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25 Weekend Getaways Near Chicago

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When you need a day trip from Chicago or a weekend getaway from the big city, you don't have to go far. These escapes—including Amish Country, Indiana; Galena, Illinois; Lake Geneva, Wisconsin; and Holland, Michigan—are within a one- to three-hour drive and offer a variety of activities that will recharge your life. Parks and gardens call to nature lovers; museums and outdoor theater provide plenty of culture; shopping abounds in towns both large and small. Here are 25 of our favorite weekend getaways from Chicago.

Indiana Dunes: 54 miles southeast of Chicago

This stretch of Lake Michigan coastline offers wide sandy beaches, towering dunes, great birding, easy bike trails and interesting history. Head to neighboring Chesterton for creative burgers at the Octave Grill and to Valparaiso for a pleasant night at Songbird Prairie Inn and Spa.

Lake Geneva, Wisconsin: 80 miles northwest of Chicago

This resort town of 7,600 has draws for summer and winter. Hotels, resorts and restaurants hug the lakeshore. Most visitors loll on the beach or cruise the lake during summer, but you can also experience the warmth of its winter in January and February during the annual Winterfest.

Michigan's southwest shore: 70 to 150 miles east of Chicago

Towns like New Buffalo, St. Joseph, Benton Harbor, Holland, Saugatuck and Grand Haven provide pristine beaches, great shopping, lakeside restaurants and front-row view of sunsets over Lake Michigan. The most accessible section of this shore extends from the Indiana line 175 miles north to Ludington. How far you drive is up to you —each town has its own personality. Take a spin on the carousel at St. Joe, tour a working windmill in Holland or just stretch out on a beach—preferably with a view of a lighthouse.

Galena, Illinois: 163 miles west of Chicago

Shops and restaurants in century-old buildings have long attracted visitors to this town of 3,500. But take time to hike, cruise the river or ski the slopes, sip local wines, taste beer and ... do some shopping.

Cedarburg, Wisconsin: 113 miles north of Chicago

A great weekend destination for both shoppers and history buffs, Cedarburg has a Main Street that's on the National Register of Historic Places and dozens of limestone buildings housing more than 70 boutiques, chocolate shops and restaurants. Explore the town's heritage at the Cedarburg History Museum and the 1849 Kuhefuss House Museum, and admire handiwork at the Wisconsin Museum of Quilts and Fiber Arts . The Washington House Inn mixes historic charm with modern amenities for a romantic getaway.

Bloomington-Normal, Illinois: 130 miles southwest of Chicago

For theater-lovers, summertime means outdoor Shakespeare. But in downstate Illinois, that takes on a fresh new form. Want improv Shakespeare? Sing-along Shakespeare? Or just a performance of his classics? Starting in June, and running through mid-August, the Illinois Shakespeare Festival in Bloomington-Normal reveals its ode to the Bard. Other draws to the area: Bloomington's restored 1800s buildings house farm-to-table restaurants, shops and live-music venues. Inside the three-story courthouse, a museum highlights the area's historical treasures.

Madison, Wisconsin: 147 miles northwest of Chicago

This town embraces the quirky and classy in its arts, museums, shops, dining venues and outdoor activities. Even its farmers market is a Bohemian rhapsody of local produce, entertainment, art and political activism on the state capitol square. Wander the paths and trails at Olbrich Botanical Gardens or the University of Wisconsin Arboretum ; admire the art at Chazen Museum of Art or the Madison Museum of Contemporary Art ; take a leisurely cruise around Lake Mendota or Menona; and be sure to work up an appetite-Madison's 600-plus restaurants offer something for every taste.

Milwaukee: 93 miles north of Chicago

Festivals, brewing history, stunning museums and water rec make Milwaukee a top weekend getaway. Just a few of your choices: Watch the Milwaukee Art Museum's striking Quadracci Pavilion open and close its "wings"; catch the Milwaukee Brewers in Miller Park ; tour the Pabst Mansion ; or take a simulated motorcycle ride at the Harley-Davidson Museum.

Mount Morris, Illinois: 100 miles northwest of Chicago

With its rolling terrain, state parks and preserves traversed by the mighty Rick and Mississippi rivers, plus biking and hiking trails crisscrossing the area, the Blackhawk Waterways region of northwest Illinois promises outdoor recreation bliss. The region also helped shape the childhood of our 40th president, whose boyhood home opens its doors to visitors.

Rockford, Illinois: 90 miles west of Chicago

Illinois' third-largest city spent years watching travelers whiz by on Interstate-90 on their way east to Chicago. Now, thanks to a revitalized downtown, an emerging foodie scene, new cultural attractions and beautiful public gardens, word is getting out: You'd be crazy not to stop. The tranquil Anderson Japanese Gardens is just one of the draws to the area.

Fox River Valley, Illinois: 60 miles west of Chicago

An hour west of Chicago's Loop, the Fox River provides a soothing backdrop to towns brimming with indulgent eats, stores housed in historical homes and posh places to stay. Three towns along the winding river offer restful diversions with a nod to history: Catch a household name playing at St. Charles' historical Arcada Theater ; 3 miles south, explore Geneva's shopping district, where boutiques fill preserved storefronts. Check out Oswego's charming Main Street—with brick-paved sidewalks—and Fox Valley Winery.

Amish Country, Indiana: 110 miles east of Chicago

In tiny Nappanee, an Amish man parks his buggy by a gas pump, a living metaphor for the way new and old coexist in northern Indiana. Come here for classic Amish Country : 31 kinds of pie at Das Dutchman Essenhaus , hand-sewn gifts and homemade jellies at Little Helpers Quilt Shop, treasure-hunting at the Shipshewana Flea Market . Towns like Goshen, Middlebury and Elkhart also draw those who just want a quiet getaway at spots like Wellfield Botanic Gardens.

Champaign-Urbana: 140 miles south of Chicago

The University of Illinois Arboretum features 160 acres of gardens.

Great outdoors, grown-up eats and classic clubs make these two cultured cities especially appealing in the summer when University of Illinois students head home. Grab a cheesy bite of nostalgia at Papa Del's Pizza or enjoy any of 3,000 dishes (really!) at Golden Harbor . Take time to admire the works at Krannert Art Museum and Spurlock Museum ; go for a stroll at the University of Illinois arboretum or Allerton Park and Retreat Center .

Starved Rock State Park, Illinois: 100 miles southwest of Chicago

Starved Rock State Park is a remarkable pocket of land along the Illinois River that includes 18 sandstone canyons, 14 waterfalls; abundant wildlife and birds; and guided hikes, special events and interpretive programs. Spend the night in rooms or cabins (and enjoy a hearty meal) at Starved Rock Lodge , built in the 1930s by the Civilian Conservation Corps. If you're up for more exploration, also visit neighboring Matthiessen State Park, where 5 miles of trails carve into the mile-long canyon, passing rocks, waterfalls and beautiful, sometimes dizzying, vantage points.

Zion, Illinois: 50 miles north of Chicago

Zion is located in Lake County , which bridges the gap between Chicago's Cook County and the Wisconsin border with family attractions and nature trails. The area is home to Illinois Beach State Park and Volo Auto Museum as well as near Six Flags Great America in Gurnee.

South Bend, Indiana: 95 miles east of Chicago

Though it's home to the Fighting Irish, it's not all football in South Bend. The St. Joseph River provides a great place for water sports and serves as a sparkling backdrop for a weekend of shopping and dining in the hometown of the University of Notre Dame.

Turkey Run Inn, Indiana: 150 miles south of Chicago

Sitting on a rocking chair on a veranda at Indiana's Turkey Run State Park inn feels surprisingly like taking refuge deep in the forest. The only sounds? Wind rustling through the trees. Owls hooting. Squirrels chattering. Brooks babbling. Maybe that's why quiet types flock here—bird-watchers, hikers and history buffs eager to explore Parke County and its covered bridges.

Grand Rapids, Michigan: 175 miles northeast of Chicago

Inspiration flows on both sides of the Grand River, particularly near downtown . Grand Rapids' ArtPrize extravaganza every other fall is part art walk, part city tour and and entirely vacation-worthy. But there's plenty to see at other times of the year, too, including the Frederik Meijer Gardens and Sculpture Park , Frank Lloyd Wright's Meyer May House and the Gerald R. Ford Presidential Library and Museum .

Elkhart Lake, Wisconsin: 150 miles north of Chicago

Sun, sand and...race cars? Most people come here for quiet weekends of swimming, sunning, boating and water-skiing in the crystal-clear lake , but the legendary Road America course is popular with amateur racers and their fans. Nearby Kettle Moraine State Forest also offers outdoor rec of another type with trails for biking, hiking and running. Round out the weekend with a stay in one of the area resorts such as the Osthoff.

Lake Mills, Wisconsin: 125 miles northwest of Chicago

Photo Courtesy of Lewis Station Winery

Famous for The Ephraim Pottery Studio and Gallery , a getaway to Lake Mills also offers plenty of outdoor recreation on Rock Lake, the Zeloski Marsh and the Glacial Drumlin Bike Trail, as well as a cozy Arts and Crafts style B&B. Snack on crackers and sip wine at Lewis Station Winery, and don't miss the old-fashioned James J. Chocolate Shop .

Glencoe, Illinois: 15 miles north of Chicago

Glencoe is one of the few cities bordering Chicago along Lake Michigan. The communities of the North Shore seem farther from the bustle of downtown, thanks to abundant green spaces, including the Chicago Botanic Garden . Make sure to visit Grosse Point Lighthouse during sunset in Evanston and take a walk along the Green Bay Trail between Winnetka and Highland Park.

Apple River Canyon State Park, Illinois: 146 miles west of Chicago

Clint Farlinger

Every day, hundreds of drivers speed past the turnoff on US-20 for Apple River Canyon State Park , bound for getaways in Galena. Those travelers admire the view from the car, not realizing that if they wanted a peek at one of the area's few remaining secrets, they should turn north on Canyon Park Road west of Stockton and drive for just 7 miles. The 297-acre Apple River Canyon State Park offers quiet amid the woods along Apple River. Hike the bluffs. Look for fossils. Listen for wildlife. Fish the river—and let the others head to Galena.

