourself a cold one or a whiskey soda and see where the night takes you.

Chicago Architecture Foundation River Cruise Arrow

Run by the Chicago Architecture Center, the Architecture River Tour is one of the most polished operations in town ( and a wonderful alternative to some of the cheesier tours ). Taking place on a barge in spring, summer, and fairer fall weather, the cruise explores Chicago's beginnings from various branches of the Chicago River—offering both day and evening tours. While groups are typically large, the Architecture Center-trained docent speaks via loudspeaker, audible from throughout the boat. (Pro-tip: Head straight upstairs when you board and snag a seat in the rear for optimal views.) In 90 minutes, you'll get to know 50 buildings along the Chicago River, hear secrets about a map of the river's topography hidden in plain sight, and learn about the only skyscraper in the skyline designed by an award-winning female architect.

Promontory Point Arrow

This man-made peninsula in Burnham Park has become a favorite gathering and photo shoot spot for locals due to its manicured landscape and rock formations along the lakefront. Our plan of attack here is to have a picnic at the point, then walk among a number of public art works edging the surrounding park. Some of the most interesting  public art installations and gathering spaces, such as Sounding Bronzeville and La Ronda Parakata, are actually within the Burnham Wildlife Corridor, which is composed of the Burnham Centennial Prairie, Burnham Nature Sanctuary, and McCormick Bird Sanctuary.

Chicago Symphony Orchestra at Symphony Center Arrow

Intuit: The Center for Intuitive and Outsider Art Arrow

Among the only museums in the world dedicated wholly to outsider art, Intuit is an impressive shrine to self-taught creators across all forms of media. Beyond an unassuming, brick facade, you’ll brush up against a concise-yet-vibrant collection of paintings, sculptures and assorted ephemera. The collected work draws you in with an air of unconventional audacity. This is a whimsical environment with an industrial edge. Exhibits are spread out with ample room for wandering and gazing at your leisure. The museum is curated by passionate docents who are committed to the cause of promoting the artistic output of marginalized creatives.

Chicago Botanic Garden Arrow

The Chicago Botanic Garden, a 385-acre living plant museum, features 28 distinct gardens and four natural areas. Those figures are impressive enough to draw more than one million visitors annually, making it one of the most frequented botanical gardens in the United States . Inside the gates, the Garden’s living collections feature more than 2.8 million plants from around the world that grow well in the Chicago area and are adapted to Midwest climate and soils. Expect to see a lush array of trees, shrubs, vines, and tropical plants, among other varieties.

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40 Best Things to Do in Chicago, From Iconic Sights to Can't-miss Museums

Planning a trip to the Windy City? Here are 40 of the best things to do in Chicago.

Meena Thiruvengadam is a lifelong traveler and veteran journalist who has visited more than 50 countries across six continents. Her writing has appeared in The Wall Street Journal , Departures , TripSavvy , and other publications.

Chicago may not be the city that never sleeps, but there is surely more to do here than you'll have time for. Whether it's world-class art, a cultural experience, or sports you seek, you'll find it in the Windy City. Here are 40 of the best things to do in Chicago.

Valerie de Leon/Travel + Leisure

See masterpieces at the Art Institute of Chicago.

This downtown museum isn't just an architectural gem, it's one of the best art museums in the United States. It's home to famous pieces, including Edward Hopper's "Nighthawks" and Grant Wood's "American Gothic," as well as the largest collection of works by Claude Monet outside of Paris.

Take an architecture river cruise.

With several buildings designed by greats like Frank Lloyd Wright and Ludwig Mies van der Rohe, Chicago is an architecture nerd's paradise. And one of the best ways to appreciate the cityscape is from the river. While there are dozens of cruise operators, Chicago's First Lady Cruises stands out for its 90-minute architecture cruise guided by experts from the Chicago Architecture Center.

Tour a submarine at the Museum of Science and Industry.

The largest science center in the Western Hemisphere, this Hyde Park museum is a great place to spend a cold or rainy day. The permanent exhibits focusing on science, technology, and nature are extensive but it's worth upgrading your ticket to include a tour of the only German submarine in the U.S. Check the schedule for special exhibitions, which can also be a treat.

Step back in time at the Chicago History Museum.

Chicago is where Al Capone once played and where Playboy was born. It's a city full of stories to tell, and there's no better place to discover them than one of the city's oldest cultural institutions, the Chicago History Museum .

Meet a dinosaur at the Field Museum of Natural History.

The Field Museum is one of the largest natural history museums in the world, and its permanent collection includes a number of fossils and the remains of Sue, the Tyrannosaurus Rex. Sue is estimated to be 67 million years old and made her debut at the museum in 2000.

Have a few laughs at a comedy club.

Several famous comedians (Tina Fey, Chris Farley, and Jim Belushi, to name a few) got their start at Chicago's well-known comedy clubs, including The Second City . New stages have since popped up, like Laugh Factory and The Revival . Who knows? You might see the next rising star of Saturday Night Live before they hit it big.

Listen to live music.

Chicago is a live music heaven, with venues that host performers of all genres throughout the year. In the mood for classical? Experience the talents of the Chicago Symphony Orchestra . Craving jazz? Head to the historic Green Mill jazz club. The city is also home to several music festivals, including Lollapalooza , Riot Fest , and world-famous blues and jazz festivals.

Go to the beach.

Believe it or not, Chicago is a beach town during the summer. Oak Street and North Avenue beaches are two sandy beaches along Lake Michigan that are close to downtown and will allow you to bask under both the sunshine and the shadows of the city's skyscrapers.

Brave the Skydeck of the Willis Tower.

Formerly known as the Sears Tower, this towering giant was once the world's largest skyscraper. That may have changed, but its expansive observation deck on the 103rd floor still offers some of the best views of the city. Those looking for a thrill can step onto The Ledge, a glass balcony extending out 4.3 feet from the building.

Stop at 875 North Michigan Avenue.

This 100-story building (formerly known as the John Hancock Center) may not be as well known as the Willis Tower, but it's another place for epic city views. There are restaurants, bars, the 360 Chicago observation deck , and occasional events like yoga classes.

Enjoy the free attractions in Millennium Park.

Located in downtown Chicago, Millennium Park is one of the city's largest green spaces. It's easy to spend a few hours here, especially since most of its attractions are free. The Frank Gehry-designed Jay Pritzker Pavilion hosts free concerts and other public events every summer. On a hot day, many cool off in the whimsical Crown Fountain , an interactive public artwork designed by Catalan artist Jaume Plensa.

Take a photo with "The Bean."

Chicago is full of public art , but this reflective sculpture by artist Anish Kapoor is one of the most recognizable pieces. While the Millennium Park attraction is officially titled "Cloud Gate," most visitors and locals affectionately call it "The Bean."

Admire Buckingham Fountain.

If you've ever watched Married with Children , this fountain set in sprawling Grant Park at the edge of Lake Michigan is one you'll definitely recognize. Opened to the public in 1927, it's one of the largest fountains in the world.

Take an architecture walking tour.

There are few better ways to experience Chicago's world-famous architecture than on foot. The Chicago Architecture Center offers several different walking tours, including some focusing on the skyscrapers that tower high above the city's streets.

See the animals at Lincoln Park Zoo.

This 35-acre zoo , founded in 1868, is one of the oldest zoos in North America. It's free to visit and hosts an annual holiday lights show .

Go to the theater.

Broadway isn't the only place to catch a show. Chicago has more than 200 theaters, including the well-known James M. Nederlander Theatre and Cadillac Palace Theatre in the Theater District. It's also worthwhile to check out the city's independent stages, such as the Tony Award-winning Chicago Shakespeare Theater at Navy Pier or the innovative Steppenwolf Theatre in Lincoln Park.

Shop the Magnificent Mile.

If you're looking to do some serious damage with your credit cards, look no further than the stretch of Michigan Avenue known as the Magnificent Mile . You'll find a mix of high-end designer stores, sprawling department stores, and more affordable retailers like Marshalls.

Tour a Frank Lloyd Wright house.

If you're a fan of architect Frank Lloyd Wright's work, head to the University of Chicago campus in Hyde Park, where you'll find the Frederick C. Robie House . The house, built in the early 1900s as a single-family home, is a fine example of Prairie School design and is among nearly two dozen homes in the area designed by the famous architect.

See the "Home Alone" house.

You'll need a car to get to this house in the Chicago suburb of Winnetka, but if you grew up on "Home Alone," it'll be worth the drive. You'll recognize it the second you pull up, but remember it's a private residence, so you'll have to appreciate it from the outside.

Go ice skating.

Chicago may get cold in the winter, but the joy of ice skating almost makes you forget about the freezing temperatures. From November to March, the Maggie Daley Ice Skating Ribbon in Grant Park and the McCormick Tribune Ice Rink in Millennium Park are popular spots for Chicagoans and visitors.

Catch a Cubs game at Wrigley Field.

Wrigley Field is one of the most charming stadiums in baseball. It's home to the former World Champion Chicago Cubs, and if you don't happen to be traveling during baseball season, you can still take a tour.

Learn about the history of Soldier Field.

The nearly 100-year-old Soldier Field is home of the NFL's Chicago Bears. Even if you're not into football, you might recognize it from the Clint Eastwood movie "Flags of Our Fathers" or the television show Chicago Fire . The stadium offers behind-the-scenes tours that pass through the locker rooms, interview room, skyline suite, and other areas.

Ride the Ferris wheel at Navy Pier.

If you're looking for a day of family fun, head to Navy Pier in downtown Chicago. The long pier features rides, games, restaurants, public artwork, and other attractions. Be sure to ride the Centennial Wheel for a truly spectacular view of Lake Michigan.

Take a walk in Oz Park.

There may not be a yellow brick road leading to Oz in Chicago, but there is a park that pays homage to the "Wizard of Oz," which author Frank Baum wrote while living in Chicago. Oz Park on the city's north side features sculptures of all your favorites, including Dorothy, Toto, and the Tin Man.

Explore a Chicago neighborhood.

Chicago is a city of neighborhoods — 77 of them, to be exact. Wicker Park, Bucktown, and Logan Square are worth exploring on the city's north side. On the south side, consider Pilsen and Chinatown. Architecture buffs are sure to appreciate the historical gems they'll find in Old Town.

Visit the DuSable Black History Museum and Education Center.

This Smithsonian-affiliated museum celebrates Black culture and pays homage to Jean Baptiste Point du Sable, the first permanent settler of Chicago. The museum holds more than 15,000 works, including paintings, sculptures, and historical memorabilia, such as the former desk of investigative journalist Ida B. Wells.

Eat your heart out.

Chicago is a foodie paradise that offers something for every palate and every budget. You'll find everything from hot dog joints like Jimmy's Red Hots to Michelin-starred restaurants like Alinea to deep-dish pizza places like Pequod's . Be sure to pack your stretchy pants, and remember, Chicagoans don't ask for ketchup on their hot dogs.

Visit the National Museum of Mexican Art.

This museum in the Pilsen neighborhood is an ideal place to immerse yourself in Mexican art and culture within Chicago's city limits. It's one of few major museums in the U.S. dedicated to showcasing Mexican, Latino, and Chicano art and culture.

Kayak along the Chicago River.

If you're craving an active adventure in the city, you can't go wrong with kayaking on the Chicago River. Urban Kayaks organizes a range of guided excursions, including tours at sunset and during the weekly Navy Pier fireworks show.

Check out the Museum of Contemporary Art Chicago.

Chicago has no shortage of museums, but when it comes to boundary-pushing exhibitions, the Museum of Contemporary Art Chicago (MCA) is second to none. The MCA's permanent collection includes more than 2,000 artworks from the 1920s to the present day, while rotating exhibits, performances, and talks are held throughout the year.

Hop between breweries.

Home to more than 160 breweries, Chicago is often dubbed the craft beer capital of the U.S. From cozy brewpubs to bustling beer gardens, there's something for everyone. Several production facilities, including Goose Island , Revolution Brewing , Lagunitas Brewing Company , and Dovetail Brewing , are also open for tours and tastings.

Stargaze at the Adler Planetarium.

You don't need to leave Chicago to see the stars – just head to the Adler Planetarium on Northerly Island. America's oldest planetarium is a destination for sky shows, exhibits, and special events. As a bonus, it stays open until 10 p.m. on Wednesdays.

Bike along the Lakefront Trail.

Chicago’s Lakefront Trail is a scenic 18-mile paved path along Lake Michigan between Ardmore Street on the north side and 71st Street on the south side. For a fun outing, rent one of the Divvy Bikes and explore it from top to bottom — including a break at one of the beaches along the way.

Celebrate St. Patrick’s Day.

Chicago's Irish pride beams as bright as the green dye in the river every March. Highlights include the annual Chicago St. Patrick’s Day Parade , river cruises, and food and drink specials at neighborhood pubs. If you're lucky (or a good planner), your trip might coincide with some of the festivities.

Stroll along The 606.

The Bloomingdale Trail Park (The 606) is an elevated recreational trail built on an abandoned railway. Similar to New York's High Line, the 2.7-mile-long path is dotted with public art installations and scenic lookouts. Access points can be found in four of the city's trendiest neighborhoods – Wicker Park, Bucktown, Logan Square, and Humboldt Park – so you can easily hop on or off.

Marvel at art among trees at the Morton Arboretum.

The Morton Arboretum was established in 1922 as a "great outdoor museum" by Joy Morton, founder of the Morton Salt Company. And with more than 1,700 acres and 22,000 plants, it certainly lives up to its mission. The park features rotating large-scale sculpture exhibitions and wellness events like forest therapy and yoga classes, making it well worth the journey 25 miles west of Chicago.

Spend an evening at the American Writers Museum.

Located in the heart of downtown Chicago, the American Writers Museum celebrates the work of historical and present-day writers, from poets to comics to novelists. The museum regularly hosts concerts and special events, including Get Lit museum nights, which bring together bibliophiles for drinks, special tours, and activities on the second Tuesday of every month.

Stop and smell the flowers at the Garfield Park Conservatory.

Garfield Park Conservatory is one of the largest conservatories in the nation, with two acres of public greenhouse space and 10 acres of outdoor gardens. The West Side centerpiece opened in the early 1900s and continues to be a destination for lovers of landscape architecture. In addition to permanent display houses, the conservatory often hosts special exhibits and spring flower shows. 

Learn about the city's criminal history.

Joining a crime tour is a fascinating way to learn about the city's prohibition-era gangsters like Al Capone, Bugs Moran, and Hymie Weiss. Opt for the Gangsters and Ghosts Tour for a storytelling stroll around the Chicago Loop, or board a bus for the Untouchable Tours' Original Gangster Tour led by guides in character as 1920s mafia members.

Admire the skyline from a cruise on Lake Michigan.

While Chicago's river cruises get a lot of attention, sailing around Lake Michigan can be just as fun. Tall Ship Windy offers a variety of cruises aboard a 148-foot, traditional four-masted schooner, including pirate-themed tours and skyline sailings that make the most of the Windy City's namesake weather.

The perfect 3 days in Chicago

Packed with towering skyscrapers, Gilded Age mansions, vibrant public art, and loads of local pride (go Cubs!), Chicago could easily take days to explore. But if you’re short on time, or visiting for a long weekend, you can do most of the must-sees in three days—all you need is the right itinerary.

That’s where we come in. We’ve created a schedule that balances hitting the highlights with downtime that doubles as sightseeing (outdoor concerts, comedy shows, and more). To save you time, we’ve bundled each day’s activities by neighborhood, so you’re not walking around in circles—even in the Loop. Best of all, we’ve used Tripadvisor reviews to find the spots travelers love most, so every stop is a winner.

MORNING: Hit the Loop

Start your day with a caffeine-and-sugar kick at Do-Rite Donuts & Chicken , a cherished Chi-town chain serving up some of the city’s best donuts. (The Buttermilk Old Fashioned never disappoints.) It’s located on the ground level of the Willis Tower —one of America’s tallest buildings— so after you’ve had your fill, ride up to the top and take in the seriously impressive 360° views of Chicago and beyond—on a clear day, you can see four states. Feeling adventurous? Stand on the glass balcony. (Note that it's always a good idea to book a timed ticket for the Willis Tower in advance, especially in summer.)

Next up, walk through downtown Chicago—also known as the Loop. Marvel at skyscrapers as you take a 15-minute stroll to Daley Plaza , home to a city market (Thursdays), Christmas market (November and December), and a public art piece by Picasso (always). Don’t miss the sculpture by Miro , nestled between two buildings in Brunswick Plaza next door.

From here, it’s just a five-minute walk to the Chicago Cultural Center . It’s free to pop inside this former public library and admire the architecture, including two giant Tiffany glass domes. Nearby, Garrett Popcorn Shops sells Chicago-style popcorn, a sweet-and-savory combo of cheese and caramel that makes for a tasty souvenir.

AFTERNOON: From deep-dish to skyscraper

We’re pretty sure you aren’t allowed to leave Chicago without eating deep-dish pizza. Legendary Chicago chain, Giordano’s , serves up a classic version—just be warned that you’ll be waiting at least 30 minutes for your pie.

Walk it off with a stroll along the Chicago Riverwalk . This is also where you’ll find the departure point for the Chicago Architecture Center River cruise . This impressive tour is a must-do, covering over 50 remarkable buildings. Chicago is the birthplace of the skyscraper, after all.

Travelers say: “I live in a Chicago suburb, and the Chicago Architecture Center River Cruise is my favorite thing to do in Chicago. Every time I take it, I am blown away by how beautiful Chicago is and am amazed by how much the docents have to teach me about Chicago architecture.”—@ Mark T

CHICAGO ARCHITECTURE TOUR OPTIONS:

• The 90-minute Chicago Architecture Center River Cruise aboard Chicago’s First Lady is the trademark architecture cruise, with informed guides from the architecture center. Cruises depart all day, plus there’s a full-service bar onboard. For about five bucks you can tack on a visit to the center itself, which has a cool diorama. Book ahead through the CAC . ( This cruise by Shoreline Sightseeing is a great alternative if the CAC is booked up.)
• Architecture buffs can also take a guided 90-minute Chicago Architecture Center Walking Tour for an up-close-and-personal look at some of the city’s most famous buildings.
• Inside Chicago Walking Tours offers affordable two-hour walking tours that take you inside famous buildings and hidden gems.

EVENING: A swanky supper club and sketch comedy

Right across the river is the chic Tortoise Supper Club (open Tuesday-Saturday, book ahead) with ‘20s vibes, inventive cocktails, and delicious Chilean sea bass. You could kick back here all night—check the schedule for live jazz shows—but we’d vote for heading north to Second City . This is one of the country’s most famous sketch comedy clubs, known for launching comedians like Bill Murray, Tina Fey, and probably half the cast of SNL. Get tickets ahead of time, and you might see the next big name.

Worthy detours along the way

MORNING: A walk in the park

Start your morning exploring Chicago’s famous Millennium Park , the city’s massive green space. Take a few selfies at the mirrored sculpture Cloud Gate , nicknamed “The Bean,” then stop by Crown Fountain , where a massive video screen displays faces of Chicagoans spitting water into the reflecting pool all summer. Hot day? Take your shoes off and splash around.

Next, walk along the BP Pedestrian Bridge to explore the winding paths of Maggie Daley Park , then make your way south to check out the three-tiered Buckingham Fountain and the surrounding rose gardens.

AFTERNOON: Art highlights, from Nighthawks to American Gothic

Grab a hearty American brunch at the Pittsfield Café , a no-nonsense diner tucked almost secretly inside the Pittsfield building.

It’s a quick hop over to your next stop, The Art Institute of Chicago . Visiting this museum is as essential as eating deep-dish. You can easily spend hours exploring the huge collection of Impressionist art, quirky paperweight exhibit, dollhouse-like miniature rooms, and plenty more. Don’t miss American classics like Edward Hopper’s Nighthawks and Grant Wood’s American Gothic, not to mention the stunning stained-glass windows by Chagall and the impressive gift shop. The museum is closed Tuesday and Wednesday, so plan accordingly.

Travelers say: “This museum went above and beyond my expectations. It is an incredibly large and diverse museum covering so many aspects of art from every corner of the world. I have been to all the impressive museums like the Met, Louvre, and Uffizi and I was still impressed with the enormous collection here.” —@ GlobeRunner22

ART INSTITUTE OF CHICAGO TOUR OPTIONS:

• The museum offers excellent free tours daily , including a 30-minute “Start Here Tour” (think of it like an orientation) and a 45-minute “Gallery Tour” that focuses on museum must-sees and hidden gems.
• If you’d rather go it alone, you can explore the highlights with interactive online guides or The Art Institute of Chicago app , where you can read about different works as you wander. The app also has a great audio tour of various collections—just don’t forget to pack your headphones!
• The Skip-the-Line Art Institute of Chicago Semi-Private Guided Tour is a major win for art lovers with knowledgeable guides that add context and history to the museum’s collection. Groups are limited to eight and tickets are included in the price.

EVENING: Dinner and an outdoor show

The Loop is overloaded with exceptional restaurants, from Michelin-starred must-try’s to Tripadvisor faves. Top of the list? The charming Italian restaurant Acanto serves up craft cocktails, award-winning wines, and a mean lobster pasta.

Round out your day with some nighttime entertainment. In the summer, Millennium Park holds free outdoor concerts and movies at Pritzker Pavilion (typically Mondays, Tuesdays, and Thursdays starting at 6:30 p.m.). You can also BYOPicnic, if lobster pasta isn’t in the budget.

In the winter, you can skate the ribbon at Maggie Daley Park . (There’s a fee to rent skates and getting tickets in advance is recommended.) Whatever the season, the skyline is sure to look stunning as the sun sets and the city lights up all around the park.

MORNING: A pretty Magnificent Mile

Start your morning at the ornate water tower on Michigan Avenue, and walk south down The Magnificent Mile , a busy main drag packed with shops (open around 10 a.m.) and skyscrapers like the famous Wrigley Building and Tribune Tower. Take a detour to visit the Richard H. Driehaus Museum (open Wednesday-Sunday), an impressive, restored Gilded Age mansion that takes you back to Chicago’s heyday. It’ll take at least an hour to admire the carved woodwork, stained glass windows, and Tiffany lamps.

Travelers say : “A meticulously renovated museum that showcases the architecture and decor of a wealthy Golden Age ‘merchant prince’… There are opulent Tiffany lamps stained glass windows, centerpieces, vases.…The walls, fireplaces, and parquet flooring is different in every room. Really a gem.” —@ janm511

AFTERNOON: Ride the Ferris wheel at Navy Pier

Hungry? Stop for lunch at the multi-award-winning Purple Pig and chow down on pork belly and crispy pig ears.

Then hop on public transit (or walk, it’s only a mile) to the massive Navy Pier, packed with carnival rides, restaurants, a Shakespearian Theater , and plenty of places to hang out and relax. It’s also home to the giant Centennial Wheel , built to honor the original Ferris wheel that debuted at the 1893 Chicago World’s Fair. The views from up top are next-level.

EVENING: Take me out to the ballgame

The pier is a great place to grab some classic Chi-town treats for dinner. Try a Chicago-style hotdog from Billy Goat Tavern (responsible for the Cub’s epic losing streak, according to legend ). Then, hit up The Original Rainbow Cone for a towering ice cream cone stacked with five flavors.

You could extend your visit to the pier through the evening; with free movies, concerts, and fireworks all summer , plus shows at Chicago Shakespeare Theater , there’s plenty to do. But since it’s your last night in Chi-town, check out a night baseball game at Wrigley Field . It’s worth it just to see the iconic 1914 Cub’s stadium—and you might even catch a celeb guest performing “Take Me Out to the Ballgame” during the seventh-inning stretch.

FOOD TOURS, CHICAGO-STYLE:

• Chicago-style food is definitely a thing. Take a deep dive on the Chicago Favorites Ultimate Food & Walking Tour and taste the city’s most iconic bites, from pizza to Italian beef sandwiches.
• Go donut shop-hopping on the Underground Donut Tour and get a taste of this city's awesome donut scene.
• If you’re here for the deep-dish (who could blame you?), Chicago Pizza Tour takes you to some of the best pizza places in the city to try four different types of pie.

Know Before You Go

Late spring through early fall are ideal times to visit Chicago, with temps in the 70s and 80s. Plus, there’s a lot going on: baseball games at Wrigley Field, music festivals like Lollapalooza and Pitchfork, and free movies in Millennium Park. If the nickname Windy City wasn’t a hint, winters in Chi-town can be downright frigid. Holiday lights and hotel deals may not warm you up, but they do help.

Chicago is a major American city with things happening every day of the week, but if you have to choose days to visit, go with Thursday-Saturday. Somewhat out of step with other big cities, Csome Chicago attractions are closed Tuesdays and Wednesdays, instead of or in addition to Mondays. The Driehaus Museum (closed Monday and Tuesday), The Art Institute of Chicago (closed Tuesday and Wednesday), and The American Writers Museum (closed Tuesday and Wednesday) are among them. Restaurants are sometimes closed on Sunday and/or Monday, and occasionally even Tuesday.

In general, cafes open at 7 a.m. and deep-dish (and everything else Chicagoans eat) is on offer from around 11 a.m. to 11 p.m., depending on the restaurant. Chicago has a strong diner scene, with most closing shop in the mid or late afternoon. Bars are open until 2 a.m. but some keep the party going until 4 a.m. Shops tend to be open between 10 a.m. and 6 p.m.

The Loop: Smack-dab in the heart of the action, hotels in the Loop are convenient to major attractions, theaters, shops, and restaurants. Plus, the area is jam-packed with architectural wonders. The Pendry Chicago is an impressive 1929 Art Deco skyscraper with a shiny black facade. Inside, the hotel is modern with a dash of Gatsby-era glam. (Picture gilded, velvet, and marble details.) You’ll also find a cozy lounge-like bar and a second rooftop bar for cocktails with a side of city views. Word of warning if you’re coming by car: Hotel parking fees in this area are steep.

Magnificent Mile: The Magnificent Mile is super central (and a sightseeing hub), with easy access to the Navy Pier and the Loop. The area is packed with upscale chain hotels—like Sofitel Chicago Magnificent Mile —that have everything you need: spacious, modern rooms, a restaurant, a bar, and more. If you’re traveling by car, expect parking to be a major added expense.

West Loop and beyond: Hostels, affordable mid-range hotels, and homey B&Bs are scattered beyond the two main tourist hubs mentioned above. Distance varies, so make sure to check where the nearest transit stop is and how long it takes to get into the city. If you want to feel like you’re staying at a friend’s really fancy apartment, check out The Publishing House Bed and Breakfast in the West Loop. Via public transit, it’s about 20 minutes to Millennium Park and 30 minutes to Navy Pier. It’s a win-win with free parking and free breakfast.

Public transportation: Chicago public transit is generally safe, affordable, and convenient. Buses and metro/trains (also called the L) are run by CTA in the city and Pace and Metra in the suburbs. After two rides, Day or Multi-Day Passes are worth it. You can buy single tickets, but a reloadable Ventra Card is more convenient—or just download the Ventra app on your phone.

By bike: With a flat landscape and hundreds of miles of bike lanes and paths, Chicago’s a surprisingly bikeable city. Bikes are affordable to borrow through the city’s bike share system, Divvy Bikes . If you’re not comfortable with urban cycling, Lakefront Trail is a very rideable 18-mile trail that runs along the water.

By taxi: Taxis are notoriously pricey in Chicago but easy to find downtown or via Chicago’s taxi app, Curb . Lyft and Uber are also available but aren’t necessarily cheaper.

By car: Parking can be difficult and pricey, particularly in the city center. It’s not uncommon for hotel parking to cost an extra $75 a day in the downtown area. It even costs a fee to park at the zoo—an otherwise free attraction.

Airport transfers: Your best bet from O’Hare International Airport (ORD) is to take the Blue Line on the L (train). It departs regularly, costs about five bucks, and you’ll get downtown in around 45 minutes. A taxi can easily take longer in traffic and cost around $50. Shared cars or shuttles will be around $35.

The fastest and cheapest option from Midway Airport (MDW) is also the L, this time on the Orange Line with a trip downtown taking about 30 minutes. Taxis can cost about $40, with trips sometimes taking an hour in traffic.

• United States

50 Best Places to Visit in Chicago

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A melting pot of eccentric culture, world-class sport, an enviable food scene (did someone say deep-dish pizza?), and a rich and vibrant history, Chicago is a quintessential Midwest destination for anyone in search of an action-packed vacation.

Straddling the shimmering shoreline of Lake Michigan and packed with top-notch attractions, Chicago is a city that has a little splash of something for everyone. With world-renowned museums, diverse art galleries, thrilling amusement rides, awe-inspiring architecture (and the home of Frank Lloyd Wright), and legendary sports teams (shout out to the Cubs finally breaking their drought), it’s easy to see why millions of people flock to this urban metropolis year after year.

And with so many options to choose from when it comes to places to visit in Chicago , you’ll never be short of ways to fill your itinerary. So, what are you waiting for? Start planning your trip to Chicago – the Windy City is waiting for you!

1 – 360 Chicago Observation Deck

Towering more than 1,000 feet above The Windy city, on the 94th floor of what was once the tallest building outside of New York City, 360 Chicago atop the former John Hancock Center dishes up spellbinding views in every direction.

Take in the busy streets of the Magnificent Mile below, the shimmering waters of Lake Michigan to the north and east, and the postcard-worthy array of skyscrapers (including the 1,451-foot Willis Tower to the south, then cap off your visit with a drink at the bar or snack at the cafe.

For a different perspective and mad adrenaline rush, test out TILT — a mechanized room full of floor-to-ceiling glass windows that angle 30 degrees over the building’s edge.

Hot tip: to experience three different, truly spectacular views – daytime, twilight, and twinkling nighttime — arrive about an hour before sunset.

• 360 Chicago Observation Deck tickets

2 – Shedd Aquarium

Straddling Lake Michigan’s shoreline of the southern end of the sprawling, elongated Grant Park, the Shedd Aquarium is a Chicago family favorite, and one of the most popular aquariums in the world.

Home to no less than 32,000 animals of all shapes, sizes, and colors (and fear factors) – from sea otters and seahorses, to beluga whales, reef sharks, and aptly-named Giant Pacific octopus — The Shedd’s galleries showcase diverse aquatic creatures from all corners of the planet, with a focus on education, conservation, and curiosity!

A surefire hit for kids and adults alike, this enormous facility (it was once the largest indoor attraction in the world) boasts highlights including a 360-degree walk-around Caribbean reef, a stingray touch pool where you can meet the ominous critters up close, a beluga whale habitat complete with underwater viewing tunnels, and a range of VIP meet-and-greet opportunities!

Don’t miss the 4D theater, and consider opting for the Beluga Encounter or Shark Feeding Experience!

Hot tip: Discover the underwater world, a family-friendly option that’s touted as one of the best indoor activities in Chicago for exploring marine life.

3 – Navy Pier

Kick-off your visit with a ride on the Centennial Wheel then wander down the 50 acres worth of parks, restaurants, docks, shops, and the tropical Crystal Gardens.

Traveling with kids in tow? Both the Chicago Children’s Museum (always free for kids) and the IMAX theater and sure to keep them entertained for at least a couple of hours. Fancy a feed? Follow the locals with a food tasting and cultural walking tour or dig into a hefty slice of  Chicago deep-dish pizza at Giordano’s!

While the area thrives year-round, during the summer months the atmosphere is electric with live music concerts, food trucks, and street performers; around the holidays it transforms into a winter wonderland of ice skating, mulled wine, and special events

• Navy Pier Centennial Wheel tickets

4 – Michigan Avenue’s Magnificent Mile

The city’s focal point for food, fashion, and fun is the world-famous Magnificent Mile – AKA Michigan Avenue.

The 13-block stretch of street runs for about a mile (hence the name) along Chicago’s northern waterfront district from the banks of Lake Michigan to Oak Street, passing dozens of department stores, chic hotels, famous museums, and picturesque landmarks en route.

Stroll down this iconic thoroughfare and you’ll uncover some of Chicago’s most renowned buildings such as The Wrigley Building, the John Hancock Center, and Tribune Tower (with its unusual facade made up of more than 150 rocks from sites around the globe) — all interspersed with high-end boutiques like Louis Vuitton and Cartier, speakeasy pubs, and revered underground eateries.

Be sure to wander over the DuSable Bridge, and, if you’re keen to learn a thing or two about the area’s history, culture, and hidden gems, consider signing up for a locally-led walking tour.

• walking tours in Chicago

5 – Zoos

Welcoming locals and visitors alike, Chicago’s two most renowned zoos — Lincoln Park Zoo in the North Side neighborhood and Brookfield Zoo over in Brooklyn — collective house hundreds of species and thousands of animals, with live educational shows, behind-the-scenes tours, reptile houses, and up-close encounters aplenty.

Easily accessed from Downtown by transport or car, the Lincoln Park Zoo is one of the last free zoos in the USA, with has a diverse array of wildlife across its 35 acres – its roughly-1,100‎ animals includes lions, gorillas, hyenas, and giraffes! Beloved by kids, the Lincoln Park Zoo also offers a children’s farm as well as some lush gardens ideal for a picnic.

Meanwhile, further inland (but worth the drive) Brookfield Zoo has more friendly creatures to check out (close to 2,300 comprised of 450 species) and is sandwiched in between the Brookfield and McCormick Woods, meaning that there’s no shortage of beautiful open space to relax in after a day of wonderful animal experiences.

6 – The Field Museum of Natural History

One for the history buffs and culture vultures, Chicago’s Field Museum of Natural History is a must-see for those interested in Earth science.

Home to more than 40 million fascinating specimens and artifacts — from fingernail-sized fossils to towering dinosaur skeletons — the museum’s exciting yet educational exhibits span everything from ancient Egyptology to geology, botany, and prehistoric evolution – so you can expect plenty of mummies, dinosaurs fossils and detailed dioramas that cover nearly 4.5 billion years worth of history!

A great spot for traveling families too, the museum is particularly interactive, with plenty of hands-on activities to keep kiddos (and kids at heart) entertained.

You’ll find the Museum tucked away at the southern end of Grant Park, around the corner from the Adler Planetarium and Shedd Aquarium — so why not check out a couple of them on the same day?

• Field Museum of Natural History tickets

7 – Millennium Park

Where the action happens and never a moment is dull, Millennium Park is one of Chicago’s best-known urban green spaces.

Located in the heart of Downtown and bordered by Grant Park, this 24.53-acre wonderland was designed as a modern public space for locals and visitors alike, with its many attractions including an outdoor concert venue (Pritzker Pavilion), Insta-worthy fountain (Crown Fountain), sculptures (Cloud Gate – nicknamed “The Bean” for obvious reasons — among others) gardens, an ice rink and plenty more to discover!