Beloit, Wisconsin: 96 miles northwest of Chicago

This area is famous for its supper clubs that serve nostalgia and hearty portions. The food at classic restaurants like The Butterfly Supper Club , Benedetti's and The 615 Club all goes down easily with an Old-Fashioned.

Midewin National Tallgrass Prairie: 60 miles southwest of Chicago

Experience landscape that once rolled across the Midwest like an ocean at this restored prairie. Spot birds, hear frogs, hike and bike, see wildflowers and unwind among the 19,000 acres at Midewin National Tallgrass Prairie.

Woodstock, Illinois: 60 miles northwest of Chicago

It's just a train ride from Chicago, but Woodstock feels anything but suburban. The historic town square (featured in the classic 1993 movie Groundhog Day ) is adorable, with great home decor shops and a cozy bookstore. Come for the summer activities or the annual Groundhog Days in early February; for full Groundhog Day vibes, stay at the Cherry Tree Inn B&B , where Bill Murray woke up over and over again in the movie.

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Best Weekend Getaways From Chicago

By Nina Kokotas Hahn

Chicagoans itching to travel right now should not underestimate the power of a great winter road trip, and not just because it may feel like the only safe option at the moment. In a break from the norm, we’ve found exciting places offering something fresh and surprising for the Midwest, making them well worth the drive. A fun, elegant cocktail experience, lakefront retreats that offer stunning views, snowy ski trips with plenty more to do off the slopes—it’s all available. Here are the best weekend getaways from Chicago .

(Editors note: Given the changing nature of the COVID-19 pandemic , the hours and accessibility of many venues are fluid and subject to change. Make sure to contact them before visiting.)

All listings featured on Condé Nast Traveler are independently selected by our editors. If you book something through our links, we may earn an affiliate commission.

LAKE FOREST, ILLINOIS

Distance from Chicago 33 miles

The Deer Path Inn

In less than 60 minutes by Metra or just over 30 minutes by car, find yourself feeling far from the city in this pretty Northshore town off of Lake Michigan. No doubt Lake Forest is fancy with its sprawling estates, Market Square, and upscale shops (check out the all-women-run Lake Forest Bookstore and Valentina boutique), and coveted waterfront views. Being here also puts you 20 minutes closer to the 385-acre Chicago Botanic Gardens , where the Japanese and dwarf confider gardens are especially sublime in winter.

Where to Stay

The main reason to go to Lake Forest now is a weekend away at the 57-room Deer Path Inn ( from $329 per night ), a fabulous, little-known gem that puts you in arm's reach of the shops and lake, and offers many experiences available only to guests. Opened in 1929 with the style of an authentic manor house, the elegant inn feels as storied and local as it does far-flung and English. Spacious, modern, and sophisticated rooms offer upscale amenities (think Frette linens and bathtubs that fill from the ceiling); recently, the inn began in-room delivery of its popular Afternoon Tea service, complete with a tower of tea sandwiches, petit fours, and tartelettes. Patio dining in the English Garden at Deer Path is scenic and doable in winter with heaters. Guests at the hotel can also reserve the inn’s hidden cellar for a new, private, and totally custom cocktail or wine tasting paired with dinner that's led by Deer Path’s fun and expert chief spirits officer, Jorge Centeno.

INDIANA DUNES NATIONAL PARK, IN

Distance from Chicago 49 miles

The dunes overlooking Lake Michigan at Indiana Dunes National Park

Drive just 60 minutes and find yourself surrounded by beauty in the 15,000-acre Indiana Dunes National Park , which packs in an astounding amount of botanical diversity thanks to its variety of lowlands, highlands, prairies, wetlands, forests, and Lake Michigan shoreline. Time your visit with cool winter conditions, when snow cloaks the park in white, and there’s a chance to see spectacular shelf ice formations on the water, not to mention you’ll get a far more secluded experience. Venture out on cross-country skis or snowshoes—the latter of which can be borrowed for free at the park’s Paul H. Douglas Center for Environmental Education. All of the park’s 50 miles of trails are available for winter activities, but opt for a one-mile loop or three-mile route on the Paul H. Douglas Trail, which takes you to the beach through a rolling black savannah, one of the rarest habitats in the country. Often confused with the national park, the two-acre Indiana Dunes State Park , immediately next door, is also open and admission is waived on weekdays in winter.

Nearby Chesterton offers a good location central to both parks, and interesting B&B’s are the way to go. Within walking distance to restaurants and shopping, Riley's Railhouse Bed & Breakfast ( from $140 a night ) is housed in a former New York Central style freight station and has rooms in real rail cars. The family-friendly DunesWalk Inn at the Furness Mansion ( from $125 a night—you can also rent the entire place out on Airbnb ) is another historic option that balances digs in an 1881 mansion with modern comfort, just a few minutes from the beach.

HARBOR COUNTRY, MI

Distance from Chicago 75 miles

A view of Lake Michigan from the Water's Edge house

Didn’t score a Michigan beach house last summer? Winter isn’t hot, but it’s a gorgeous and secluded time to experience the dramatic Lake Michigan coast from the comfort of a luxury beach home, most of which can be had now at low season rates. Take your pick of towns on the state’s south coast like Union Pier, New Buffalo, and little-known Harbert. Sans summer crowds, this is the time to stop at the harborside Stray Dog Bar & Grill . Even better, book an igloo for outdoor dining at small-batch Beer Church Brewing , try alfresco wine tastings at Round Barn Estate , or get takeout from Red Arrow Roadhouse (try the buffalo cauliflower and nachos) and locally made whiskey from the Journeyman Distillery to bring back home. As everyone does, give into the pull of the lovely Lake Michigan coast, where dune walks and sledding at Warren Dunes State Park should be high on your list.

Bluefish Vacation Rentals (from $100 a night ) is your best option for a well-curated assortment of homes throughout Harbor Country, plus the bonus concierge-like guidance of the local husband-and-wife team who run it, Jason and Erika Milovich. In winter, most of their homes can be had at low season rates and don’t require summer’s usual full week stay. The scenery can’t be beat in Harbert at three-bedroom Water’s Edge , a splurge-worthy find tucked into a forested bluff overlooking a private stretch of Lake Michigan shoreline; spend $750 a night in winter verses the nearly double rate of $1,429 a night in summer. Walk the beach and watch glacier-like ice form with the waves, warm up in the hot tub, and light a bonfire under starry winter skies framed by trees. Other notable options include the three-bedroom Harbor Time , new five-bedroom Darby Cottage with its massive showroom-worthy open kitchen, and new four-bedroom Lake Life that puts spectacular lake views right in your lap.

KOHLER, WISCONSIN

Distance from Chicago 149 miles

By Steph Koyfman

By Todd Plummer

By Rachel Chang

By Caitlin Gunther

One of the Kohler luxury Cabins

On a drive of just over two hours, cruise past Mars Cheese Castle in Kenosha (hit the brakes to load up on Wisconsin gold), and lakefront Milwaukee, on your way to Kohler. Popular in temperate months for its jaw-dropping golf courses, which regularly feature on the PGA Tour, Destination Kohler is a find in winter with fewer visitors, killer spa treatments at its Kohler Waters Spa, and invigorating outdoor adventures at its lesser-known River Wildlife preserve. Like Kohler’s golf courses, the 500-acre wilderness playground showcases the natural beauty of the landscape here. Try hikes and horseback rides through rolling trails, ice skating and curling at Winter Wonderland, guided trap shooting in a forest canyon, and brunch or hot toddies at River Wildlife Lodge, the preserve’s atmospheric log cabin outpost.

Options at the resort include classic hotel rooms at the 241-room American Club ( from $189 ), but four chic and splurge-worthy cabins (f rom $842 a night ) are the way to go, especially if you want privacy and space wrapped in some gorgeous nature. The two-bedroom Lake Cabin ( from $1009 a night )—one of two opened just last summer—positions you on a staggering bluff just above Lake Michigan. The beach is inaccessible from this rugged perch, but you won’t care with endless, ocean-like views from the back porch and firepit, and the sprawling evergreen forest at the front of the house that doubles as a wildlife crossing (watch for deer and wild turkeys). It’s all the more magical with a dusting of snow on the beach grass, a warm fire, and dinners inside your own beautiful kitchen—everything from tenderloin and ricotta gnocchi takeout from the new Taverne on Woodlake to whiskey pairings, curated Wisconsin cheese boards, and gourmet groceries delivered from Woodlake Market .

Distance from Chicago 164 miles

Downtown Galena

With rolling forested landscapes, an historic downtown on the Mississippi River, and the best (one of the only!) ski mountain in Illinois, Galena is as charming as ever in winter. Even the two-hour-and-45-minute drive sets the mood as flat highways turn to one-lane roads that climb gentle hills and weave through farmlands and woods, eventually dropping you into this once-thriving river port town. Stroll the downtown’s Main Street for a superb array of local shops and studios; new options include Galena Book & Paper , the Galena Spoon Company for handcrafted spoons and carving classes, and Scent Workshop , where you can learn French perfuming techniques. There are loads of restaurants and boozy options here, too; go for especially good take-home dining and cocktail kits from French-meets-German Fritz and Frites , Miss Kitty’s Grape Escape , and the drive-thru Galena Brewing Co . Downhill skiers won’t want to miss Chestnut Mountain Resort, just 15 minutes from the downtown, with 19 runs that race to a halt at the bank of the Mississippi River.

It’s a-okay to vape in the new guest-only “potting shed” outside the pretty five-bedroom Aldrich House , Illinois’ only cannabis-friendly bed and breakfast ( from $145 a night ). For something upscale and romantic, it’s hard to do better than the luxury six-suite Jail Hill Inn , set in a former jailhouse at the end of Main Street and serving a three-course breakfast ( from $345 a night ). Families settle in nicely at the stylish, condo-like Ulysses Suites ( from $214 a night ), while south of downtown on 6,800 acres of Galena Territory, Eagle Ridge Resort & Spa offers a robust nordic activities program and everything from simple hotel rooms to full homes ( from $99 a night ).