This vibrant spot is also home to some fun seasonal activities like open-air movies during summer months and winter ice rinks to boot; so whatever time of year you visit, bet your bottom dollar that long-lasting memories will be made!

Directions in Google Maps

8 – Willis Tower SkyDeck

Located on the 103rd floor of Willis Tower (formerly Sears Tower), this popular tourist attraction offers visitors sweeping panoramic views of Chicago and its surrounds in all their glory, making it one of the most elevated spots in not just the city but all of America too.

On a clear day, you can see for around 40 miles in every direction – from neighboring states like Wisconsin and Indiana to the vast expanse of Lake Michigan and far beyond!

Tickets are relatively affordable (especially when bought online) and timed entry means that there’s never too long a wait; so whether you want to snap some selfies against the iconic skyline, grab a drink at the bar, or take in an incredible sunset over the Midwest plains, make sure to add this spot to the top of your list of places to visit in Chicago.

• SkyDeck tickets

See also: Cheap Skydeck Chicago Tickets – How to Save up to 20%

9 – Six Flags Great America

A quintessential stop for anyone who even remotely deems themselves a thrill-seeker, Six Flags Great America up in Gurnee, about 50 minutes drive north of Chicago, is a theme park that has it all.

Expect riveting roller coasters, heart-in-your-mouth thrill rides, and refreshing water slides galore in this amusement park that spans over 300 acres of land — plus plenty of kid-friendly activities too!

A great spot for adrenaline junkies, the park is known for its many world-class rides and rollercoasters, including the iconic American Eagle (the world’s tallest and fastest racing wooden coaster), Goliath (which boasts a gut-wrenching 180-foot feet drop), and Raging Bull, the tallest, longest, and fastest coaster at the park.

If you’re looking for something a little tamer, there’s also a charming riverboat ride, Buccaneer Battle, Columbian Carousel, live theater and dance shows, and plenty of restaurants and food trucks; so no matter what your age or thrill-seeking level, you’re sure to have a blast at Six Flags Great America!

10 – Art Institute of Chicago

One for the culture vultures, the world-famous Art Institute of Chicago, located in Downtown’s Grant Park, is one of America’s oldest and largest art museums (operating since the late 1800s and covering a whopping one million square feet).

Here you can explore a mammoth collection of over 300,000 works spanning more than 5000 years – from ancient Egyptian artifacts to over 25,000 pieces of European Decorative Arts, to one of the world’s most significant Impressionist and Post-Impressionist collections outside of France. paintings. Throw in sections dedicated to modern masterpieces by the likes of Picasso, Warhol, and Pollock, and you’ve got to accommodate every artistic fancy!

A true highlight for anyone who has even a passing interest in art (and let’s face it: that’s pretty much everyone), this famous museum also boasts an incredible school where budding artists are given the opportunity to hone their skills in areas like architecture design; so if it tickles your fancy why not check out some classes too?

• Art Institute of Chicago tickets

11 – Chicago Riverwalk

Dedicated to pedestrians and teeming with shopping, dining, entertainment and recreational activities, the Chicago Riverwalk stretches 1.25 miles from Lake Michigan to Lake Street through the heart of Downtown, dishing up cozy cafes, hidden wineries, rowdy bars, and quirky boutiques to boot.

Besides the chance to pop into the shops en route, this charming spot along the city’s scenic waterfront also offers visitors a unique vantage point from which to admire the city’s skyline and, with a walking tour, explore Chicago’s rich history and cultural landscape.

So whether you’re looking for a romantic stroll, an hour or two of people-watching, a spot of afternoon tea, or a day of impromptu walkabout, this waterfront promenade is not to be missed!

12 – North Avenue Beach

Perfect for those toasty summer days, North Avenue Beach is one of the city’s most popular and iconic spots to soak up some sun.

Here you can expect clear views of Chicago’s skyline, a plethora of beach activities (think kayaking, paddleboarding and volleyball), as well as plenty of waterside restaurants where you can kick back with an ice-cold drink and some hearty seafood.

Though it can get a little crowded during the summer months, there’s plenty more sand than people in this shoreline stretch so it seldom feels overwhelming; so grab your sunscreen, your favorite book and prepare for a day of fun in the sun!

Located in Lincoln Park directly on Lake Michigan, it’s also a stone’s throw from myriad hiking and biking trails, as well as the free-to-enter Lincoln Park zoo.

13 – Buckingham Fountain

Set in Chicago’s Grant Park, this iconic landmark was constructed in 1927 to commemorate Clarence Buckingham (a philanthropist who gave his name to the fountain) and has been wowing locals and visitors alike with its impressive 20-minute long water shows ever since, which take place every hour on the hour. So whatever you do, don’t forget your camera!

The basin itself measures an incredible 280 feet in diameter while its central jet shoots a whopping 15,000 gallons of water per minute 150 feet into the air – making it an eye-popping spectacle that couldn’t be missed if you tried.

Hot tip: stroll past the landmark at night for a different perspective – the post-dusk shows are choreographed with brilliant light and music performance!

14 – Lake Michigan

Offering everything from quick one-hour trips focused purely on checking off the main landmarks to longer excursions with buffet-style food and strong drinks included, and even VIP romantic cruises, there’s a boat tour for everyone – no matter your budget or timeframe.

What’s more, many of the cruises offer unbeatable perspectives of iconic landmarks you won’t find from land, like Navy Pier, Willis Tower (formerly known as Sears Tower), and the Hancock Building; so whether you’re looking to snap some postcard-perfect shots or just take in the amazing architecture and natural beauty of Chicago from a different perspective, this is definitely the way to do it.

Seel also: best architecture boat tours in Chicago

Choose from luxury yachts, family-friendly ferries, or heart-racing speedboat rides; book your ticket in advance to save a few bucks, and enjoy the sail!

• boat tours in Chicago

15 – Garfield Park Conservatory

An enchanting slice of nature in an otherwise chaotic metropolis, the Garfield Park Conservatory is a haven of tranquility in the heart of Chicago.

Boasting thousands of species of plants from all around the world, this award-winning conservatory is one of the largest indoor gardens in North America and makes for a peaceful and educational day out for visitors of all ages.

What’s more, entry is free 365 days per year so you can come as often as you like; just be sure to check the opening hours as they do vary depending on the season.

Hot tip: don’t miss the marvelous permanent glasswork by artist Dale Chihuly.

16 – Maggie Daley Park

Sandwiched in between Millennium Park (home of The Bean) and the Lake Michigan shoreline, Maggie Daley Park is a relatively recent addition to the Chicago tourist scene — but it hasn’t taken long for it to become a magnet for locals and visitors alike.

Opened in 2014, gentrifying the old three-level East Monroe Street Parking Garage, the park is all about fun for the whole family, with a whimsical play garden full of climbing towers, slides, swings, and splash zones, as well as the ice skating ribbon, sports fields, and plenty of picnic areas – not to mention some amazing views!

Whether you’re bringing your kids along or just want an excuse to act like one yourself, this sprawling 25-acre green space offers plenty of entertainment options no matter what time of year it is. And, best of all, admission is always free.

17 – Adler Planetarium

The first planetarium in the Western Hemisphere (opening back in 1930) and one of Chicago’s most famous sights, this incredible museum is home to three full-size theaters where visitors can get a glimpse of what life would be like on Mars or learn about Jupiter, the moon and more through amazing high-tech displays and interactive exhibits.

There are also fascinating rotating exhibitions focusing on everything from telescopes to space travel (including the actual Gemini 12 space capsule); plus an observatory deck with beautiful views over Lake Michigan – all set within a striking Art Deco building designed by Ernest Grunsfeld Jr., which was declared an official National Historic Landmark back in 1987.

With so much going for it, as well as regular neighborhood skywatching events (check the events calendar), this interstellar attraction is one of the best places to visit in Chicago.

• Adler Planetarium tickets

18 – Soldier Field

The locally beloved stomping ground of the Chicago Bears NFL team, Soldier Field delivers a roar and energy matched by few stadiums in the Midwest, regularly packing every seat in the house for home games.

But even when the Bears are on the road, this massive structure (the third-largest in the NFL) is worth a visit for its impressive architecture and unique history – after all, it’s been around for the better part of a century. Tours are available on non-game days, while a range of concerts dots the calendar too — or you can simply enjoy a walk around the perimeter and (thanks to its location at the southern end of Grant Park) take in some amazing views of downtown Chicago.

19 – Chicago Children’s Museum

A Navy Pier crowd favorite, the Chicago Children’s Museum is the perfect place to take your little ones for a day of fun peppered with a whole lot of learning.

With three floors of interactive exhibits designed specifically for children, this colorful museum provides hours of entertainment with a wide variety of hands-on exhibits that dive into the wonderful worlds of science, culture, construction, art, and more.

Best of all, admission is free for children under 17 (and affordable for everyone else), and free to Illinois residents every Tuesday from 2 pm onwards, so it’s a great place to take the whole family for a day of immersive creativity and learning without breaking the bank.

20 – Glessner House

Standing since 1887, the Glessner House is one of Chicago’s oldest and most beautiful homes, attracting visitors from all over the world with its exquisite architecture and fascinating history.

Designed by architect Henry Hobson Richardson (one of America’s first masters of the Romanesque Revival style) this iconic structure was once at the forefront of innovative home design, incorporating features like central heating and indoor plumbing (which were still pretty new ideas back in the day).

These days it serves as a museum open to the public, housing rotating exhibitions on everything from furniture design to decorative arts. DIfferent tours (focused on topics like architecture, history, or arts and crafts) are available daily, or you can simply admire it from the outside while enjoying a stroll around the Prairie Avenue Historic District.

21 – Loop district

In the heart of downtown Chicago, you will find The Loop – an area that was once a tangled maze of train tracks and elevated trains. Nowadays it’s a vibrant commercial district where many locals work, shop, dine out and hang out.

Its name comes from its circular shape – created by the “loop” made when trolleys traveled around the street block that encircled this central business district (the tracks have since been removed).

Attracting tourists like fish to water, The Loop is home to some of Chicago’s most famous buildings (including Willis Tower and the Chicago Board of Trade Building) as well as numerous theaters and museums (including the Chicago Cultural Center).

Take a stroll — or a guided walking or biking tour — around and you’ll uncover dozens of iconic sculptures on display along its streets, as well as some of the best donuts, pizza, architecture interiors, and shopping and dining in the city.

• The Loop tours in Chicago

22 – Oz Park

Made famous for its whimsical statues of Scarecrow, Lion, Tinman, and Dorothy and Toto, Oz Park is a small (but charming) public park over in the Lincoln Park neighborhood on Chicago’s north side that blends the peace and quiet of nature with the childish wonder of one of the world’s most beloved stories.

Named for L. Frank Baum’s classic book The Wonderful Wizard of Oz, the underrated park features a range of fun attractions like a playground (called Dorothy’s Playlot), a lush Emerald Garden, tennis courts, basketball courts, and more. Best of all, it’s free to enter and explore!

And, during the balmy summer nights, grab a lawn chair for Movies in the Park!

23 – Baháʼí House of Worship

An architectural masterpiece, the Baháʼí House of Worship (also known as a “Lotus Temple”) is one of only seven Baha’i temples in the world and the only one located in North America.

The beautiful, lotus-shaped, nine-sided building dates back to the mid-1900s and has become iconic in its beauty, combining neoclassical symmetry, with Gothic, Renaissance dome, Romanesque and Islamic elements — all combining to make a structure that is both spiritual and stunning.

The temple is open to all, regardless of religious affiliation (or none), and visitors are welcome to come to explore the interior prayer hall, which features marble floors, fine woodwork, and beautiful stained-glass windows, as well as the large garden that offers plenty of space for visitors to stroll around, relax or meditate on life’s big questions.

24 – Congress Plaza Hotel

One of Chicago’s most iconic hotels and a piece of living history, The Congress Plaza Hotel on Michigan Avenue is a grand Beaux-Arts building dating back to 1893.

Over its near-130-year timeline, it’s hosted visitors, heads of state, and celebrities from near and far, dishing up wondrous views over both Downtown and Lake Michigan, with a prime spot opposite the Art Institute of Chicago, just minutes from Millennium Park.

Its history goes way beyond that though — the hotel has been labeled one of America’s most haunted hotels with ghost stories galore, including that of gangster Al Capone and his men who stayed here in the 1920s!

Learn all about the topsy-turvy tales of this longstanding landmark on a spine-tingling ghost and gangsters tour that dives into the dark side of Chicago’s history.

• Gangsters and Crime tours in Chicago

25 – Music Box Theatre

One of Chicago’s oldest and most beloved movie theaters, The Music Box Theatre on Southport Avenue in Chicago’s Lakeview district has been screening all kinds of indie and art-house films since 1929.

What began as a single-screen theater showing silent movies (and later “talkies”) quickly became known as one of the city’s most unique venues, thanks to its charming art deco facade and intimate seating that always guarantees a great view from any seat in the house.

These days, it’s still going strong with a busy schedule of new releases and cult classics, plus occasional live stage shows and events.

Check out what’s playing during your next visit to see if you can snag tickets to an old-school flick at this classic Chicago cinema!

26 – LEGOLAND Discovery Center

Inside visitors will find everything from an awesome Miniland featuring replicas of some of America’s most famous landmarks made entirely out of Lego bricks (including a replica of the entire Windy City!), a 4D cinema, no less than 10 different hands-on play zones, a couple of rides, and a store chock-full of over 900 unique builds and souvenirs.

The center also hosts regular events like Master Builder Workshops and holiday celebrations, so be sure to check what’s happening during your visit before you go! And, since it’s located over in Schaumburg, it’s a good excuse to check out the nearly Ned Brown Preserve (Busse Woods) on the same day.

• LEGOLAND Discovery Center tickets

27 – Indiana Dunes National Park

For when you want to get out of the city and experience a little bit of nature, Indiana Dunes National Park is only an hour away from Chicago via car or train, straddling the southern shores of Lake Michigan in neighboring Indiana.

An adventurer’s heaven on earth, the sprawling park encompasses over 15,000 acres of dunes, beaches, grasslands, wetlands, prairies, and meandering rivers, and a whopping 50 miles worth of hiking trails — the most picturesque of which tackles dune formations that rise as high as 200 feet above sea level!

Hiking aside, visitors can swim at its many beaches (including some dog-friendly beaches), try horseback riding, cycle down the Calumet Trail, camp overnight, or just enjoy soaking up the immense beauty on offer here — it’s all about getting back to nature for a day and letting Mother Nature work her magic.

28 – Promontory Point at Burnham Park

One of the most iconic spots on Chicago’s South Side for a leisurely stroll, Promontory Point at Burnham Park is a narrow peninsula that juts out into Lake Michigan between 53rd and 57th Streets and offers sensational views of Downtown and the city’s famed skyline.

The 40-acre point has been popular with locals and visitors alike since it first opened in the 1930s and these days is home to lovely gardens, a couple of sculptures, plenty of local birds and wildlife, and a handful of benches where you can sit back and take in all the beauty on show.

29 – Museum of Science and Industry

One of the largest science museums in the world, Chicago’s Museum of Science and Industry is a sprawling complex that takes up the equivalent of an entire city block in the middle of Jackson Park, diving into fascinating exhibits on everything from aviation and outer space to WWII, natural disasters, dinosaurs, chemistry, and energy.

In addition to its over 35 permanent exhibits, the museum also hosts regular temporary exhibitions (just check the website to find out the flavor of the month), features an Omnimax theater, a carousel, and plenty of hands-on activities for kids (and adults

With myriad interactive elements, curious visitors can climb aboard a WWII German submarine, take a spin in a human-sized hamster wheel, navigate through a mirror maze

• Museum of Science and Industry tickets

30 – United Center

Sports fans, listen up! Exuding a roar and an energy that can send shivers down your spine, Chicago is home to one of the most iconic and renowned sports arenas in the world: the United Center .

Home to not just the Chicago Bulls (of Michael Jordan fame) and Chicago Blackhawks (of the NHL), but also a whole range of other top-level events like concerts (think Iron Maiden; Elton John; Tyler, The Creator, and everyone in between) family shows, and more, United Center welcomes millions of guests through its doors every year.

With a capacity of close to 20,000 spectators, this arena — which, mind you, is officially the largest indoor arena in the country — really knows how to pack in the crowds for some unforgettable live action.

31 – Alfred Caldwell Lily Pool at Lincoln Park

A tranquil oasis in the heart of bustling Lincoln Park, Alfred Caldwell Lily Pool is a historic slice of nature and one of the most picturesque — and underrated — attractions in the city.

Designed by celebrated Prairie School architect Alfred Caldwell with roots going all the way back to 1889, the lily pool pays homage to the Midwest’s natural prairie landscape with its flowing curves and earthy hues, while offering visitors a chance to take a break from the go-go-go mentality of city life.

Open from early May until mid-November each year, this little slice of paradise welcomes locals and tourists alike for a relaxing stroll, a guided tour, or an enchanting and educational wildflower walk.

32 – Great Wolf Lodge Water Park Illinois

Perfect for energetic kids (and kids at heart); if you’re in the mood for some serious water park action, look no further than the Great Wolf Lodge .

Located over in Gurnee, Illinois (just a short drive from downtown Chicago), this massive water park resort is home to an impressive dozen towering slides (thrillseekers, make a beeline for the Double Whirlwind), a wave pool, lazy river, kiddie splash zones, and a whole lot more.

Not only will you find something for everyone here, but with its on-site restaurants, arcade games, live shows, mini-golf course, climbing walls, ropes course, pint-sized bowling alley, ever-popular Build-A-Bear workshop, and themed suites (we’re talking everything from log cabin-themed to cave-themed), there’s bounds of entertainment around every corner!

33 – Museum Of Contemporary Art

If you’re in the mood for some cutting-edge contemporary art, the Museum of Contemporary Art sells itself as one of the more intriguing places to visit in Chicago. Located in the trendy and vibrant neighborhood of River North, this museum has been showcasing boundary-pushing artwork since it opened its doors back in 1967.

Boasting an ever-changing roster of exhibitions (some permanent, others rotating), that cover paintings, sculptures, film, and photography, as well as a busy schedule of talks, performances, and educational programming geared towards all ages, MCA is always worth a visit if you want to see what’s new and exciting in the world of contemporary art (it is, after all, one of the biggest contemporary art venues on the planet).

Traveling in July or August? You’re in luck! Admission is free for everyone during the summer.

• Museum Of Contemporary Art tickets

34 – Wrigley Field

A beloved American pastime, baseball is taken to a whole new level at Wrigley Field . Home of the Chicago Cubs (who recently overcame a 70+ year World Series drought), this stadium is one of the most iconic and hallowed venues in all of sport, not just baseball.

From its ivy-covered walls to the hand-turned scoreboard, there’s plenty of charm and character to be found at Wrigley. And, of course, there’s the history. Opened all the way back in 1914, this is one of America’s oldest ballparks still in use today.

If you’re a fan of baseball (or just want to experience some truly iconic Americana), be sure to plan a visit to Wrigley Field during your time in Chicago — or, take your experience to the next level with a 90-minute behind-the-scenes stadium tour that takes you into the Cubs’ dugout, the Bleachers, and the Press Box!

35 – Chicago Cultural Center

Home to a staggering variety of free art exhibits, performances, and educational programs (not to mention the occasional blockbuster traveling exhibition), the Chicago Cultural Center is one of the city’s most beloved and well-used attractions.

Located in the heart of downtown Chicago, this Beaux-Arts beauty was originally built back in 1897 as the city’s central library. However, fast forward to 1976 and it reopened as the Chicago Cultural Center we know and love today, with grand staircases, foreboding entrancement ways, coffered ceilings, and bronze-framed doors that make the building a piece of art in its own right — the Preston Bradley Hall and Tiffany glass dome, which contains some 30,000 pieces of glass, are shining examples.

Boasting an impressive five floors of exhibition space, there’s always something new to see at the Chicago Cultural Center — from contemporary art to historical artifacts, and several educational workshops to boot.

36 – Robie House

Tucked away off the beaten track in Hyde Park, on the University of Chicago campus, architecture buffs will drool over one of the most important examples of Prairie School architecture in the world; Frank Lloyd Wright’s Robie House is a must-see for fans of 20th-century design.

Commissioned by wealthy University of Chicago trustee and businessman Frederick C. Robie, this stunning home was designed by Wright in 1908 and completed in 1910.

Its clean lines and geometric shapes are an early example of Wright’s signature “Prairie Style” that would come to define his career — and it continues to be known today as the first uniquely American architectural style.

Now a National Historic Landmark, the Robie House is open to the public for tours (check out their website for more information on guided or self-guided tours). If you’re lucky, you might even catch one of their special events held throughout the year.

• Robie House tickets

37 – DuSable Museum of African American History

Named after Jean Baptiste Point du Sable, widely considered to be the first non-indigenous settler to explore the area and as such the ‘Founder of Chicago’, this museum tells the story of Africans and African Americans from pre-colonial times to the present day.

The DuSable Museum is home to a wide variety of exhibits on everything from art and music to politics and civil rights, as well as an impressive research library containing tens of thousands of volumes, and a regular even calendar that features concerts, films, kid-friendly events, and debates.

Take a stroll around the peaceful outdoor sculpture garden which displays works by some of today’s leading African American artists, and make sure to visit the museum’s gift shop for some unique souvenirs and books to further your learning.

38 – Chicago Architecture Center

If you’re at all interested in architecture, or in just taking a stroll around one of the most beautiful cities on Earth, then the Chicago Architecture Center is a must-visit. Located in the heart of Downtown Chicago, this center offers free tours (both guided and self-guided) of some of the city’s most iconic buildings, as well as lectures, exhibitions, and family activities.

The CAC’s main attraction is their 90-minute walking tour that takes visitors through downtown Chicago’s Loop district to see some of the city’s best-known (and sometimes controversial) buildings up close. From grandiose skyscrapers like The Willis Tower and John Hancock Center to classical masterpieces like Louis Sullivan’s Carson Pirie Scott store, there’s something for everyone to marvel at.

All up, the CAC offers some 85 tours of the city’s neighborhoods, including boat tours along the Chicago River (which come highly recommended!), and even a tour of Frank Lloyd Wright’s home and studio in Oak Park. Simply check out their website for more information on what’s on offer.

39 – Tribune Tower

No trip to Chicago is complete without a visit to the Tribune Tower, one of the city’s most iconic and best-loved buildings. Located on Michigan Avenue, smack-bang in the center of the Loop district, this neo-gothic tower was completed in 1925 and has been home to the Chicago Tribune newspaper ever since.

Besides boasting a fascinating century’s worth of history, it’s the building’s facade that gleans the most interest: the exterior of the building is covered in over 150 different types of famous marble, limestone, and granite building fragments from all over the world — we’re talkin’ pieces of the Parthenon, the Notre Dame cathedral, the White House, and even the Berlin Wall.

40 – Illinois Beach State Park

Located in northern Lake County (about an hour’s drive north of Chicago, halfway to Milwaukee), the Illinois Beach State Park is a nature lover’s paradise.

With its sprawling grassy dunes, lakeside forests, and stunning sandy beaches, it’s no wonder over 2.5 million people flock to this park every year — although, at a whopping 4,160 acres, it never feels even remotely crowded.

Full of family-friendly activities to escape the city and soak in the best of Mother Nature, the park offers plenty to keep you occupied during your stay: go hiking along dozens of miles worth of trails and enjoy the 650+ species of plants that cover the area;

Keep your eyes peeled for rare and majestic birds flying above the North Unit (the park is split into two units); fish for salmon or trout in Sand Lake; take a dip in Lake Michigan — swimming and sunbathing are popular pastimes here — or simply grab yourself a picnic table and soak up all that fresh air!

41 – Chicago Theatre

This grand old movie palace, located on North State Street in the Loop district and able to seat 3,600‎ people, has been entertaining theater-goers since 1921 — it was the first lavish movie palace in the nation, setting the standard for all that followed, and today remains one of the most popular venues in the city for live performances.

The theatre’s facade is an impressive sight, towering seven stories tall with a postcard-worthy neon sign juxtaposing Romanesque Revival details, and inside you’ll find a beautifully restored auditorium with gilded ceilings, marble flooring, and luxury touches galore.

Check the calendar, choose from comedy nights, live music shows, film screenings, or Broadway shows (or even a behind-the-scenes theater tour), and get ready to be entertained!

• Chicago Theatre tours

42 – National Museum of Mexican Art

Portraying the rich culture, history, and artistry of Mexican heritage in America (and beyond), the National Museum of Mexican Art is definitely worth a visit while you’re in Chicago if you’re looking to expand your cultural horizons.

The museum’s collection spans over 35 centuries — with archeological finds dating back to ancient Mesoamerica covering everything from traditional crafts and jewelry to fine art painted by some of Mexico’s most renowned artists and modern takes on photography and pop-art — making it one of the largest collections of its kind in the US.

You can also get more out of your visit by checking out their calendar for upcoming events: workshops are regularly available (think writing classes or guest speakers), as well as performances and expert-led tours.

Plus, thanks to its location in Harrison Park in the Pilsen neighborhood, there’s plenty of space to take a stroll and stretch the legs afterward.

43 – Frank Lloyd Wright Home and Studio

When it comes to architectural wonders, Frank Lloyd Wright is a name you can’t ignore. And here in Chicago, you can visit his original home and office — now officially known as The Home & Studio of Frank Lloyd Wright — which was built in 1889 by the famed architect himself, serving as the place where he’d pen over 150 different designs that would eventually manifest into a legacy of world-famous buildings.

The studio has been meticulously restored to its 1890s appearance and today offers guided tours that highlight pieces of furniture and dive into the life and works of the iconic architect.

Craving more Frank Lloyd Wright? See inside the architectural gem that is the Robie House in Hyde Park, or visit the Unity Temple in Oak Park to see another of his works — both spots are listed on many a list of the quintessential places to visit in Chicago.

44 – Waterfall Glen Forest Preserve

Located just southwest of the city limits in Darien, about 25 minutes inland from Chicago, Waterfall Glen Forest Preserve is a vast tract of land covering over 2000 acres (and featuring 11 miles of trails) that’s ideal for hiking, biking, horseback riding, and cross-country skiing, or simply basking in the fresh and quiet air.

Families and adventurers alike can easily spend an entire day out here exploring all it has to offer: there are wooded areas and open meadows, wildflower fields to roam through, rock formations, and over 300 species of wildlife roaming around to admire — along with the main attraction that is the waterfall (read: a dam), of course.

For a wonderful viewpoint, check out the Sawmill Creek bluff overlook, and for something unexpected, make your way to the model-airplane field at Mile 3 on the loop trail.

45 – Orchestra Hall

Home to the highly esteemed Chicago Symphony Orchestra , Orchestra Hall is an architectural gem in itself. Built in 1904 and designed with the help of architect Daniel Burnham (who was also responsible for Manhattan’s Flatiron Building), it’s one of those buildings that feels like you’re stepping into a movie set.

Curious travelers can take a guided tour to learn more about its history — from construction back when Symphony Center first opened up as Orchestra Hall through to modern times where it now hosts over 300 concerts each year — or simply sit down and enjoy some world-class music within the walls of a National Historic Landmark; tickets are available online and at the box office, just be sure to book in advance to avoid missing out).

46 – Cantigny Park

Calm and green and always free to visit, Cantigny Park is a 500-acre oasis located in Wheaton, about 40 minutes island from downtown Chicago, that’s perfect for a relaxing day out of the city.

The park was once the estate of Colonel Robert R. McCormick (the founder and publisher of the Chicago Tribune), and it’s now open to the public with plenty to keep visitors entertained: from gardens and nature trails to picnic areas and playgrounds, there’s something for everyone here.

Culture vultures and history buffs flock here too, for good reason. Cantigny is home to The Robert R. McCormick Museum, which dives into the life and work of the media mogul; and The First Division Museum, which immerses visitors in the sights, sounds, and stories of the military unit.

47 – Peggy Notebaert Nature Museum

Charming locals and tourists alike with its interactive exhibits that explore all aspects of nature — from animals and plants to insects (the Judy Istock Butterfly Haven is by far one of Chicago’s cutest attractions) — since 1999, the Peggy Notebaert Nature Museum is a must-visit for anyone with an appreciation for the natural world.

The museum also offers up educational programs and events, like animal feedings, the regular Critter Connection where you can meet and greet snakes and turtles, yoga in the Butterfly Haven, birdwatching excursions, and a host more, so keep an eye out on their website to see what’s happening during your visit.

Make sure to take a stroll on the outdoor walkways to observe the local wildlife doing its thing, and learn about the importance of climate change at the fascinating Weather to Climate exhibit.

48 – The Green Mill

A hidden gem beloved by locals and jazz aficionados the world over (and frequented by Al Capone and his goonies way back yonder), The Green Mill is a Chicago institution that’s managed to keep its Prohibition-era speakeasy charm intact over a century later.

First opened all the way back in 1907, it was originally a venue for vaudeville and variety shows (Green Mill is actually a nod to the famous Moulin Rouge in Paris, which translates to the ‘Red Mill’) before becoming one of the most popular jazz clubs in America, even hosting performances by legends like Louis Armstrong, Billie Holiday and Charlie Parker along the way.

While nowadays it’s not quite as rowdy as it once was in the Capone era, the club still offers up toe-tapping live music every night of the week and some of the best cocktails around; just be sure to arrive early It gets busy so get there early as there are no reservations.

With plenty to see in do in the neighboring Uptown streets, including restaurants and shopping galore, The Green Mill is a great spot to end an evening after exploring the neighborhood.

49 – Illinois Holocaust Museum & Education Center

A somber and eye-opening look at one of the darkest moments in human history, the Illinois Holocaust Museum & Education Center is a confronting but important experience for anyone making a trip to the Chicago area.

Dedicated to Holocaust remembrance and education, the Museum features exhibits that tell the personal stories of survivors, provides reflecting rooms and powerful tributes, and showcases a range of artifacts from WWII, concentration camps, and ghettos.

The museum also offers educational programs on genocide awareness, and historian-led tours to get the most out of your trip.

What sets this museum apart from other Holocaust museums is its new virtual reality exhibition, The Journey Back. Using VR technology, visitors are taken on walks through concentration camps alongside Holocaust Survivors, hearing their captivating memories and stories first-hand.

50 – Morton Arboretum

An outdoor wonderland full of the most beautiful trees and flowers, the Morton Arboretum is undeniably one of the best places to visit in Chicago not just for nature-lovers, but for every type of visitor, entertaining locals and tourists alike for over 100 years.

With 16 miles of hiking trails that twist and turn their way through more than 1,700 acres, plus stunning sculpture-filled gardens, a maze garden, tourist trolley, library, and a herbarium, there’s plenty of fun to be had at this lush oasis just outside Chicago (about 25 minutes outside, to be exact).

Hot tip: if visiting during the winter, be sure to check out the magical illumination show, where towering trees are lit up with 150 colorful lanterns and colorful projections, providing a beautiful splash of color on the usually snowy-white backdrop, made all the more memorable by roasting marshmallows and crackling fires along the way.

Want a travel hack? Grab a city tourist pass!

We are undoubtedly spoiled for choice in this midwestern metropolis. Thankfully, to take the confusion and hassle out of selecting and choosing where to start, how to get around, and which destinations to prioritize, the folks behind the City Pass and Go City Chicago Explorer Pass have already done all the hard work for us.

Tailored specifically to those excited tourists who visit Chicago every year in search of hearty deep-dish pizza and brilliant museums (and all the other goodies we’ve mentioned) these passes offer great value-for-money deals and allow you to see and experience as much, or as little of the city as you please.

With a bounty of options to choose from for every budget, interest, and timeframe, these passes are a great way to see the best of Chicago’s attractions — like the Field Museum, Skydeck Chicago, and Hop-on-Hop-off bus – and save a few bucks along the way. In fact, you can save up to 44% of the regular costs if you were exploring solo!

Looking for a hotel?

Hundreds of hotels of all shapes, sizes, and price tags line the streets of Chicago, so rest assured that there’s something for every style (luxury VS basic) and every location (right in the city center, or a bit further out).

Craving a little luxury? The Waldorf Astoria oozes elegance, the Gwen on the Magnificent Miles comes with complimentary shoe shines and clothes pressing (which should say just enough about the opulence of this place); the Ritz-Carlton and the Langham boast fine reputations that precede them, and the 5-star Peninsula Hotel , which welcomes celebrities on the regular, is often voted the #1 Hotel in Chicago.

For excellent yet slightly more affordable options, any of the Sofitel, Marriott, or Radisson are popular choices, while if you can snag it at a bargain rate, the Drake dishes up splendid lakeside views.

Pinching pennies? You’ll find myriad hostels and budget options too, like the HI Chicago Hostel and the Wrigley Hostel .

Hot tip: check online to find the best deals on hotels all around Chicago — from budget-friendly motels to luxurious five-star resorts. With so many options to choose from, it’s easy to find something that suits your travel needs and budget. And, compared to walk-in prices, you could save hundreds.

Save yourself hassle: book an airport transfer

Is there anything worse than arriving at an airport and having to wait in lengthy queues for a taxi or public transport? Especially when you’re tired after your flight, not sure where you’re going, and don’t know the local lay of the land.

Thankfully, with so many tourists flocking to Chicago every year, there are lots of companies who offer pre-booked transfers from both of the city’s airports – O’Hare and Midway – to your hotel or accommodation. This way, you can avoid long queues, get straight to your destination without any fuss, and start exploring as soon as possible. Plus, if traveling as a group, it’s often cheaper than the total cost of transport tickets (and far more comfortable)!

Final thoughts

And that’s a wrap! We hope this article has given you a little taste of the best places to visit in Chicago! So whether you’re visiting in the summer, winter, or any time at all, you can expect a warm welcome from locals and tourists alike.

Have any questions about the different attractions? Want more recommendations on where to eat, drink, or stay? Or perhaps you’re looking for some tips on how to get around the city (and which neighborhoods are worth exploring)? Let us know in the comments below! As always, happy travels!

The perfect 3-day itinerary in Chicago

May 9, 2022 • 6 min read

Only have three days? Chicago is the perfect city to visit © Mlenny / Getty Images

The nation’s third-largest city covers a lot of ground, but you can take in a good chunk of Chicago during a weekend if you have a plan. And we’ve got one with sky-high buildings and star art collections, along with dive bars and Route 66 diners.

Here's our guide to the perfect weekend itinerary in Chicago. 

Head to the docks beneath Michigan Avenue downtown and hop on a boat tour with the Chicago Architecture Center . Yes, it’s touristy, but it’s also marvelous. Grab a seat on deck and look up as the finest collection of buildings in the country glides by. Guides’ architecture lessons carry on the breeze, so you’ll know your Beaux Arts from International Style by journey’s end.

After stuffing your head with knowledge, it’s time to stuff your face with deep-dish pizza, Chicago’s premier local specialty. Giordano’s makes “stuffed” pie, which is a bigger, doughier version – like deep-dish on steroids. Loosen the belt, because each cheese-laden slice weighs a half-pound or so.

Next, motor north a few miles to catch a show at Second City , the launching pad of jokesters from Bill Murray to Tina Fey. The outlandish sketch revues are always high-quality laugh fests. They’re also popular, so book tickets well in advance.

Before the night ends, get a drink at the Old Town Ale House , across the avenue from Second City. It’s a wonderfully democratic institution (some might call it a dive bar), where beautiful people and seen-it-all regulars mingle on barstools under the nude celebrity paintings until last call at 4am. You might even see cast members from your show hanging out over a wee-hour brew.

Start at downtown’s western edge and fuel up at Lou Mitchell’s , a diner from the days when Route 66 rolled by the area. The old-school waitresses call you “doll” while delivering fluffy omelets and plate-defying flapjacks to the table. Lines can be long, but Lou’s soothes the pain with free donut holes and Milk Duds as you wait for your table.

Walk a few blocks east to Willis Tower . Chicago’s tallest building pokes 1450ft into the heavens and its 103rd-floor Skydeck provides a panorama over four states. Brave souls can step onto the glass-floored Ledges to be suspended (almost) in stomach-lurching mid-air. Be sure to book tickets beforehand.

Stay downtown and mosey to the Art Institute of Chicago (advance reservations required). The second-largest art museum in the country hangs masterpieces aplenty, especially impressionist and post-impressionist pieces.

Georges Seurat’s pointillist A Sunday Afternoon on the Island of La Grande Jatte is here; so is Grant Wood’s American Gothic . Marc Chagall’s glowing stained glass America Windows fill a room, too.

When you’ve seen your fill, head to the Art Institute’s 3rd floor sculpture terrace, and step onto the silvery pedestrian bridge arching into Millennium Park . Make a beeline for the shiny “Bean” sculpture for the obligatory photo op. Splash around in Crown Fountain, where video images of locals spout gargoyle-style. Admire Frank Gehry’s swooping silver band shell. Then contemplate it all over a Nutella soufflé pancake and ginger tea at Hanabusa Cafe .

Take the Blue Line L train to Logan Square, a buzzy neighborhood 20 minutes northwest of downtown – prime for chowhounds and tipplers. Drop in at Revolution Brewing to knock back a Rosa hibiscus ale or other inventive beer with the local crowd.

Make your way a mile southwest to Giant , a small storefront cooking up big flavors in modern American comfort food. Advance reservations are essential. If you can’t score a seat, no worries: nearby Ground Control earns praise for its tofu fried chicken, beer-braised greens and other vegetarian dishes served with a side of local brews and budget cocktails.

From here it’s a stone’s throw to Rosa’s Lounge . The electric blues became Chicago’s tune when Muddy Waters, Howlin’ Wolf and friends plugged in their amps in the 1950s, and Rosa’s is an authentic spot to hear a fret-bending set.

The humble venue brings real-deal players to its arm’s-length-away stage where guitars wail into the night. It’s wise to buy tickets in advance, though you usually can walk up and get in after the first set (around 11pm). 

Chicagoans go gaga for brunch, and the West Loop provides loads of stylish hot spots to get your eggs on. The Publican delivers honey butter waffles, pork belly hash and hefty Bloody Marys, while Top Chef winner Stephanie Izard’s Little Goat shows how it’s done with cheesy hash browns and spiced apple pancakes. Roister makes chicken and waffles and biscuits and gravy that go way beyond the traditional versions.

If it’s baseball season and the Cubs are playing, hop on the Red Line train to Wrigley Field . The 1914 ballpark charms with retro touches like ivy-covered outfield walls and a hand-turned scoreboard. Shoveling down hot dogs and drinking beer in the raucous bleacher seats makes for an exceptional afternoon.

Otherwise, aim for the Pilsen neighborhood, a mash-up of Chicago’s Mexican community and hipster underground. Wild murals radiate off the buildings on practically every street.

A walkabout with Pilsen Public Art Tours is a good way to explore. Hungry? Bite into sublime pork tacos at Don Pedro Carnitas or complex, mole-rich dishes at 5 Rabanitos . The Pink Line L train to 18th Street gets you there.

Where to stay

Downtown (aka the Loop): Cool boutique and architectural properties fill the core, where you’re steps away from Millennium Park, the Art Institute and other top sights. The playful Virgin Hotel offers large, cleverly conceived rooms in an old art deco bank tower, while the Silversmith flashes gem-inspired, vintage-cool rooms in a Gilded Age jewelers building.

West Loop: Chicago’s most trendsetting accommodations pop up in the West Loop, surrounded by heaps of fashionable bars and restaurants. The Publishing House Bed & Breakfast puts you in the thick of it, with 11 stylish rooms named after Chicago writers. The Hoxton Chicago brings mid-century-modern-inspired decor to its creative digs, along with free bicycles and a festive rooftop cafe.

How to get to Chicago 

O’Hare International Airport is on the city’s northwest side; it’s larger and where most international flights arrive. Smaller Midway International Airport is on the south side. Both have easy links to downtown via the L train, which costs $5 and takes 40 minutes from O’Hare, and $3 and 30 minutes from Midway. Amtrak arrives downtown at Union Station.

You might also like:

How to spend a perfect weekend in Chicago Out of the Loop: a tour of Chicago's off-the-beaten-path neighborhoods The best day trips from Chicago

This article was first published Sep 9, 2019 and updated May 9, 2022.

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52 Best Places to Visit in Chicago

Natalija Marković - Travel Writer

Last Updated: January 4, 2024

Hey there! I'm Natalija, a travel enthusiast and writer who is thrilled to share with you the 52 best places to visit in Chicago in 2024. With captivating photos and insider tips, this article will help you create unforgettable memories in the Windy City.

The bustling metropolis of Chicago, also known as the Windy City , is home to many amazing places that tourists can discover. Everyone can find something to do in Chicago, from famous landmarks to thriving neighborhoods.

This city has something for everyone, whether you're a history buff, foodie, or art aficionado. 

In this post, we’ll introduce you to 52 of the best places to visit in Chicago, all of which are sure to play with your senses and leave you with priceless memories.

Most Recommended Thing to Do

Millennium Park

Top Choice Hotel

The Peninsula Chicago

Our Top Choice Restaurant

Our Top Choice Bar for Nightlife

The Underground

Best Time to Visit

Summer and spring offer best weather and festivals.

Average Temperature

Cold winters, hot summers: average temperature in Chicago.

Transportation Options

Bus, train, subway, taxi, rideshare, bike sharing, walking

Average Cost ($, $$, $$$)

My Top Recommendation

Chicago, the Windy City, offers a plethora of experiences for travelers. Start your day by taking a leisurely stroll along the picturesque Lakefront trail, where you can soak in stunning views of Lake Michigan while catching the morning breeze. Afterwards, head to Millennium Park to marvel at the iconic Cloud Gate sculpture, also known as "The Bean," and snap a selfie or two.

In the afternoon, immerse yourself in the vibrant culture of Chicago by paying a visit to the Art Institute of Chicago, home to an extensive collection of masterpieces spanning centuries. Indulge in a deep dish pizza for lunch, a Chicago specialty, at one of the city's famed pizzerias. In the evening, venture to Navy Pier and catch a breathtaking sunset while taking a ride on the iconic Ferris wheel. Wrap up your day by exploring the lively neighborhoods like Wicker Park or Lincoln Park, where you can enjoy a lively atmosphere, live music, and delicious cocktails.

What You'll Need to Bring

Passport, comfortable shoes depending on the season/weather

What Not to Miss

The art institute of chicago, willis tower skydeck.

• Wrigley Field
• Magnificent Mile
• Museum of Science and Industry

Chicago Riverwalk

• Cloud Gate (The Bean)

What to Avoid

• Rush hour traffic
• High crime areas
• Paying for parking in the city center
• Expensive tourist traps
• Overpriced hotels and accommodations
• Poorly reviewed restaurants
• Countless hours of wait time at popular attractions
• Ignoring local customs and etiquette
• Overpacking and unnecessary baggage
• Taking public transportation during late hours

Table of Contents

1. Lincoln Park Zoo

The Lincoln Park Zoo , one of the country's oldest zoos, is a must-see attraction for tourists in Chicago. This free-admission zoo offers a distinctive and comprehensive animal experience and is located only a short distance from downtown Chicago.

The Lincoln Park Zoo is a mesmerizing location for animal lovers of all ages with its varied variety of animals from throughout the world, including lions, tigers, monkeys, and more.

It is a wonderful complement to any schedule for Chicago because visitors can also take advantage of the beautiful gardens, educational exhibitions, and special events. This zoo is one of the various tourist attractions in Chicago , so don't miss it.

2. Millennium Park

Without visiting the famous Millennium Park , no trip to Chicago is complete. This urban sanctuary, which is located in the center of Chicago, offers an alluring fusion of art, architecture, and nature.

Millennium Park is a sensory feast, from the captivating Cloud Gate sculpture reflecting the city skyline to the tranquil Lurie Garden and engaging Crown Fountain . Just a few feet away, enjoy a leisurely stroll along the Chicago Riverwalk or attend summertime music at the Jay Pritzker Pavilion.

Everyone who wants to visit Chicago should see Millennium Park because of its distinctive fusion of modern design and unspoiled beauty.

3. Chicago Riverwalk

A lovely location that provides a distinctive perspective of the city's architecture and history is the Chicago Riverwalk . This waterfront promenade, which stretches along the Chicago River, offers picturesque views, colorful gardens, and busy eateries.

Visit the famous Chicago Water Tower , a historical site that withstood the Great Chicago Fire of 1871, while strolling slowly.

The Riverwalk is a must-visit location for both tourists and locals because of its stunning scenery, attractive atmosphere, and convenient location to other places to visit in Chicago.

Discover the rich history of the city while taking in the beauty of the Chicago River as you stroll along this lively waterfront promenade.

4. The Magnificent Mile

The Magnificent Mile in Chicago is a must-visit location for locals and tourists alike because it is a shopper's paradise with an entire city block of top-notch shopping.

This famous retail area offers a dizzying assortment of dining, entertainment, and shopping options along its streets of premium shops, department stores, and best hotels in Chicago .

The Magnificent Mile is a favorite choice for tourists wishing to indulge in a genuinely remarkable shopping experience in the center of Chicago because of its energetic ambiance, gorgeous architecture, and numerous offerings.

Additionally, the Wrigley Building is situated on the famed Magnificent Mile, just opposite Michigan Avenue from the Tribune Tower.

5. The Field Museum

Any visitor should not skip the Field Museum in Chicago, which is a veritable treasure trove of information and wonder.

This renowned museum provides a fascinating look into Chicago's history, natural history, and fine arts through its enormous collection of artifacts and exhibitions.

The Field Museum captivates visitors of all ages with its breathtaking gem and jewelry displays as well as its astounding dinosaur bones.

For anyone wanting an educational and engaging experience in the Windy City, the Field Museum is one of the best museums in Chicago .

6. Museum of Science and Industry

Tourists shouldn't pass up the opportunity to embark on a discovery expedition at the Museum of Science and Industry in Chicago.

This top-notch museum provides an interesting and dynamic experience for visitors of all ages and is conveniently close to well-known destinations like the Field Museum, Millennium Park, and Michigan Avenue.

The Museum of Science and Industry offers a fascinating look into the wonders of science and innovation, with engaging exhibitions on biology, physics, and other subjects in addition to interactive exhibits on space exploration and cutting-edge technology.

7. Wrigley Field

For fans of both sports and history, Wrigley Field , the storied home of the Chicago Cubs , is a must-see location.

This iconic baseball stadium offers an unforgettable experience and is situated in the lively Clark St area, close to other well-liked tourist attractions like the Wrigley Building and the City Center.

Wrigley Field is an iconic location that has been a part of Chicago's sports culture for more than a century, from the nostalgic appeal of the ivy-covered outfield walls to the electrifying atmosphere of a Cubs game.

8. Willis Tower Skydeck

For tourists looking for stunning vistas and exhilarating experiences, a trip to Chicago's Willis Tower Skydeck , once known as the Sears Tower , is a must.

This famous tower, which lies in Chicago's city center, provides expansive views of Lake Michigan , the city skyline, and beyond.

Feel your heart accelerate as you gaze out onto the glass-floored Skydeck, 1,354 feet above the ground, and take in the breathtaking landscape. You'll develop a new respect for Chicago's architectural wonders, from Grant Park to the Willis Tower itself.

9. Navy Pier

One of the most popular Chicago attractions, Navy Pier , is a distinctive and energetic location that guarantees visitors an amazing experience. 

Navy Pier offers something for everyone, from breathtaking panoramas of the city skyline to exhilarating rides at the amusement park. Take a leisurely boat tour on Lake Michigan, enjoy delectable food, catch a live music performance at an outdoor concert venue, or stroll along the pier.

The must-see attraction Navy Pier, which is close to Grand Ave, is sure to be the highlight of any visit to Chicago.

10. The Art Institute of Chicago

Your decision to attend T he Art Institute of Chicago will not be one you regret. This well-known museum displays works of art from all over the world and has a large collection of artwork that ranges from classical to current.

The Art Institute of Chicago is a veritable gold mine of artistic marvels that will fascinate your senses, from Van Gogh's "The Bedroom" to Grant Wood's "American Gothic."

This national museum invites you to explore the colorful collection of Mexican art , awe at the superb contemporary art, and become fully immersed in the rich cultural legacy.

11. Chicago Children's Museum

The Chicago Children's Museum , which is housed on the Navy Pier, is a popular attraction for families. 

The Chicago Children's Museum provides a vibrant and enriching environment for kids to explore, learn, and have fun. It features hands-on exhibits that inspire creativity and curiosity as well as interactive displays that encourage problem-solving skills.

This Museum is a standout of the city's thriving cultural scene and a top pick among places to visit in Chicago for families because of its ideal location in downtown Chicago and its concentration on kid-friendly activities.

12. Lake Michigan

A popular tourist destination, Lake Michigan , the recognizable body of water that borders Chicago, has a wide range of sights and activities.

Lake Michigan is a must-see destination for travelers in Chicago because of its breathtaking shoreline views, sandy beaches, and recreational activities.

In the winter, try ice skating or take a stroll along the lakefront while admiring the Chicago Water Tower. Chicago, the third-largest city in the US, is defined by its proximity to Lake Michigan, which offers countless options for outdoor leisure, relaxation, and enjoyment.

13. Maggie Daley Park

A premier tourist destination in Chicago, Maggie Daley Park offers a distinctive fusion of outdoor activity and family-friendly attractions.

This vast park is home to a variety of activities, including a spectacular ice skating rink in the winter, making it a well-liked destination for people looking to have some frosty fun.

Maggie Daley Park is a must-visit spot for tourists wishing to immerse themselves in the beauty and excitement of Chicago's outdoor offerings because of its central location and close proximity to other tourist attractions like Lincoln Park.

14. John Hancock Center

Tourists shouldn't skip the John Hancock Center at 875 North Michigan Avenue, a renowned architectural wonder in Chicago.

This landmark skyscraper features amazing architectural and technical marvels, including its recognizable X-bracing structure that stands out on the Chicago skyline .

Visitors to the John Hancock building can take in the stunning scenery of Michigan Ave, marvel at its remarkable design, and enjoy panoramic views of the city and Lake Michigan from its observation deck.

15. Garfield Park Conservatory

For tourists seeking peace and beauty in the middle of the city's activity, the Garfield Park Conservatory is a hidden gem in Chicago that they must explore.

The Garfield Park Conservatory is ideally situated next to well-known tourist destinations like Cloud Gate and others that provide distinctive attractions like a historic carousel and a mini-golf course .

The Garfield Park Conservatory is the ideal location thanks to its peaceful atmosphere, educational exhibits, and stunning scenery.

16. Shedd Aquarium

One of the most well-liked tourist attractions in Chicago and a must-see location for tourists is the Shedd Aquarium . Over 32,000 aquatic creatures, including sea otters, penguins, and sharks, call this amazing aquarium home.

Visitors can engage with interactive displays, touch tanks, and even go dolphin swimming. The Shedd Aquarium is conveniently close to well-known sites like the Buckingham Fountain and is reachable by public transit.

The Shedd Aquarium is a must-see attraction for any visitor to Chicago because of its enormous collection of aquatic life and interesting exhibits.

17. Jackson Park

Jackson Park , a sizable park overlooking Lake Michigan, is well-known for its extensive size and rich historical value, offering a peaceful retreat from the bustling city center.

Situated in the Woodlawn neighborhood, Jackson Park is a central and easily accessible location. It also borders the South Shore and Hyde Park communities.

Jackson Park exemplifies the cultural and natural history of Chicago with its wide variety of attractions and lakeside location.

18. The Chicago Cultural Center

If you want to fully experience the rich cultural heritage of the city, you must visit the Chicago Cultural Center . Numerous exhibitions that focus on African American history , natural history, and other topics are housed in this architectural treasure.

The Chicago Cultural Center is a real masterpiece that exemplifies the dedication of the city to the fine arts and culture with its gorgeous Beaux-Arts architecture and elaborate mosaics.

The Chicago Cultural Center is a must-visit location for anybody wishing to delve into the rich cultural fabric of Chicago, from its interesting exhibits to its historic significance.

19. Washington Park

Chicago's Washington Park is a thriving, historic park that provides a wide range of leisure and cultural possibilities. This vast park is renowned for its breathtaking scenery and extensive history.

It is home to well-known sites including the DuSable Museum of African American History , which offers an in-depth understanding of the past and accomplishments of African Americans in American culture.

This Park is a well-liked destination for families, visitors, and locals alike because of its lovely gardens, recreational facilities, and playgrounds.

A trip to this park is a wonderful way to experience Chicago's natural beauty and cultural diversity.

20. Burnham Park

Burnham Park , which is situated along Lake Shore Dr and stretches along the beautiful Lake Michigan waterfront, is a must-see location for travelers in Chicago.

Burnham Park, a contemporary of Lincoln Park, provides a distinctive fusion of scenic beauty, leisure pursuits, and cultural attractions.

Burnham Park is the ideal place to relax, take in amazing vistas, and savor the lively ambiance of Chicago's lakefront thanks to its stunning lakefront position.

21. Robie House: The Architectural Masterpiece of Frank Lloyd Wright

Anyone interested in design and history must see the University of Chicago's Robie House , a masterpiece of modern architecture. Robie House is a well-known example of the Prairie School architectural style of Frank Lloyd Wright .

Numerous educational opportunities, such as guided tours, displays, and events that highlight the value of this historic site are available at the museum campus that surrounds Robie House.

An opportunity to appreciate Frank Lloyd Wright's creative work and become fully immersed in Chicago's rich architectural legacy is provided by a visit to Robie House.

22. Oriental Institute Museum

Both history buffs and tourists will find the Oriental Institute Museum to be a fascinating place. Also called the Institute for the Study of Ancient Cultures, West Asia and North Africa , this is a renowned museum.

Located in Chicago, the museum provides a fascinating look into the prehistoric cultures of the Middle East and North Africa.

Explore displays of ancient sculptures, manuscripts, and archaeological finds at this history museum. A visit to this Chicago history museum is a captivating journey through time, offering a deeper understanding of our shared human heritage.

23. Chicago Shakespeare Theater

Both theater enthusiasts and tourists should visit the Chicago Shakespeare Theater .

Shakespeare's classic plays are displayed with more modern works at this theater. This Chicago theater is conveniently located inside Navy Pier, one of Chicago's most well-known tourist destinations, making it simple for tourists to include it on their schedule while seeing the city.

The Chicago Shakespeare Theater is a must-see location that ensures an outstanding theatrical experience, whether you're a theater fan or simply looking for a distinctive cultural experience when you visit Chicago again.

24. Buckingham Fountain

Chicago's Buckingham Fountain is a captivating icon and popular tourist destination. One of the biggest fountains in the world, it can be found in Grant Park and is renowned for its magnificence and beauty.

The fountain, which is a feature of Grant Park , provides breathtaking panoramic views of the city skyline and Lake Michigan, making it the ideal location for priceless pictures.

Buckingham Fountain is a must-see location that captures the magnificence of Chicago's urban setting, whether you visit during the day or at night to experience the fountain's mesmerizing light and music presentations.

25. Hyde Park

The flourishing Chicago neighborhood of Hyde Park has a wide variety of tourist attractions. The Robie House on the University of Chicago campus is just one of its highlights.

This neighborhood is a bustling and diversified destination that tourists to Chicago should not miss, in addition to its architectural and natural beauties. It is also home to numerous cultural institutions, restaurants, and stores.

26. Tribune Tower

For lovers of architecture and history, the Tribune Tower in Chicago should not be missed. With its distinctive style and historical significance, it stands as an iconic landmark on North Michigan Avenue.

The Tribune Tower is a fascinating visit for those interested in the history and architecture of the city. It was once the home of the Chicago Tribune newspaper and features a wide variety of architectural styles from throughout the world.

27. North Avenue Beach

Tourists looking for leisure and pleasure frequent Chicago's North Avenue Beach . This sandy sanctuary, which is tucked away within the enormous Lincoln Park, offers a lovely setting with far-off views of the famous John Hancock Center and Lake Michigan.

Visitors can enjoy a relaxing swim, relax on the beach, or stroll along the lovely lakefront promenade. The beach is the ideal location for a day of fun and relaxation because it also has a variety of services like beach volleyball courts, refreshments, and bike rentals.

28. Adler Planetarium

The Adler Planetarium in Chicago, the first planetarium in the US , is a fascinating destination for all visitors as well as a haven for science enthusiasts.

The Adler Planetarium offers stunning panoramic views of the Chicago skyline and is located near the scenic Lake Michigan waterfront.

Visit the Adler Planetarium in Chicago to learn about the wonders of the cosmos.

29. Frank Lloyd Wright Home and Studio

For those who love architecture and are fans of the famous architect's work, a visit to the Frank Lloyd Wright Home and Studio in Chicago is a must.

This famous location, which can be found in the Oak Park district , provides a look into Wright's formative years and his avant-garde architectural concepts.

Admire the distinctive characteristics, minute details, and organic design components that are emblematic of Wright's distinctive style.

Guided tours offer insights into his revolutionary ideas and the sources of inspiration for his outstanding creations.

30. Wrigley Building

For tourists interested in renowned architecture, the Wrigley Building in Chicago is a must-see. 

It has spectacular views of the Chicago River, is adjacent to well-known department stores, and is situated on the renowned Magnificent Mile.

The Wrigley Building stands out as a landmark due to its distinctive fusion of Gothic and French Renaissance styles, so be sure to check it out when you visit Chicago. 

31. Chicago History Museum

Both history buffs and interested travelers should visit the Chicago History Museum , which is situated in Lincoln Park at the intersection of North Avenue and Clark St.

Explore the exhibits and collections to become fully immersed in the rich history of Chicago, which spans from its earliest days to the present.

Explore the city's rich cultural history, significant historical events, and enduring people that have influenced its identity. An educational and inspiring trip through time awaits visitors to this Museum.

32. Museum Of Contemporary Art Chicago

For lovers of art and culture alike, the Museum of Contemporary Art Chicago is a must-visit location. This renowned institution offers a stimulating experience with its varied collection of cutting-edge modern art.

Discover cutting-edge styles in art and ground-breaking creations by both well-known and up-and-coming artists. At the Museum of Contemporary Art Chicago, immerse yourself in the world of contemporary art and be inspired by its dynamic and constantly changing displays.

33. The Chicago Botanic Garden

For those who enjoy the outdoors and plants, the Chicago Botanic Garden is a true haven, making it a popular tourist destination.

A remarkable diversity of flora from all over the world is displayed in this world-class garden's 27 stunning gardens, which are spread out over 385 acres.

The Chicago Botanic Garden provides a tranquil getaway from the busy city center with its calm lakes, winding trails, and gorgeous settings. Seasonal flower displays, interactive exhibitions, and educational activities are available to visitors of all ages.

34. The 360 Chicago Observation Deck

One of the places to visit in Chicago is the 360 Chicago Observation Deck , which provides unrivaled panoramic views of Chicago's famous skyline.

This observation deck on the 94th level of the John Hancock Building offers amazing views that extend for miles in every direction.

The 360 Chicago Observation Deck is a popular attraction that provides an amazing perspective of the gorgeous city of Chicago. It includes interactive displays, an exhilarating TILT experience, and a bar serving refreshments.

35. The Chicago Architecture Center

Anyone interested in the rich architectural history of the city must visit the Chicago Architecture Center .

It provides a fascinating tour through Chicago's architectural history and is housed in the renowned One Illinois Center.

Through entertaining tours, interactive displays, and educational presentations, visitors may find out more about the designs of Frank Lloyd Wright and other well-known architects.

The center also presents unique exhibits, talks, and workshops that explore the various architectural innovations and styles found throughout the city.

36. The Chicago Theatre

Visitors may expect to have an outstanding time at the storied Chicago Theatre . This historic location is a masterpiece of imposing construction.

The Chicago Theatre, with its recognizable marquee and brilliant marquee lights, is a magnificent sight to behold.

You can savor the splendor of the elaborate interior, which has opulent chandeliers and gilded furnishings. The theater provides a magical setting for concerts, comedic performances, and other events thanks to its long history as a cinema palace and its present status as a prominent live entertainment facility.

37. The Peggy Notebaert Nature Museum

For people who love the outdoors and are interested in natural history, the Peggy Notebaert Nature Museum in Chicago is a fascinating place to visit.

This museum, which is nearby the famed Field Museum, provides an interactive experience that highlights the varied ecosystems of the Midwest.

For nature lovers of all ages, the museum's stunning butterfly paradise, which is home to hundreds of local butterflies, is a highlight.

38. The Chicago River Cruise

A popular and picturesque way to tour the city's famous river and take in its magnificent architecture is to take a Chicago River Cruise .

By boarding a ship, tourists may cruise along the storied Chicago River while passing by famous sites including the Tribune Tower, the Wrigley Building, and the Willis Tower.

The Chicago River Cruise is a must-do activity for Chicago visitors because it features knowledgeable guides, beautiful views, and easy access to nearby sites.

39. The Chicago Cultural Mile

The Chicago Cultural Mile , a bustling section of Michigan Avenue close to Lincoln Park, is a treasure trove of art, history, and culture. This hub of culture is home to top-notch theaters, galleries, museums, and more.

The Museum Campus , a gorgeous lakefront park where three of the city's best museums—the Field Museum, the Shedd Aquarium, and the Adler Planetarium—are located, is one of the highlights of the Chicago Cultural Mile.

Visitors can experience the wonders of science, history, and marine life like never before at this famous location. The Chicago Cultural Mile is a destination in and of itself thanks to its ideal position on the shores of Lake Michigan.

40. The Chicago Pedway

The Chicago Pedway is a unique and fascinating underground network of tunnels and walkways that lies in the city center.

This gem offers a convenient and weatherproof way to explore downtown Chicago, connecting iconic landmarks, hotels, offices, and shopping centers.

The Pedway provides a distinctive perspective of the city, with its labyrinthine passages and vibrant art installations.

Whether you're looking to escape the elements or simply discover a lesser-known side of Chicago, the Pedway is a must-visit destination for urban explorers.

41. The National Museum of Mexican Art

In a dynamic and culturally significant location, the National Museum of Mexican Art presents a distinctive viewpoint on Mexican art and culture.

This museum, which is located in the center of Chicago, is a must-see for art lovers and people who are curious about a variety of cultural experiences.

The vast collection of the museum displays a variety of artistic traditions from Mexico. 

42. The Museum of Broadcast Communications

For anyone interested in the background of radio and television, the Museum of Broadcast Communications in Chicago is one of the city's most fascinating tourist attractions.

This museum, which is located in the center of Chicago, honors the development and influence of broadcasting on American culture.

By displaying legendary shows, well-known presenters, and behind-the-scenes glimpses into the world of broadcasting, the museum provides a nostalgic walk down memory lane.

For anybody interested in media, history, or the intriguing world of radio and television broadcasting, it is a must-see.

43. The 606: An Elevated Park and Trail System

A unique and cutting-edge urban paradise in Chicago, The 606 is an elevated park and trail system that provides a welcome respite from the bustle of the city.

A former elevated railway track has been converted into a vibrant green area for enjoyment, relaxation, and community interaction.

The 606 is the ideal location for a leisurely stroll, jog, or bike ride thanks to its gorgeous landscaping, public art pieces, and stunning views of the city.

Its proximity to luxury hotels and a mini golf course makes it an ideal place for Chicago visitors who want to see the city's natural splendor.

44. The Chicago Public Library (Harold Washington Library Center)

A cultural treasure in the center of Chicago, the Harold Washington Library Center is home to the Chicago Public Library and provides access to a plethora of information, tools, and opportunities for community involvement.

With its iconic design and soaring atrium, this magnificent library—named after Chicago's first African American mayor, Harold Washington—is a grand architectural wonder.

You can browse a sizable collection of books, digital media, and educational resources inside, as well as take advantage of the free events, workshops, and activities available for people of all ages.

The Harold Washington Library Center is a hub of knowledge, exploration, and community connection because of its welcoming environment and closeness to the Navy Pier.

45. The Richard H. Driehaus Museum

In the city center of Chicago, the Richard H. Driehaus Museum provides a window into the sumptuous Gilded Age.

This museum displays the magnificence of late 19th-century architecture and design and is housed in a magnificent estate that has been painstakingly restored to its full brilliance.

The elaborate interiors, luxurious furnishings, and stunning decorative arts collections will leave visitors in awe.

46. The Money Museum at the Federal Reserve Bank of Chicago

For those interested in the development, function, and activities of the Federal Reserve System, the Money Museum at the Federal Reserve Bank of Chicago is a fascinating stop.

This distinctive museum, which is situated in downtown Chicago, provides visitors with an immersive look into the financial and banking industries.

You will learn about the role of the Federal Reserve, the development of currency, and the significance of monetary policy through engaging demonstrations, multimedia displays, and interactive exhibits.

The Money Museum also provides a unique chance to observe up close the complex procedures involved in creating and handling money. 

47. Chicago Food Planet Culinary Tours

Chicago Food Planet is a firm that organizes culinary tours that provide a special and delectable way to discover Chicago's thriving food industry.

These food tours take guests on a culinary trip through several neighborhoods, displaying the city's rich food culture, history, and local cuisine. The tours are led by professional guides.

A mouthwatering experience for foodies and cultural enthusiasts alike, Chicago Food Planet excursions feature everything from deep-dish pizza to Chicago-style hot dogs, gourmet chocolates to ethnic delights.

These excursions provide an enjoyable, educational, and unique opportunity to experience the flavors of the City while learning about its culinary legacy, with an emphasis on local companies and sustainable methods.

48. The Rookery Building

The Rookery Building in Chicago is a masterpiece of architecture that mesmerizes tourists with its old-world charm and cutting-edge style.

This famous structure, which can be found in downtown Chicago's Loop neighborhood , is a must-see for both history buffs and fans of architecture.

The Rookery Building, created by renowned designers Daniel Burnham and John Root, has an impressive interior atrium with a spectacular cast-iron staircase and a gorgeous skylight.

It is ideally situated near the Art Institute of Chicago, making it the ideal stop for anybody wishing to enjoy the city's rich architectural history and world-famous art collections.

49. DuSable Black History Museum and Education Center

A crucial cultural organization that recognizes and protects the rich history and contributions of African Americans is the DuSable Black History Museum and Education Center in Chicago.

This museum offers a potent forum for learning, introspection, and celebration of Black history, culture, and accomplishments .

It is named after Jean Baptiste Point DuSable, a Haitian of African and French heritage who is largely regarded as the first non-indigenous settler in Chicago.

The DuSable Museum provides a distinctive perspective on African American history, art, and culture through its exhibits, events, and educational initiatives, developing understanding, awareness, and appreciation of the Black experience.

For people who want to learn more about African American ancestry and contributions to American society, it is a must-visit location.

50. Brookfield Zoo

Wildlife fans of all ages can find world-class entertainment at the Brookfield Zoo in Chicago. This renowned zoo, which is just outside of downtown Chicago, is spread across 216 acres and is home to more than 2,300 animals from all over the world.

The Brookfield Zoo provides a fascinating and immersive experience for visitors to learn about and enjoy the beauty and diversity of the animal kingdom because of its dedication to conservation, education, and animal care.

The Brookfield Zoo offers a wide variety of exhibits and environments, including cutting-edge and award-winning animal enclosures, from African savannahs to tropical rainforests. The Brookfield Zoo is a must-go location for both nature and animal lovers because of its focus on conservation and education.

51. American Writers Museum

A literary gem that honors the vast and varied literary heritage of the United States is the American Writers Museum in Chicago.

This distinctive museum is devoted to displaying the literary accomplishments of American writers throughout history, from classical literary giants to modern authors, and is situated in the center of downtown Chicago.

The American Writers Museum provides visitors with a one-of-a-kind trip through American literature, exploring the power of words and the influence of writers on society and culture. It does this with interactive exhibits, compelling displays, and immersive experiences.

The American Writers Museum is a must-see location for literature lovers, aspiring writers, and anybody who values the beauty and power of the written word, from Mark Twain to Maya Angelou.

52. Chicago Lakefront Trail

For 18 miles along the gorgeous Lake Michigan shoreline, the Chicago Lakefront Trail is a picturesque gem that provides outdoor enthusiasts and nature lovers with an unforgettable experience.

This legendary trail offers unmatched vistas of the lake , the Chicago skyline, and lovely parks along the way and is ideal for walking, running, biking, or simply strolling.

The Chicago Lakefront Trail is a well-liked attraction for both locals and tourists due to its well-maintained routes, practical access locations, and breathtaking panoramas.

The Chicago Lakefront Trail is a must-see location that provides an unforgettable experience for everyone, whether you're looking for a revitalizing workout, a serene getaway, or to stay near Michigan Avenue.

FAQs About Things to Do in Chicago

Let’s take a look at some frequently asked questions about the best places to visit in Chicago.

What are 5 things that Chicago is known for?

Chicago is known for many things, including the Lincoln Park Zoo, Millennium Park, Grant Park, the Art Institute of Chicago, and the Chicago Cubs.

How can I spend a day in Chicago?

If you have one day to spend in Chicago, you can stroll along the Magnificent Mile, visit the Art Institute, head to North Avenue Beach, or take a selfie with the iconic Cloud Gate. If you have time, stop for a drink at Navy Pier to end your day.

What is Chicago famous for?