INDIANAPOLIS, IN

Distance from Chicago 185 miles

The Bottleworks Hotel in Indianapolis' Bottleworks District

Every worthwhile weekend getaway from Chicago isn’t a charming small town or lakeside retreat. For those who want some city culture that isn’t their own, Indy’s Bottlework’s District is calling. Stop in Merrillville for proper road trip junk food—fresh Indiana-made gummy bears—at Alabanese Confectionery Group on the three-hour drive south to Indy. Once there, head to the new 12-acre, mixed-use neighborhood that spans the north side of Mass Ave in downtown Indianapolis and brims with local indie shops in historic industrial buildings. Explore the mix of offerings at Circle City Industrial Complex , a 500,000 square-foot warehouse opened in the old Schwitzer car manufacturing facility, where you should check out newly opened SoChatti dairy-free chocolate tasting room and a class at Indy Fused Glass. Other new places worth a visit are Good Neighbor for fresh duds and the Living Room movie theater. For dinner, head out of the district for romantic outdoor dining in the new fireside greenhouse huts at Public Greens , a modern, community-driven restaurant that shares its profits to feed nearly 2,000 of Indy’s less fortunate youth every week.

Opened in December in what was formerly the world’s largest Coca Cola bottling plant, the 139-room Bottleworks Hotel ( from $249 a night ) is the stylish new anchor for the Bottleworks District. The industrial, art-deco-inspired hotel occupies the top two floors of the historic building, showing off a white terra-cotta exterior and brass-patterned doors. High-style rooms have velvet couches, loft ceilings, and terrazzo-tiled floors. Adjacent to the hotel, find more dining options at Garage Food Hall , Indy’s first food hall opened this month in the factory’s former garages, with nearly two dozen vendors serving everything from lobster rolls and poke to Pakistani-Indian fare and Brazilian steak.

BOYNE, MICHIGAN

Distance from Chicago 346 miles

A look down Boyne Mountain

Make your winter ski trip happen at Boyne Mountain Resort , one of the most exciting ski mountains within a reasonable drive of Chicago—five and a half hours, plus a one-hour time change. Rising up from the northern part of Michigan’s lower peninsula, the mountain offers 500 feet of vertical with 60 downhill trails for a range of skiers and riders, though the biggest perk of a visit here is the abundance of high-quality outdoor adventures that go beyond skiing. Rent a new sno-go ski bike and shred downhill runs, fat-tire bike on forest trails, zipline 50 feet in the air across the mountain, cross country ski or snowshoe on dedicated trails, ice skate or snow tube, and even dine outdoors in one of five igloos serving at Forty Acres Tavern. If you have a little extra time you can also tack on the 40-minute drive north to Boyne Highlands , the mountain’s sister resort, for even more challenging ski terrain plus the new “Enchanted Trail,” an illuminated two-mile trail for nighttime winter walks and snowshoeing. NOTE: Like other ski resorts around the country, both mountains are limiting capacity during the pandemic and booking lift tickets and gear rental in advance is recommended.

Spread out in one of the fully-equipped three- and four-bedroom Mountain Cabins that are part of the resort (f rom $607 per night ). Each is set in the woods with a hot tub on the deck, fully equipped for cooking your own meals, and offers ski-in/ski-out access. Some of the cozy one- and two-bedroom condos at the Village at Disciples Ridge also offer ski-in/ski-out access ( from $488 per night ). Pro tip: the best way to guarantee access to the slopes this season along with your accommodations is to book a “ Ski & Stay Package ,” which bundles lodging and lift together and lets you ski both resorts.

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• Jun 21, 2022

26 Best Weekend Getaways from Chicago (within a 4-hour flight)

Updated: Jan 21

Deep dish pizza, sports, great bars, and awesome summers. Chicago has it all (except the ocean and nice winters). If you're looking to take a break from the norm in Chicago or escape the brutal winter, read on for some ideas about where to go for a quick weekend.

With a vast array of short domestic destinations, there are also many international destinations within reach. Here are some weekend getaway ideas for locals in the Chicago area within a non-stop 4-hour flight. More importantly, these trips are all possible without having to request PTO (for you M-F 9-5'ers), it just depends on what you want to do at your destination.

Miami, Florida (MIA, FLL) - Just Over a 3 Hour Flight

Beaches, outdoors activities, clubs, restaurants, culture. I just ask that you please please please venture out beyond Miami Beach.

When to go?

Any time of the year, but best is October - February for perfect weather. Avoid the spring break crowd in late Feb/early March the best you can.

Who can fly you there?

AA from ORD - See flight deals

Spirit Airways from ORD - See flight deals

Southwest from ORD, MDW - See flight deals

United from ORD - See flight deals

How much will it cost to get there?

Airfare: $100+

Where can you stay?

See hotels in Miami

See hotels in Miami Beach

Visit the following neighborhoods to step away from the "typical Miami": Wynwood, Brickell, Coral Gables, Coconut Grove, Midtown, Edgewater.

Orlando, Florida (MCO) - Just Under a 3 Hour Flight

Disney & Universal Studios. Bring bug spray and an umbrella if you go during the summer.

Frontier from ORD - See flight deals

Airfare: $150+

See hotels in Orlando

New York, New York (JFK, LGA, EWR, ISP, HPN) - 2 Hour Flight

It might not be the same city it was a few years ago, but it'll always make for a great weekend getaway.

Summer for the best weather, but peak rates for solid hotels.

Winter for Christmas festivities!

Delta from ORD - See flight deals

JetBlue from ORD - See flight deals

Airfare: $50+

See hotels in New York

Toronto, Ontario (YYZ, YTZ) - Just Under a 2 Hour Flight

Food, people, cleanliness, Hockey Hall of Fame.

Air Canada from ORD - See flight deals

WestJet from ORD - See flight deals

Swoop from ORD - See flight deals

Porter Airlines from MDW - See flight deals

See hotels in Toronto

Philadelphia, Pennsylvania (PHL) - 2 Hour Flight

History, sports, cheesesteaks

Summer and Fall

United Airlines from ORD - See flight deals

Airfare: $200+

See hotels in Philadelphia

Washington, DC (IAD, DCA, BWI) - Just Under a 2 Hour Flight

Museums, walking tours, great mass-transit and cherry blossoms. Fly to DCA for convenience.

Year-round (spring season for cherry blossoms)

See hotels in Washington DC

For avid runners, pack your running shoes and go for daily runs around the White House, Washington Monument, Lincoln and Jefferson memorials.

Discover the ease of weekend escapes from Chicago with ING Chauffeured Transportation , your trusted choice for dependable ground transportation.

Kansas City, Missouri (MCI) - 1.5 Hour Flight

BBQ! BBQ! BBQ!

Southwest from MDW - See flight deals

See hotels in Kansas City

Visit the Power & Light District for a unique nightlife experience & go to Arthur Bryant's for BBQ.

Nashville, Tennessee (BNA) - 1.5 Hour Flight

Music (not just country), endless bars, brewpubs, hot chicken.

Spring, Summer and Fall

See hotels in Nashville

Stay in the Gulch or near printer's alley.

New Orleans, Louisiana (MSY) - 2.5 Hour Flight

Jazz music, other music, culture, architecture, partying, passionate football fans.

Spring, Summer, Fall

See hotels in New Orleans

Check out Bourbon Street for a little bit, but don't get sucked in. It's absolutely disgusting. Chartres Street is better for those looking to maintain their cleanliness.

Atlanta, Georgia (ATL) - 2 Hour Flight

Brew pubs, art, nightlife, Mexican food.

Delta from ORD, MDW - See flight deals

Frontier from MDW - See flight deals

See hotels in Atlanta

Walk some of the BeltLine and stop at stores, bars, and restaurants.

Raleigh, North Carolina (RDU) - 2 Hour Flight

Outdoors activities, restaurants, college sports, booming tech sector.

See hotels in Raleigh

Glacier National Park, Montana (FCA) - Just Over a 4 Hour Flight

Glacier National Park and the great town of Whitefish. I recommend camping, but you can get a boutique hotel in Whitefish or Kalispell.

SkyWest from ORD - See flight deals

Airfare: $350+

See hotels in Whitefish

Austin, Texas (AUS) - Just Under a 3 Hour Flight

Food, Art, Music, BBQ, Tech, Bach Parties, and All-Around Fun!

See hotels in Austin

Cancun, Mexico (CUN) - Just Under a 4 Hour Flight

Your money goes a long way: all-inclusive hotels, nightlife, and activities.

December to April for the best weather.

Avoid March Spring Break travel if you want to be at peace.

See hotels in Cancun

Jackson Hole, Wyoming (JAC) - Just Over a 3 Hour Flight

Bears, Yellowstone National Park, Grand Teton National Park, skiing, golfing, horseback riding, rustic boutique hotels, cool people.

Airfare: $400+

See hotels in Jackson Hole

Make sure you have time to visit both Yellowstone and Grand Teton. Jenny Lake is a must.

Aspen, Colorado (ASE) - Just Over a 3 Hour Flight

Skiing, great scenery, luxury.

See hotels in Aspen

It's very expensive, but worth a shot. 3.5 hour drive if you wish to save some $$.

Boston, Massachusetts (BOS) - Just Over a 2 Hour Flight

History and cool summertime temps!

Intercontinental Boston

See hotels in Boston

Las Vegas, Nevada (LAS) - 4 Hour Flight

Gambling, Hoover Dam, Death Valley National Park, Valley of Fire State Park, Partying, more Gambling.

See hotels in Las Vegas

Denver, Colorado (DEN) - Just Under a 3 Hour Flight

Mountains, beer, National Parks, hiking, clean city, nice people.

Year-round. Ski in the winter. Hike in the summer.

Airfare: $250+

See hotels in Denver

Salt Lake City, Utah (SLC) - 3.5 Hour Flight

Skiing, Salt Flats, Mormons, and great National Parks within a moderate drive.