Chicago is also famous for its stunning skyline, which includes the Sears Tower (Willis Tower), Chicago Water Tower, and the various structures on the Magnificent Mile. With so many great tourist attractions, it is hard to pinpoint just a few famous sites in Chicago.

What should tourists do in Chicago?

Tourists in Chicago should visit the Sears Tower, the Art Institute of Chicago, Lincoln Park Zoo, Millenium Park, and the Magnificent Mile. If you are traveling with kids, you should also stop at the Shedd Aquarium and Grant Park.

Summing up: The Best Places to Visit in Chicago

Chicago is a city with a rich history , a diverse population, and a thriving arts community. Chicago has countless options for exploration and discovery with its famous sites, multicultural neighborhoods, and distinctive attractions.

In the Windy City, there is something for everyone to enjoy, from the Lincoln Park Zoo and Millenium Park to Grant Park and the Magnificent Mile.

Keep this list of 52 fantastic locations in Chicago for when you plan your trip. Make unforgettable experiences by booking your vacation to Chicago right away.

Lincoln Park Zoo

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The Perfect 3 Days in Chicago Itinerary (2024 Edition)

• Last Updated: February 4, 2024

If you’re planning a long weekend trip to the Windy City and aren’t quite sure what to do, keep reading for our epic 3 days in Chicago itinerary!

While Chicago is the 3rd-largest city in the US, it’s often overlooked by travellers who jet for one of the coasts.

In my opinion, Chicago is the best city in the country. New York and LA are great and all, but I’ll gladly take the friendly Midwestern vibe of Chicago instead.

Situated on Lake Michigan, the Chicago skyline is one of the most beautiful in the world. After all, it was here that the first skyscraper was built in 1885!

There’s so much going on here that you could spend a lifetime there and never run out of things to do.

With a solid Chicago itinerary, you can definitely check out the best of the city in 3 days. Let’s get to it!

Table of Contents

When to Visit Chicago

Chicago citypass, getting around chicago, loop walking tour, chicago hot dog, millennium park, art institute of chicago, willis tower, dinner and drinks, museum campus, riverwalk or river cruise, magnificent mile, chicago deep dish pizza, choose your own adventure, museum of your choice, 360 chicago, lincoln park, best hostel in chicago – hi chicago, best mid-range hotel – congress plaza, best luxury hotel – peninsula, brunch/lunch, how to spend a perfect 3 days in chicago itinerary.

Our 3 days in Chicago itinerary includes:

• Shedd Aquarium
• Skydeck Chicago
• Field Museum
• Adler Planetarium
• 360 CHICAGO Observation Deck
• Navy PierMuseum of Science and Industry
• Ferris Wheel
• Crown Fountain

Looking for more awesome things to add to your Chicago itinerary? Be sure to read our guide to the best things to do in Chicago !

Travel Tips for Visiting Chicago

The first step in figuring out what to do during your 3 day Chicago itinerary is planning when you’ll visit.

Winter in Chicago can be painfully cold, which can definitely put a damper on your trip. Unless you enjoy frigid temperatures and cold, biting wind, I recommend skipping out on December-March.

Your best bet is to visit Chicago between May and October. It gets hot and crowded in the summer, but there’s so much going on that it’s worth dealing with those minor inconveniences.

Read Next: Don’t miss out on the best Chicago day trips !

Another huge tip I have before you visit Chicago is to purchase a Chicago CityPASS .

Essentially this is just a multi-use ticket that actually saves you a bunch of money (50% to be precise!) on many great Chicago attractions.

You buy the pass for USD$109, and it includes access to the following:

• Skydeck Chicago and
• Adler Planetarium or the Art Institute of Chicago
• 360 CHICAGO Observation Deck or the Museum of Science and Industry

Best of all, those entrances are mostly express or premium tickets included with the CityPASS , meaning it not only saves you money but saves you time as well.

We highly recommend you pick one up when using our Chicago itinerary to make the most of your time in the city.

Thankfully, getting around Chicago is a breeze thanks to the CTA network of train and bus lines. Chicagoans refer to the train as the “L” because it’s mostly on “el-evated tracks.”

If you’re spending 3 days in Chicago, your best bet is to just pick up an unlimited CTA pass. These cost $20 and are added to a Ventra card.

You can pick up a Ventra card at vending machines for $5 and it’s credited back to your account after you register the card. Read all about getting around Chicago on the CTA website .

You can count on the CTA getting you as far south as the Museum of Science and Industry all the way north to Lincoln Park.

Or consider jumping on and off the open-top bus that will take you all over the city!

In the city center, lots of Chicago attractions are all within walking distance as well.

Now that some of the logistics are taken care of, let’s get this show on the road for your 3 day Chicago itinerary!

Day 1 – Morning

For day 1 of your Chicago itinerary , you’ll need to hit the ground running if you want to maximize your time.

Get a nice early start, crush a substantial breakfast and some coffee, and get ready to rock.

The best way to kick-off your Chicago itinerary is by taking a walking tour of the Loop. This area of downtown is where you’ll find a majority of the sights in Chitown.

You have several options for exploring the Loop. If you enjoy meeting people and getting the insight of a local guide, you can sign up for one of the many options with Free Tours by Foot .

If it’s your first time in Chicago I suggest joining their 10 AM tour of the Loop and Millennium Park. Or if you’re really into architecture, check out their 10:30 Birth of the Skyscraper tour. Both are excellent options!

Those who prefer a DIY approach can check out the many self-guided tours of Chicago from MetroWalkz. This Architecture/Loop tour makes for a fantastic introduction to the city and is pretty easy to follow.

Whichever option you choose, you’ll get to see some of the most iconic places in the city in just a few short hours. A few of the highlights include the historic start of Route 66, the great Chicago Theatre.

READ NEXT: While you’re exploring the Midwest, be sure to check out the best things to do in Minneapolis, Minnesota !

Day 1 – Afternoon

At this point, the order in which you do things depends on which type of tour you chose. You can be flexible, as it’s a short walk between the next couple of destinations.

Before we move along with the 3 day Chicago itinerary, it’s time for lunch! If you’re down in the Loop and you want to try a local favourite, the choice is easy…

There are countless restaurants to choose from in the Loop, but you don’t want to travel all the way to Chicago to get stuck eating at some overrated chain or overpriced tourist trap.

Al’s is a classic local joint serving up the famous Chicago style hot dogs and their specialty Italian beef sandwiches.

One thing to know, a Chicago dog is an all-beef dog on a sesame seed bun. It comes topped with tomato, chopped onions, pickled peppers, relish, a pickle spear, and yellow mustard. Quite simply put, it’s heaven on a bun.

I would be remiss if I didn’t also mention Portillo’s. They also make one of the best Chicago style hot dogs out there.

While they’re a bit out of the way for today’s itinerary, keep them in mind if you’re craving another hot dog during your 3 days in Chicago (and trust me, you will).

Read More: Spending time exploring the Midwest? Be sure to check out our post on all of the best things to do in Kansas City !

Even if you visited on your walking tour, it’s worth it to double back to Millennium Park for further exploration.

There’s a lot of cool stuff to see here, including the Crown Fountain and the Cloud Gate.

The latter is commonly referred to as “The Bean” and is one of Chicago’s most popular places to take photos in the city. Don’t forget to snap that quintessential Chicago shot for the ‘gram and keep on moving.

Other Chicago attractions you must see in Millennium Park include the Jay Pritzker Pavilion, the BP Pedestrian Bridge, the Chicago Cultural Center, and the Lurie Garden.

You can easily spend a couple of hours in Millennium Park, especially on a nice day.

Buckingham Fountain and Grant Park are within this same area as well if you want to keep exploring on foot.

While there’s plenty of amazing public art in the Loop, you can’t top the collection at the Art Institute of Chicago. Art lovers will definitely want to include this on their 3 day Chicago itinerary.

Tucked away on Michigan Avenue on the south end of Millennium Park, the Art Institute of Chicago has a seriously impressive collection here and there are always new exhibits featuring modern and contemporary art.

Make the most of your Chicago CityPASS to gain fast entry into the Art Institute of Chicago.

The museum is open daily from 10:30 AM to 5 PM and stays open until 8 on Thursdays.

Day 1 – Evening

Before the day turns into night, it’s time to hustle over to your next destination of your 3 day Chicago itinerary. Try to time it just right so you make it there about an hour before sunset. Trust me, it’s worth it!

Whether or not you hit the museum, your next stop should be the Willis Tower. This is one of Chicago’s most iconic skyscraper in the city that invented them!

Formerly known as the Sears Tower, this was the tallest building in the world for 25 years. It stands at 442 meters (1,450 feet) tall and is currently the 2nd-tallest building in the US.

If you plan to visit Chicago in 3 days, you definitely need to check the Willis Tower off your to-do list.

Head to the 103rd floor to access the Skydeck Chicago and step out onto “The Ledge” – a glass balcony that lets you look straight down. You’ll want to see views of the city from this spectacular perspective!

Don’t forget, the best time to go to the Willis Tower is just before sunset. It stays open until 10 PM from March through September and tickets cost $25 for adults and $17 for children.

Once again though, no need to pay extra for a ticket, because the entrance to the Skydeck Chicago is included with your CityPASS .

To celebrate making it through a massive day 1 of the Chicago itinerary, it’s time for dinner and drinks! When it comes to wining and dining, the world really is your oyster in the Loop.

After such a big day, you may want to call it a (somewhat) early night. We’ve still got a lot of ground to cover with this 3 days in Chicago itinerary! Of course, if you want to go out and rage, go for it!

Day 2 – Morning

If you don’t have breakfast included at your hotel, I highly advise you to start day two off at Yolk’s South Loop location.

This is the perfect spot to load up with a big breakfast and coffee before another big day in the city. Go ahead and carb up – there’s going to be a lot of walking today!

After breakfast, walk across the street to check out Agora – a sculpture composed of 106 headless figures.

Keep walking east towards Lake Michigan to reach the Museum Campus. Here you’ll find the Field Museum, Shedd Aquarium, and the Adler Planetarium.

With just 3 days in Chicago, you’ll probably want to just visit one. Having been to all three, I’ll cast my vote for the Field Museum.

There are so many cool exhibits at the Field Museum and they’re always changing.

At the moment, they have: Inside Ancient Egypt, Bird’s of America, and Brewing Up Chicago, among others. Check their website to see what’s going on before you visit.

Tickets for the Field Museum cost $26 for adults and $19 for children for basic admission.

If you got the CityPASS, your admission is included in all three, unless you hit the Art Institute on day one. If you’ve got the pass, you might as well hit the aquarium as well.

To be honest, the aquarium is pretty sweet. Even if you don’t have the CityPASS, you should probably try to squeeze it in.

Tickets are $40 for adults and $30 for kids and you’ll definitely get your money’s worth.

Day 2 – Afternoon

There are a few cafes and food stands around the museum campus, so go ahead and grab a snack and a drink before powering on.

This is one of those days where it’s best to have a big breakfast and dinner and just graze during the day. When you’re trying to cross off so many things to do in Chicago in 3 days, you gotta keep moving!

The museum campus is the southern part of Grant Park. Known as “Chicago’s Front Yard,” this massive green space is to Chicago what Central Park is to NYC.

Take a stroll through the park to see such landmarks as the Buckingham Fountain, the Rose Garden, and the Seated Lincoln Statue. There are plenty of benches if you need to sit down and chill for a bit.

Grant Park also hosts some of the biggest events in the city, such as the Taste of Chicago and Lollapalooza.

Some are free and others cost hundreds of dollars, so be sure to check the calendar of events to see what’s happening before you book your trip.

Hug the coast and keep walking north along the Lake Michigan until you reach the Riverwalk. This scenic pedestrian path along the Chicago River is the perfect place for a leisurely stroll.

If your feet are feeling a bit tired from all the walking, you can enjoy the spectacular Chicago architecture on this fantastic river cruise instead .

Taking in the sights along the Chicago River is definitely one of the top things to do in a 3 day Chicago itinerary.

Wendella Boats has an architecture river cruise that comes highly recommended. Make sure you have your camera for this one, as you’ll get some epic views of the city.

Day 2 – Evening

I’m sure you’re ready to eat your hand by now, but you’ve just got to soldier on for a bit longer. Trust me, it’s going to be worth the wait!

On the other side of the Chicago River, you’ll find the Magnificent Mile, a short stretch of Michigan Avenue in downtown Chicago. This is the city’s premier commercial district, full of high-end shops, nice restaurants, and boutique hotels.

Along the Magnificent Mile, you’ll also see several historic skyscrapers, such as the Wrigley Building, Tribune Tower, and the Old Watertower.

The latter is home to the City Gallery, which has Chicago-focused photography exhibits. It’s totally free to visit, so you may as well check out while you’re in the area.

Even if you’re not doing any shopping, it’s worth a quick stroll along the famous Michigan Avenue. That’s because it’s leading you to…

You had the hot dog on day one, so it’s time to dig into some Chicago-style deep dish pizza.

Since it’s cooked in such a deep pan, a Chicago-style deep dish pizza can be stuffed with mountains of cheese. Of course, you can add whatever other toppings you like as well.

Now you see why I’ve been torturing you by making you walk around all day waiting for dinner! This deep dish pizza is seriously delicious and filling, so I wanted to make sure you could at least have a few slices.

There are plenty of places cooking up Chicago-style deep dish pizza, but I brought you here because two of the best are easily accessible.

Get to the corner of Michigan and Superior and you have an important choice to make. Take a left and you’ll go to Giordano’s. Hook a right and you’ll be at Gino’s East.

Just go ahead and flip a coin because you win either way. Both places are legendary for their deep dish pizzas, so you really can’t go wrong.

Not far from the Magnificent Mile, you’ll find Navy Pier. If you’re spending 3 days in Chicago on a long weekend, this is the perfect place to be on a Saturday night.

First up, you can take a ride on the Centennial Ferris Wheel. Tickets cost $18 for adults and $16 for children, but you can save a few bucks if you book online .

From the end of May until the end of August, Navy Pier also hosts bi-weekly fireworks shows. These happen on Wednesdays at 9:30 PM and Saturdays at 10:15.

To take in the spectacle, you can find a spot to stand on the Navy Pier or sign up for an evening cruise. Enjoying the fireworks as you cruise around is a great addition to your Chicago itinerary.

If you have any gas left in the tank after all of the activities at the Navy Pier, congratulations! I just ran you ragged all over Chicago on day two. That’s why it’s time to choose your own adventure!

For many, that will probably involve grabbing a casual drink from the hotel bar and getting some sleep. That’s totally fine. I’m getting to the age where that sounds like a perfect Saturday night!

For the young whipper-snappers among us, you’re probably itching to enjoy a big night out on the town. Go for it, you crazy kids!

Your options are endless. There’s live music of all varieties, comedy clubs, and just about every type of bar under the sun.

Whether you’re looking for a speakeasy that whips up creative cocktails, a classy wine & jazz joint, or just a good ole’ fashioned dive, you can find it in Chicago.

In this part of the city, one of my personal favourites is Three Dots & a Dash. This awesome tiki bar has an impressive selection of cocktails that will transport you to the Caribbean in no time.

If you’re going to go hard one night, this is the one to do it! Bars in Chicago typically close at 2 AM, but there are several that stay open as late as 4 on the weekend. You’ve been warned…

Day 3 – Morning

How early the last day of your 3 day Chicago itinerary starts depends entirely on how late your night went!

Those who already regret ordering that last round may need to sleep in a bit and smash a greasy brunch, while the go-getter set who actually slept will be up and at them. Life is all about choices, people!

Whatever you did the night before, get some food and caffeine in your system and get out there to wind down this 3 day Chicago itinerary.

Our third and final day in Chicago starts off with a leisurely museum visit. Within a few blocks of each other, you can take your pick between three excellent museums.

Art enthusiasts will gravitate towards the Museum of Contemporary Art, which highlights post-WWII art.

Those more interested in architecture and antiques may want to hit the Richard H. Driehaus Museum. It’s in a restored 19th-century mansion and brings you right back to the Gilded Age.

Chicago is very much a sports city, as people here are very passionate about their teams. Check out the Chicago Sports Museum, which is full of memorabilia and plenty of fun exhibits.

I know I already sent you to the Willis Tower on day one, but it’s still worth a trip to John Hancock’s 360 Chicago on Michigan Avenue.

This observation deck on the 94th floor of the John Hancock Building provides a whole different perspective on the city that you will definitely want to see.

Plus, if you bought a CityPASS your admission to the John Hancock building is already included! If you didn’t grab the pass, a ticket is $25 for adults or $15 for children.

Those who are feeling adventurous (and not hungover) may want to take a ride on Tilt – Chicago’s highest thrill ride.

If you need some hair of the dog instead, you can grab a ticket that includes your choice of adult beverage. Sunday Funday!

If you don’t purchase the Chicago CityPASS consider purchasing this ticket to enjoy the views from the 94th floor of the John Hancock building’s 360 Chicago.

Day 3 – Afternoon

Once you come down from 360 Chicago in John Hancock building, you have plenty of options for lunch. Within a few blocks, you can find Cuban, Vietnamese, Mediterranean, and the Chicago staple of deep dish pizza.

If you want a lunch with a view, consider eating at The Kennison. This upscale bar and restaurant offers sweeping views of Lincoln Park. The menu is modern American and they have lots of amazing cocktails and drinks.

Hop on the bus, order an Uber, or walk 30 minutes to our next destination – Lincoln Park.

There’s a lot to do in this huge park on the shores of Lake Michigan. North Avenue Beach is at the south end.

On a beautiful day in Chicago, it’s hard to beat lounging on the beach and swimming in the lake. You can also play some beach volleyball and rent a SUP or bike if you want some more activity.

In the middle is the Lincoln Park Zoo, which is totally free to visit. Sightseeing gets expensive, so this awesome free attraction is definitely one of the top things for any Chicago itinerary.

After such an action-packed 3 days in Chicago, you should definitely just take it easy and enjoy all that Lincoln Park has to offer. You’ve covered some serious ground in a short time, so congrats on that!

Day 3 – Evening

At this point in the journey, you have absolutely crushed 3 perfect days in Chicago. Order a celebratory drink or two and enjoy your last evening in the city!

What you choose to do with your final night all depends on when you’re visiting and what your interests are. That’s why it’s time once again to…

In a perfect world, the Cubs would be playing a night game while you are visiting Chicago. You could head north to Wrigley Field and enjoy America’s pastime at the 2nd-oldest ballpark in the country.

The Cubs play about 80 home games between April and September, so there’s a good chance they’ll be in town when you are. Even if you’re not a baseball fan, I recommend hitting a game if at all possible.

Chicago actually has two MLB teams. But the White Sox ballpark is way south of where you’ll be on day three and not worth the trip if you ask me.

If you’re making a trip to Chicago between October and April, you may be able to catch the Bulls (NBA), Blackhawks (NHL), or the Bears play a home game. Check their schedules to see what’s going on when you’re in town.

Those who prefer a good laugh can head back to the south end of Lincoln Park. Just a block away, you’ll find three of the city’s best comedy clubs – Second City, UP, and Zanies.

I pretty much always travel to Chicago for live music, so you know I’m going to toss that in here!

The city has an epic music scene and there’s always something playing here. Whether you’re into rock, hip-hop, jazz, electronic, blues, pop, or whatever it is you wacky Millenials listen to these days, there’s a show for you.

I usually check Jambase to see what shows are playing.

Congratulations, my friend. You made it through an insane 3 days in Chicago itinerary and experienced the best that the Windy City has to offer.

I’d say that calls for a toast! If you want to finish up with a true Chicago experience, order a shot of malort. This infamous Chicago liquor is pretty hard to describe, so I’ll let its label do the work:

“ Malort has the aroma and full-bodied flavor of an unusual botanical. Its bitter taste is savored by two-fisted drinkers .”

I’m not going to sugar coat it – this stuff is awful. It’s a rite of passage here in Chicago, though. Eat the hot dog. Drink the malort. Praise be to Ditka. You’re now a little bit Chicagoan.

After you finish that putrid shot of malort, switch to a delicious Chicago craft beer. There are plenty of choices here, including Lagunitas, Revolution, and Goose Island.

I hope you enjoyed this massive tour of Chicago!

From Navy Pier, to Millennium Park, the Chicago riverwalk, the famous Chicago hot dogs and more, visiting Chicago is never dull.

Hopefully this 3 day Chicago itinerary has been inspiring and gives you an idea of what to do in the Windy City.

Chicago Itinerary Travel Guide

Now that you know what to do with a long weekend in Chicago, I’ve gone ahead and put together a mini-guide to this awesome city to help you decide where to stay, where to eat, and of course where to drink!

Where to Stay in Chicago

You’re probably wondering where to stay, especially if it is your first time in Chicago.

Most first-time visitors choose to base themselves in downtown Chicago, and for good reason. Here are countless options for accommodation, sightseeing, dining, and nightlife.

As you might expect, staying downtown comes with a price tag. Other popular places to stay that are a bit cheaper include River North, Lincoln Park, Bucktown, and Wicker Park.

When it comes to places to lay your head, Chicago has it all. The city has 5-star luxury hotels, quaint B&Bs, dingy motels, fun hostels, and plenty of options on sites like Airbnb.

Here are a few options to suit all budgets:

Hostelling International is a trusted name in backpacker accommodation, and their downtown Chicago location is definitely the best hostel for visiting Chicago.

They have several different options for both private and dorm rooms. You can get a bunk for under $40 a night here – a steal for this fantastic location.This includes a free breakfast, and they also have free walking tours during the day and free activities at night.

That’s not all, though. They’ve also got a huge lounge with a ping pong table and a TV room with plenty of movies. Best of all, this hostel is environmentally-friendly. They have reusable products in the kitchen and recycling points all around the building.

This historic downtown Chicago hotel dates all the way back to 1893. Don’t worry – it’s had several updates over the years!

You really can’t beat the location of this place. I usually stay with friends in more residential neighbourhoods, but this is my go-to spot when I want to be in the middle of all the action.

From here, you’re just across the street from Grant Park. Many of the rooms here even boast a nice view of Lake Michigan. With rooms starting as low as $115 a night, it’s a pretty awesome deal staying here.

The 5-star Peninsula Chicago was recently named the 2nd best hotel in the country by US News & World Report. This place is fancy, people!

It’s located right on the Magnificent Mile, so it’s surrounded by high-end shops. This is definitely where the fabulous people stay.

In addition to the super swanky rooms, you can enjoy the hotel’s three different restaurants and its impressive fitness centre.

Taking up the top two floors of the building, it features a 25-meter pool and an award-winning spa. Rooms start at around $600 a night here.

Where to Eat and Drink in Chicago

I’m very fortunate to have a good friend who is heavily involved in the hospitality scene in Chicago.

I reached out to him to get a list to add to this guide. He’s never done me wrong with food & drink recommendations, so you can take these to the bank the next time you visit Chicago!

• Dove’s Luncheonette
• Joe’s Stone Crab: It’s a steakhouse and it’s hard to get into at night, but if you go for boozy brunch it’s great.
• Parson’s Chicken & Fish: Not really brunch but just a great people-watching patio.
• Big Star: Chicago classic taco joint with highly sought after patio
• 3 Arts Club

• Bavette’s Bar & Boeuf
• The Roister
• Green Street Smoked Meats: A great BBQ joint and High Five Ramen is below.
• Maple & Ash
• Nico Osteri
• Billy Sunday
• Aviary (try to get down to the office)
• Violet Hour
• Start at Scofflaw and work your way over to Best Intentions
• Longman & Eagle 
• The California Clipper: Been around since before prohibition!

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I would love to visit Chicago in 2024! This itinerary looks perfect!

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• 15 Best Places To Visit In Chicago That Add Charm To Your American Vacay!

23 Mar 2023

The beautiful city of Chicago has some of the best attractions like museums, skyscrapers and local spots that are worth a visit whether you are a local or a traveler. Being one of the top cities of USA, Chicago has some of most spectacular attractions to be witnessed once in a lifetime. While there are a number of places to see in Chicago , these 15 attractions are must-visit on your next trip.

15 Fascinating Places To Visit In Chicago

1. Millenium Park 2. Art Institute of Chicago 3. Riverwalk 4. Navy Pier 5. John Hancock Observatory 6. Cloud Gate 7. The Magnificent Mile 8. Lincoln Park Zoo 9. Chicago History Museum 10. Glessner House 11. Crown Fountain 12. Shedd Aquarium 13. Buckingham Fountain 14. Garfield Park Conservatory 15. Promontory Point at Burnham Park

1. Millenium Park

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Known for hosting the concerts and festivals, this is one of the most popular Chicago attractions which is all about the city’s weekend vibe. You’ll find interesting sculptures and contemporary installations all over this 25-acre park while taking an evening stroll. The Millenium Park is definitely one of the best places to visit in Chicago for all kinds of tourists.

Location: 201 E Randolph St, Chicago Timings: 6 AM to 11 PM

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2. Art Institute of Chicago

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When talking about the most exquisite places to see in Chicago , the Art Institute has to be on the list as it houses a collection of more than 300,000 pieces of artwork. Even if you’re not an art connoisseur, the gorgeous Greek sculptures, Japanese prints, and stained glass installations will make you an admirer in no time. Other than that, one can also dine at the Art Institute’s restaurant – Terzo Piano that offers spectacular views of the Millenium Park.

Location: 111 S Michigan Ave, Chicago Timings: 10 AM to 5 PM

3. Riverwalk

Image Credit: MK Feeney by flickr

When it comes to Chicago sightseeing , taking a stroll along the Riverwalk is totally mandatory. One can adore the city lights next to the Chicago river while choosing your dinner menu from a range of bars, pubs and restaurants. The Riverwalk has some of the best restaurants in Chicago and the other amazing places to go in Chicago can easily be explored via Water Taxi.

Location: Chicago Riverwalk, Chicago Timings: 6 AM to 11 PM

4. Navy Pier

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For a relaxed evening, drop by the Navy Pier which boasts of a Giant Ferris Wheel, a beer garden, and live entertainment. If you’re thinking about what to see in Chicago , you can listen to live music by the pier or attend one of the classic plays at the renowned Chicago Shakespeare Theatre. A number of restaurants and take-out places at the Navy Pier makes it one of the best places to visit in Chicago .

Location: 600 E Grand Ave, Chicago Timings: 10 AM to 7 PM

5. John Hancock Observatory

Image Credit: GPA photo archive by flickr

The most iconic structure and also known as 360 Chicago, the John Hancock Observatory gives you a complete view of the city from 1000 ft. above which is a sight not to be missed. Hop onto TILT that will ‘tilt’ you from the 94th floor and indulge in an experience you will not forget in a lifetime. Being the only place from where you can see upto five states as well as the infamous Lake Michigan, this is one of everyone’s favourite places in Chicago .

Location: 875 Michigan Avenue, Chicago Timings: 9 AM to 11 PM

6. Cloud Gate

Image Credit: Dhilung kirat by flickr

The infamous Cloud Gate is a spectacular piece of art which undoubtedly is one of the places to visit in Chicago . It’s the perfect spot for a selfie and since it’s inception, it has been an Instagram-favourite for all tourists around the world. Sometimes known as the beanbag, this fun installation works as a house of mirrors and is a must-see place for all visiting the Millenium Park.

Location: AT&T Plaza at Millennium Park Timings: 6 AM to 11 PM

7. The Magnificent Mile

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You are never done with Chicago till the time you visit its commercial district known as the Magnificent Mile. Find the best selection of fashion outlets and topnotch stores at this vibrant location where one can also be a part of the Magnificent Mile Shopping festival that is held each summer. Also, the Magnificent Mile Lights Festival is also a must-attend event when in the city. Dedicate an entire day and indulge in the cosmopolitan experience at one of the best places to visit in Chicago .

8. Lincoln Park Zoo

Image Credit: Pelican by flickr

In Chicago, places to visit are so many that it won’t disappoint you. Bring back your childhood memories with a trip to the infamous Lincoln Park Zoo , especially if you’re a nature and an animal lover. Located in the middle of the city and surrounded by skyscrapers and buildings, this prime location happens to be one of everyone’s favourite places to visit in Chicago .

Location: 2001 N Clark St, Chicago Timings: 7 AM to 4:30 PM

9. Chicago History Museum

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With over 20 million artifacts, this museum is an important part of Chicago’s tourist destinations. Needless to say, if you appreciate history, you will find an abundance of sites to visit within this museum. Be it the hands-on model of the Hancock Building or the real story behind the Great Chicago Fire, there’s a lot more to this museum being one of the best Chicago’s places to visit  than what meets the eye.

Location: 1601 N Clark St, Chicago Timings: 9:30 AM to 4:30 PM

10. Glessner House

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One of the top architectural places to visit in Chicago , the Glessner House is a popular landmark in the State of Illinois. There are different tales associated with this timeless monument while the museum inside contains unbelievable collections of 19th Century life. An inspiration to domestic architecture, the Glessner House is a fortress waiting to be explored by tourists.

Location: 1800 S. Prairie Ave. Timings: 11 AM to 4 PM

11. Crown Fountain

Being one-of-a-kind installations in the city, this fountain is a 50-foot glass block which projects the images of the locals while the water flows through an outlet strategically placed at the mouth of the installation. This 21st century art is clearly one of the spectacular places to visit in Chicago that is located in the Millenium Park. Make sure you capture both the screen during middle of Spring and Fall, as the water effects are operational only then.

12. Shedd Aquarium

Image Credit: smart destinations by flickr

Closer to the Lake Michigan, resides a very popular tourist attraction of Chicago – the Shedd Aquarium . As one of the largest aquariums in the world, this indoor setup is the place to spend a lazy afternoon with your family, especially children. From Beluga whales to white-sided dolphins, you can witness over 1500 mammals and fishes here, which makes it one of the most exciting places to visit in Chicago .

Location: 1200 S Lake Shore Dr, Chicago Timings: 8.30 AM to 6 PM

13. Buckingham Fountain

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Inspired by the Art Deco movement, this extraordinary fountain is located at the centre of Grant Park. It is operational during the peak hours of the day while it shows its magic with lights in the evening. As 15,000 gallons of water move around to make beautiful designs, this fountain becomes a must-visit spot for all tourists who are looking for iconic places to visit in Chicago .

Location: 301 S Columbus Dr, Chicago

14. Garfield Park Conservatory

The ‘landscape art under glass’ consists of rare and exotic plant species that are displayed on the indoors as well as on the outdoors in the garden. There are regular art exhibitions, flowers shows, and even lectures that one must visit if their interest lies in horticulture. As a matter of fact, one will not find a better place to visit in Chicago , and relax away amidst the gorgeous flora.

Location: 300, North Central Park Avenue, Chicago Timings: Thursday to Tuesday – 9 AM to 5 PM; Wednesdays – 9 AM to 8 PM

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15. Promontory Point at Burnham Park

Enjoy a lovely picnic in the summer sun at the Chicago Promontory Point, which is a relaxing spot for everyone in search of a calm and a quiet place. Named as one of the best summer places to visit in Chicago , simply unwind in the evenings, ride a bike, go running along the greenery, enjoy a swim by the shore, or have a barbeque with friends and family, and much more.

Further Read: 22 Best Things To Do In Chicago: The City With A Magnetic Charm

Still confused about Chicago’s tourist attractions? This list of top 15 places to visit in Chicago should be your go-to guide for your next vacation. Having said that, plan your US trip with TravelTriangle and make sure you visit each of these places to get the real taste of city life.

For our editorial codes of conduct and copyright disclaimer please click  here . 

Frequently Asked Questions About Places To Visit In Chicago

What is Chicago known best for?

If you are visiting Chicago for the first time, some of the things that this city has to offer are Chicago-style hot dogs and deep-dish pizza along with a great jazz music scene that you can explore.

What is the most visited tourist attraction?

Being one of the top cities of USA, Chicago has some of most spectacular attractions to be witnessed once in a lifetime. Some of the most popular attractions are: 1. Millenium Park 2. Art Institute of Chicago 3. Riverwalk 4. Navy Pier 5. John Hancock Observatory 6. Cloud Gate 7. The Magnificent Mile 8. Lincoln Park Zoo

Where can I go for free in Chicago?

There are numerous interesting free places to explore in Chicago. Check out the following free places in Chicago: 1. Millennium Park 2. Lincoln Park Zoo And Conservatory 3. Chicago Cultural Center 4. Buckingham Fountain 5. Garfield Park Conservatory 6. National Museum of Mexican Art 7. Oriental Institute, Smart Museum & Renaissance Society 8. Museum of Contemporary Photography

Which are the most popular tourist destinations in Chicago?

The most popular tourist destination in Chicago is Millennium Park, followed by Willis Tower, Navy Pier, and Cloud Gate.

Are museums free in Chicago?

Alike other places to visit in the USA, the museums in Chicago are free for members of the US Armed Services, Chicago Fire Department, Chicago Police Department, and Illinois teachers.

Is the Skydeck free?

The Skydeck in Chicago is not free. You need to pay INR 2,348.08 for adults whereas the same for kids above the age of 3 years will be charged INR 996.24. However, kids below the age of 3 are absolutely free to enter the Skydeck.

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A Snob’s Guide to Chicago

Is this list exhaustive? Maybe not. But it is highly opinionated, and that’s all that really matters.

I started visiting Chicago regularly after college, when my closest friends moved there. We went to the old Bistro 110 and felt very proud when we graduated to drinks at the Violet Hour and the Aviary, and then dinner at the Publican and Girl & the Goat (still favorites). There are things on this list I’ve loved for 30 years. Others became musts more recently. I also get a little help from my highly opinionated friends and family. Let’s call them the HOFs.

1. Check into the recently refreshed and perfectly located Park Hyatt Chicago. Ask for a lakeside room (on an upper floor). The Lake Michigan and Park Suites feel as if you are actually on the water.

2. “Walker Bros. for breakfast!” HOF and Chicago native Brooke Garber Neidich advises. “49ers pancakes, very crispy bacon, fresh-squeezed OJ.”

3. Take an architecture cruise. I like the Chicago Architecture Center River Cruise. I do this every time.

4. Have lunch at RL. Before Polo Bar in New York, before Ralph’s in Paris, there was RL in Chicago. It’s the OG.

5. Check into the Peninsula Chicago. Also right there on the Magnificent Mile. Have afternoon tea in the lobby and dumplings at the Shanghai Terrace. In winter ask about the skating rink!

6. The Langham (and its big, gorgeous rooms) is also a favorite.

7. Walk along Michigan Avenue to the Art Institute. (On the way, take your Kapoor Bean selfie.) The Thorne Miniature Rooms are a must, as is the Seurat that inspired Sondheim and Grant Wood’s American Gothic . The museum website has a great “what to see in an hour” guide.

8. ”The Field Museum of Natural History is also fabulous,” interjects HOF William Li. “The Hall of Jades! Go.”

9. “And the Fairy Castle at the Museum of Science and Industry!” Brooke says.

10. Riverwalk? Yes, says HOF Kate Chappell, news anchor for NBC Chicago. “End with sunset views at Tiny Tapp.”

11. Do the Frank Lloyd Wright Home and Studio tour in Oak Park. Ice cream at Petersen’s (around since 1919) afterward.

12. “Go see Robie House,” says my HOF niece and Chicago undergrad, Cayla, of Wright’s landmark. Reservations required. Afterward “get a Mediterranean omelet ­cafeteria-style at Valois, and try to sit at President Obama’s table, or have excellent Southern-inspired food at Roux.”

13. See a show at the Goodman Theatre. The hot ticket for 2024 will be Taylor Mac and Rob Ashford’s Midnight in the Garden of Good and Evi l (June 25–August­ 4).

14. And at the Steppenwolf. Laurie Metcalf will star in an as yet untitled show. It doesn’t get more Chicago than that.

15. And anything at the Lyric Opera.

16. “ The chorizo-stuffed bacon-wrapped ­medjool dates at Avec,” I say.

17. “A steak and a martini at Gene & Georgetti!” Brooke says.

18. “The tuna crudo and stracciatella appetizer at Rose Mary,” Cayla says. (I second this, and also a walk around the Fulton Market District.)

19. “The Hong Kong–style roast meats at Sun Wah BBQ,” William says.

20. “ The chicken pot pie, truffle bucatini, and the burger at Armitage Ale House,” Cayla says.

21. “Pasta at Monteverde. Any of them,” says basically everyone you will ever talk to.

22. “The thin crust pizza at Nancy’s in West Loop,” Kate says. That’s all I’ll say on the pizza matter.

23. The Kalamata chicken at the Athenian Room. It’s how Chicago theater royalty Carrie Coon and Tracie Letts celebrate their anniversary. (If that doesn’t matter to you, the rest of this list might not either.)

24. Wait in line for the Au Cheval burger. It’s a rite of passage. Same goes for dinner at Alinea. I have never been, and am ashamed.

25. Go to a Garrett Popcorn shop before you leave. Get tubs of the cheddar-and-caramel. Bring me some.

Editor-in-Chief Stellene Volandes is a jewelry expert, and the author of Jeweler: Masters and Mavericks of Modern Design (Rizzoli).

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THE 15 BEST Things to Do in Chicago

Things to do in chicago.

• 5.0 of 5 bubbles
• 4.0 of 5 bubbles & up
• 3.0 of 5 bubbles & up
• 2.0 of 5 bubbles & up
• Near North Side
• Downtown / The Loop
• Good for a Rainy Day
• Budget-friendly
• Good for Couples
• Good for Big Groups
• Good for Kids
• Hidden Gems
• Honeymoon spot
• Adventurous
• Good for Adrenaline Seekers
• Things to do ranked using Tripadvisor data including reviews, ratings, photos, and popularity.

1. The Art Institute of Chicago

2. Millennium Park

3. Chicago Architecture Center

4. Museum of Science and Industry

5. The Magnificent Mile

6. Skydeck Chicago - Willis Tower

7. Wrigley Field

8. Cloud Gate

9. Field Museum

10. 360 Chicago Observation Deck

11. Chicago Riverwalk

12. Lincoln Park Zoo

13. Chicago Cultural Center

14. Medieval Torture Museum

15. Chicago River

16. Navy Pier

17. Richard H. Driehaus Museum

18. Garfield Park Conservatory

19. Buckingham Fountain

20. Shedd Aquarium

21. United Center

22. Lakefront Trail

23. Holy Name Cathedral

24. American Writers Museum

25. Lincoln Park Conservatory

26. Chicago History Museum

27. Lincoln Park

28. Route 66

29. Chicago Skyline

30. The Chicago Theatre

What travellers are saying.

3 Days in Chicago: The BEST Weekend Itinerary (By a Local!)

Planning 3 days in Chicago and seeking the perfect itinerary? I have lived in Chicago almost my entire life so I have created the perfect detailed Chicago 3 day itinerary with the best things to do, best places to eat, where you should stay, and all of my top tips, so that you can spend less time planning and more time enjoying the Windy City.

There is so much to do in Chicago but three days is enough to see most of Chicago’s top attractions . I have grouped each day by neighborhood so you don’t have to waste time getting around.

3 Days in Chicago Itinerary

3 Days in Chicago – Day 1

Lets start Day 1 in Chicago by enjoying some of the best views Chicago has to offer.

360 CHICAGO

For panoramic views of Chicago, head to 360 CHICAGO (formerly John Hancock Observatory), a public observatory on the 94th Floor of 875 N Michigan that offers breathtaking 360 degrees views of the city skyline and Lake Michigan.

The 360 Chicago observation deck is also home of TILT – Chicago’s highest thrill ride – an enclosed moving platform that literally tilts you out over Michigan Avenue from the 94th Floor.

Tip: 360 Chicago tends to be less busy and has shorter lines that the taller Willis Tower (on Day 2) but it is still best to visit in the morning to avoid crowds. (Click here to buy a skip the line ticket ).

Shop (or Window Shop) on the Magnificent Mile

After visiting 360 Chicago, walk south on Michigan Avenue and join the throngs of visitors and locals shopping (or window shopping) on The Magnificent Mile. The Magnificent Mile (or The Mag Mile), is an upscale section of Michigan Avenue, running from Oak Street to the Chicago River. Although some of the stores on Michigan Avenue are pricey, it is totally free to window shop. Landmarks on the Mag Mile include the historic Chicago Water Tower, the Tribune Tower and the Wrigley Building skyscraper.

Take an Architecture River Cruise

Chicago has amazing architecture and the best way enjoy it is by taking an architecture river cruise . Because the water sometimes freezes, river cruises don’t usually run in the winter.

If you are visiting Chicago in the summer, you can do a longer combined architecture river and lake cruise to see the skyline from the lake as well.

An alternative to a river cruise is to take a walk along the Chicago Riverwalk . The Riverwalk is one of the best spots in Chicago for people watching and there are also restaurants , shops and places to sit along the way. You can see a map of attractions on the Riverwalk here .

Go on a Gangsters Tour

Chicago has a long  history of organized crime and is famous for being the home of mafia figure Al Capone. There are many mob tours for those that want to learn more about the history of organized crime.

Food or Drinks with a View

Chicago has several rooftop bars and restaurants with amazing views of Chicago.

Cindy’s (12 S Michigan Ave) is a restaurant and bar on the rooftop of the Chicago Athletic Association Hotel located across Millennium Park which offers panoramic instagram worthy views of Millennium Park and Lake Michigan. This is a popular spot and the wait for the elevator can be long but if you visit around the time it opens (10 am on the weekends and 11 am on some weekdays) you can enjoy the great views without the crowds.

LH ON 22 (85 East Wacker Drive) -Enjoy classic cocktails and small bites from the outdoor LH terrace of LondonHouse Chicago which offers great views of the Chicago River, Lake Michigan and the Magnificent Mile.

The J. Parker (1816 N Clark St) is a stylish bar and restaurant on the rooftop of the Hotel Lincoln with great views of Lincoln Park.

3 Days in Chicago – Day 2

From the highest vantage point of the city to the famous Bean, Day 2 in Chicago will take you to Chicago’s best and most famous attractions.

Skydeck at Willis Tower

The Skydeck at Willis Tower (formerly known as the Sears Tower and what locals still call it) is the most well known of Chicago’s two tall skyscrapers with public observatories. The Willis Tower is the tallest building in the Western Hemisphere and was the tallest building in the world from 1974 until 1998.

If you are not scared of heights, you can stand on the Ledge’s glass boxes that extend out over 4 feet from the Skydeck.

Tip:   Lines for the Skydeck can get very long (especially on weekends) so avoid the crowds it is best to visit first thing in the morning as soon as it opens or in the evening. (Click here to buy a skip the line ticket ).

See The Bean at Millennium Park

If you have seen photos of Chicago on social media, chances are you have seen photos of Cloud Gate (also called The Bean), the famous mirrored sculpture in Millennium Park.

Please note that due to construction, public access and views of Cloud Gate are limited through spring of 2024.

Although The Bean is very touristy, don’t skip it. It is one of the most instagrammable places in Chicago and it is a great spot to take photos to remember your trip to Chicago.  The Bean is usually crowded especially in the summer and on weekends so if you don’t want other people in your photos visit early in the morning.

The free Millennium Park is part of Grant Park and also includes the Jay Pritzker Pavilion, the Crown Fountain sculpture and Lurie Garden. In the winter, there is a free ice skating rink right in front of the park. On hot summer days, kids (and some adults) love to splash in the water from the Crown Fountain .

If you are visiting Chicago with toddlers and young kids, you might want to also visit Maggie Daley Park , a large public park connected to Millennium Park that has play areas for kids of various ages, a fieldhouse, climbing wall and another ice-skating ribbon in the winter.

Art Institute of Chicago

Chicago has many great museums which are worth visiting but my top pick is the  Art Institute of Chicago conveniently located next to Millennium Park. It is one of the oldest and largest art museums in the United States and is frequently found on lists of the top museums in the world. (Click here to buy a skip the line ticket if you want to avoid long lines).

Some locals consider Navy Pier a bit of a tourist trap, but it is a not to missed attraction especially for those visiting Chicago with kids. Navy Pier is full of fun things to do including a large Ferris wheel, rides and games, the Chicago Children’s Museum and several shops, restaurants (including Giordano’s and Garrett Popcorn Shops) and bars. Navy Pier is also the starting point for various sightseeing cruises and boat rides.

Tip: If you are visiting Chicago in the summer, stay or come back for the free fireworks at Navy Pier every Wednesday at 9 pm and Saturday night at 10 pm. You can even watch the show from the water on a sightseeing cruise .

3 Days in Chicago – Day 3

Here are my suggestions for your third and final day sightseeing in Chicago. If you are visiting Chicago on a Sunday morning, head to Maxwell Street Market , one of the best places for Mexican food.

Visit One or More Museums

Chicago has many great museums which are worth visiting. The Field Museum , the  Shedd Aquarium and Adler Planetarium are all located close to each other on The Museum Campus. The Adler Planetarium Skyline Walk has one of the best skyline views of Chicago .

The Museum of Science and Industry is located in Hyde Park and is a bit out of the way from downtown Chicago but it is a really fun museum with hands-on activities and interactive exhibits. If the weather allows and you have extra time in Hyde Park, you might want to check neighboring Jackson Park . This park has cherry blossom trees in the spring and it also has a free Japanese garden.  Promontory Point is about a half mile away and has great skyline views of Chicago.

Tip:   If you are visiting a few museums and indoor attractions, consider purchasing a Chicago CityPASS or Go Chicago Card to save money on entrance fees.

Explore the Lakefront Trail and Beaches

Chicago’s Lakefront Trail is a paved path on a 18-mile-long stretch along Lake Michigan and it is a great spot to people watch and get some exercise.  In the summer and weekends, the lakefront is packed with locals and visitors walking, running and riding bikes.  You can find a map with the access points here .

Most people don’t think of Chicago as a beach destination but Chicago has many beaches on Lake Michigan.   Oak Street Beach and Ohio Street Beach are conveniently located close to the major tourist attractions. North Avenue Beach is more of a party beach and is located close to Lincoln Park.

More Things to Do in Chicago

If you have more time or not a fan of museums or tall buildings, here are some more fun things to do in Chicago:

Find Street Art

Chicago is full of street art and there are always new murals popping up.  One of the most famous Chicago murals is “Moose Bubblegum Bubble” (pictured above) by Jacob Watts which located at 33 E. Ida B. Wells Drive (formerly 33 E. Congress Parkway). It is part of the Wabash Arts Corridor which is walking distance to Millennium Park, The Art Institute of Chicago and other well known tourist attractions. You can find more detailed mural walks in the Loop here .

Another famous mural is The Greetings From Chicago Mural at 2226 N Milwaukee Ave, in Chicago’s Logan Square neighborhood. You can see this mural and other street art on this street art tour .

Another neighborhood that has a high concentration of street art (as well as great Mexican food) is Pilsen.

Watch a Cubs Game at Wrigley Field (or attend another sporting event)

Chicago is known for their love of their sports teams, so if you are visiting during the season you might want to attend a sporting event. To those unfamiliar, historic Wrigley Field is home to one of the city’s baseball teams – the Cubs.  Whether a fan of the Cubs, baseball in general or just a fun atmosphere, a day at the 100 year old ballpark is a must for locals and tourists alike.  You don’t need to enjoy baseball to enjoy a Cubs game – it is fun to just soak in the atmosphere while drinking and eating. (There are also tours of the stadium offered during the off season).

Enjoy One of Chicago’s Many Festivals

Chicago always has at least one or more festivals or events happening every weekend especially in the summer .  Some Chicago festivals are very well known and attract thousands of tourists, but there are many festivals and events in Chicago where you will mostly find locals. For great food, music and people watching, check to see if there are any festivals or events  going on while you are in town.

Walk The 606

The 606 is Chicago’s version of The Highline in NYC , an elevated trail goes through 2.7 miles of the city’s northwest side neighborhoods: Wicker Park, Bucktown, Humboldt Park, and Logan Square.  It is a bit off the beaten tourist path but it great place to walk, run or bike.  There are several access points so you can get off the trail to explore the various neighborhoods.

Where to Eat in Chicago

Chicago is known for its food so get ready to eat! Chicago is one of the best cities in the world for food and I could easily write a whole post just about the food! Although Chicago is famous for food like deep dish pizza and Chicago-style hot dogs – there is so much more great food in Chicago.  Don’t limit yourself to just deep dish pizza and hot dogs, but you should try those if you are visiting Chicago for the first time.

Lou Malnati’s and Giordano’s  are two of the best restaurants for deep dish pizza. Giordano’s can be found in several spots throughout the city including Navy Pier, near Michigan Avenue and near Millennium Park.

Many locals consider Pequods in Lincoln Park to have the best deep dish pizza in Chicago. Their version has a caramelized crust.

For Chicago style hot dogs (remember, no ketchup allowed) try Portillos , a popular chain.

Al’s Italian Beef (169 W Ontario St.) is famous for its Italian beef sandwiches.

For original Chicago-style popcorn head to Garrett Popcorn Shops, with a location near Millennium Park and Navy Pier.

To get an overview of the food scene consider a food tour:

Where to Stay in Chicago

Most people visiting Chicago stay in the downtown area including the Loop, River North, Gold Coast, Streeterville and Michigan Avenue since they are close to most of the major tourist attractions. If you are visiting during the weekend, the Loop is a great option as it is more quiet at night. River North (where I live) is close to nightlife and restaurants, but noise can be a problem especially during the weekends. Here are some of my top picks for the best hotels in Chicago :

The Peninsula Chicago.   If you are looking for a luxury hotel, The Peninsula Chicago is one of the best hotels in Chicago with a world renown spa and a half-Olympic length swimming pool overlooking the Chicago skyline. It has a central and convenient location right off the Magnificent Mile, close to shopping and less than a block from the Water Tower and 360 Chicago. Click here to see the latest prices and click here to read reviews .

Hilton Chicago/Magnificent Mile Suites.  Recently renovated all-suite hotel with fridge and microwave in room. Great location just steps from Michigan Avenue and one block from Lake Michigan.   Click here to see the latest prices and click here to read reviews .

ACME Hotel Company. This modern, stylish and unique hotel is located in downtown Chicago 2 ½ blocks from the Magnificent Mile in River North. Offers great value and great service. Click here to see the latest prices and click here to read reviews .

Best Western River North Hotel. Convenient located in the heart of River North close to the Chicago River as well as many restaurants and bars. Amenities include free high-speed Wi-Fi, deeply discounted parking, room service, fitness center, indoor pool and sun deck.  Click here to see the latest prices and click here to read reviews .

The Best Time to Visit Chicago

Chicago has plenty of things to do year round whatever the season. Summer is one of the best (and busiest) times to visit Chicago as the city comes alive and there are always outdoor festivals, concerts and events going on where you can take advantage of the warm weather. Restaurants and bars open their rooftops and sidewalk patios so you can dine outside. The temperature in the summer is usually hot but not unbearable (but some days can be very hot and muggy).

Winter can be very cold and snowy but some years can have mild winters with hardly any snow. Late November and December are busy with holiday events and festivities and the temperatures are usually still not that cold.  January and February tend to be the coldest months but attractions are less crowded. Even if you hate cold weather, there are enough indoor attractions to keep you entertained in Chicago during the winter .

Fall and spring are generally great times to visit Chicago – the popular attractions are not as busy as summer and the weather is usually more pleasant (but temperatures can be very unpredicable). The weekend before St. Patrick’s Day and the weeks during spring break can get very busy but the rest of spring is considered shoulder season.

Personally, I think the best time to visit Chicago is September and early October because students are back in school but temperatures are still warm but not as hot and humid as summer.

If you still need help deciding when to visit Chicago, check out The Best Time to Visit Chicago – A Month By Month Guide  for more details regarding weather and events by month.

Getting Around in Chicago

Chicago is an easy city to get around in with many public transportation options. Both Chicago airports – Chicago O’Hare (ORD) and Chicago Midway (MDW) – are connected to downtown Chicago by train.

For longer distances you can use public transportation , taxi, rideshare or rent bikes through Divvy (Chicago’s bike share program).

Taxis are plentiful and very easy to find downtown and at popular tourist attractions. You can also use the Curb app (for taxis) or ridesharing apps ( Lyft and Uber) to get around Chicago .

A hop on hop off bus is a great way to see all the attractions without having to figure out how to get around.

These are my top choices for the best things to do if you have 3 days in Chicago .

Planning a trip to Chicago? Check out more of my Chicago guides and itineraries:

• Best Things to Do in Chicago in the Summer
• 24 Hours in Chicago: A Perfect One Day Itinerary (From a Local)
• Most Instagrammable Places in Chicago
• Best Free Things to Do in Chicago
• Best Day Trips From Chicago

Related Posts

savvyglobetrotter

One comment.

Hi, I have also lived in Chicago and yes, although Summer is great, the best time to visit I’d also say it’s Aug/Sept. This is one, if not THE one, of the best places on Earth. I’d even say, if you can stay longer than 3 days in Chicago, do so. You are not going to regret it, since the city offers so much to do year round. Lovely post!

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• 3 Days in Chicago: The Perfect Itinerary for First-Timers

Looking to spend 3 days in Chicago but don ’t know where to start? Well, this guide is here to help you out!

Chicago is one of the most populated cities in the United States and sits on the shores of Lake Michigan. Known as ‘the Windy City’, Chicago attracts millions of visitors each year and it’s no surprise why.

With its iconic attractions, towering skyscrapers, and scenic views, this city has made it onto many people’s bucket lists. 

But how should you spend your 3 days in Chicago? This guide will go through the must-visit sites, how to get around the city, and the best places to stay. 

Without further ado, here is the ultimate 3-day Chicago itinerary!

* Disclosure: This post contains a few affiliate links, which means I may receive a small commission, at no cost to you, if you make a purchase through my link. *

No time to read now? Pin it for later!

Table of Contents

Useful Info for Spending 3 Days in Chicago

How to get to chicago.

Chicago O’hare International Airport is the city’s primary airport and is located just 16 miles (26 km) from Downtown Chicago. However, you’ve also got Chicago Midway International airport too. 

Flying is one of the most popular ways to reach Chicago as between them, both airports offer inbound and outbound flights to over 240 destinations across the world. You’ll also find plenty of great deals on domestic flights within the United States too.

If you’re wanting to save some money you can catch a bus or train to Chicago from other major cities in the U.S. 

The most popular coach routes are from New York, Buffalo, Dallas, Minneapolis, and Detroit. However, Greyhound also runs 20 express routes to and from major cities and has five locations within the city.

Catching a train is another popular choice, and the best option is Amtrak . They offer routes to over 500 destinations within the United States and Canada, so you’ll easily be able to reach the city. 

Many of the coach and bus trips to Chicago often run overnight if you’re traveling a long way, which will also help you save on accommodation costs. 

Best time to visit Chicago

Chicago’s high season runs from June to August, and temperatures range from 61°F (16°C) to 85°F (29°C) during this time. 

You’ll also find plenty of festivals and sports games to attend in the summer months, but be prepared to pay top prices for accommodation. 

If you’d prefer a quieter and cheaper experience, then visiting Chicago during the shoulder season is a great option.

The city’s shoulder season falls between April-May and September-October, and you’ll also find the tourist attractions to be much less crowded. 

Between April and May, temperatures range from 39°F (4°C) to 71°F (22°C) while during September and October, the temperature fluctuates between 45°F (7°C) to 76°F (24°C).

Although the weather is cooler and you’re likely to see more rain, you can get great bargains on accommodation and transport.

How to get around in Chicago

Chicago is super easy to get around as public transport is efficient and runs regularly. 

The best way to explore the city is by using the ‘L’ Train. There are 8 colored network lines that will take you to most of the areas and attractions in Chicago. Two of these run 24 hours a day, while the others typically operate between 4 am to 1 am. 

You can purchase single standard passes, but it’s cheaper to purchase a one-day or three-day pass depending on your itinerary. 

Buses are also a great way to get around as 129 routes run throughout the city. Some of these bus routes run on a 24-hour basis, while others operate until 11 pm or  2 am. 

If you’re looking to head out into the suburbs then you can take the Metra Rail. 

Taxis can also be found throughout the city but they aren’t cheap, although Uber and Lyft are available here. 

However, one of the coolest ways to get around the city is by water taxi. They offer a fast and affordable way to travel along the Chicago River, Lake Michigan, and between tourist attractions. 

They do only run between May and September/October though so you’ll need to keep this in mind. 

Although you can hire a car and drive around the city center, I wouldn’t recommend it – especially if you only have 3 days in Chicago. The traffic is a nightmare and parking is extremely limited (and very pricy).

Where to stay in Chicago

There are endless neighborhoods within the city so deciding where to stay in Chicago isn’t an easy decision. So, here is a quick guide to the main areas of the city: 

• Downtown Chicago/The Loop  – perfect for first-time visitors
• River North – the best place to stay for nightlife
• Wicker Park – one of the coolest areas in Chicago
• The Gold Coast – a beautiful area along Lake Michigan
• Magnificent Mile – known for luxury stays and shopping

There are plenty of great areas to stay within the city, but these are just a few of the most popular ones. If you’re interested in knowing more about each neighborhood, make sure to read my detailed guide about the best areas to stay in Chicago .

If you ’re in a rush, here are my top recommendations for different budgets.

LUXURY – Viceroy Chicago

Viceroy Chicago is situated in the scenic Gold Coast area and is just minutes away from the Magnificent Mile and Lake Michigan. This hotel has all the facilities you could need for a luxury stay including a rooftop bar and lounge, a fitness center, on-site dining, and a seasonal rooftop pool.

MID-RANGE – Hotel EMC2

Hotel EMC2 is located in Streeterville and is right by the Magnificent Mile and Downtown Chicago. Millennium Park and Navy Pier are also just 1 mile (1.6 km) away. Not only are the rooms beautiful and spacious, but this hotel also has on-site dining available, a fitness center, and a dry-cleaning service. 

BUDGET – Central Loop Hotel

All guest rooms at Central Loop Hotel have custom-designed furnishings and comfortable beds with down duvets and plush pillow-top mattresses. They also include work desks with ergonomic chairs. Complimentary exercise equipment and air purifiers are available for room delivery upon request.

Overview of Your 3 Day Chicago Itinerary

Breakdown of your 3 days in chicago.

• Day 1: Breakfast at ​​Goddess and the Baker, Millennium Park (Cloud Gate, Crown Fountain, Lurie Garden), The Art Institute of Chicago, Navy Pier, Dinner at Giordano’s, Sunset at Milton Lee Olive Park
• Day 2: Breakfast either at Beatrix or Wildberry Pancakes & Cafe, Starbucks Reserve Roastery, Magnificent Mile, Chicago Riverwalk, Chicago Theatre, Chicago River Architecture Cruise, Nature Boardwalk at Lincoln Park Zoo, Sunset at North Avenue Beach, Dinner at Portillo’s Hot Dogs
• Day 3: SkyDeck Chicago, Breakfast at Mojo Coffee, Grant Park & Buckingham Fountain, Museum Campus (Shedd Aquarium, Field Museum, Adler Planetarium, Soldier Field), Dinner at Lou Malnati’s Pizzeria

Map for your 3 day Chicago itinerary

Below you can find a customized map that includes all the locations you’re going to visit on this Chicago itinerary.

I marked your 3 days in Chicago with different colors – I used blue for the first, yellow for the second, and green for the third day, so you can easily see which places you’re going to visit each day.

If you open up this post on your phone and you click on the bracket in the upper right corner of the map, it will open up in your Google Maps app so you can always have it with you. Super convenient, right?

Day 1 of Your 3 Days in Chicago

Breakfast at ​​goddess and the baker .

Grabbing a bite to eat at the Goddess and the Baker is the perfect way to fuel your day of exploring. It’s famous for its great food, amazing coffee, and fun treats!

They have a wide selection of breakfast options including yogurt parfait, omelets, bagels, and waffles so you won’t have a problem finding something to your taste here.

There are multiple locations of Goddess and the Baker, but this one is right across from Millenium Park (the next stop on your 3 day Chicago itinerary). You can either have breakfast first thing in the morning or after you’ve visited the park – it’s completely up to you! 

Millennium Park and The Bean

After (or before) breakfast, make your way to Millennium Park which is one of the most famous landmarks in Chicago. 

Spanning over 24.5 acres, this park is home to many popular attractions including the Cloud Gate (aka ‘The Bean’).

The Cloud Gate is a public sculpture that was designed by British artist Anish Kapoor. It’s made up of 168 stainless steel plates and weighs in at a whopping 110 tons!

You can walk around the sculpture, take photos, and even go underneath it. Thanks to its reflective surface, it has quickly become one of the most Instagrammable places in Chicago . So be prepared for the crowds as this is one of the most popular things to do in Chicago!

After you’ve had your fill of The Bean, continue exploring Millennium Park. There’s plenty to see and do here including visiting the Lurie Garden, which is a 2.5-acre public garden, or checking out the Crown Fountain which is a work of art in itself!

The Art Institute of Chicago

The Art Institute of Chicago is another popular attraction as it’s one of the world’s largest (and oldest) art museums. 

Aside from its ever-changing exhibitions, the museum has a permanent collection of around 300,000 art pieces which is pretty impressive. 

These ongoing exhibitions include the ‘Of Gods and Glamor’ exhibit, ‘a New View of African Art’, and the ‘Landscape in Light’ exhibit. 

The museum attracts around 1.5 million people annually and is a must-visit on your 3 day trip to Chicago. 

It’s important to note that the Art Institute of Chicago is closed on Tuesdays and Wednesdays, so you’ll have to time your visit right if you want to visit this spot.

Otherwise, it ’s open between 11 am – 5 pm from Thursday to Monday and general admission costs $25 per person.

TOP TIP: In case you want to visit multiple attractions, take a look at the Chicago CityPASS which can help you save 48% or more on the top attractions. It includes access to The Art Institute of Chicago, Shedd Aquarium and SkyDeck Chicago among many other popular sites.

Next up on your 3 days in Chicago itinerary is a visit to Navy Pier, a 3,300-foot-long pier that sits on the shores of Lake Michigan.

It’s one of the most popular tourist destinations in the city and it’s easy to see why with its many attractions, shops, and restaurants.

You’ll find plenty to do here including fairground rides, live music performances, theater productions, and special events. Not to mention the incredible views to be had from the pier itself!

One of the unmissable things to do in Navy Pier is going on a ride on the Centennial Wheel, which is a 200-foot tall Ferris wheel. From the top, you’ll be able to see amazing views of the cityscape and beyond! Since it’s a fairly popular attraction, it’s best to purchase your tickets in advance .

If you’re looking to do some shopping, Navy Pier is also home to a variety of stores selling everything from souvenirs to clothing.

Dinner at Giordano’s 

And when you’re ready to refuel, there are plenty of restaurants and cafes in Navy Pier to choose from including the food court which has options to suit all tastes.

My personal recommendation for today ’s dinner is Giordano ’s . They have multiple locations throughout the city but this one is actually at Navy Pier so you won’t have to wander far. 

Giordano ’s is home to the best deep dish pizzas in all of Chicago, and you’ll find plenty of tasty topping options here.

Some of the most popular choices include ‘meat and more meat’, the ‘Chicago classic’, and the ‘super veggie’. You can even make your own if you fancy!

In case you’re not in the mood for pizza, they also have a delicious range of pasta dishes and sandwiches. If you’re looking to see (and taste) the best of Chicago in 3 days, this is the restaurant you need to visit!

Sunset at Milton Lee Olive Park

Watching the sunset at Milton Lee Olive Park is the perfect way to end the first day of your 3 days in Chicago. 

The park is named after Milton Lee Olive who was given a medal of honor for his actions in the Vietnam War. 

It’s located on a man-made peninsula that juts out onto Lake Michigan, so naturally, it boasts spectacular views – especially at sunset. You’ll also find plenty of walks here that offer superb views of the Chicago skyline.

However, the highlight of Milton Lee Olive Park has to be the fountains! There are five circular fountains in total and each one is connected by walking trails. 

Day 2 of Your 3 Days in Chicago

Breakfast either at beatrix or wildberry pancakes & cafe .

Breakfast is the most important meal of the day, and these two places are incredible! 

Both Beatrix and the Wildberry Pancakes & Cafe have multiple locations throughout the city and you’ll find one relatively close to the Magnificent Mile (the next attraction on your 3 day Chicago itinerary).

Wildberry Pancakes & Cafe is one of the best choices when it comes to breakfast places in Chicago. As the name suggests, pancakes are their specialty and you’ll be spoiled for choice with all of the different flavors on offer.

There are also plenty of other breakfast options available including eggs, bacon, sausage, bagels, and more. Their French toasts are also incredible!

If pancakes aren’t your thing, another great option for breakfast is Beatrix . This restaurant has a focus on healthy and flavorful food with plenty of vegan and vegetarian options available.

You’ll find everything from avocado toast to quinoa bowls on the menu, as well as a selection of fresh juices and smoothies.

Starbucks Reserve Roastery

After breakfast, make your way to the Starbucks Reserve Roastery . This is a must-visit for any coffee lover!

Starbucks Reserve Roastery is home to a selection of the rarest and most extraordinary coffees on earth. Not only that, but it’s the largest Starbucks in the world with five floors covering over 35,000 sq ft. 

Usually, you’d head to a Starbucks for a quick coffee but not here! The Starbucks Reserve Roastery offers interactive tours, a rooftop deck to admire the city views, and delicious pastries. 

Trust me, if you’re into coffee then you don’t want to miss out on this place during your 3 day trip to Chicago.

Magnificent Mile

The Magnificent Mile is without a doubt one of the most popular places to visit in Chicago. It’s one of the most famous shopping destinations in the world and is home to huge shopping centers, boutique stores, and plenty of designer shops. 

However, there is so much more to do here than just shop! Some of the most popular attractions include the John Hancock Center, the Wrigley Building, and the Tribune Tower. You can also head to the free gallery within the Water Tower.

If you’re looking to do some shopping, you’ll find everything from high-end stores to budget-friendly options. And when you need a break from shopping, there are plenty of restaurants and cafes to choose from.

Chicago Riverwalk

After exploring the Magnificent Mile, make your way to the Chicago Riverwalk. This is a great spot to relax and take in the views of the city.

The Chicago Riverwalk is a 1.25 mile (2 km) path that is made up of four districts; the Arcade, the Civic, the Confluence, and the Esplanade. 

The path starts from Lake Street and runs along the Chicago River until it reaches Lake Michigan. 

Along the way, you’ll get to see a variety of public art including banners, murals, and sculptures so make sure you take your time walking this path. 

However, the highlights of the Chicago Riverwalk have to be the iconic Wrigley Building and the DuSable Bridge. With so much to offer, this riverwalk needs to be on your 3 days in Chicago itinerary! 

Chicago Theatre

The Chicago Theatre was constructed in 1921 and designed by Cornelius Ward Rapp and George L. Rapp. It was the first lavish movie palace in the United States and was incredibly successful. 

This led to the owners (Balaban & Watz) constructing other theaters of its design throughout America. 

The whole design of the theater is based on luxury, which is clear just by taking a look at the grand lobby inside.

During your stay in the city, I’d recommend catching a show here to fully experience this incredible building. You can take your pick from comedy shows, live music performances, and theater productions.

However, if you don’t have time then simply head inside and go on a tour – trust me you won’t regret it!

Chicago River Architecture Cruise 

If you’ve only got 3 days in Chicago, then going on a river cruise has to be at the top of your list. Chicago River architecture cruises usually last around 1.5 hours and typically start at DuSable Bridge. 

One of the best choices is this river cruise that will take you down the Chicago River and past some of the city’s most iconic buildings.

You’ll also learn all about the history and architecture of each building from your knowledgeable tour guide. Best of all, it allows you to skip the ticket office and board straight away!

Alternatively, this 1.5-hour river cruise is a great option as well.

If you’re a bit short on time or want to keep the children entertained, then this family-friendly river cruise is a great choice. It’s only 45 minutes long but will still show you the city’s most breathtaking landmarks.

Nature Boardwalk at Lincoln Park Zoo 

After your architecture cruise, make your way to the Nature Boardwalk at Lincoln Park Zoo. This is a great spot to unwind and take a break from all the hustle and bustle of the city.

The Nature Boardwalk is an oasis within the city with plenty of trees, flowers, and greenery. There’s also a pond where you can spot turtles, ducks, and other wildlife.

One of the unmissable sights within the Nature Boardwalk is the Educational Pavilion which is one of the most unique things you’ll see during this 3 day Chicago itinerary.

The honeycombed shaped pavilion is constructed of prefabricated wood elements and the arched structure forms a place to shelter during your exploration of the park.

If you have some extra time on your hands, I also recommend checking out the Lincoln Park Zoo. It’s one of the oldest zoos in the country and it’s completely free to visit!

Sunset at North Avenue Beach

There’s no better way to appreciate a new city than by admiring an epic sunset. Chicago has plenty of incredible opportunities for this but watching the sunset at North Avenue Beach just hits differently! 

It’s one of the city’s most popular beaches and is located within Lincoln Park so you won’t have to walk far after visiting the Zoo or the Nature Boardwalk. 

Not only is North Avenue Beach beautiful, but you’ll also find an awesome beach house here too. The building is inspired by an ocean liner and offers a top deck where you’ll get spectacular views – especially at sunset. 

Make sure to stay a bit longer after the sunset to see the city all lit up. It ’s truly an incredible experience!

Dinner at Portillo ’s Hot Dogs

Chicago has endless options for dining, but you definitely need to try Portillo’s Hot Dogs during your 3 days in Chicago.