See hotels in Salt Lake City

Nassau, Bahamas (NAS) - 3.5 Hour Flight

Turquoise waters, friendly people, and close proximity to Florida make the Bahamas a popular destination.

December to July to avoid hurricanes and tropical storms.

May to August to avoid crowds and surcharges.

November to February to avoid the summer heat.

Airfare: $500+

See hotels in Nassau

Rent a car ! Be prepared to drive on the left side of the road.

Charleston, South Carolina (CHS) - 2 Hour Flight

History, culture, family-friendly attractions, and watersports.

See hotels in Charleston

Asheville, North Carolina (AVL) - Just Under a 2 Hour Flight

Art, craft beer, and the Smoky Mountains. I'd recommend driving instead of flying, but it's your call!

Allegiant from MDW - See flight deals

See hotels in Asheville

Montreal, Quebec (YUL) - 2 Hour Flight

More restaurants per capita than any other North American city.

See hotels in Montreal

Bozeman, Montana (BZN) - 3.5 Hour Flight

Skiing, Hiking, Waterfalls, Museums, Rivers, and of course Yellowstone National Park (1.5-hour drive). It's possible to do the park in one day from Bozeman, but if going to the park is your goal, I'd recommend staying closer to the park in West Yellowstone.

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See hotels in West Yellowstone

Rapid City, South Dakota (RAP) - 2.5 Hour Flight

You'll find nature and parks galore in one of the most unique areas of the country. Mt. Rushmore National Monument, Custer State Park, Black Hills National Forest -- all within a 35 min drive from Rapid City, in the same direction. Do all 3 in one day and be sure to visit Sylvan Lake in Custer. Just incredible. Badlands National Park is 1 hour away and that's doable in a separate day. Devils Tower National Monument is just under 2 hours in the opposite direction across the Wyoming border.

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10 Essential Destinations For Day Trips And Weekend Getaways From Chicago

If you're looking to get out of the city for a minute, whether for nature, small-town living, or just a different city, these are our favorite places to go!

As our thriving metropolis moves into the glorious spring and summer temperatures, riverside bars, lakefront beaches, and our plethora of parks all blossom with jubilance. But at the same time, our urban jungle can sometimes become too much, and weekend getaways from Chicago are much-needed. While Lake Michigan offers respite from the summer heat, there’s peace found in escaping the city clamor during its more restless months.

As unique as Chicago is, getting out of the city once in a while to explore new pastures, even just for a day or two, is good for the mind, body, and soul. To give readers some ideas of accessible weekend getaways from Chicago , we’ve picked out our favorite places a short drive away that would make for superb day trips and weekend destinations as they all begin to flourish in the coming months.

1. Starved Rock State Park, Illinois

If you are cooped up and want to escape into nature for fresh air, look no further than Starved Rock State Park in Illinois. Added to the National Register of Historic Places in 1998, Starved Rock is an incredible spectacle offering over 13 miles of hiking trails , 14 waterfalls , and 18 glorious sandstone canyons, all less than two hours outside Chicago.

Currently, the Starved Rock State Park and Starved Rock Lodge are open, in addition to the Veranda, The Starved Rock Cafe, and Trailheads Concessions for food and drinks. Steeped in history and beauty, Starved Rock State Park offers a wonderful break for outdoor enthusiasts and those looking for a nonchalant trip outside the city.

📍98 miles outside Chicago

2. Indiana Dunes State Park, Indiana

However, our favorite spot across the eastern border has to be Indiana Dunes State Park. Here you’ll find one of the best views of Chicago’s sensational skyline imaginable. With 2,000 acres of sand and shore, there is so much to explore and plenty of space to enjoy. You can bound up mountainous dunes (and then roll back down them), go spelunking in one of Indiana Dunes State Park’s many caves , take a moment to relax on the beaches of Lake Michigan, and much more.

All of the park’s inns, restaurants, all nature preserves, forest, fish, and wildlife areas are open for you to explore this spring and summer!

For real-time updates on what’s available at the Indiana Dunes State Park, follow Indiana State Parks on their social media.

📍50 miles outside Chicago

3. Galena, Illinois

A little journey to the top western corner of Illinois, but still just a one-tank trip, and you’ll find Galena. Listed on the National Register of Historic Places, the city is renowned for its rich history, charming 19th-century architecture , rolling hills, and numerous resorts. It’s a quaint but enjoyable historic getaway named after the mineral galena, which was the reason for the first major mineral rush in the United States.

It’s one of our favorite small towns near Chicago , where visitors can enjoy views of three states from Horseshoe Mound, just outside of Galena. At the same time, the Great Galena Balloon Race happens yearly and offers the chance to enjoy the magic of more than 20 hot air balloons, three races, a night glow extravaganza, bounce houses, live music, and much more at a spectacular three-day event.

📍150 miles outside Chicago

4. Lake Geneva, Wisconsin

Lake Geneva has long been a vacation haven for Chicagoans. The resort city features 21 miles of beautiful shoreline with amazing beaches and a sea of water activities. Whether you’re looking to kick back and relax at a resort, gear up for the many outdoor activities the city has on hand, or relish in its variety of restaurants, retailers, and nightlife attractions, Lake Geneva has what you’re looking for.

📍80 miles outside Chicago

5. Rockford, Illinois

With the exception of Gary, Indiana — every one of these destinations will give you a chance to step back and relax. If relaxation is your intention, Rockford is one of your best bets. The city is flush with blooming gardens and a network of streaming rivers . Like Chicago, it boasts terrific eateries and fantastic amenities and attractions, such as the sublime Anderson Japanese Gardens. This award-winning landscape was named one of the highest-quality Japanese Gardens in North America by Sukiya Living Magazine.

📍89 miles outside Chicago

6. Milwaukee, Wisconsin

While it is the second-largest city on Lake Michigan’s shore behind Chicago, taking a drive up to Milwaukee provides a nice change of scenery but a similarly vibrant urban experience in another ethnically and culturally diverse city. Take your pick from the plethora of top-notch breweries around the city for the full taproom experience.

See what else is on tap in the city by checking out their amazing food, scenic drives, outdoor art, beaches, parks, and their famous Riverwalk, making it this part of weekend getaways from Chicago you need to check out. From the Harley-Davidson Museum to the Milwaukee Art Museum , there are also an array of great museums if you’ve spent too much time in Chicago’s many museums.

📍92 miles outside Chicago

7. Holland, Michigan

With this town’s dazzling display o f 4.5 million blooming tulips , it’s no wonder that Holland, Michigan made it on our weekend getaways from Chicago list. The town is rich in Dutch culture. Throughout the year, the town regularly holds a variety of parades in honor of its Dutch heritage. Visitors can explore wonderful Dutch cuisine , architecture, windmills, and art collections around the city. If you visit Holland, be sure to stomp by the DeKlomp Wooden Shoe & Delft Factory for the ultimate experience.

8. Door County, Wisconsin

Take your partner on a romantic getaway to Door County, Wisconsin. Door County is home to 300 miles of shoreline, acres of orchards, five state parks, and 11 historic lighthouses . Choose your lodgings in a bed & breakfast, log cabin, a cozy cottage, or do it big at a resort. Wherever you hang your hat at night, know there’s much to do during the day.

Explore the county’s beautiful parks , caves, and forestry, or voyage out to one of its islands by sea — whether by boat, kayak, or paddleboard — though the latter might take a minute. Go cherry-picking and finish the day with fine wine, local brew, or cider while dining down on home-cooked cuisine.

📍244 miles outside Chicago

9. Shawnee National Forest, Illinois

While it is certainly a bit of a trek to this spot on the opposite side of Illinois, the natural landscapes make it worth the trip of weekend getaways from Chicago. Shawnee National Forest is our state’s only national forest, spanning approximately 280,000 acres in Southern Illinois between the Mississippi and Ohio rivers.

It is home to some awe-inspiring natural landscapes , unique ancient rock formations, sprawling panoramic views, and breathtaking hikes. The 300-million-year-old sandstone rock formations known as The Garden of the Gods offer some of the most stunning scenery in Illinois and are one of the most photographed places in the state. The famous Observation Trail takes you through the abundance of natural beauty.

The forest is also home to some extraordinary caves, such as Ox-Lot Cave and the enormous 55ft wide cave overlooking the Ohio River by the name of Cave-In-Rock, which was once a refuge stronghold for frontier outlaws. There are plenty more natural spectacles like the monolithic 30 feet high and eight feet Pomona Natural Bridge extending 90 feet over a verdant ravine and numerous beautiful waterfalls like Jackson Falls to explore on a hot day. An abundance of camping spots means it’s an easy task for keen campers, but Shawnee Forest Cabins with Wi-Fi, hot tubs, and fireplaces, as well as rentable treehouses, offer memorable experiences.

📍309 miles outside Chicago

10. Gary, Indiana

A world away from the waterfalls of Starved Rock, but under two hours by car, we’d be remiss, not to mention the casinos in Indiana. If you are ready to roll the dice, drive to Gary, Indiana, to visit the Majestic Star Casino. There you’ll find six floors packed with all the classic casino games — poker, blackjack, baccarat, roulette, and a wide — in a whirling atmosphere of bright blinking lights, buzzing slots, and high-rolling energy.

The casino has been revamped since a return to normalcy following the pandemic and offers a cutting-edge experience with added safety and sanitary measures.

📍30 miles outside Chicago

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35 Best Weekend Getaways From Chicago — Quick Trips!

By: Author Cole Evans

Posted on Published: January 12, 2023  - Last updated: September 5, 2023

There’s no better way to discover the heart of America than through Chicago.

It’s the third largest city in the country, where its skyline meets the shoreline.

And your best weekend getaways from Chicago start the moment you arrive.

Its modern architecture, museums, vibrant music scenes, clubs, and outdoor activities are just some of the many things you can see and do here.

But in a city this vast, you may think and ask what to do and where to stay.

It is a question relatable to many.

As a traveler with years of experience, I visited Chicago and explored its beauty.

I stayed in some of the best properties and toured the city.

And to help you out, I compiled and ranked those places based on different and practical criteria.

Are you keen on knowing more?

Then check out my review with tips below.

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Best Weekend Getaways From Chicago Compared

For your best weekend getaway in Windy City, review my guide below.

Editor’s Choice

Four Seasons Chicago

Four Seasons Chicago is the best place where you can marvel at the beauty of the city’s skyline.

• Room Variety: 5/5
• Comfort and Cleanliness: 5/5 
• Location: 5/5
• Affordability: 3/5
• Family-Friendliness: 4/5

#2nd Best Choice

Waldorf Astoria Chicago

If you want exclusivity in your stay in Chicago, choose Waldorf Astoria. It has 215 elegant guest rooms inclusive of oversize bathrooms with tubs.

• Room Variety: 4.5/5
• Comfort and Cleanliness: 5/5
• Family-Friendliness: 

#3rd Best Choice

The Peninsula Chicago

It is a five-star hotel that will surely level up your stay in the city.

• Affordability: 2.5/5
• Family-Friendliness: 5/5

Here are the top 35 weekend getaways in Chicago.

1. Four Seasons Chicago (Editor’s Choice)

120 E Delaware Chicago, IL 60611 (312) 280-8800 Visit Website Social Media Open in Google Maps

Ratings Criteria

• Beautiful city view
• Ideal for business or family trip
• Not so spacious lobby area

Chicago is the home to some of the world’s earliest skyscrapers.

And it is still renowned for its inspiring architectural design.

But it doesn’t stop there.

A luxurious stay here is guaranteed with exceptional service, facilities, and amenities.

Its lobby and lounge are designed ideally for entertainment and socializing.

And its restaurant and bar offer nothing but the perfect taste of Chicago. 

What’s more notable is its perfect location where you can revel in food, drinks, art, and music in the city center.

2. Waldorf Astoria Chicago

11 E Walton St Chicago, IL 60611 (312) 646-1300 Visit Website Social Media Open in Google Maps

• Complete amenities
• Spacious rooms
• Quite expensive

If you want exclusivity in your stay in Chicago, choose Waldorf Astoria.

It has 215 elegant guest rooms inclusive of oversize bathrooms with tubs.

Its suites are furnished with terraces where you’ll see the allure of the city’s skyscrapers right before your eyes.

Surrounded by the city’s highlights, you won’t miss a thing.

Go-to spots, shops, restaurants, and bars are just a breeze away.

And after a long day of being a tourist in Chicago, its spa and indoor lap pool is just waiting for you.

Or better yet, stay in your room or sit on the terrace and appreciate the glowing Chicago at night.

3. The Peninsula Chicago

108 E Superior St Chicago, IL 60611 (312) 337-2888 Visit Website Social Media Open in Google Maps

• Unsurpassed service
• Nice location
• Too expensive for what it offers

Whether it’s a weekday or weekend getaway you’re in, The Peninsula Chicago is just a step away.

Each part of it is designed for your perfect Chicago getaway.

Everything is incomparable, from its sophisticated rooms and suites to its fancy restaurant and rooftop spa.

Do you intend to stay longer?

Think about it as your third night is on them when you book at least three consecutive nights.

That’s a pretty reasonable offer, quite hard to resist.

Moreover, almost every must-visit spot is just a walk away from this property.

4. Grand Geneva Resort & Spa

7036 Grand Geneva Way Lake Geneva, WI 53147 (262) 248-8811 Visit Website Social Media Open in Google Maps

With its luxurious facilities, this 1,300 acres of AAA Four-Diamond resort is an excellent alternative to Waldorf Astoria Chicago and The Peninsula Chicago.

This resort encompasses 1,300 acres of countryside in Wisconsin.

It features two lodging options: The Grand Geneva and the Timber Ridge.

By car, Grand Geneva Resort & Spa is 1 hour and 27 minutes away from Chicago.

Enjoy an incredible getaway with the family in this popular resort.

The kids will enjoy the resort’s health and fitness facility, with its programs crafted especially for them.

They can participate in many kid-friendly activities in the adventure center, too.

If they prefer outdoor activities, they can go horseback riding or meet the animals in the zoo instead.

As for the adults, how does a spa treatment sound?

If you opt for physical activities, you can play water sports in Timber Ridge’s park or go wall climbing in the gym.

5. Milwaukee

Milwaukee, WI (414) 286-2489 Visit Website Social Media Open in Google Maps

This city in Wisconsin encompasses over 61,000 acres of land on Lake Michigan’s western shore.

It features breweries, museums, and event venues.

If you’re coming from Chicago, you can reach Milwaukee in 1 hour and 27 minutes.

Here’s one cool overnight trip you won’t forget.

Milwaukee has everything you need for the best weekend adventure.

Want some history?

Check out the Milwaukee Public Museum, with its beautiful recreation of the city at the turn of the 20th century.

If you’re more into nature, the Mitchell Park Horticultural Conservatory is the perfect destination.

It features three domes that each function as a greenhouse and botanical garden.

Enjoy the blushing peonies and firs for the complete nature experience.

Recommended Hotel: The Pfister Hotel

Related: Fun Day Trips From Milwaukee

Related: Hotels in Chicago

6. Indiana Dunes National Park

1215 North State Road 49 Porter, IN 46304 (219) 395-1882 Visit Website Social Media Open in Google Maps

This park stretches for 15,349 acres in northwestern Indiana.

It’s home to a visitor center, park trails, and historical structures.

The travel time from Chicago to Indiana Dunes National Park is 42 minutes.

Are you looking for short trips from Chicago for your weekend getaway with friends?

Head to the Indiana Dunes National Park.

Hike the Dunes Succession Trail, with its vast array of paths perfect for adventurers.

Wear comfortable shoes because you’ll have to walk sandy and wooden trails at the same time.

If you’re up for a challenge, climb 192 feet to the top of Mount Tom.

You’ll get rewarded with stunning views of the dunes and the lake.

Recommended Hotel: Spring House Inn

Madison, WI (608) 255-2537 Visit Website Social Media Open in Google Maps

Madison is the capital city of Wisconsin.

It’s on an isthmus surrounding Mendota, Monona, Waubesa, and Kegonsa lakes.

It’s also home to botanical gardens and architectural gems like the Wisconsin State Capitol.

You can reach Madison from Chicago in 2 hours and 18 minutes if you use a vehicle.

Madison is one of the best places near Chicago for vacation.

Visit any of the city’s nine national historical landmarks, including Jacobs I, a single-family home constructed in 1937.

Not much of a history buff?

Marvel at Jacobs I’s architecture instead.

The home built by architect Frank Lloyd Wright has been touted as the first Usonian home.

The Wisconsin State Capitol is a must-see, too, with its majestic dome and elegant gilded bronze statue on top.

Recommended Hotel: The Madison Concourse Hotel

Holland, MI (616) 355-1370 Visit Website Social Media Open in Google Maps

Spanning over 11,000 acres, Holland is the largest city in Ottawa and Allegan counties.

It’s a popular tourist destination for its rich Dutch heritage.

From Chicago, Holland is only 2 hours and 33 minutes away by car.

If you’re looking to have the perfect weekend getaway, Chicago and its nearby areas offer many options.

Chicago has beautiful parks and skyscrapers.

Meanwhile, Holland has deep Dutch roots evident in many of its landmarks.

In the Windmill Island Gardens, you’ll find the last working mill allowed to leave The Netherlands in 1964.

Check out Nelis’ Dutch Village, too.

The amusement park is home to a gorgeous reproduction of an 1800s Dutch village.

Recommended Hotel: CityFlatsHotel Holland, Tapestry Collection by Hilton

9. Wisconsin Dells

Wisconsin Dells, WI (608) 254-4636 Visit Website Social Media Open in Google Maps

Nestled on the Wisconsin River, this city stretches over 5,200 acres in Adams, Columbia, Juneau, and Sauk counties.

It features a wide array of water parks and nature spots.

You can reach Wisconsin Dells in 2 hours and 56 minutes if you’re driving a car from Chicago.

You and the kids will agree this is one of the best getaways in Chicago and nearby.

After all, who doesn’t like swimming in beautiful blue waters and going down long slides?

If you get tired of swimming in water parks, go on a duck boat tour instead.

Marvel at the beautiful creatures while floating on Lake Delton under the blue Wisconsin skies.

Recommended Hotel: Hilton Garden Inn Wisconsin Dells

Related: Restaurants in Wisconsin Dells, Wisconsin

Related: Weekend Vacations in Illinois

Geneva, IL (630) 232-7494 Visit Website Social Media Open in Google Maps

Geneva is in Kane County, located on the western side of Chicago.

It features an extensive bike trail system and historical sites, some dating back to the 1800s.

It’s a 49-minute drive from Chicago to Geneva.

Geneva is just the place to be if you want to bond with your significant other.

The city is one of the best romantic getaways from Chicago for its natural beauty.

Take a stroll in the beautiful Fabyan Forest Preserve.

Amid the lush greenery stands the majestic Fabyan Windmill, built between 1850 and 1860.

Check out the Fabyan Japanese Garden, too.

It’s a lovely oasis with a small pond and flora that stand out.

Recommended Hotel: Comfort Inn & Suites Geneva- West Chicago

11. Fox River Valley

Fox Valley Aurora, IL 60504 (630) 256-4636 Visit Website Social Media Open in Google Maps

Also known as the Fox Valley, this region extends from Antioch in northern Illinois to Ottawa in the south.

It’s home to the Fox River Trail, green spaces, and water bodies.

The travel time from Chicago to the Fox River Valley is 42 minutes.

This place will make any traveler’s list of inexpensive weekend getaways near Chicago.

The Fox River Valley, after all, is pure nature anyone can explore.

Bike a portion of the 32-mile Fox River trail for stunning views of Carpenters Dam and Tyler Creek.

You can rent a kayak if you prefer a water adventure.

Soak in the gorgeous nature views while gliding along the Fox River.