This Chicago born-chain is famous for its juicy hot dogs, tasty burgers, and delicious chocolate cake. Their Italian beef sandwiches are also a big hit. They even have vegan hot dogs so they cater to every dietary requirement. 

After a long day of exploring, eating at Portillo’s Hot Dogs is the best (and tastiest) way to refuel. 

Day 3 of Your 3 Days in Chicago

Skydeck chicago.

To truly make the most out of your 3 days in Chicago, you’ll want to head up to Skydeck Chicago during your visit. Located on the 103rd floor in the Willis Tower, Skydeck Chicago offers breathtaking views of the city.

If you head up there on a clear day you’re really in for a treat, as you’ll be able to see up to 50 miles (80 km) away including four American states! 

Are you feeling daring? If so, you should head out onto the ledge. The ledge is made up of four glass view boxes, and you’ll get a completely unobstructed view of Chicago. However, this probably isn’t suitable for people with a fear of heights, as it’s pretty daunting!

Since it ’s one of the most popular attractions in Chicago, I recommend heading there first thing in the morning right when it opens (usually around 8.30 am – 9 am). It ’s also advisable to book your tickets in advance so you don ’t lose any time waiting in the line.

Breakfast at Mojo Coffee

Mojo Coffee is a great place to fuel yourself for the last day of this 3 day Chicago itinerary.

You’ll find plenty of locations throughout the city but I’d recommend heading to this one as it ’s located right next to the Willis Tower. Plus, it ’s the very first cafe they ’ve opened in Chicago after their success in New Zealand!

Mojo Cafe offers plenty of tasty food options, including waffles, shakshuka, salads, poached eggs, and avocado on toast for starters.

They also have a delicious range of smoothies including ‘cold brew & chocolate’ and ‘pear, pineapple & spirulina’.

Also, if you ’re a coffee lover, grabbing a cup here is mandatory – and you can also take some freshly roasted coffee beans home with you.

Grant Park & Buckingham Fountain

After you’ve had your fill of the views from Skydeck Chicago and you ’re stomach is full, make your way to Grant Park. This is one of the most popular spots in the city and it’s easy to see why.

The park is huge (319 acres to be exact!) and there’s so much to see and do here. From gardens and sculptures to museums and fountains, there’s something for everyone in Grant Park.

One of the most popular attractions in the park is Buckingham Fountain. This iconic fountain is one of the largest in the world and uses around 15,000 gallons of water per minute.

The fountain also performs a water show hourly so make sure you time your visit right to witness it. You can also decide to come back after nightfall when you can enjoy a light and music display with the water show.

Museum Campus 

After you’ve explored Grant Park, make your way to Museum Campus. This 57-acre park is home to some of the best museums in the city including the Field Museum, the Shedd Aquarium, and the Adler Planetarium.

If you’re visiting with kids, they’ll definitely want to check out the Field Museum . This world-renowned museum is home to Sue, the largest and most complete Tyrannosaurus Rex fossil ever found.

Adults will appreciate the Shedd Aquarium which is one of the largest indoor aquariums in the world. And if you’re interested in space, the Adler Planetarium is a must-visit.

Visiting all 3 museums is pretty time consuming so I would recommend choosing one or two that take your fancy, so you can take your time and not rush around. No matter which museum you choose to visit, you’re sure to have a great time at Museum Campus!

TOP TIP: To make the most out of your visit and to save some cash, I’d recommend getting the Chicago CityPASS . It allows you to visit five of the city’s top attractions (including all 3 museums in Museum Campus) and you can save up to 48% off the normal ticket prices.

Dinner at Lou Malnati’s Pizzeria 

After a day of exploring, you’re going to want a delicious dinner. And there’s no better place for that than Lou Malnati’s Pizzeria .

This iconic pizzeria has been serving up delicious deep dish pies since 1971 and is hands-down the best place to get pizza in the city. They use an exclusive sausage blend, vine-ripened plum tomatoes, and Wisconsin cheese to make the most delicious toppings. 

You can either create your own pizza here, or you can try one of their many tasty options including the ‘Malnati Chicago Classic’, ‘The Lou’, and the iconic pepperoni. 

Lou Malnati’s Pizzeria also has a wide variety of pasta dishes, salads, sandwiches, and desserts.

They have multiple locations throughout the city, this one is the closest to Millenium Park. There is no better way to end your 3 days in Chicago, than by dining here!

Planning a trip to Chicago?

Then you might want to take a look at all our other travel guides about Chicago. I promise, they are just as awesome as this article was!

• Top 8 Best Areas to Stay in Chicago
• 22 Amazing Hotels with the Best Views in Chicago
• 13 Stunning Chicago Hotels with Lake Views
• 15 Most Instagrammable Places in Chicago You Can’t Miss
• 107 Incredible Chicago Captions for Instagram

Read about more US States: California | Massachusetts | Maine | Nevada | New Hampshire | New York | Vermont

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Travel, Hiking, Food

Long Weekend in Chicago: Essential Itinerary to Spend 3 Days in Chicago For First Timers

Spending a long weekend (3 days) in chicago this 3 day chicago itinerary shows you the best places to go and eat in chicago. this itinerary also gives you many chicago planning tips if this is your first time in chicago..

Planning a trip to the Windy City for 3 days or a long weekend? You are in the right place!

From iconic architecture and world-class museums to deep-dish pizza and blues music, Chicago has something for everyone. Whether you’re a history buff, foodie, art lover, or just looking to soak up the urban energy, Chicago won’t disappoint.

I had been to Chicago previously in the winter and it was pretty miserable to be honest. But going there in the summer and early fall is a completely different (and amazing) experience.

In this 3 day long weekend Chicago itinerary I will show you the best places to see in Chicago and how to most efficiently spend 3 days in Chicago. I will also address practical information like how to get around Chicago, how to save money on attractions, where to eat and stay in Chicago for your perfect Chicago trip.

This blog contains occasional affiliate links, where I receive a small commission on sales of the products/hotels that are linked at no additional cost to you. In addition, as an Amazon Associate, I earn from qualifying purchases .

When’s the Best Time to Visit Chicago For A Long Weekend?

NOT in the winter! Ok I think we all know winter is brutal in Chicago so that’s the worst time to visit Chicago. I went to Chicago once in February and it was just pure misery.

Early Summer and early fall are the best time to visit Chicago with the warmer temperature and beautiful weather. In particular, the month of June, September, and October are great to visit Chicago because it does get quite hot and humid in July and August.

The shoulder seasons are generally cheaper and less crowded than the peak summer season and you can enjoy a lot of outdoor activities. Although if you do have to visit Chicago in the summer at least you can enjoy the beach near the city center.

Where to Stay in Chicago?

As a first time visitor, the best areas to stay in Chicago would be either near the Magnificent Mile or in the Loop . Other great areas to stay in Chicago include West Loop and Gold Coast.

The reason I suggest these two areas is because of the access to restaurants, museums, and other attractions. You can walk easily from place to place or take a local bus to get around. There are also a lot of accommodation options in these two touristy areas.

The Magnificent Mile

There are a ton of hotels near on Michigan Avenue as well as between Dearborn St. and Michigan Avenue.

I stayed at the Intercontinental which was very centrally located. Rooms were average size and service was good. I loved that I could walk everywhere, from 360 CHICAGO to Millennium Park, making it super convenient to explore.

Other hotels near the Magnificent Mile include Courtyard , Royal Sonesta or Hyatt . You will find a lot of chain hotels here so you know quality is guaranteed.

The Loop is a vibrant area where you will find the Bean at Millennium Park and all the famous museums in Chicago. You will inevitably spend a lot of time in the Loop area, so it’s a good area to stay.

Some of the best places to stay in the Loop include CitizenM , Arlo Chicago , the Blackstone .

West Loop & Fulton Market

If you want to stay somewhere close to good food, then you should consider Fulton Market and West Loop, an area west of the Loop. Formerly known as the meat-packing district, the West Loop is super walkable with industrial aesthetics and amazing restaurants.

In fact West Loop is one of my favorite areas in Chicago. I went there a few nights in a row just to try different restaurants and coffee shops.

So if you don’t mind walking or taking the bus to get around Chicago, then consider staying in the West Loop.

Some of the best places in the West Loop include the Hoxton , Nobu Hotel Chicago , and the Hyatt House .

If West Loop is my 2nd favorite area in Chicago, then Gold Coast is my absolutely favorite area in Chicago.

Gold Coast is north of the Loop and it is one of the most luxurious neighborhoods in Chicago. It is the home of beautiful mansions (like the original Playboy Mansion), upscale restaurants and stores (like RH).

You can easily walk to the beach and Lincoln Park and it is a short ride down to the Loop.

Some of the best hotels to stay at in Gold Coast include Ambassador Chicago and Viceroy Hotel .

Long Weekend (3 Day) Chicago Itinerary (With Maps)

Now you know some of the basics of how to get around and where to stay in Chicago, let’s talk about what you will actually do (and eat) in Chicago for a long weekend!

I am just so excited for you. Really, Chicago is such a nice place to visit when the weather is good (yeah don’t visit in the winter). With Lake Michigan to the east and tons of parks to relax and explore, Chicago really is beautiful when the weather is warm.

Coming from New York City, I am just so impressed with how clean and neat Chicago is and it also is not super crowded compared to New York City. So if you want a taste of Chicago as a first time visitor, you will love all the suggestions on this itinerary.

For your convenience, I mapped out all the major attractions and awesome restaurants in Chicago on this map below.

Day 1 : Famous Museums in the Loop + Skydeck (Orange Pins) Day 2 : Art Museum, Parks, Architectural Tour, 360 CHICAGO (Purple Pins) Day 3 : Magnificent Mile, Near North Side, Lincoln Park area (Green Pins) Where to Eat : Red pins

Day 1 in Chicago: Museums + Skydeck

Start your first day in Chicago with a bang! You will see some of the best museums in Chicago in what’s known as the Museum Campus.

Museum Campus is in the southern end of the Loop; it is an area that houses 3 of the most famous museums in Chicago: Adler Planetarium , Shedd Aquarium , and Field Museum .

It is also a beautiful area to walk around, with plenty of greens (and parks) and the view of Chicago skyline and Lake Michigan.

All 3 museums open at 9am, but I would actually recommend going to Shedd Aquarium first because it gets really crowded with school tours and just kids running around especially during the summer months.

So we will start our 3 day Chicago itinerary with Shedd Aquarium.

Shedd Aquarium

Hours of Operations : 9am – 9pm Ticket Price : $42-$45 (if not Chicago resident) with tax Time Needed : 2-3 hours at least

Shedd Aquarium is one of the largest and most renowned aquariums in the US.

It houses an impressive collection of marine life from around the globe. It features diverse exhibits that showcase a wide range of aquatic creatures, including fish, sharks, dolphins, sea turtles, penguins, and more. In fact it has over 32,000 animals representing 1,500 species; that number is just mind blowing to me.

One of the highlights of Shedd Aquarium is the Oceanarium, a massive exhibit that replicates a Pacific Northwest coastal environment. Here, visitors can observe majestic beluga whales, playful dolphins, sea otters, and a variety of marine birds as they interact.

Funny story here : I was watching the “Animal Spotlights” program with the beluga whales when I visited. After the show finished as I was walking out, the beluga whales swam very close to me and jumped out of the water. Of course I couldn’t miss the opportunity to take photos of it. Little did I know he came over to splash me, so as you can imagine, I got super wet after taking that photo.

There are also other activities such as penguin encounters which require additional ticket.

Overall, if you want to avoid the crowd it’s best to visit Shedd Aquarium right at opening.

Shedd Aquarium is included in the Chicago Pass and Chicago CityPASS .

Adler Planetarium

Hours of Operations : 9am – 9pm (9am – 10pm on Wednesdays) Ticket Price : $35 (entry + 2 shows) Time Needed : 2-3 hours at least if you watch the shows

Adler Planetarium is the first planetarium in the western hemisphere!

At Adler Planetarium, you can explore the wonders of the universe, learn about space science, and engage in immersive experience.

Adler Planetarium is perfect if you have kids traveling with you. Depending on the ticket you get, you can watch 1 or 2 planetarium shows.

The reason I suggest going to Adler Planetarium after Shedd Aquarium is that many shows are in the early afternoon, so if you arrive at 9am when they open you will need to wait a long time before showtime.

Adler Planetarium is included in the Chicago Explorer Pass and Chicago CityPASS and it comes with 2 shows.

Field Museum

Hours of Operations : 9am – 5pm Ticket Price : $30 ( general admission ); $37 (3D movie or 1 of the 3 ticketed exhibitions) Time Needed : 2 hours at least

The Field Museum is a renowned natural history museum that lets you explore the wonders of our planet and its history.

It has a vast collection of artifacts, specimens, and interactive exhibits as well as special temporary exhibits.

The Field Museum is home to an extensive range of exhibits that cover a wide array of topics, including anthropology, paleontology, geology, biology, and more. One of the museum’s most famous and beloved attractions is Sue, the largest and most complete Tyrannosaurus rex fossil ever discovered.

The museum also showcases exhibits that delve into human cultures and civilizations from around the globe, from ancient Egyptian mummies and artifacts to Native American artifacts and cultural displays.

Field Museum tickets are included in the Chicago Explorer Pass and Chicago CityPASS . Chicago CityPASS gives you all access rights to see all the ticketed exhibitions and 3D film; the Chicago Pass gives you access to 1 ticketed exhibition.

I forgot to mention that you can eat at the cafes inside the museums or planetarium or walk 10 minutes to get Chicago hot dogs at Devil Dawg (or eat at other restaurants).

Hours of Operations : 9am to 8 or 9pm depending on day and months. See official website . Ticket Price : $30+ ( general admission ); $55+ (expedited entry) Time Needed : 45 min – 1.5 hours

Skydeck is an iconic observation deck in Chicago. It was formerly known as the Sears Tower and now known as Willis Tower (the naming right will change in a few years so it might be called something else).

The Skydeck is situated on the 103rd floor of the Willis Tower, making it one of the highest observation decks in the United States. It offers unparalleled panoramic views of the Chicago skyline, Lake Michigan, and the surrounding area.

On clear days, you can see for miles, taking in the beauty of the city’s architecture and the vastness of the landscape.

The most famous feature at Skydeck is “The Ledge” , which are 4 glass bottom “boxes” that extend out from the building. You can step onto the transparent surface suspended over 1300 feet in the air.

If you have a fear of heights like I am, you might get scared standing on it.

For different sized parties, there is a different time limit. For a party of 1-3 people, you have 1 minute to take photos/ videos after the official photos finish (they have cameras latched above the ledge to take photos of you and sell you the pictures).

For parties of 4 or more you get 90 seconds. The attendant will set an alarm and can help you take photos if you are traveling alone.

I highly recommend going to Skydeck around sunset time so you can see the colorful sky as well as all the lights come on in the city. So if you finished your museums early you can grab dinner first then go to Skydeck for sunset.

Skydeck is included in the Chicago Explorer Pass and Chicago CityPASS . CityPASS gives you expedited entry but I didn’t really need that when I went.

Day 2 in Chicago: Art Museum, Parks, Architectural Tour, 360 CHICAGO

After a whole day of touring the most famous museums in Chicago, you will spend day 2 doing a variety of things. This is going to be an action packed day so be prepared to walk.

Start your second day in Chicago by checking out the Bean and Crown Fountain for some photos. Proceed to walk through Millennium Park and Grant Park before heading back to the Art Institute of Chicago to see world famous artwork.

If time allows, stop by the Chicago Cultural Center for a quick (and free) self-guided tour to see the beautiful ceilings before heading back north to the Chicago River for a fun and educational architectural cruise . Finish your evening at 360 CHICAGO for another amazing view of Chicago at sunset.

The Bean and Crown Fountain at Millennium Park

The Bean, officially known as the Cloud Gate, is one of the most iconic symbols of Chicago. Located in Millennium Park (which is in Grant Park), it is a must-see attraction for all first-time visitors.

Designed by renowned British artist Anish Kapoor, the Bean is a massive, highly polished stainless steel sculpture that reflects and distorts the surrounding cityscape.

You can walk around and under the sculpture and take some artistic photos with it. But be warned that the bean does get crowded so if you want an instagram worthy photo you will have to go fairly early.

Close to the Bean is another famous art installation called Crown Fountain.

Designed by Spanish artist Jaume Plensa, the fountain consists of two towering glass block towers facing each other across a shallow reflecting pool. The fountain uses digital technology within the glass block towers to display the ever-changing faces of Chicago residents.

Millennium Park & Grant Park

Chicago has no shortage of parks, in fact public parks make up around 9% of total Chicago land (according to my architectural guide).

During your second day in Chicago you will get a chance to see two of the most famous parks in Chicago, Millennium Park and Grant Park. Millennium Park is technically inside Grant Park.

The Bean and Crown Fountain are in Millennium Park, so you have already seen part of the park. As you explore the park, you will see some other highlights, such as the Jay Pritzker Pavilion , an outdoor concert venue, Lurie Garden , a tranquil oasis in the middle of Millennium Park, and the BP Pedestrian Bridge , a famous stainless steel bridge that connects Millennium Park with Maggie Daley Park.

As you continue to walk south, you will actually pass by The Art Institute of Chicago (we will go back to that in a second) and arrive at Grant Park.

Grant Park is often known as “Chicago’s front yard”.

Grant Park is right next to Lake Michigan, so you have an incredible view of the waterfront and the Chicago skyline.

Within Grant Park, you’ll find several notable landmarks and attractions. Buckingham Fountain , one of the park’s most iconic features, serves as a grand centerpiece with its majestic water displays and ornate design.

Other landmarks in Grant Park include MAGMA , an art installation, the Turtle Boy , Dove Girl , Fisher Boy and Crane Girl fountains , a farm and rose gardens .

Art Institute of Chicago (Closed Tue & Wed)

Hours of Operations : 11am – 5pm (8pm on Thursday) Ticket Price : $32 for general admissions; $10 extra for special admission; $40 to skip the line Time Needed : 2 hours at least

The Art Institute of Chicago is a world-renowned art museum and cultural institution. Founded in 1879, it is one of the oldest and largest art museums in the US.

There are over 300,000 works of art in the Art Institute’s collection, from ancient Egyptian artifacts to European and Asian masterpieces to contemporary arts and photography.

The collection features renowned works by legendary artists such as Vincent van Gogh, Pablo Picasso, Claude Monet, Georgia O’Keeffe, and Grant Wood, among many others.

There are also temporary special exhibitions featured at the Art Institute that cost additional $10.

The Art Institute is included in the Chicago CityPASS only.

Chicago Cultural Center

Hours of Operations : 10am – 5pm Ticket Price : Free! Time Needed : 30 min – 1 hour

The Chicago Cultural Center is in a beautiful historical building right across from the Bean.

Originally built in 1897 as the city’s first central public library, the Chicago Cultural Center is a stunning example of Beaux-Arts architecture. The building itself is a work of art, featuring grand marble staircases, intricately designed mosaics, and ornate decorative elements.

There are 2 beautiful stained glass domes in the Cultural Center and an art gallery. There are also cultural events and programs that are hosted at the Cultural Center regularly.

Chicago Architectural Cruise

Hours of Operations : 9:30 – 8:45pm (see schedule here ) Ticket Price : $45-50 Time Needed : 75 min – 90 min

The Chicago Architectural Cruise tours are a popular and highly recommended way to explore the stunning architecture of the city. These boat tours take you along the Chicago River, providing a unique perspective and an in-depth look at the iconic buildings that define the city’s skyline.

Led by knowledgeable guides, the architectural cruise tours offer fascinating insights into Chicago’s rich architectural history and the visionary architects who shaped the city. You’ll learn about the different architectural styles, from Beaux-Arts to Art Deco to modernist designs, and how they contribute to the unique character of Chicago’s skyline.

There are several different companies that offer architectural cruises. I took the Shoreline Cruise because it was covered by my Chicago Explorer Pass (and also Chicago CityPASS ) but you can also choose other ones like this one .

360 CHICAGO

Hours of Operations : 9am – 11pm Ticket Price : $30+ for general admissions ; $39+ to Tilt & View; $46.5 for View & Sip Time Needed : 1-2 hours

360 CHICAGO, formerly known as the John Hancock Observatory is one of the two popular observation decks in Chicago.

Located on the 94th floor of this iconic building, it offers breathtaking panoramic views of the city’s skyline and Lake Michigan.

The main highlight of 360 CHICAGO is its observation deck, which provides visitors with an unparalleled 360-degree view of the cityscape.

One of the unique features of 360 CHICAGO is the TILT experience. This exhilarating attraction allows you to step into a glass-enclosed moving platform that tilts outward from the building, giving you a thrilling downward-facing perspective of the city below.

There is also a bar and some seating areas at 360 CHICAGO so you can relax while enjoying the view.

I visited during sunset and I thought the view was amazing. This is why I suggest going to 360 CHICAGO before sunset time so you can grab an early dinner before visiting.

If you can only visit one observation deck in Chicago, you should check out my detailed comparison guide between 360 CHICAGO and the Skydeck to see which one is better for you.

360 CHICAGO general admission is included in the Chicago Explorer Pass and Chicago CityPASS .

Day 3 in Chicago: Magnificent Mile, Lincoln Park, Navy Pier, Food Tour

Your last day in Chicago is pretty chill. You have the option to do everything or just chill, eat, shop or check out some other museums.

You can start your day at the Starbucks Reserve Roastery to grab some coffee and pastries before window shopping on the Magnificent Mile to do some shopping (or window shopping). If you are visiting on a Friday or Saturday, you can do a tour inside the magnificent Chicago Theatre . If not, wander on the Riverwalk and take in all that Chicago has to offer.

Get lunch then take the bus over to Lincoln Park where you can check out the free Lincoln Park Zoo and Conservatory. Finish your day by having some fun at Navy Pier , check out the West Loop area for great food or have a fun night at a comedy club .

You can also take a food tour and try all the iconic food of Chicago.

Starbucks Reserve Roastery

Hours of Operations : 8am to 8pm M-Th; 8am to 9:30pm Fri – Sun

Located on the magnificent mile, the Chicago Starbucks Reserve Roastery is a fantastic place to stop by for some coffee and pastry early in the morning.

This is no ordinary Starbucks Reserve, in fact this particular location is the largest Starbucks in the world. It has 5 stories and each story has something different.

It also offers a bakery with a wide selection of freshly baked goods, artisanal bread, and delicious pastries.

Magnificent Mile

The Magnificent Mile, often referred to as “Mag Mile,” is a world-famous stretch of North Michigan Avenue. It is renowned for its upscale shopping and beautiful architecture.

Stretching for approximately one mile, the Magnificent Mile is lined with a dazzling array of high-end boutiques, department stores, luxury brands, and flagship stores of renowned fashion designers. You can find brands like Burberry, Cartier, Rolex on Michigan Avenue.

Aside from shopping, the Magnificent Mile is also home to a plethora of renowned landmarks and architectural gems such as the Wrigley Building , the Tribute Tower , the John Hancock Center (where 360 CHICAGO is), and the Chicago Water Tower .

You will also see street performers, Architectural Cruise ticket booths, Chicago Riverwalk, theaters, and Museum of Ice Cream on the Mag Mile.

The Chicago Theatre

Marquee Tour Hours : 12pm Friday & Saturdays Ticket Price : $24 ( ticket link ) Time needed : 75 min

The Chicago Theatre is a famous landmark in downtown Chicago.

Built in 1921, this theater is known for its grandeur, architectural beauty and its significance in Chicago’s cultural and entertainment scene.

If you are not watching a show in the theater, your only option to visit the inside of this magnificent building is to do the Marquee Tour.

The tour will lead you inside to see the grand lobby, sweeping staircase and beautiful auditorium. You will get a chance to stand on the stage and learn about the history of the building.

The Chicago Theater Marquee Tour is included with the Chicago Pass and Chicago Explorer Pass .

Chicago Riverwalk

If you are not doing the Chicago Theater Marquee Tour don’t worry, you can either spend more time shopping or check out the Chicago Riverwalk.

The Chicago Riverwalk is a scenic and vibrant promenade that runs along the south bank of the Chicago River. It stretches for 1.25 miles and you can stroll, relax, dine, and enjoy the stunning views of the city’s iconic architecture.

Lincoln Park Zoo

Hours of Operations : 8am – 5pm on weekdays; 8am – 7pm on Sat & Sun. See seasonal hours here . Ticket Price : Free! Time Needed : 1-2 hours

Located at Lincoln Park, the zoo is one of the oldest zoos in the US and it is completely free to visit!

Spanning over 35 acres, the Lincoln Park Zoo is home to a diverse collection of animals, from gorillas to lions to exotic birds and reptiles.

The Farm-in-the-Zoo is a popular attraction where children can interact with farm animals, learn about agriculture, and engage in hands-on activities.

Lincoln Park Conservatory (Closed Monday and Tuesdays)

Hours of Operations : 10am – 5pm Wed – Sun Ticket Price : Free, but reservation needed . Time Needed : 45 min – 1 hour

Located right next to the Lincoln Park Zoo, the conservatory is a hidden gem that should not be missed.

The conservatory, built in the late 1800s, showcases an impressive collection of tropical plants, flowers, and trees from around the world. As you step inside, you’ll be greeted by a lush and vibrant environment, with soaring palm trees, colorful blooms, and cascading vines that create a truly enchanting atmosphere.

The conservatory is divided into several distinct rooms, each with its own unique theme and plant life. The rooms include the Palm house, the Fern Room, the Orchid Room and the Show House.

If you are visiting the zoo you should definitely stop by the conservatory and enjoy the tranquility from the bustling city.

After an eventful day, you can either stop by Navy Pier to check out the Centennial Wheel , the ferris wheel that can be seen from all the observation decks and cruise tours or go to the West Loop to eat at some of the most iconic restaurants in Chicago.

If you are into comedy shows , Chicago also has a number of comedy clubs such as The Comedy Bar, the Comedy Clubhouse, Zanies Comedy Night Club and many others.

Is 3 Days Enough For Chicago?

3 Days in Chicago is the perfect amount time for a first time visitor to see the highlights of Chicago.

From world class museums to renowned restaurants to beautiful parks, you can see the best of Chicago over a long weekend (3 days) in Chicago.

Of course you can always spend more time in Chicago to explore things a little further away from city center, such as Garfield Park Conservatory , the largest conservatory in the US, relax on a beach , check out Hyde Park and the Museum of Science and Industry , explore the trendy area of Wicker Park , or venture out to the beautiful Baha’i temple or the magnificent Hindu Temple of BAPS Shri Swaminarayan Mandir .

How to get to Chicago?

Unless you are traveling from nearby cities, most likely you will have to fly to Chicago.

Chicago is served by two major airports: O’Hare International Airport (ORD) and Midway International Airport (MDW).

O’Hare International Airport , located about 17 miles northwest of downtown Chicago, is one of the busiest airports in the world and serves as a major hub for domestic and international flights.

Midway International Airport , situated about 10 miles southwest of downtown Chicago, primarily serves domestic flights and is known for its convenient location and smaller size compared to O’Hare. There are only a number of airlines that fly to Midway International Airport, such as Allegiant, Avelo, Delta, Frontier, Porter, Southwest and Volaris.

Besides flying, you can take the Amtrak train to Chicago to Union Station or take a long distance bus such as Greyhound to Chicago. Union Station, the city’s major train station, often serves as a hub for various bus services as well.

How to get around Chicago?

You can use a combination of public transportation, biking, walking and ride share apps to get around Chicago during your long weekend Chicago trip.

Chicago is a super walkable city if you are planning to stay in the downtown area and do touristy things! You can literally walk from museum to museum or just walk along Michigan Avenue.

I walked A LOT when I was in Chicago and when I got tired, I used other forms of transportation below.

Public Transportation in Chicago

Public transportation in Chicago includes the “L” (or the CTA trains), buses and the Metra Rail.

The CTA train, otherwise known as the “L” (short for “elevated”) is a convenient way to get around the city with over 140 stations located throughout Chicago and the surrounding areas.

The “L” has 8 lines, known by their colors (Blue Line, Red Line, Green Line, etc). The Blue Line and Red Line run 24 hours.

I was super confused when I was looking up directions in Chicago because some blogs would say take the “L” train but Google Maps was telling me to take the Blue Line and the airport sign says “CTA trains”. Well I am here to tell you that they all mean the same thing. L = CTA trains = whatever color Line .

The bus network is also expansive, with 129 bus routes covering places that may not necessarily be served by the L.

The Metra Rail is a commuter rail train that goes from downtown Chicago to the suburbs. The closest Metra stop to downtown is at Millennium Park. You can see the Metra Rail system map .

Navigating & Paying for the public transportation station in Chicago

Google Maps and City Mapper both work well in Chicago when looking up directions with public transportation. You can also download the Ventra App which shows you public transportation information.

Paying for public transportation in Chicago is easy and there are a lot of options.

Apple Pay/ Google Pay/ Contactless Cards can be used to pay for the bus and L trains. You just have to tap your card and you are good to go. However I did notice that using contactless cards on buses costed me $5 for the full price (instead of $2.25) the first time I used it on a bus.

Ventra App : The Ventra App allows you to load money into the app and add the Ventra card to Apple Pay and Google Pay, then you can tap and pay on buses and L trains. I used this in Chicago and the bus fare was the $2.25 fare.

CTA/Pace Pass : You can purchase a 1, 3, 7, or 30 day CTA/ Pace Pass from either the ticket machine or load onto your Ventra account.

For a full list of fares and options, see the official CTA website .

Taking Uber/ Lyft in Chicago

Uber and Lyft both operate in Chicago and you can easily get a car when it is too late or you simply do not want to bother with public transportation.

While I was in Chicago, I found Lyft to be a lot cheaper than Uber and the cars came faster. You may have a different experience but check both apps.

Biking in Chicago

When I was in Chicago I saw public bikes called Divvy Bikes all over Chicago.

You can buy a Pass from Divvy, find an available bike, unlock the bike and take short rides. In fact Lyft operates the Divvy system in Chicago. When you look for cars on Lyft, you can actually see options for Divvy bikes.

For more information on Divvy Bike, see their official website .

Hop-on-hop-off bus in Chicago

If you just want to go to the main attractions in Chicago then a hop on hop off bus may be worth it.

I saw a lot of people using Big Bus Tours when I was in Chicago and they are very conveniently located with stops at all the popular spots. They are also covered under the Chicago Pass and Chicago Explorer Pass if you want to save money.

Where to Eat in Chicago

Chicago is a food lover’s paradise, with a vibrant culinary scene that offers a diverse range of dining options. Whether you’re craving deep-dish pizza, sizzling steaks, ethnic cuisine, or innovative fine dining, the city has something to satisfy every palate.

If you are in Chicago you probably want to try the iconic Chicago hotdog, deep dish pizza, and Italian beef sandwiches.

For Chicago hot dogs , I would recommend Superdawg Drive-in , the Wiener’s Circle , Portillo’s and Devil Dawg .

For deep dish pizza , the three most famous places are Lou Malnati’s Pizzeria , Giordano’s , and Pequod’s Pizza .

When it comes to Italian beef sandwiches , be sure to check out Portillo’s or Al’s Italian Beef .

There are just so many amazing and famous restaurants in Chicago that I can’t list them all. Some of the most noteworthy restaurants include Alinea , Girl & the Goat , Au Cheval , XOCO , Grand Lux Cafe , and the Purple Pig . If you want a really beautiful restaurant then head to the RH store and eat in their 3 Arts Club Cafe (super overpriced though!).

I bookmarked all of these restaurants (and more) on my Google Maps above. You should definitely aim to get reservation at least 2 weeks in advance for many of these restaurants (except Alinea, that’s a whole different story).

Alternatively you can just book a walking food tour and get a taste of everything famous and iconic.

Saving Money on Chicago Attractions

If you are planning to visit all the major attractions in Chicago, then the best way to save money is to get one of the Chicago discounted attraction passes.

The individual attractions do cost between $30 – $50, and they add up to quite a lot of money if you want to see all the famous ones.

With these Chicago discount passes you pay upfront for the pass then you can visit the available attractions for free (within a particular time period or with a particular number of attractions).

Using the first day of this 3 day Chicago itinerary as an example, visiting the 3 museums and Skydeck turn out to be about $144 but with a one day Chicago Pass you only pay $112 (after discount) so you can save quite a bit of money.

You can read this detailed Chicago pass comparison to see which pass is the best for you (hint: my favorite is the Chicago Explorer Pass because of its versatility).

Other ways to save money in Chicago is to take public transportation and walk instead of taking Uber everywhere unless it’s late night.

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37 BEST Places to Visit in Chicago (2024)

Everyone’s heard of the windy city and it’s an incredibly popular destination for tourists from inside and outside of the US. Chicago is known for its amazing food, especially the unusual pizzas they have there, as well as iconic buildings that reflect this city’s tumultuous past. And if you’re looking for entertainment, there’s always something going on in Chicago for every taste, from concerts to theater and a vibrant nightlife.

But Chicago isn’t all pizza, history and entertainment. It also has a darker side that makes some people reluctant to visit the city. It’s sometimes called one of the most dangerous cities in the US, with a higher than average crime rate, and yet this isn’t the full story. Careful travelers rarely ever see this side of the city. Instead, they spend all their time enjoying everything that Chicago has to offer. If this is what you want for your trip to Chicago, we’ve created a guide on how to stay safe while exploring this exciting part of the US.

Need a place quick? Here’s the best neighbourhood in Chicago:

These are the best places to visit in chicago, faq on the best places to visit in chicago, final thoughts on the coolest places to visit in chicago.

Downtown/The Loop

Home to the city’s business district, this area of Chicago is packed with skyscrapers, lively theatres, and picturesque architectural landmarks. Walking distance away from Chicago’s best attractions, you’ll get to explore a lot.

• Take a picture at Cloud Gate, the iconic Bean sculpture.
• Climb to the 99th floor of Willis Tower and enjoy sweeping views out over the city.
• Dig into an exquisite Italian dinner at Trattoria No. 10.

Hold off on that deep dish for a second because although we know you want to get going, we think you should check out where to stay in Chicago first. It’s a sprawling and diverse city, so we’ve condensed all of our recommendation options down for you. Give it a whirl and then get back to your deep dish.

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#1 – Shedd Aquarium – Awesome place to visit in Chicago with kids!

• More than 80 different habitats.
• Great for kids and adults as well.
• Has live animal shows and encounters if you want to get up close and personal.

Why it’s so awesome : There’s nothing like a great aquarium. They’re a chance to get out of the heat and spend time marvelling at a whole different world. The animals that live under the sea are some of the strangest and most amazing creatures in the world, which is why spending time learning about them can create a fascination that lasts a lifetime.