Recommended Hotel: Best Western Oswego Hotel

12. Harbor Country

Three Oaks, MI (269) 469-5409 Visit Website Social Media Open in Google Maps

This region consists of eight towns in southwest Michigan: New Buffalo, Three Oaks, Lakeside, Harbert, Michiana, Grand Beach, Sawyer, and Union Pier.

It features gorgeous beaches and wineries.

You can get to Harbor Country from Chicago in 1 hour and 12 minutes.

Harbor Country differs from many Chicago weekend getaways.

Unlike your cheap Chicago vacations, this one entails a bit of shelling out money.

After all, Harbor Country is an upscale weekend getaway destination.

Think of it as the Hamptons of New York or the Cape Cod of Boston.

But even if you’d need to shell out a bit, it’s worth it.

You can enjoy the region’s beaches with delicious wine.

Then spend the night in a luxurious bed and breakfast with amenities.

Recommended Hotel: Fairfield Inn and Suites New Buffalo

13. St. Joseph

St. Joseph, MI (269) 983-5541 Visit Website Open in Google Maps

This city stretches for over 3,000 acres on the shores of Lake Michigan.

It’s home to the sandy Silver Beach and parks.

You can get to St. Joseph in 1 hour and 35 minutes if you’re coming from Chicago.

If you prefer cheap vacations from Chicago, head to St. Joseph.

The city is a nature oasis you can enjoy anytime.

Have a picnic on the Silver Beach shore and enjoy the beautiful landscape.

If you prefer a more strenuous activity, go swimming in the gorgeous blue waters.

Are you a fitness enthusiast?

Go on a hike for your dose of exercise in Tiscornia Park.

Recommended Hotel: The Inn at Harbor Shores

14. South Haven

South Haven, MI (269) 637-0700 Visit Website Social Media Open in Google Maps

This city encompasses 2,240 acres of land in Van Buren and Allegan counties.

It features a gorgeous harbor and beaches.

If you’re driving from Chicago, you can reach South Haven in 2 hours and 2 minutes.

Commune with nature in this popular tourist destination.

The city’s seven public beaches aren’t just the perfect spots for swimming.

They make for beautiful pictures, too, with their gorgeous sea waters and shores.

If you get tired of the beach, check out the beautiful South Haven harbor.

Enjoy the stunning water views, then walk downtown for the perfect meal.

Recommended Hotel: Hampton Inn South Haven

Gurnee, IL (847) 599-7500 Visit Website Social Media Open in Google Maps

This village borders Waukegan in the Chicago metropolitan area.

Located 35 miles from Chicago, it’s home to the Six Flags Great America amusement park.

If you drive a vehicle from Chicago, you can get to Gurnee in 50 minutes.

Enjoy pure family fun in Gurnee, with its amusement park known for its adrenaline-pumping rides.

Try all 17 of Six Flags’ heart-stopping roller coasters for the complete adventure.

But if you’re not a thrill-seeker, don’t worry.

You can enjoy the park’s entertaining shows instead.

Or just explore Gurnee Mills, a mall that features over 170 stores.

Recommended Hotel: Country Inn & Suites by Radisson, Gurnee, IL

16. South Bend – Indiana

South Bend Indiana, United States (574) 233-0311 Visit Website Social Media Open in Google Maps

An hour and 44-minute drive from Chicago lies South Bend, Indiana.

It’s a great day trip destination to explore more of what’s outside Chicago.

This city is home to the University of Notre Dame, a prestigious university known for its gold-domed main building.

And if you proceed to the city center, you’ll witness its thriving art scene.

There lies the Studebaker National Museum which has numerous displays of classic cars.

Morris Performing Arts Theater, a 2,564-seat concert hall, is a shouldn’t-miss part, too.

Surely you’ll see all the must-sees in the city within a day; a perfect place for your weekend getaway from Chicago.

Recommended Hotel: Antioch Inn & Suites Near Gurnee

17. Lake Geneva

Lake Geneva, WI (262) 248-3911 Visit Website Social Media Open in Google Maps

Located on Geneva Lake, this resort city features gorgeous beaches, parks, and Gilded Age mansions.

It is 65 miles northwest of Chicago.

If you use a car, you can get to Lake Geneva in 1 hour and 24 minutes.

Head to Lake Geneva, and you’ll see why it’s one of the best long weekend trips from Chicago.

Although small in size, the city has a lot to offer the traveler.

Explore Shore Path for stunning views of spectacular mansions, some dating back to the 1800s.

Check out the Stone Manor built by real estate magnate Otto Young in 1899.

Blackpoint, constructed in 1888 by Chicago beer baron Conrad Seipp, has 74 species of evergreen trees in front of his mansion.

If you’re not into architecture, you can immerse in nature instead.

Ride a boat on the 5000-acre Geneva Lake and soak in the beautiful views.

Recommended Hotel: Mill Creek Hotel

18. Turkey Run State Park

8121 Park Road Marshall, IN 47859 (765) 597-2635 Visit Website Open in Google Maps

This park, created in 1916, is Indiana’s second state park.

It stretches for 2,382 acres of land in Parke County.

It’s also home to historical sites, a pool, and public sitting areas.

If you use a vehicle, the travel time from Chicago to Turkey Run State Park is 3 hours.

You won’t run out of things to do in this park.

Experience nature at its finest while hiking a portion of the 14 miles of trails with varying degrees of difficulty.

Are you a history enthusiast?

The park has individual sites listed on the National Register of Historic Places.

Check out the Lusk Home and Mill Site, which date back to 1822 and 1826, respectively.

The Richard Lieber Log Cabin, built in 1848, is a must-see, too.

Recommended Hotel: Turkey Run Inn & Cabins

19. The American Club Resort Hotel

419 Highland Drive Kohler, WI 53044 (800) 344-2838 Visit Website Social Media Open in Google Maps

Built in 1918 as a male dormitory for Kohler employees, this lodging institution is now a five-star hotel that offers wellness and recreational opportunities.

By car, The American Club Resort Hotel is 2 hours and 22 minutes away from Chicago.

Who says you can’t have some incredible me-time in one place?

At The American Club Resort Hotel, you can.

Have the ultimate relaxing experience at the Kohler Waters Spa.

After your spa, enjoy your favorite book in the hotel’s reading area.

You can also check out the Kohler Design Center instead, with its stunning bathroom designs.

Enjoy an upscale meal in The Immigrant for the perfect bonding moment with yourself.

20. Whistling Straits

N8501 Lakeshore Road Sheboygan, WI 53083 (800) 444-2838 Visit Website Social Media Open in Google Maps

This luxury golf resort, owned by Kohler Company, is along the Wisconsin coastline.

The resort consists of two golf courses: the Straits and the Irish.

You can reach Whistling Straits in 2 hours and 28 minutes if you travel by car from Chicago.

If you love golf, Whistling Straits should be your go-to place.

Enjoy state-of-the-art 36-hole links-style golf courses set against a beautiful nature landscape.

Whistling Straits offers incredible views of Lake Michigan and rolling hills.

The Irish, meanwhile, will transport you to the gorgeous European country with its rugged coastline and smooth grassy terrain.

You won’t just get to play your favorite sport here.

Recommended Hotel: Harbor Winds Hotel

21. Parke County

Parke County, IN (765) 569-3394 Social Media Open in Google Maps

This rural county stretches for over 284,000 acres of land along the Wabash River.

It lays claim to being the Covered Bridge Capital of the World.

If you’re coming from Chicago, Parke County is 3 hours and 26 minutes away by car.

Do you love architecture?

Go on a weekend getaway to Parke County, then.

You need more than enough time to visit the county’s 31 covered bridges, each with its unique architectural design.

The Portland Mills Covered Bridge is a must-see.

Built in 1856, it’s a single-span Burr Arch truss-covered bridge that’s also the second oldest in the county.

Check out the Jackson Covered Bridge, built on a base of hewn stone in Rockport.

Constructed in 1861, it’s the oldest standing bridge built by the acclaimed J.J. Daniels.

Galena, IL (815) 776-9200 Visit Website Social Media Open in Google Maps

This city in Illinois is the largest in Jo Daviess County.

Located in an unglaciated area in the northwest portion of the state, it’s famous for its rolling hills and 19th-century architecture.

Galena is a 3-hour drive from Chicago.

Although a city by classification, Galena exudes a small-town vibe, making it a popular destination.

Picture gorgeous red-brick structures lining the main road where traditional carriages occasionally ply.

Go kayaking along the river to experience stunning views of nature wherever you look.

You can walk through native prairies and interact with goats here, too.

Cap off your weekend with a challenging game of golf on any of the city’s 11 picturesque courses.

Recommended Hotel: Country Inn & Suites by Radisson, Galena, IL

23. Dubuque

Dubuque, IA (563) 589-4100 Visit Website Social Media Open in Google Maps

Nestled along the Mississippi River, Dubuque encompasses over 19,000 acres of land at the junction of Iowa and Wisconsin.

It’s a go-to place for its unique architecture and historical sites.

You can get to Dubuque from Chicago in 3 hours and 16 minutes by car.

Dubuque is heaven for architecture and history buffs.

Head downtown, and you’ll find the Dubuque County Courthouse.

It’s in the Beaux Arts architectural style, built from 1891 to 1893.

The Holy Ghost Catholic Church in the North End is a must-see, too.

Formed in 1896, the beautiful church’s Romanesque Revival style stands out.

In the South End, check out St. Raphael’s Cathedral.

The church traces its roots way back in 1833.

Enjoy its Gothic Revival Style amid Dubuque’s nature landscape.

Recommended Hotel: Hotel Julien Dubuque

24. Field of Dreams

28995 Lansing Road Dyersville, IA 52040 (563) 875-8404 Visit Website Social Media Open in Google Maps

Built in 1988 for the movie Field of Dreams, this baseball field now functions as a sports venue and pop culture destination.

It’s also home to a souvenir shop and a 2,600-square-foot barn that serves as an event center.

By car, Field of Dreams is 209 miles away from Chicago. So you can get to the iconic baseball field in approximately 4 hours.

This isn’t your ordinary baseball field.

It has pop culture significance as the filming site of the Academy Award-nominated movie Field of Dreams.

So when you get to the place, you can also tour the Kinsella family house as shown in the movie.

You can also purchase official Field of Dreams apparel from Baseballism, the movie’s on-site official retail store.

Spend a night in the newly remodeled three bed-room farmhouse for the complete movie experience.

Recommended Hotel: Super 8 by Wyndham Dyersville

25. Ann Arbor

Ann Harbor, MI (734) 794-6000 Visit Website Social Media Open in Google Maps

This city stretches for over 18,600 acres in the Midwestern state of Michigan.

It is home to the University of Michigan, museums, and parks.

The travel time from Chicago to Ann Arbor is 4 hours and 33 minutes by car.

Ann Arbor has everything you need for the perfect weekend getaway.

The University of Michigan Museum of Art will give you a one-of-a-kind artistic experience, with its collection spanning over 150 years.

If you’re more of a history buff, the Kelsey Museum of Archaeology is just the place for you.

It’s home to over 100,000 artifacts, including mummies.

Don’t worry if you’re not much of a museum-goer.

Ann Arbor has gorgeous parks you can explore, too.

Go paddle-boarding on the Huron River for fantastic views of the Michigan skies, flora, and fauna.

You can also hike the trails of Gallup Park and explore its 69 acres of open green spaces and water bodies.

Recommended Hotel: Graduate Ann Arbor

26. Traverse City

Traverse City, MI (231) 947-1120 Visit Website Social Media Open in Google Maps

This city stretches for over 5,500 acres in Grand Traverse and Leelanau counties.

It’s the largest city in the Northern Michigan region.

It’s home to beaches, at least 30 public parks, and historical sites.

By car, you can get to Traverse City in 5 hours and 8 minutes if you’re coming from Chicago.

The trip from Chicago to this city may take longer than your usual day trips outside.

However, it’s worth it.

Immerse in history with a tour of landmark sites, such as the City Opera House and Novotny’s Saloon.

Take the kids to Indian Woods Park, where they can also use playground equipment in a beautiful nature landscape.

If you want some physical activity, try hiking.

Just take your pick from the over 30 trails that meander through gorgeous woodlands and open green spaces in the city.

Recommended Hotel: Country Inn & Suites by Radisson, Traverse City, MI

27. Louisville

Louisville KY (502) 379-6109 Visit Website Social Media Open in Google Maps

Nestled on the Ohio River, Louisville is Kentucky’s largest city.

It features boxer Muhammad Ali’s home, some Fortune 500 companies, and a wide array of dining options.

If you’re driving from Chicago, you can reach Louisville in 4 hours and 47 minutes.

Experience the big city life in Louisville.

Marvel at the gorgeous skyscrapers that jut into the Kentucky skies.

The 400 West Market stretches 549 feet above the ground.

A close second is the National City Tower, with a height of 512 feet.

Then head to Mall St. Matthews for your shopping needs.

The mall features over 140 specialty retailers, which means you’re bound to find something to take home.

Recommended Hotel: The Brown Hotel

28. St. Louis

St. Louis, MO (314) 421-1023 Visit Website Social Media Open in Google Maps

This city is along the Mississippi River.

Commonly known as the Gateway to the West, the city has independent frontier-town roots and a vibrant blues music scene.

From Chicago, St. Louis is 4 hours and 35 minutes away by car.

If you love history, don’t miss out on St. Louis.

The city is home to majestic structures, some of them dating way before the Civil War.

Drop by the Basilica of St. Louis, built between 1831 and 1834.

The Christ Church Cathedral is a must-visit, too, with its Gothic Revival style completed in 1867.

Don’t forget to check out the arch that gave St. Louis its Gateway to the West moniker.

Completed in 1965, the long arch is also an architectural beauty, standing 630 feet tall.

Recommended Hotel: Angad Arts Hotel

Related: Fun Day Trips From St Louis

Zion, IL (847) 746-4000 Visit Website Social Media Open in Google Maps

This city encompasses over 6,300 acres of land in Lake County at an elevation of 187 meters.

It boasts beautiful parks and historical structures.

You can get to Zion in 58 minutes if you’re coming from Chicago.

Have the ultimate nature experience in Zion, with its 24 parks offering incredible views of flora.

Go biking through Edina Park, with its serene pond and open spaces

Hermon Park is perfect for picnics, with its tall trees surrounding green grass.

If you still have energy for more workout activities, hike a portion of the trail that cuts through Carmel Park.

You’ll get stunning views of the clear Illinois skies and lush greenery.

Recommended Hotel: The Inn On Sheridan

30. Elkhart Lake

Elkhart Lake, WI (920) 876-2231 Visit Website Social Media Open in Google Maps

This village in Sheboygan County runs along Elkhart Lake.

It’s famous for its natural beauty, museums, and road race events.

If you drive from Chicago, you can reach Elkhart Lake in 2 hours and 30 minutes.

You’ll enjoy your weekend getaway in Elkhart Lake with the tons of activities you can do here.

Hike the 3.35-mile segment of the Ice Age National Trail for beautiful views of rolling hills.

If you get tired of hiking, visit Road America, which stretches over 4 miles around the lake.

The track that has been around since the 1950s continues to host racing events.

Time your visit to the city based on the racing schedule so you can attend one.

Recommended Hotel: Baymont by Wyndham Plymouth

31. Richland County

Richland County, WI (608) 647-8821 Visit Website Social Media Open in Google Maps

This county stretches for 376,960 acres in southwestern Wisconsin.

Richland County is home to Frank Lloyd Wright architecture, parks, and museums.

Richland County is 3 hours and 37 minutes away from Chicago by car.

Richland County has something to offer, whether you’re a history buff or a nature enthusiast.

Check out the Albert D. German Warehouse, designed by acclaimed architect Frank Lloyd Wright in 1915.

You can unwind at Alana Springs Campground, where you can set up your tent amid gorgeous nature.

The Pier County Park is a must-see, too, with its layered and blocked sandstone rising for about 60 feet.

Recommended Hotel: Ramada by Wyndham Richland Center

Related: Best Weekend Getaways From Minneapolis

32. Door County

Door County, WI (920) 743-5511 Visit Website Open in Google Maps

Situated on a peninsula between Green Bay and Lake Michigan, Door County is home to many beaches and parks.

Chicago is 244 miles away from Door County.

If you travel from Windy City by car, you can get to Door County in 3 hours and 48 minutes.

Door County has a little bit of everything for everyone.

For the nature buff, Cave Point County Park is a must-visit.

The park is home to gorgeous underwater caves and limestone cliffs you can explore.

For the history enthusiast, check out the Eagle Bluff Lighthouse, built in 1868.

The Door County Maritime Museum is a great destination, too, with its comprehensive exhibits on Great Lakes history.

Door County even has something for the wine lover.

Enjoy delightful wines made from California grapes in Stone’s Throw Winery.

Recommended Hotel: Gordon Lodge

33. Vilas County

Vilas County, WI (715) 479-3600 Visit Website Open in Google Maps

This county stretches for 548,480 acres in northern Wisconsin.

It’s home to nearly 90 scenic forest trails and over 1,300 lakes.

From Chicago, the drive to Vilas County will take you 5 hours and 44 minutes.

It’s quite a long journey from Chicago to Vilas County.

But when you get to the place, you’ll conclude the trip is worth all your time and effort.

After all, the place is a nature oasis.

Go boating on Eagle Lake and soak in the gorgeous lush greenery around you.

You can hike the 1.5-mile loop near Eagle River afterward.

Whatever you do, you’re in for a beautiful nature immersion.

Recommended Hotel: Hiawatha Lodge Inn

34. Shawnee National Forest

Herod, IL 629646 (618) 253-7114 Visit Website Social Media Open in Google Maps

Nestled in southern Illinois between the Ohio and Mississippi Rivers, this national forest stretches for 289,000 acres.

It’s home to forests, lush canyons, and ridges.

The travel time from Chicago to Shawnee National Forest is 5 hours and 25 minutes.

Travel to one of nature’s wonders for the perfect weekend trip.

Experience Cedar Lake a different way, on board a beautiful horse and under the gorgeous Illinois skies.

You can hike in the park if you prefer to walk.

How about exploring a portion of the 160-mile River Trail that will take you to gorgeous forest streams and greenery?

Recommended Hotel: Baymont by Wyndham Marion

35. Pictured Rock National Lakeshore

N8391 Sand Point Road Munising, MI 49862 (906) 387-3700 Visit Website Social Media Open in Google Maps

This tourist destination encompasses the south shore of Lake Superior in Michigan.

It’s home to unusual sandstone formations and shipwrecks.

You can reach Pictured Rock National Lakeshore in 6 hours and 12 minutes by car.

This is one of the best weekend getaways from Chicago for a reason.

The place is a visual treat, with its magnificent cliffs.

The cliffs can go as high as 200 feet above sea level, with formations ranging from human profiles to castle turrets.

Bring your camera because you’ll want to take pictures of everything here.

Recommended Hotel: Comfort Inn & Suites Munising – Lakefront

Getaway Guide 

Comparing destinations: which one is right for you.

Knowing the pros and cons of each destination will help you decide which one is ideal for you.

And remember that your preference also plays a vital role in picking what’s best.

The Four Seasons Chicago lives up to what it promises guests: a luxurious and relaxing stay.

But for years in business, some parts need an update already.

Meanwhile, Waldorf Astoria Chicago is indeed a luxury hotel with unsurpassed facilities and amenities, but it also comes with a high cost.

On the other hand, The Peninsula Chicago has everything you need and expect from a five-star hotel.

But just like other luxury hotels, it’s also quite expensive.

Finally, Grand Geneva Resort & Spa has an array of activities for fun and relaxation for everyone.

But its customer service could be better. 

How I Picked The Destinations 

With years of experience as a blogger and traveler, I have learned much about picking the best destination and property to stay.