What to do there : Spend some time while you’re at this aquarium so you get the chance to see all the exhibits. The Shedd Aquarium has more than 80 different habitats, so you’ll probably see a few sea animals that you’ve never even heard of before let alone seen. But if you still want more, you can have a penguin encounter and be introduced to one of these adorable, tuxedoed animals, or see a live animal show featuring some of the aquarium’s most amazing residents. Some of Chicago’s best hostels are located nearby so you could go multiple times and not pay for transport if you wish!

#2 – The Art Institute of Chicago

• Voted one of the best art museums in the world by travelers.
• Home to some of the most famous paintings in the world.
• A great place for art lovers.

Why it’s awesome : Have you ever heard of American Gothic with the farmer and his wife standing with the pitchfork? Or wanted to see a work created by Van Gogh in real life? Well, you can do all of that here. The Chicago art museum is one of the best in the world and now it includes the recently completed Modern Wing, which houses artwork from around the world and from different times in history.

What to do there : Make sure you take a look at the Modern Wing with its artwork from ancient Greece and Rome. Another favorite houses the Thorne Miniature rooms, which have tiny, detailed houses from key times in European and American history. You’ll quite literally be able to see how people from other times lived and marvel at the amount of detail in each piece.

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#3 – Second City

• Some of the best comics in the world started out here!
• A fun night out for groups and people on their own.
• Make sure you stick around for the encore to see new material.

Why it’s so awesome : Steve Carrell, Tina Fey, Bill Murray and Chris Farley all started out at this venue. Second City has been the home of the best comedy in the city for a long time and that hasn’t changed. When you attend a show at this location, you’ll get to see some of the best comedy sketches in the world, which will make for a laughter-filled evening.

What to do there: Check what’s on and when while you’re in the city and make sure you reserve your seat! And once the show’s over, stay there until the encore’s finished too, because this is when the comedians improvise, and that’s sometimes funnier than the rest of the show!

#4 – The Empty Bottle – A nice non-touristy place to visit in Chicago

• One of the best rock and roll clubs in the US!
• A chance for you to see the best newcomers to the music scene.
• Is the perfect location for a night out with friends.
• This club is mostly for the locals, so you probably won’t see too many tourists while you’re there.

Why it’s so awesome : If you like rock and roll then you must spend an evening at the Empty Bottle. This is a small club that books some of the best music acts in town, and the venue has become a rite of passage for up-and-coming bands. If you are lucky enough to visit Chicago on a weekend then this place will really come alive.

What to do there : Take your friends, get there early, and enjoy the music. The club has a maximum capacity of about 300, so make sure you’re there early so you don’t get locked out. And if you’re there on a Monday, take advantage of the slow night special to see a free show.

#5 – The 360 Chicago

• Has a one of a kind open Skywalk.
• Gives a gorgeous view of some of Chicago’s prime tourist spots.
• Great for photographers.

Why it’s so awesome : This attraction boasts the fastest elevator in North America, which will take you up to the 94th floor in 40 seconds. There you can look out over the city and spot some of Chicago’s best tourist attractions from a bird’s eye view. The site also has educational features where you can learn about the city’s history, its culture, and some of the architecture that you’re looking at.

What to do there : While you’re there, see how many of the city’s attractions you can spot from your sky-high view. And if you’re a history buff, you can explore the city’s past by spending some contemplating the history wall. But if you want a little more from your experience, try the TILT, which allows you to lean over the edge of the building to see the city from high up without any barriers. It’s hair-raising but almost worth the terror!

#6 – Adler Planetarium

• Great for kids and adults.
• A place to indulge the science geek in you.
• Includes hand on exhibitions and display that will fascinate you even if you aren’t a science buff.

Why it’s so awesome : This planetarium does its best to push back the pollution that crowds the skies of most big cities and show visitors the stars. With some of the most technologically advanced theaters in the world, you’ll get a closeup view of the universe in living color in this Planetarium, and walk away with a whole new appreciation of the size of the universe and our tiny place in it.

What to do there : Make sure you spend some time at the Galaxy Wall, which shows the largest and most complete picture of the Milky Way that we have at the moment. And check what shows they have on in the theaters too. Whether you’re a child or an adult who’s curious about the world, you’ll love learning about this side of the universe that most people only see through a telescope. This is one of the best things to do in Chicago by far.

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#7 – Museum of Science and Industry – Cool place to see in Chicago with friends!

• The largest science museum in the western hemisphere.
• The first museum in North American to get interactive displays.
• Great for kids and science lovers.

Why it’s so awesome : This museum is all about encouraging visitors to interact with the displays and this makes it one of the most interesting and personally relevant museums that you can spend time in. There is also a 5 story, wrap around theater where you can watch Omnimax shows and learn even more about the world around you!

What to do there : This is a museum where you should wander around and try everything. You can explore the weather through the Science Storms display, play basketball with a virtual instructor, and wander through a German submarine from World War II. Whatever you’re interested in, you’ll find something here that will help you learn more about it. School was never as fun as this!

#8 – The Field Museum – A fascinating educational place to visit in Chicago

• Travel through time billions of years in one place.
• Great for history buffs and people who want to learn more about how the world came to be.
• Kids will love the animal and dinosaur displays.

Why it’s so awesome : If you want to understand the history of the planet then this is the place to do it. The Field Museum explores billions of years of the world’s history in living, exciting color. And if you like your displays a little closer to home, there are also displays showing the history of human civilization as well as exciting exhibitions that will make you see the world from a whole new, much smaller perspective.

What to do there: Check out the Egyptian tomb with all the trimmings including a book of the dead, mummies and other artifacts. And make sure that you spend some time in the Underground Adventure exhibition, where you’ll explore the world from the view point of a creature that’s 1/100th of your size. From this perspective, spiders are enormous, and you’ll get to experience what it’s like to be hunted by one!

#9 – Navy Pier – An awesome place to visit in Chicago for half a day!

• A city within the city.
• Truly one of Chicago’s most iconic spots.
• There’s no end to the activities that you can indulge in here.

Why it’s so awesome : Navy Pier is one of the most popular spots in the city for tourists and locals alike. It consists of more than 50 acres of lakefront territory and is home to shopping centers, restaurants, gardens and lots of other attractions. This area is like a city within a city, with its own energy and vibe, and you could literally spend days here just seeing what it has to offer.

What to do there : Well, what are you interested in? Some of the most popular options are the river or dinner cruises, where you can take in the city from the water. There’s a 150-foot Ferris wheel that operates year-round as well as fireworks twice a week during the summer. And if you enjoy the theater, then you must go to one of the shows put on at the Chicago Shakespeare theater, which is one of the best in the world and dedicated to groundbreaking productions. And if none of that appeals, you can just wander the area, sightsee and shop!

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#10 – Skydeck Chicago – One of the most amazing places in Chicago!

• The tallest building in the Western Hemisphere.
• Great for photographers and anyone who wants a shot of the iconic skyline of Chicago.
• The best place to take in the whole city.

Why it’s so awesome : This is the tallest building in the Western hemisphere and that makes it a great spot to get photographs of Chicago’s famous skyline . The observation deck is on the 103rd floor and you’ll be able to see some of Chicago’s most famous buildings from this vantage point. This is definitely not a place for people who are scared of heights, but it’s the best view in the city!

What to do there : If you’re really brave, you can step out onto The Ledge, a glass-enclosed balcony where there’s nothing between you and the city but air. Make sure you have a strong stomach if you try this because you’ll have a clear view all the way down. And it’s a really long way down. Otherwise, just take some great pictures with the skyline in the background and try to pick out some of the buildings you’ve already seen in your travels around the city!

#11 – Millennium Park – One of the most incredible free places to go to in Chicago

• A brand-new attraction that’s become one of the city’s hotspot.
• Holds hundreds of free concerts and events, so you’ll definitely get to see something good!
• A lovely natural area where you can escape from the busyness of the city.

Why it’s so awesome : Chicago is a busy city and sometimes it’s nice to get away from the streets and the pollution and spend time in a natural area. Millennium Park is the best place in the city to do that. Not only is it a beautiful park, but there are also lots of unique art pieces throughout the area for you to enjoy and sometimes puzzle over.

What to do there : While you’re in the Millennium Park, make sure you check out the Jay Pritzker Pavilion, where the city holds free concerts and events throughout the year. Even if you don’t catch a concert, the park is a lovely natural area so spending some time wandering around. And if you don’t like to walk, you can hire a bike or a Segway and see the park on wheels!

#12 – The Magnificent Mile – A great place in Chicago if you love to shop!

• Shopping, shopping, shopping.
• One of the busiest, most popular areas for tourists in the city.
• This area is also the heart of Chicago’s restaurant scene.

Why it’s so awesome : If you love to shop then this is where to come! The Magnificent Mile is basically a collection of streets where every shop you can imagine has a home. No matter what you’re looking for, you’ll find it here. And when you get tired, some of the best restaurants in Chicago are in this area. So, the only thing you’ll have to worry about is how to choose one!

What to do there : There are a lot of shops and a lot of streets included in this area so make sure you visit every one of them if you’re looking for something in particular! Whatever you’re looking for, from clothes to pet goods to jewelry, you’ll find it here, so just explore until you find some treasure!

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#13 – Grant Park – One of the most incredible free places to go in Chicago

• Over 300 acres of natural space.
• It includes bike trails and softball diamonds so you can play sports.
• It’s also known as a public art space, so there’s no shortage of things to see.

Why it’s so awesome : Grant Park is located between the city and the riverfront so it’s basically Chicago’s front yard. This is the perfect place to enjoy a bit of nature, get your blood pumping with some sports, or take advantage of the free music concerts that are frequently held in the area. There are also a number of art installations around the park, so no matter what you’re interested in, you’ll find something to occupy your time here.

What to do there : While you’re in the area you can go biking, play some softball or baseball, or just sit on the grass. The gardens themselves are gorgeous and well worth a look on their own, but you should also have a look at the headless figures dotted throughout the landscape. These art installations are striking and make an interesting statement about modern life.

#14 – Cloud Gate

• An odd, fascinating piece of artwork.
• A great place for photos.
• The ‘Bean’, as it’s known, as become Chicago’s most iconic piece of art.

Why it’s so awesome : Cloud Gate is a futuristic, silvery bean that was put in place during the grand opening of Millennium Park. It has a shiny exterior surface that reflects everything around it in a distorted and highly entertaining way. Looking at the bean is a little like being in a mirror house, except for the fact that everything from the sky to the buildings to the people are reflected, versus just a single person.

What to do there : There are pictures of the ‘bean’ all over social media, so why not join the crowd? You can get a great shot of the Chicago skyline all twisted by the surface of this slightly odd piece of artwork. But you can do more than look at it. This piece of art is meant to be touched and its shiny, smooth surface makes it irresistible, so don’t try to fight the urge!

#15 – The Chicago Theater

• Interesting architecture.
• The theater has played host to lots of big stars, so if you’re interested in celebrity culture then this is the place to go.

Why it’s so awesome : The theater itself is beautiful. It boasts a vertical Chicago sign that’s almost six stories high and lights up the night. But even if you aren’t interested in architecture than go for the shows. This theater is known as a hub for great entertainment and has hosted stars like Dolly Parton, Aretha Franklin, Oasis and Ellen Degeneres. So, if you’re looking for a great show to watch, you’ll probably find it at this theater.

What to do there : Get dressed up and see a show. This theater used to be a movie mansion, but now it hosts live theater with amazing productions and stars. So, if you feel like having an elegant night on the town, then make this a part of your evening.

#16 – Chicago Lakefront Trail – A beautiful and scenic place to check out in Chicago

• Great views of Lake Michigan!
• The most scenic route you can take to Chicago’s hotspots.
• A great way to get some exercise in beautiful surroundings.

Why it’s so awesome : Lake Michigan is iconic, and you’ll never be able to get a better view than along this trail. It’s 18 miles of stunning views of both nature and the city and is the ideal way to travel when you have a little extra time and don’t mind the walk. There are also several beaches, parks and attractions along the way, so you don’t have to go one more step than you want to.

What to do there : Run, walk or job along the lakefront if you want to get some exercise in during your stay. And if you’re just there for the views and the experience, walk a little way and then stop off at some of Chicago’s best attractions. The Field Museum of Natural History and the Shedd Aquarium are both easily accessible from the walk, so you don’t have to stick it out for the whole 18 miles.

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#17 – Wrigley Stadium – A must visit place to visit in Chicago on the weekend!

• Home to Chicago’s iconic sports team, the Cubs!
• If you manage to grab a game, it’s a great afternoon out with snacks and an exciting vibe!
• You can also visit the souvenir store and take home some Cubs memorabilia!

Why it’s so awesome : Chicago is a city that loves its sports which, is why going to a game is a must-do while you’re in Chicago. Even if you don’t like sports, the trashy food, the excitement, and the entertainment that goes on throughout the day make it well worth the trip.

What to do there : If it’s the right time of year, then you absolutely must go and see a game. There’s something about seeing a sport in real life, with thousands of other fans, that just can’t be missed. Games are a big deal in this city, so there’s no shortage of food and non-stop entertainment for you to enjoy on game days.

#18 – Chicago Cultural Center

• Great for music and lovers of art of all kinds.
• Lots of free public events are held in this building.
• Brings culture, history and art together in a stunning and fascinating display.

Why it’s so awesome : If you want to learn more about any facet of Chicago then you’ll probably be able to learn it here. This beautiful building is a masterpiece on its own, but it’s also home to the city’s best music and art scene. You can see movies, dance performances, theater, and art exhibitions at any time of year. And there’s always something going on, so make sure you check out what’s on offer while you’re in the city.

What to do there : There’s so much to do in the Cultural Center that it can be hard to choose what to do first. Visit the building for Chamber Mondays and delight in the shows put on by jazz, classical and ethnic musicians. Or take the building tour and learn about its many stunning features including the world’s largest stained glass Tiffany dome that holds pride of place at the top of the building.

#19 – Lincoln Park

• The park is a beautiful natural area by day.
• At night it’s part of Chicago’s exciting night life.
• Great for photographers and nature lovers.

Why it’s so awesome : Most of the attractions in Lincoln Park are free, which makes the area the perfect place to spend an afternoon without spending all your money. And it’s great for the family too, with a range of exhibits that kids of all ages will enjoy as well as some great dining options.

What to do there : Make sure you check out Lincoln Park Zoo if you’re visiting with the family or just enjoy seeing animals without paying an admission fee. You can also check out the Lincoln Park Conservatory and other attractions dedicated to different types of plants and the most beautiful parts of nature. And when you’re tired of all that green, you can head up to the beach area to get your feet wet or visit one of the cafes in the area for a nice relaxing snack and sit down.

#20 – Chicago Botanic Garden

• A great place to have a break from the city.
• The beautiful displays look great in photos.
• There’s a tram tour of the garden if you don’t feel up to walking it.

Why it’s so awesome : There’s nothing like exploring a bit of nature when you’re spending most of your time in the city. The Chicago Botanic Gardens are beautiful, expansive, and include a number of displays that will delight anyone. You will be able to relax in this area while you’re entertained and educated at the same time, and even the kids will like it so much that they won’t notice they’re actually learning!

What to do there : Take the narrated tram tour around the gardens to you can get an idea about the layout of the area. This will help you to find your favorite places later! And also make time to explore the Waterfall Garden and the English Oak meadow to glimpse beautiful and vibrant natural worlds that will make you feel like you’re a world away from the busy city!

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#21 – Logan Arcade – Easily one of the most fun places to check out in Chicago

• A chance to revisit some old favorite pastimes.
• You’ll get to play arcade games and drink at the same time.
• This is one of the best and the biggest arcade bars in the city.

Why it’s so awesome : Arcade bars are extremely popular in Chicago and the city has a few of them. Logan’s Arcade has one of the largest collections of well-maintained arcade games, which makes it a standout in this group. You’ll get to play all your old favorites and see for yourself if you still have the knack.

What to do there : Unapologetically retro, these types of venues play into the best parts of the past and will probably be a lot more fun than you think. Make sure you have a look around at the arcade games and find the ones you remember playing when you were younger. They have old favorites like Mario Kart, Ms. Pac Man and Jurassic Park, and you can have a drink while you play too, which just doubles the enjoyment.

#22 – Neo Futurarium

• A theater with a difference.
• The shows are different every time.
• Great for people who enjoy the unusual and the quirky.

Why it’s so awesome : This is a show that prides itself on leaving behind the restrained, polite world of the theater in favor of pure madness. It’s a 60-minute show that includes 30 miniature shows, all of them different and with a zany energy that’s infectious and sometimes just crazy! You’ll never know what you’ll get to see here, so just sit back and enjoy the spectacle!

What to do there : When you buy your ticket for this venue, you’ll have to pay a price that’s based on the roll of a dice. So, if you’re really lucky you could end up paying almost nothing. And this barrier to entrance is indicative of the tone of the entire show, so you have been warned. Strange as it sounds, you need to sit back, enjoy the show, and expect to be surprised when you spend time here.

#23 – The Robie House – A great place to see in Chicago if you love architecture

• Created by the famous architect Frank Lloyd Wright.
• A marvel of engineering and naturalistic lines and shapes.
• Take a tour to get the most from the experience.

Why it’s so awesome : Frank Lloyd Wright was a maverick in the field of architecture and his work stands as a symbol of the new style he inspired. The Robie House is one of his best pieces of work and you don’t have to leave the city to see it. The art-glass windows alone are worth the trip there, and the rest of the house is one of the best examples of Wright’s Prairie School style that you’ll ever see. We really wish this place was an Airbnb, but you’ll have to settle for one of the great Chicago Airbnb’s nearby and hope they’ve copied the architecture.

What to do there : Unless you’re an architecture student or an architect yourself, make sure that you take the tour through the Robie House. This is the best way to ensure that you get the full effect and that you understand just how significant this architectural style was in the past and how it still affects our present.

#24 – Boystown

• The center of homosexual culture in Chicago.
• One of the best places in the city to go bar hopping.
• Has everything from cocktail bars to drag shows and famous gay bars.

Why it’s so awesome : If you like to bar hop then this is one of the most colorful places in the city to do it. Make sure you visit a few different venues while you’re in the area because this location boasts everything from amazing cocktail bars to drag shows that will have you in stitches. And the lively atmosphere is something that must be seen to be believed, so add it to your Chicago itinerary!

What to do there : There are a lot of bars and restaurants in this area but make sure you check out perennial favorite Sidetrack, have a cocktail at the Elixir bar, and watch a drag show at the Kit Kat bar.

#25 – Half Acre Brewery Balmoral

• A behind the scenes look at the brew scene.
• This venue has beers that you can’t get anywhere else, so if you enjoy unusual beer, then try some of what’s on offer.
• A quick, educational tour that ends with a beer. Does it get any better than that?

Why it’s awesome: Unusual brews, free samples, and a cheap and interesting tour that teaches you the basics about what you’re drinking. No matter what brew you enjoy you’ll find it and learn about it here, and you might find a new favorite while you’re at it!

What to do there : For 10 dollars you can take a tour of the brewery and learn about how your favorite drinks get from field to the bottle. You’ll learn a little something and get some free samples as an added bonus. Sounds like the perfect lazy afternoon!

#26 – The United Center

• Home of the Chicago Bulls.
• Once home of that legendary player, Michael Jordan!
• A great place to see a game and enjoy fattening snacks.

Why it’s so awesome : Chicago is a town that loves its sports, all sports, and this stadium is a great place to see a game and start to understand why. During basketball and hockey season you can see games here. And in the off-season, the venue holds some of the biggest music concerts in the city!

What to do there: When you’re going to see a sporting event you need to get into the spirit and try everything that’s on offer. Eat fattening food, cheer for your favorite team, and generally get caught up in the madness. And if you admire Michael Jordan, and who doesn’t, make sure you get a photo with his statue in the venue’s public atrium. If you don’t like sports, keep an eye out for any musical events the venue has planned. Everyone from U2 to Madonna has played here, so if there is a concert on, it’ll probably be amazing!

#27 – Rainbow Cone

• An iconic ice cream shop in Chicago.
• Home to some of the most amazing flavors as well as some more unusual choices!
• Great for kids and anyone who has a sweet tooth.

Why it’s so awesome : This shop is iconic in Chicago and one of the best places to get a sweet treat on a hot afternoon. The shop first opened in 1926 and is colored bright pink, so there really is no way to miss it.

What to do there: What else? Try some ice cream. You’ll find old favorites here such as delectable strawberry and diet busting worthy chocolate as well as some unusual flavors you probably haven’t tried before. And if you’re not in the mood for ice cream, they have some great sundaes, cakes and shakes as well.

#28 – The Signature Lounge – A great place to visit in Chicago at night

• An iconic bar.
• Panoramic views of the city at night that you can take in through the floor to ceiling windows.
• A long popular bar with great cocktails.

Why it’s so awesome : Taking in the lights of a city at night is amazing and it’s even better when you can do it with a drink in your hand. This bar, located at 875 N Michigan Avenue, has been the place to look at the lights with a drink in hand for years. Locals never get sick of that view, and neither will you once you relax and take it in.

What to do there : This is a place to relax, order your favorite drink, and take in the lights. It’s located on the 96th floor above the Hancock Observatory. So, rather than paying the entrance fee to the Observatory, just pay for your drink and take in the view from a comfortable chair.

#29 – Stony Island Arts Bank

• An old bank that was converted into an art gallery and media archive.
• It has free art exhibitions on the ground floor showcasing some of the best parts of the city’s media history.
• A great place to experience a slice of Chicago’s past.

Why it’s so awesome : Sometimes we forget that the internet and CD’s and online music haven’t always existed. In reality, these things are fairly new, and not so long ago there were other ways for artists to share their work with the world. And this is the place where you can experience that slice of the past and gain an appreciation for the changes and how lucky we are to live in an age driven by technology.

What to do there : Firstly, spend some time on the bottom floor and take in the art, which often showcases some of the best artists in the US. And when you’re done with that, go upstairs to see the permanent collections. You’ll see record collections, slides from Chicago University, and other ways that people showed off their work in times gone by.

#30 – Jackson Park – Quite the quirky place in Chicago!

• Home to one of Yoko Ono’s quirky creations.
• A very photogenic place where you can take a more unusual picture of your travels.
• Great for art lovers.

Why it’s so awesome : Yoko Ono is a controversial figure even today, and most people don’t even know that she was also an artist in her own right. This display of her work in the Garden of the Phoenix in Jackson Park is an indication of her talent and her vision. it’s become a major draw for tourists in recent years, so make sure you check out what all the hype is about.

What to do there : Take a photo next to one of the quirky, slightly strange looking installations before you move on to explore other parts of the garden. There’s actually a beautiful Japanese garden known as the Osaka Japanese Garden in the park as well. It’s laid out in a traditional style and is a relaxing, restorative place to spend some time.

#31 – Kingston Mines

• One of the oldest blues bars in the city.
• Two different stages where you can experience different sides of this soulful sound.
• Great for music lovers.

Why it’s so awesome : Chicago has an exciting music scene and blues music is a mainstay here, so you absolutely must catch a show and see what all the hype is about. The Kingston Mines is the oldest continuously operating blues club in the city, and it has an infectious energy that always makes for a fun night.

What to do there: This bar is open most nights of the year until late and features some of the best blues music in the city. It’s a high energy place, so make sure you come expecting to have a loud and lively night!

#32 – Montrose Beach

• A quieter beach that’s slightly off the beaten track.
• There are less tourists here, which makes for a more relaxing atmosphere.
• A great place to soak up the sun!

Why it’s so awesome : You probably don’t think of beaches in connection with Chicago and yet there are a number of them in the city. The closer the beach is to the Loop, the busier it is, which is why you should spend your time at Montrose Beach. It’s a little further away from the center of the city so it’s less crowded and more conducive to a relaxing afternoon!

What to do there : This beach is great for relaxing, but it also has the same amenities as some of the more popular choices. If you’re feeling energetic you can hire a kayak or play volleyball on the beach. And when you get hungry, there are lots of food places nearby to choose from too.

#33 – Pequod’s – A must-see for foodies!

• A local secret that has amazing Chicago style pizza.
• The place to go for great pizza at non-tourist prices.

Why it’s so awesome : You can’t go to Chicago without trying one of their famous pizzas. They’re super thick, with layers of cheese and sauce, and you can even get a stuffed crust if you want to really ruin your diet. There are a lot of places that sell these pizzas for tourists, but if you’re looking for a more local restaurant then Pequod’s is a great choice. There are two locations in the city, one of them in Lincoln Park, and you’ll get amazing pizza at local prices whichever one you find!

What to do there : Eat one of Chicago’s famous pizzas! This is where the locals come, so you know it’s good, and the prices are excellent. Going at lunchtime is an especially good idea, as you’ll get a pizza for a fraction of the price you’d pay at a more touristy spot.

#34 – Pilsen

• Chicago’s Hispanic Neighborhood.
• Great for foodies who enjoy Mexican dishes.
• There’s also some great street art in this area.

Why it’s so awesome : Spending time in Pilsen is a good way to see another side of Chicago. You’ll eat some amazing Mexican food, learn about another culture, and enjoy the rebellion and color of street art at the same time.

What to do there: This is a great neighborhood if you like to eat. There are a number of incredible eateries in the area including 5 Rabanitos , which offers some of the best meals in the city. Make sure you check out the National Museum of Mexican Art while you’re there and spend some time on 16th and 18th streets, where there are some colorful murals brightening up the buildings.

#35 – Chinatown

• The best dim sums in the city.
• Some amazing teahouses where you can get out of the heat and enjoy some varieties of tea.
• Check out the Chinese-American Museum while you’re there.

Why it’s so awesome : If you want some authentic Chinese food then you’ll find it in this area. Spread out over Cermak Road and Wentworth Avenue, this is a lively area where you can eat, shop and drink tea. There’s also a museum that explores the history of the area and its people which will give you an insight into another facet of Chicago and its culture.

What to do there: While you’re there, make sure you eat. You’ll find some of the best dim sums in the area here, especially in landmark locations like Dolo Chicago , which has a full bar, and Duck Duck Goat , which has a weekend menu to die for.

#36 – Museum of Contemporary Art Chicago

• A smaller, but no less impactful art museum than others in the city.
• Has a permanent collection that showcases Andy Warhol, Francis Bacon and Alexander Calder.
• The venue’s eatery  Marisol  is well worth checking out for the food and the ambiance.

Why it’s so awesome : This imposing building fits perfectly with the contemporary art that it showcases. It houses a smaller collection that’s absolutely fascinating for art lovers and people who are curious about modern art. The restaurant also has a range of startling dishes for brunch, lunch and dinner, so whatever time you go make sure that you check it out!

What to do there : If you’re an art lover then you’ll probably recognize many of the famous names that showcase their art in this museum. But if you don’t know as much about contemporary art then it’s a chance to wander and maybe find some new favorites! Make sure you check out the rotating display as well as the regular one to get the full effects. And grab a snack or a meal at the Marisol restaurant to experience some truly innovative dishes while you’re there.

#37 – Oz Park

• A quirky and whimsical place to spend a couple of hours.
• Great for kids and lovers of the movie or the books.
• A magical wonderland in the middle of the city!
• You’ll get some amazing and slightly quirky photos here too.

Why it’s so awesome : It’s a whole park dedicated to the Wizard of Oz movie and world, how could it not be awesome? This park started its transformation in 1974 and is now filled with Oz-inspired amenities and images. But the best part has to be the statues of the iconic characters who are on display throughout the park.

What to do there : This is a place to wander around and let your imagination go wild. You’ll see a playground called Dorothy’s Playlot and a green space known as the Emerald Gardens as well as all your favorite characters. The park is meant to provide a clean and safe space for children, one that excites their imagination, and it does that very well indeed.

Get insured for your trip to Chicago!

ALWAYS sort out your backpacker insurance before your trip. There’s plenty to choose from in that department, but a good place to start is Safety Wing .

They offer month-to-month payments, no lock-in contracts, and require absolutely no itineraries: that’s the exact kind of insurance long-term travellers and digital nomads need.

SafetyWing is cheap, easy, and admin-free: just sign up lickety-split so you can get back to it!

Click the button below to learn more about SafetyWing’s setup or read our insider review for the full tasty scoop.

Find out what people want to know about the best places to visit in Chicago

What is the number 1 place to visit in Chicago?

The Navy Pier is the most popular tourist attraction in Chicago and is full of gardens, shops, restaurants and parks.

Is 2 days enough for Chicago?

If you only want to see the highlights of Chicago, then two days should be enough time to see them all.

What is Chicago famous for?

Chicago is famous for is skyscrapers, deep dish pizzas and mobster routes.

What is the most famous place to visit in Chicago?

Millenium Park and Navy Pier are the most famous places to visit in Chicago.

Chicago’s reputation has suffered a bit over the last few years, but this doesn’t mean that you should avoid the city. As long as you’re careful and stay away from certain key areas, your visit to Chicago should be safe and filled with great food, entertainment and amazing sites! So make sure you visit some of your favorite sites on this list, and you’ll see why people say that Chicago is one of the most exciting and interesting cities in the world.

And for transparency’s sake, please know that some of the links in our content are affiliate links . That means that if you book your accommodation, buy your gear, or sort your insurance through our link, we earn a small commission (at no extra cost to you). That said, we only link to the gear we trust and never recommend services we don’t believe are up to scratch. Again, thank you!

Aiden Freeborn

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Le Travel Style

by Courtney Delfino • a San Diego based travel + lifestyle blog inspiring you to travel in style

Travel , Travel Guides , USA · Last Updated: February 17, 2024

How to Spend 3 Days in Chicago: a Chicago Itinerary

A full 3 days in chicago itinerary.

So you only have 3 days in Chicago? Well, that is the perfect amount of time to explore the Windy City. Chicago, also known as the “Windy City”, is one of the largest and most vibrant cities in the United States. This Midwestern metropolis has something for everyone, from world-class museums and stunning architecture to trendy neighborhoods and delicious food.

It’s one of my favorite cities because it has a little something for everyone to enjoy. The people are pure gold, the food is *chefs kiss*, and there are ample things to do in Chicago. In this “3 Days in Chicago Itinerary”, I’m sharing everything to know before visiting so you can truly enjoy all it has to offer!

Best Time to Visit Chicago

They don’t call it the windy city for anything! The temperatures in Chicago can drop below zero in the winter so it’s best to travel to Chicago from May-July and September-November. Where the weather is mild and you’ll be able to enjoy walking around the city without freezing. Finally, St. Patricks Day is the most popular time to visit Chicago. The riverwalk turns green to celebrate the occasion and the entire city takes place in the festivities.

While all opinions and recommendations are always my own, my content on this blog post may contain affiliate links for hotels I’ve traveled to, tours I’ve completed, and products I recommend. This means I get a small commission (at no additional cost to you) if you book a stay or purchase a product after clicking one of these links. As always, I am so thankful for your support so I can continue to offer free resources.

Where to Stay in Chicago

Chicago has no shortage of beautiful hotels to choose from. If you’re like me and love a little luxury then I highly recommend these two hotels:

• The Langham Chicago: luxury at its finest with the best views of the riverwalk. Make sure to take advantage of their club access when staying it includes breakfast, lunch, and dinner. Experiencing the Langham Club was incredible I think about those stunning views often. Book your stay here !
• The Four Seasons: the ultimate 5-star hotel close to all the major shops. This hotel offers incredible service and rooms, beautiful views of the lake, and the tastiest in-house restaurant, Adorn. Book your stay here !

Mid-range hotels:

• The Pendry: located right across from Millennium Park this hotel is in a prime location. Book your stay here !
• Kimpton Gray Hotel: also located near millennium park this hotel offers packages that include food as well. Book your stay here !

Best Things to Do in Chicago

Millennium park.

Home to the infamous bean (which is properly named the Cloud Gate sculpture), Millennium Park is a must-see for every visitor. Take a stroll through the park and enjoy the public art and green spaces. The bean sculpture is the most famous landmark in this city and with the Chicago skyline in the background, it makes for the perfect photo opportunity.

Another popular feature of Millennium Park is the Jay Pritzker Pavilion, an outdoor concert venue that hosts concerts, festivals, and other events throughout the year. The pavilion is famous for its unique design, which includes a trellis made of stainless steel that curves over the stage and a sound system that provides excellent acoustics.

Millennium Park is open year-round and admission is free. It’s a popular destination for both tourists and locals, and there are always events and activities happening in the park. Whether you’re looking to take in some art, catch a concert, or simply enjoy a sunny day in the city, Millennium Park is a must-visit destination in Chicago. Finally, it’s magical to visit during the fall.

Architecture River Cruise

If you’ve seen “My Best Friends Wedding” then you’ll remember when Julia Roberts is dancing with Michael atop the Architecture River Cruise. It’s one of the most popular things to do in Chicago. A must-see for your 3 days in Chicago.

During the 90-minute tour, knowledgeable guides provide insight into the history and design of each building, offering a fascinating look at the city’s rich architectural heritage. Some of the highlights of the tour include the Wrigley Building, the Tribune Tower, the Marina City complex, and the Willis Tower (formerly known as the Sears Tower).

There is nothing like admiring architecture from the water. Overall, the Chicago Architecture Foundation River Cruise and walking tours are a must-do for anyone interested in architecture, history, or just taking in the stunning views of the city. There are ample architecture tours to choose from!

Walk the Chicago Riverwalk

The Chicago Riverwalk is a picturesque pedestrian walkway along the Chicago River that offers stunning views of the city skyline. Visitors can enjoy drinks at one of the waterfront bars, take a boat tour, or simply stroll along the river.

This 1.25-mile path is a treasured natural amenity for residents and tourists alike. You choose to walk, run, or just sit on a bench and admire you’ll experience the prettiest views of the city. It’s open from 6 am – 11 pm and is best experienced in the early morning while the city is still sleeping. Furthermore, you’ll recognize this spot from many movies including one of my personal favorites, While you Were Sleeping .

Visit the Art Institute of Chicago

Chicago is also home to several world-renowned museums, such as the Art Institute of Chicago, the Museum of Science and Industry, and the Field Museum. The Art Institute houses an impressive collection of art, including works by famous artists such as Monet, Van Gogh, and Picasso. The Museum of Science and Industry features fascinating exhibits on space exploration, genetics, and other scientific topics. The Field Museum is a natural history museum that has exhibits on dinosaurs, ancient cultures, and much more.

Depending on your preference either of those museums are a great way to spend an afternoon in Chicago. Book your tickets in advance!

Walk around Lincoln Park

Lincoln Park is Chicago’s largest park bordering the most affluent neighborhoods in the city. It’s an oasis to the locals from the bustling city of Chicago. One of the main attractions in Lincoln Park is the Lincoln Park Zoo, which is free to the public and open year-round. The zoo features a wide variety of animals, from big cats and primates to reptiles and birds. It also has a beautiful nature boardwalk that provides stunning views of the Chicago skyline.

Another popular attraction in Lincoln Park is the Honeycomb. This structure is unique and offers unique views of the chicago skyline. When visiting, you’ll be surrounded by nature while admiring the skyline from afar. Make sure to wear your walking shoes when exploring this beautiful part of the city. Finally, it’s especially pretty to visit in the fall to witness the changing leaves against the cityscape.

Willis Tower/Skydeck Chicago

The Skydeck Chicago is an observation deck located on the 103rd floor of the Willis Tower (formerly known as the Sears Tower) in downtown Chicago. It’s one of the city’s most popular attractions, offering stunning views of the city and Lake Michigan.

The Skydeck experience begins with a high-speed elevator ride to the top of the tower, which takes less than a minute. Once you arrive, you can step out onto the glass-floored Ledge, a series of glass boxes that extend out from the side of the building. The Ledge provides a unique and thrilling experience for visitors, as they can see the city from a completely different perspective, with nothing between them and the street below but a layer of glass.

Fun fact, you can see four states from the observation deck. It’s most definitely an experience everyone needs to try when visiting. Because of it’s popularity, it is extremely busy so make sure to book your time slots in advance!

The Chicago Theatre

An icon! The Chicago Theatre rivals “the bean” for the most photographed part of the city. This legend was built in 1921 and was America’s first large movie palace. Even if you’re not going to a show, you need to visit the famous marquee. Click here for a show schedule.

The Magnificent Mile

If you’re an avid shopper then The Magnificent Mile is the place for you. This street spans one mile of high-end luxury stores, beautiful architecture, and top-notch eateries. It’s the perfect place to spend an afternoon and grab lunch when you only have 3 days in Chicago.

Visit Milton Lee Olive Park

Located close to Navy Pier is Milton Lee Olive Park. It’s lesser known spot overlooking Lake Michigan featuring stunning views of the skyline. Finally, it’s a secluded spot to the city often with runners and locals taking their daily walk.

Other things to do in Chicago if you have time:

• Visit Navy Pier
• Catch a ball game at Wrigley Field
• 360 Chicago Observation Deck
• Garfield Park Conservatory
• Admire the Architecture at the University of Chicago
• Visit North Avenue Beach
• Visit the Chicago Water Tower

3 Days in Chicago Itinerary

Here’s a summary of a suggested 3-day itinerary for exploring Chicago:

• Visit the Sky Deck for panoramic views of the city
• Walk the Chicago Riverwalk for waterfront views, drinks, and boat tours
• Take an Architecture River Cruise
• Dinner at Beatnik on The River
• Visit Millennium Park
• Explore the Art Institute of Chicago for impressive art collections
• Shopping on the Magnificent Mile
• Lunch at Three Arts Cafe
• Walk around the Gold Coast Neighborhood
• Stroll through Lincoln Park and visit the Honeycomb
• Breakfast in the trendy River North neighborhood
• Explore Navy Pier for entertainment, shopping, and dining
• Check out Milton Lee Park for unique views
• Have dinner at Pequod’s restaurant and catch a show at The Chicago Theatre

Where to Eat in Chicago

When it comes to food, Chicago is famous for its deep-dish pizza. There are several restaurants throughout the city where you can try this classic dish. However, Chicago is also home to a diverse range of cuisines, from hot dogs and Italian beef sandwiches to Korean BBQ and sushi. I’ve listed the top picks below:

• Three Arts Cafe ($$$$): Did you really visit Chicago if you didn’t go to Three Arts Cafe? The prettiest restaurant in Chicago. Located inside the Restoration Hardware store this cafe is heaven. Don’t sleep on the burger, the best one I’ve ever had in my life!
• Beatnik on the River ($$$): amazing views of the riverwalk and delicious Mediterranean-inspired foods.
• Adorn ($$$$): located in the Four Season Hotel, Chef Jonathon Sawyer is cooking up award-winning dishes featuring global-inspired cuisine. Get the poutine and thank me later!
• Pequod’s ($$): the locals love this spot for the most famous Chicago dish, deep-dish pizza. Being from New York, I’m a hard one to judge but this was surprisingly good. Chicago deep-dish pizza is not your average pizza and reminds me more of a casserole dish. But nonetheless, still tasty!
• Portillo’s ($): when visiting Chicago you NEED to get a famous Chicago dog. Portillos is the most famous spot with locations all around the city. What makes Chicago Dogs special is its poppy seed bun.
• Do-Rite Donuts & Chicken ($)
• Girl & The Goat ($$$)

What to Pack for Chicago

• If you’re traveling during the colder months make sure to have a warm coat. I’m talking about a puffer jacket. We all want to look cute but when walking around Chicago I highly suggest this puffer coat .
• Warm socks to keep your feet warm
• A comfortable but cute pair of booties . I love these chic ones, they’re comfortable for walking!
• A warm beanie
• A good scarf
• My favorite leather leggings that pair nicely with the booties

Thank you for reading my 3 day Chicago itinerary. Chicago is a city that has something for everyone. Whether you’re interested in museums, food, architecture, or simply exploring unique neighborhoods, Chicago is a destination worth visiting.

I hope you have a fabulous time exploring the windy city. If you need more help packing you don’t want to miss my “ 22 Travel Essentials for your next trip ” post. Enjoy your trip!

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XX, Courtney

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February 21, 2023 at 7:41 am

Chicago during the fall is so gorgeous! These are all really great suggestions, especially all the pretty photo spots near Lincoln Park.

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Fun Places to Eat in Chicago: A Guide to the Best

I f you’re looking for fun places to eat in Chicago, you’re in luck. The city is known for its diverse and vibrant food scene, with something for everyone. From quirky and unique dining experiences to classic Chicago-style deep-dish pizza, there’s no shortage of delicious options.

Whether you’re in the mood for something quirky or upscale, Chicago has plenty of fun places to eat that are sure to satisfy your cravings.

Iconic Chicago Eateries

If you’re looking for a taste of Chicago, you can’t miss out on these iconic eateries. From deep-dish pizza to Chicago-style hot dogs, these spots are a must-visit for any foodie.

Deep Dish Pizza Spots

Chicago is famous for its deep-dish pizza, and for good reason. These spots serve up some of the best pies in town:

• Lou Malnati’s : With locations all over the city, Lou Malnati’s is a Chicago staple. Their deep-dish pizza is a must-try, with a buttery crust and plenty of cheese and toppings.
• Giordano’s : Another classic Chicago pizza joint, Giordano’s is known for its stuffed pizza. The pizza is so thick and filling that one slice is often enough to satisfy even the hungriest of diners.
• Pequod’s Pizza : If you’re looking for a unique take on deep-dish pizza, check out Pequod’s. Their pizza has a caramelized crust that adds a delicious sweetness to every bite.

Ethnic Cuisine in Chicago

If you’re looking for a taste of the world, Chicago is the place to be. With a diverse population, you can find a wide range of ethnic cuisines here. Here are a few neighborhoods and restaurants to check out:

Chinatown Dining

Chicago’s Chinatown is a vibrant neighborhood that’s home to some of the best Chinese food in the city. Here are a few restaurants to try:

• MingHin Cuisine : This popular restaurant is known for its dim sum. They have a huge selection of steamed and fried dumplings, as well as other traditional Chinese dishes.
• Cai : If you’re looking for something a little more upscale, check out Cai. This restaurant serves modern Chinese cuisine in a sleek, contemporary setting.
• Lao Sze Chuan : This restaurant is famous for its spicy Szechuan cuisine. If you’re a fan of heat, you won’t be disappointed.

Little Italy Favorites

Chicago’s Little Italy neighborhood is home to some of the best Italian food in the city. Here are a few restaurants to check out:

• Tuscany : This cozy restaurant serves classic Italian dishes like lasagna, spaghetti carbonara, and chicken parmesan. They also have an extensive wine list.
• Rosebud : This popular chain has several locations throughout the city, but the Little Italy restaurant is the original. They serve classic Italian-American dishes like meatballs and spaghetti, as well as steaks and seafood.

Mexican Food in Pilsen

Pilsen is a predominantly Mexican neighborhood that’s home to some of the best Mexican food in the city. Here are a few restaurants to try:

• Carnitas Uruapan : This casual restaurant is known for its carnitas, which are slow-cooked pork that’s crispy on the outside and tender on the inside. They also serve other traditional Mexican dishes like tacos and tamales.
• Nuevo Leon : This family-owned restaurant has been serving Mexican cuisine for over 40 years. They’re known for their homemade tortillas and mole sauce.
• La Casa Del Pueblo : This grocery store has a small restaurant inside that serves delicious Mexican food. They’re known for their tacos al pastor, which are made with marinated pork that’s cooked on a spit.

Upscale Dining

If you’re looking for a fancy dining experience in Chicago, you won’t be disappointed. The city is home to some of the best upscale restaurants in the world, with Michelin star ratings and stunning rooftop views.

Want a Michelin-Starred Restaurant?

Chicago has a total of 25 Michelin-starred restaurants, making it one of the top cities for fine dining in the world. Here are a few of the most notable ones:

• Alinea : This three-star restaurant is one of the most famous in the city. The 15-course tasting menu is a culinary journey that combines flavors from around the world.
• Oriole : This two-star restaurant is known for its contemporary American cuisine. The tasting menu changes frequently to reflect the seasons and the chef’s inspiration.
• Next : This two-star restaurant offers a unique dining experience with a constantly changing theme. Past themes have included Paris 1906, The Hunt, and Hollywood.

Rooftop Dining

Chicago’s skyline is one of the most iconic in the world, and there’s no better way to enjoy it than from a rooftop restaurant. Here are a few of the best options:

• Cindy’s : Located on the rooftop of the Chicago Athletic Association Hotel, Cindy’s offers stunning views of Millennium Park and Lake Michigan. The menu is a mix of classic American dishes and creative cocktails.
• The J. Parker : This rooftop bar and restaurant is located on top of the Hotel Lincoln in Lincoln Park. The views of the city skyline are breathtaking, and the menu features small plates and craft cocktails.
• The Terrace at Trump : This upscale restaurant is located on the 16th floor of the Trump International Hotel and Tower. The views of the Chicago River and the Magnificent Mile are unparalleled, and the menu features classic American cuisine with a modern twist.

Whether you’re celebrating a special occasion or just want to treat yourself to a fancy meal, Chicago’s upscale dining scene has something for everyone.

Unique Dining Experiences

Chicago is known for its food scene, and there are plenty of unique dining experiences to be had in the city. From themed restaurants to waterfront dining, there’s something for everyone. Here are some of the best unique dining experiences in Chicago.

Themed Restaurants

If you’re looking for a dining experience that’s a little out of the ordinary, Chicago has plenty of themed restaurants to choose from. Here are a few of the most popular:

Waterfront Dining

Chicago is located on Lake Michigan, and there are plenty of restaurants that take advantage of the city’s waterfront location. Here are a few of the best:

Whether you’re looking for a themed dining experience or a meal with a view, Chicago has plenty of unique options to choose from.

Late Night Eats

Chicago is a city that never sleeps, and that means you can get a great meal at any time of the day or night. Whether you’re craving a hearty burger, a slice of pizza, or something a little more exotic, there’s always somewhere to satisfy your hunger. Here are some of the best late-night eats in Chicago.

Location: 2833 W Armitage Ave Chicago

Gretel is a Logan Square restaurant that’s open until midnight on weekdays and 1 a.m. on weekends. The food is a mix of German and Scandinavian cuisine, with dishes like schnitzel, spaetzle, and gravlax on the menu. The atmosphere is cozy and intimate, with wood-paneled walls and dim lighting. The cocktails are also excellent, with creative twists on classic drinks like the Old Fashioned.

Location: 2521 N Milwaukee Ave Chicago

The Owl is a 4 a.m. bar and restaurant in Logan Square that’s been a favorite of Chicagoans for years. The menu is simple but satisfying, with classic bar food like burgers, fries, and wings. The drinks are also excellent, with a wide selection of beers on tap and creative cocktails like the Spicy Margarita. The atmosphere is laid-back and welcoming, with a mix of locals and tourists hanging out until the early hours of the morning.

Furious Spoon

Location: 2410 N Milwaukee Ave Chicago

Furious Spoon is a ramen restaurant with locations all over Chicago, including one in Wicker Park that’s open until 2 am on weekends. The menu is simple but delicious, with a variety of ramen bowls to choose from, including vegetarian options. The atmosphere is casual and fun, with a hip-hop soundtrack and graffiti-covered walls. The cocktails are also worth trying, with creative twists on classic drinks like the Moscow Mule.

The Chicago Diner

Location: 2333 N Milwaukee Ave Chicago

The Chicago Diner is a vegetarian and vegan restaurant that’s been a staple of the city since 1983. The Logan Square location is open until midnight on weekdays and 1 am on weekends, making it a great spot for a late-night meal. The menu is extensive, with everything from burgers and sandwiches to salads and smoothies. The atmosphere is cozy and welcoming, with a retro diner vibe that’s perfect for a late-night hangout.

The Wiener’s Circle

Location: 2622 N Clark St Chicago

The Wiener’s Circle is a late-night hot dog stand in Lincoln Park that’s been around since 1983. The menu is simple but satisfying, with classic Chicago-style hot dogs, burgers, and fries. The real draw, though, is the atmosphere, which is loud, raucous, and often profane. The staff is known for their insults and banter, which can be both hilarious and offensive. If you’re looking for a true Chicago experience, The Wiener’s Circle is a must-visit.

Family-Friendly Restaurants

Chicago is a great place to take your family out for a meal. There are a variety of restaurants that cater to families with children of all ages. Here are some of the best family-friendly restaurants in Chicago.

Wildberry Pancakes & Cafe

Location: 130 E Randolph St Chicago

Wildberry Pancakes & Cafe is a great place to take your family for breakfast or brunch. This restaurant is located across from the iconic Millennium Park and offers a variety of delicious pancakes, waffles, and other breakfast items. They also have a kids’ menu with options like chocolate chip pancakes and French toast sticks.

Do-Rite Donuts & Chicken

Location: 233 E Erie St Chicago

Do-Rite Donuts & Chicken is a casual restaurant that serves up some of the best-fried chicken and donuts in Chicago. They have a kids’ menu with options like chicken tenders and grilled cheese sandwiches. Plus, their donuts are a hit with kids and adults alike.

The Polo Inn Bridgeport U.S.A.

Location: 3322 S Morgan St Chicago

The Polo Inn Bridgeport U.S.A. is a family-owned restaurant that has been serving up classic American dishes for over 60 years. They have a kids’ menu with options like mac and cheese and chicken tenders. Plus, their friendly staff will make you and your family feel right at home.

Revival Food Hall

Location: 125 S Clark St Chicago

Revival Food Hall is a great place to take your family if you’re looking for a variety of options. This food hall features a little bit of everything from some of Chicago’s best restaurants. They have options like tacos, pizza, sushi, and more. Plus, there’s plenty of seating so you can enjoy your meal with your family.

Overall, Chicago has plenty of family-friendly restaurants that will make your dining experience enjoyable for both you and your children.

Chicago is known for its hot dogs, and for good reason. The city has a long history of unique and delicious hot dog stands, each with their own take on the classic Chicago-style dog. Here are a few of the best places to grab a hot dog in the Windy City:

Gene & Jude’s Red Hot Stand

Location: 2720 N River Rd River Grove

Located in the suburbs, Gene & Jude’s Red Hot Stand is a must-visit for hot dog enthusiasts. The stand has been around since 1946 and is known for its simple, no-frills approach to the classic Chicago-style dog. Don’t ask for ketchup here – they don’t have it.

Instead, enjoy your hot dog topped with mustard, relish, onions, and sport peppers. Don’t forget to order a side of their famous fries, which are served on top of the hot dog for a truly unique experience.

Location: 3343 W. Addison Street Chicago

Portillo’s is a Chicago institution and a popular spot for locals and tourists alike. Their hot dogs are made with Vienna Beef and topped with mustard, relish, onions, tomatoes, pickles, and sport peppers. They also offer a variety of specialty hot dogs, such as the Jumbo Chili Cheese Dog and the Bacon Chili Cheese Dog. Be sure to save room for one of their famous chocolate cake shakes!

Tip: Be sure to join their app and get a free dessert with your birthday dinner.

Location: 6363 N Milwaukee Ave Chicago

Superdawg is a classic drive-in hot dog stand that has been around since 1948. The stand is known for its signature “Superdawg,” which is a hot dog topped with mustard, piccalilli, a dill pickle spear, chopped onions, and a hot pepper. The stand is also known for its unique decor, which includes two giant hot dogs on the roof.

Fatso’s Last Stand

Location: 2258 W Chicago Ave Chicago

Fatso’s Last Stand is a popular spot in Ukrainian Village for late-night eats. Their hot dogs are made with Vienna Beef and topped with a variety of creative toppings, such as giardiniera, bacon, and mac and cheese. They also offer vegetarian and vegan options, including a vegan hot dog topped with vegan chili and vegan cheese.

Whether you’re a Chicago native or just visiting, be sure to check out one of these hot dog stands for a true taste of the city.

Best Burgers

Chicago is famous for its deep-dish pizza, but it’s also home to some of the best burgers in the country. Whether you’re in the mood for a classic cheeseburger or something more creative, Chicago has got you covered. Here are some of the best places to grab a burger in the Windy City.

Location: 800 W Randolph St Chicago

Au Cheval is a must-visit for any burger lover. This West Loop spot has been named the best burger in America by numerous publications, and for good reason. The burger is made with two thin patties, American cheese, dijonaise, and house-made pickles, all served on a toasted bun. It’s simple, but it’s executed perfectly. Be prepared to wait, though – Au Cheval is always packed.

The Loyalist

Location: 177 N Ada St Ste 001 Chicago

The Loyalist is a cozy basement bar in the West Loop that serves up one of the best burgers in the city. The Loyalist Original Cheeseburger is a double patty burger topped with American cheese, lettuce, onion, and a special sauce. It’s juicy, flavorful, and incredibly satisfying. The Loyalist also has a great cocktail menu, so be sure to grab a drink while you’re there.

Kuma’s Corner

Location: 852 W Fulton Market Chicago

Kuma’s Corner is a heavy metal-themed burger joint with several locations throughout the city. The burgers are named after metal bands and are piled high with toppings. The Slayer, for example, is a burger topped with chili, cherry peppers, andouille sausage, andouille aioli, and jack cheese. The burgers are big and messy, but oh so delicious.

Edzo’s Burger Shop

Location: 1571 Sherman Ave Evanston

Edzo’s Burger Shop is a casual spot with locations in Evanston and Lincoln Park. The burgers are made with fresh, never frozen beef and are smashed on the griddle for maximum flavor. The menu is simple, with classic burgers, cheeseburgers, and a few specialty burgers. The truffle aioli burger is a standout – it’s topped with truffle aioli, gruyere cheese, and crispy onions.

Small Cheval

Location: 1732 N Milwaukee Ave Chicago

Small Cheval is the more casual offshoot of Au Cheval, located in Wicker Park and Old Town . The burger is similar to the one at Au Cheval – two thin patties, American cheese, dijonaise, and pickles – but it’s served on a sesame seed bun instead of a toasted bun. The fries are also a standout – they’re crispy and perfectly seasoned.

Chicago has no shortage of great burgers, but these five spots are some of the best in the city. Whether you’re a die-hard burger fan or just looking for a tasty meal, you can’t go wrong with any of these options.

Navy Pier Nibbles

If you’re looking for a fun place to eat in Chicago, Navy Pier is a must-visit destination. This iconic landmark offers a variety of dining options that cater to different tastes and budgets.

Savor the Flavors

One of the best things about Navy Pier is that it offers a diverse selection of cuisines. Whether you’re in the mood for American, Italian, Mexican, or Asian food, you’re sure to find something that satisfies your cravings.

For a taste of Chicago’s deep-dish pizza, head to Giordano’s, which is known for its delicious stuffed pizza. If you’re looking for something more upscale, Riva Crab House offers fresh seafood dishes and stunning views of Lake Michigan.

Grab-and-Go

If you’re short on time or want to eat on the go, Navy Pier has plenty of options for quick bites. From classic Chicago-style hot dogs at America’s Dog to sweet treats at Garrett Popcorn Shops , there’s something for everyone.

Iconic Eats

No visit to Navy Pier is complete without trying some of its iconic eats. The famous Navy Pier Funnel Cake is a must-try, with its crispy fried dough and a generous dusting of powdered sugar.

For a unique twist on a classic dish, head to Lirica , which offers Latin-inspired cuisine with a modern twist. Don’t miss their signature dish, the paella, which is bursting with flavor and served in a traditional cast-iron pan.

Overall, Navy Pier is a great place to grab a bite to eat while enjoying the sights and sounds of Chicago. With so many options to choose from, you’re sure to find something that satisfies your taste buds.

Great Outdoor Patio

When it comes to dining in Chicago, nothing beats the experience of eating outdoors on a beautiful day. Granted, this is only during the summer months, but only the people in the Midwest know how to make the most of downtown Chicago.

Luckily, the city is full of great restaurants with outdoor patios that offer stunning views and delicious food. Here are some of the best outdoor patios in Chicago that you should definitely check out:

Piccolo Sogno

Location: 464 N Halsted St, Chicago

Piccolo Sogno , located in River West/West Town, is a charming Italian restaurant with a beautiful outdoor patio. The patio is surrounded by ivy-covered walls, creating a lush and romantic atmosphere that is perfect for a date night or a special occasion. The menu features classic Italian dishes like pasta, pizza, and seafood, all made with fresh and high-quality ingredients.

Las Fuentes

Location: 2558 N Halsted St Chicago

Las Fuentes is a popular Mexican restaurant with a secret weapon: a beautiful private patio that is perfect for private events, including weddings. The patio is located near the restaurant’s main entrance and is surrounded by lush greenery, creating a peaceful and relaxing atmosphere. The menu features traditional Mexican dishes like tacos, burritos, and enchiladas, as well as a wide selection of margaritas and other cocktails.

Porter Kitchen & Deck

Location: 150 N Riverside Plz Chicago

Porter Kitchen & Deck is a riverside spot with two outdoor seating areas, including a waterfront patio and an elevated deck with city views. The patio is the perfect place to enjoy a delicious meal and a refreshing drink while taking in the stunning views of the Chicago River. The menu features American comfort food like burgers, sandwiches, and salads, as well as a variety of craft beers and cocktails.

Location: 1402 W Randolph St Chicago

Bambola is a recently opened spot in the West Loop that is quickly becoming a favorite among locals. The restaurant features an intimate, sun-drenched patio that is the perfect place to enjoy the new happy hour menu.

The patio is surrounded by greenery and features comfortable seating and a relaxed atmosphere. The menu features modern Italian dishes like pasta, pizza, and seafood, as well as a selection of craft cocktails and wines.

No matter what type of cuisine you’re in the mood for, Chicago has plenty of great outdoor patios to choose from. Whether you’re looking for a romantic date night spot or a casual place to grab a drink with friends, these restaurants are sure to impress.

Final Thoughts

Chicago is a city that has it all, from world-class museums to stunning architecture, and of course, fantastic food. Whether you’re a local or a visitor, there’s no shortage of fun and exciting places to eat in the Windy City.

From the quirky and unusual to the sophisticated and stylish, Chicago’s dining scene has something for everyone. Whether you’re in the mood for pizza, steak, seafood, or something more exotic, you’re sure to find a restaurant that fits the bill.

One thing to keep in mind when exploring the city’s dining options is that many of the most popular restaurants can get quite busy, especially on weekends or during peak tourist season. It’s always a good idea to make a reservation in advance, or consider visiting during off-peak hours if you want to avoid the crowds.

Another tip for dining out in Chicago is to be prepared for a wide range of prices. While there are plenty of affordable options available, some of the city’s most famous restaurants can be quite expensive. If you’re on a budget, consider exploring some of the city’s lesser-known neighborhoods, where you’re more likely to find affordable eats.

Overall, Chicago is a food lover’s paradise, with an incredible range of dining options to suit every taste and budget. Whether you’re looking for a fun night out with friends or a romantic dinner for two with great food, you’re sure to find a restaurant that fits the bill. So why not start exploring the city’s culinary scene today?

Frequently Asked Questions

What are some popular restaurants in chicago that don’t require reservations.

Chicago has plenty of popular restaurants that don’t require reservations. Some of the best include Lou Malnati’s Pizzeria , Portillo’s , and The Purple Pig . These restaurants are known for their delicious food and casual atmosphere, making them perfect for a spontaneous night out.

What are some of the hottest new restaurants in Chicago?

Chicago is always buzzing with new restaurants to try. Some of the hottest new spots include Aviary , Kumiko , and Pacific Standard Time. These restaurants offer unique menus and trendy atmospheres that are sure to impress.

What are some of the best restaurants to try during Restaurant Week in Chicago?

Chicago Restaurant Week is a great opportunity to try some of the city’s best restaurants at a discounted price. Some of the top picks include Girl & the Goat , The Capital Grille , and RPM Steak . These restaurants offer delicious prix-fixe menus that showcase their signature dishes.

What are some fun kid-themed restaurants in the Chicago suburbs?

If you’re looking for a fun dining experience for the whole family, check out Rainforest Cafe , Medieval Times , or Chuck E. Cheese’s . These restaurants offer interactive experiences that kids will love, from animatronic animals to jousting knights.

What are some interactive restaurants to try in Chicago?

Chicago has no shortage of interactive dining experiences. Check out The Melting Pot for a fondue feast, or Korean BBQ restaurant Gogi for a DIY grilling experience. For a truly unique meal, head to Alinea , where the chefs create stunning dishes right in front of your eyes.

What are some cool and fun restaurants to check out in the Chicago suburbs?

If you’re willing to venture outside the city, there are plenty of cool and fun restaurants to check out in the suburbs. Some top picks include The Lucky Monk in South Barrington, which offers craft beer and delicious burgers, and The Bavarian Lodge in Lisle, which serves up authentic German cuisine and a wide selection of beers.

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These Chicago hotels are the best in the U.S. according to the Michelin Guide

The Peninsula Chicago, Chicago Athletic Association and more all earned the inaugural U.S. Michelin Keys.

The Michelin Guide has long been one of the most prestigious evaluators of culinary experiences, and now it’s expanding its expertise to hotels. 

The inaugural recipients of Michelin Keys in the U.S. have just been announced by the French tire company. Hotels in Atlanta, California, Chicago, Colorado, Florida, New York and Washington D.C.—the cities where the Michelin Guide also recommends restaurants—were eligible for the awards. Similar to how it judges eateries, Michelin inspectors took anonymous stays or visits to hotels across the country. In total, 124 accommodations received either one, two or three Michelin Keys, including eight spots in Chicago.

The Peninsula Chicago , Pendry Chicago and The Langham, Chicago all earned two Keys. The designation is bestowed upon places that are “truly unique and exceptional in every way, where a memorable experience is always guaranteed,” Michelin explained. “A hotel of character, personality and charm that’s operated with obvious pride and considerable care. Eye-catching design or architecture, and a real sense of the locale make this an exceptional place to stay.”

One Key was awarded to the Chicago Athletic Association , Nobu Hotel Chicago , The Gwen , Viceroy Chicago and Waldorf Astoria Chicago . These hotels are “a true gem with its own character and personality,” according to Michelin. “It may break the mould, offer something different or simply be one of the best of its type. Service always goes the extra mile and provides significantly more than similarly priced establishments.”

These hotels join Chicago’s acclaimed collection of Michelin-starred restaurants as the best of the best in their industry.

No Chicago hotel earned three Michelin Keys. The company plans on announcing Key winners in other U.S. destinations later this year.

• Jeffy Mai Editor, Time Out Chicago

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News & Insights

3 Airline Stocks to Watch From a Promising Industry

April 30, 2024 — 10:29 am EDT

Written by Maharathi Basu for Zacks  ->

About the Industry

The Zacks Airline industry players are engaged in transporting passengers and cargo to various destinations globally. Most operators maintain a fleet of multiple mainline jets in addition to several regional planes. Their operations are aided by their regional airline subsidiaries and third-party regional carriers. Additionally, industry players utilize their respective cargo divisions to offer a wide range of freight and mail services. The players invest substantially to upgrade technology. The industry, apart from comprising legacy carriers, includes low-cost players. The well-being of companies in this group is linked to the health of the overall economy. This is evident from the fact that the aviation space was one of the worst-hit corners during the pandemic, with passenger revenues taking a beating. However, air travel demand is strong now.

Factors Relevant to the Industry's Fortunes

Upbeat Passenger Volumes : Air travel demand remains strong, leading to impressive top-line performance by airlines.  While air travel demand is particularly strong on the leisure front, it is heartening to note that business demand has made an encouraging comeback. UAL’s top line increased 9.7% year over year in first-quarter 2024. This was driven by a 10.1% rise in passenger revenues.

Boeing-Led Woes : Jet delivery delays from Boeing have forced airlines to cut expectations for plane deliveries. While releasing first-quarter 2024 results, United Airlines management trimmed its current-year guidance for capital expenditure. The company now expects full-year 2024 total capital expenditure to be approximately $6.5 billion, down from $9 billion expected earlier. Due to aircraft delivery delays, UAL now anticipates 61 narrowbody aircraft and five widebody aircraft deliveries in 2024.  The earlier expectation was for a delivery of 101 narrowbody jets. Chicago-based UAL, with 79 Boeing Max 9 planes in its fleet, is the largest operator of such jets across the globe.

Plane manufacturer Boeing has been under intense regulatory scrutiny following the Jan 5 mid-air scare involving an Alaska Airlines plane. Alaska Airlines’ Ontario, CA-bound flight (1282) saw a panel and window being blown out of the Boeing 737 MAX 9 jet shortly after takeoff from Portland, OR.

Northbound Fuel Costs : The increase in fuel expenses is another headwind for the industry. Notably, oil price spiked 16% in the January-March period. This does not bode well for the bottom-line growth of airlines. This is because fuel expenses are a significant input cost for airline stocks. The northward movement in crude price is primarily due to the ongoing production cut by major oil-producing nations and geopolitical tensions.

Strong Returns for Shareholders : With economic activities becoming normal after the pandemic, more and more companies are allocating their increasing cash pile by way of dividends and buybacks to pacify long-suffering shareholders. This underlines their financial strength and confidence in business. Among airline players, Alaska Air resumed share buybacks in 2023. The restrictions, under the CARES Act, prohibited airlines from paying dividends or buying back shares till Sep 30, 2022. During 2023, ALK repurchased nearly 3.5 million shares for $145 million Uptick in Labor Costs : The increase in expenses on the labor front represents another challenge for airlines. With U.S. airlines grappling with a labor shortage in the post-COVID-19 high-demand scenario, the bargaining power of various labor groups has naturally increased. As a result, we have seen pay-hike deals being inked in the space. This is resulting in a spike in labor costs. For example, at United Airlines, consolidated cost per available seat mile, excluding fuel, third-party business expenses, profit-sharing and special charges, increased 4.7% year over year in first-quarter 2024.

Zacks Industry Rank Signals Bright Prospects

The Zacks Airline industry is a 30-stock group within the broader Zacks  Transportation  sector. The industry currently carries a Zacks Industry Rank #85, which places it in the top 34% of 250 plus Zacks industries.

The group’s  Zacks Industry Rank , basically the average of the Zacks Rank of all the member stocks, indicates encouraging near-term prospects. Our research shows that the top 50% of the Zacks-ranked industries outperforms the bottom 50% by a factor of more than 2 to 1.

Before we present a few stocks that you may want to add or retain in your portfolio, let’s look at the industry’s recent stock-market performance and its valuation picture.

Industry Surpasses S&P 500 and Sector

Over the past year, the Zacks Transportation - Airline industry has gained 34.9% compared with the S&P 500 composite’s rise of 23.5%. The broader sector has gained 9% in the said time frame.

One-Year Price Performance

Valuation Picture

The price/sales (P/S) ratio is often used to value airline stocks. The industry currently has a forward 12-month P/S of 1.04X compared with the S&P 500’s 3.86X. It is also below the sector’s forward-12-month P/S of 1.87X.

Over the past five years, the industry has traded as high as 1.04X, as low as 0.40X and at the median of 0.65X.

Forward 12-Month Price-to-Sales Ratio (Past Five Years)

3 Airline Stocks to Watch

Alaska Air:  The company, based in Seattle, WA, is being aided by the uptick in air travel demand. The carrier’s shareholder-friendly attitude also bodes well.

Over the past 60 days, the Zacks Consensus Estimate for 2024 earnings has been revised 8.3% upward. ALK currently carries a Zacks Rank #2 (Buy).

You can see the complete list of today’s Zacks #1 Rank (Strong Buy) stocks here

Price and Consensus: ALK

Latin American carrier Copa Holdings is being aided by upbeat air travel demand. We are also encouraged by Copa Holdings' initiatives to modernize its fleet. 

Over the past 60 days, the stock has seen the Zacks Consensus Estimate for 2024 earnings being revised 1.2% upward. CPA currently carries a Zacks Rank #2.

Price and Consensus: CPA

United Airlines  is based in Chicago. The gradual increase in air travel demand (particularly for leisure) is aiding AAL. However, high operating costs are hurting the bottom line.

Over the past 60 days, the stock has seen the Zacks Consensus Estimate for 2024 earnings being revised 1.5% upward. UAL currently carries a Zacks Rank #3 (Hold).

Price and Consensus: UAL

Zacks Names "Single Best Pick to Double"

From thousands of stocks, 5 Zacks experts each have chosen their favorite to skyrocket +100% or more in months to come. From those 5, Director of Research Sheraz Mian hand-picks one to have the most explosive upside of all.

It’s an American AI company that’s riding low right now, but it has rounded up clients like BMW, GE, Dell Computer, and Bosch. It has prospects for not just doubling but quadrupling in the year to come. Of course, all our picks aren’t winners but this one could far surpass earlier Zacks’ Stocks Set to Double like Boston Beer Company which shot up +143.0% in little more than 9 months and NVIDIA which boomed +175.9% in one year.

Want the latest recommendations from Zacks Investment Research? Today, you can download 7 Best Stocks for the Next 30 Days. Click to get this free report

United Airlines Holdings Inc (UAL) : Free Stock Analysis Report

The Boeing Company (BA) : Free Stock Analysis Report

Copa Holdings, S.A. (CPA) : Free Stock Analysis Report

Alaska Air Group, Inc. (ALK) : Free Stock Analysis Report

To read this article on Zacks.com click here.

Zacks Investment Research

The views and opinions expressed herein are the views and opinions of the author and do not necessarily reflect those of Nasdaq, Inc.

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