I thoroughly researched where to stay and what to do in Chicago.

My fellow travelers also gave reliable suggestions, and when I got there, I tried them myself.

My research and experience in the city strengthen my conclusion of what’s best.

Our Property Rating Method 

I rate these properties based on the following criteria:

• Room Variety: I use this to rate the room options offered by every property. What room types are available? Can it accommodate different budgets, group sizes, and preferences? I ask myself these questions when evaluating the property’s room variety. 
• Comfort and Cleanliness: This measures the overall cleanliness and comfort of the accommodations. Does it have comfortable beds? Are the rooms spotless and dust-free? These are important factors I consider when rating comfort and cleanliness. 
• Location: This is used to evaluate how convenient and accessible the property is. How close is it to the attractions? Are there good public transportation options near the location? Is it easily accessible for families? These questions are important when I rate the location of every accommodation. 
• Affordability: I use this to evaluate the property’s affordability. Are the room rates reasonable? Does the property have any additional fees? Does the property offer discounts or packages? I ask myself this in order to rate affordability. 
• Family-Friendliness: This evaluates the family-friendliness of each property. Does it offer babysitting services and children’s activities? Does it have connecting rooms for families? I use these questions to rate the family-friendliness of the property. 

Frequently Asked Questions 

What are cities 3 hours from chicago.

Milwaukee, Rockford, and Michigan City are within a two-hour drive from Chicago.

How Far Is Lake Geneva From Chicago, And What Can I Do There?

Lake Geneva is about a 90-minute drive from Chicago. It offers a range of activities including boating, fishing, golfing, hiking, and skiing in the winter. The area is also home to several spas and wellness centers.

A stay in a property with a perfect location will give you nothing but only the best weekend getaways from Chicago. 

My Waldorf Astoria Chicago experience was beyond impressive.

I had a relaxing and with-a-view room.

The excellent location for shopping and restaurants was what I love most about The Peninsula Chicago.

And the variety of activities I did at Grand Geneva Resort & Spa was immense.

My favorite was the view of the calm lake

But the top pick of the bunch is the Four Seasons Chicago.

The welcoming staff, fancy and modern facilities, and countless amenities made me enjoy my stay. 

During my stay at the Four Seasons Chicago, I particularly enjoyed their renowned spa, indulging in a rejuvenating massage and a soothing swim in the indoor pool.

My family and I savored the diverse breakfast options, with my children relishing the fluffy pancakes. 

When exploring the surrounding areas, we appreciated the hotel’s proximity to the iconic Magnificent Mile, making it easy to shop and dine.

My kids had a blast at the nearby Navy Pier, where we enjoyed a fun-filled afternoon. 

Four Seasons Chicago offered the ideal blend of relaxation and adventure for our family getaway.

10 Easy Weekend Getaways from Chicago—No Flights Required

Escape chicago for a few days with one of these 10, drivable weekend getaways and short road trips starting in chicago..

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Door County, Wisconsin, is one of the many easy-to-reach day trip destinations from Chicago.

Photo by Bailey Berg

Despite cries about that winter weather, Chicago is inarguably blessed with a little something we like to call location, location, location : With prime real estate on Lake Michigan, the Midwest city is about as far by car from Minneapolis (six hours) as it is Toronto (eight hours) and Nashville (seven hours). In this sense, it’s an ideal jumping-off point for a drivable trip. There are several weekend getaways from Chicago, whether you want to put some serious miles on your car or be somewhere new by the time your kids are done watching Cars. Read on for ten easy weekend getaway ideas from Chicago.

What cities are under three hours from Chicago by car?

• Milwaukee, Wisconsin (1 hour, 30 minutes)
• Madison, Wisconsin (2 hours, 25 minutes)
• Grand Rapids, Michigan (2 hours, 47 minutes)
• Peoria, Illinois (2 hours, 41 minutes)
• South Bend, Indiana (1 hour, 39 minutes)
• Indianapolis, Indiana (2 hours, 56 minutes)

The Dane County Farmers’ Market in Madison is one of the largest in the U.S.

Photo by MarynaG/Shutterstock

Geneva, Illinois

• Distance: An hour by car
• Best for: Singular art and great shopping

OK, OK. Geneva is technically a suburb of Chicago, but it feels worlds away, thanks to its small-town charm. Drop your bags at the boutique Herrington Inn & Spa , located on the Fox River, and set out to explore the city’s walkable downtown on foot. Public art abounds here, as do independent shops and restaurants (all told, there are more than 150 of them in the historic district).

Michigan City is a breath of fresh air not far away.

Photo by Andy Konieczny / Shutterstock

Michigan City, Indiana

• Distance: An hour and a quarter by car
• Best for: Hiking (and swimming for the brave)

On a clear day from Michigan City, you can see Chicago’s skyline across the water. Enjoy towering sand dunes, the cool waters of Lake Michigan, and nearly 50 miles of trails at Indiana Dunes National Park ; in Michigan City proper, attractions include the 19th-century Barker Mansion —listed on the National Register of Historic Places—and family-friendly Washington Park Zoo .

A lighthouse in New Buffalo, Michigan

Photo by Suzanne Tucker/Shutterstock

Harbor Country, Michigan

• Best for: A beach and wine combo trip

Comprising the eight towns of Michiana, Grand Beach, New Buffalo, Three Oaks, Union Pier, Lakeside, Harbert, and Sawyer, Harbor Country is a favored weekend escape from the Windy City, thanks to its beach and country offerings. There are also a number of world-class wineries and breweries in the area, including the popular Lehman’s Farmhouse and Dablon Vineyards and Winery , in nearby Baroda.

Milwaukee is home to one of the largest German populations in the U.S.

Photo by Jayne Lipkovich / Shutterstock

Milwaukee, Wisconsin

• Distance: An hour and a half by car
• Best for: Brats and brews

Milwaukee has a rich German heritage, which means the city is full of places to get a good beer and brat (and more beer, if that’s your thing). Both Pabst Blue Ribbon and Miller are based here, but don’t sleep on the smaller guys, including Milwaukee Brewing and Lakefront .

Mary stands atop the Golden Dome of the University of Notre Dame Main Administration Building.

Photo by Jonathan Weiss/Shutterstock

South Bend, Indiana

• Distance: An hour and forty minutes by car
• Best for: Whitewater rafting

There’s more to South Bend than Fighting Irish football, though we absolutely cosign the idea of a walk around Notre Dame’s scenic campus. Hit the rapids on East Race Waterway , North America’s first artificial white-water course, which cuts through the city, or visit the historic Robinson’s department store to throw your own pottery at the Pigeon and the Hen . Play arcade games—for free!—at the Garage Arcade and Bar , which has all the classics, Galaga and Ms. Pac-Man included.

The Fredrick Meijer Gardens spans 158 acres and features a host of outdoor art exhibits.

Photo by SNEHIT PHOTO / Shutterstock

Grand Rapids, Michigan

• Distance: Around three hours by car
• Best for: Beer, of course, but also outdoor sculptures

Voted “Beer City USA” in several national polls, Grand Rapids is known for its suds: Check out the Beer City Ale Trail , a map showcasing all of the options in the city. For food, we’re partial to strolling Downtown Market , which counts more than 20 vendors in the hall south of Heartside Park (a perfect picnic location, if you ask us). For an outdoor experience that requires a bit more activity, head to the 158-acre Frederik Meijer Gardens & Sculpture Park : here, you’ll find art by Auguste Rodin as well as a hall dedicated solely to carnivorous plants.

A dinosaur breaks out of the Children’s Museum in Indianapolis.

Photo by James Kirkikis/Shutterstock

Indianapolis, Indiana

• Distance: Three hours by car
• Best for: Museums, both traditional and quirky

Indianapolis is an incredible museum city. Although two of its most popular attractions are the Children’s Museum and the sprawling indoor-outdoor Indianapolis Museum of Art , don’t miss some of the city’s quirkier options: the Indiana Medical History Museum (not for the faint of heart) and the Kurt Vonnegut Museum and Library . Visit Indy’s famed City Market to sample more than 25 locally owned eateries; when you’ve had your fill, descend underground on a public catacombs tour, which takes place on the select Saturdays, May through October, between 10 a.m. and 3.15 p.m. (Private tours can be booked with Indiana Landmarks .)

Ann Arbor is known for its university, but a host of delights awaits all visitors.

Photo by Dark Vader / Shutterstock

Ann Arbor, Michigan

• Distance: Around three hours and 45 minutes by car
• Best for: Adventures on the river

Activities for all seasons abound in Ann Arbor, best known as the home of the University of Michigan. Tube, kayak, SUP, or canoe down the peaceful stretch of the Huron River—accessed from the 69-acre Gallup Park—or stroll U of M’s famed Matthaei Botanical Gardens and Nichols Arboretum . Be sure to make time for the city’s Kerrytown Market and Shops , a picturesque neighborhood full of independent boutiques and restaurants. ( Zingerman’s Deli , one of the best spots in Ann Arbor for a sandwich, is here.)

An aerial view of Door County, Wisconsin

Photo by Matt Sampson Photography/Shutterstock

Door County, Wisconsin

• Distance: Four and a half hours by car
• Best for: Exploring rugged coastline

A 70-mile-long peninsula, Door County is often called the “ Cape Cod of the Midwest” —and rightfully so. Just 50 miles northeast of Green Bay, Door County has stunning coves, cherry orchards, harbors, lighthouses, wineries, and some 300 miles of coastline. Newport State Park is an International Dark Sky Reserve , and the 900-acre Rock Island State Park has no cars; for a dose of small-town charm, stop by Ephraim, a Scandinavian-style village .

Traverse City might be a bit further away, but it’s worth the drive—especially in the fall.

Photo by Gary R Ennis Photos / Shutterstock

Traverse City, Michigan

• Distance: Five hours by car
• Best for: Exploring shops and galleries in a justifiably popular small town

No wonder Traverse City was named one of the sweetest small towns to visit in summer : a lakeshore beauty with art deco architecture, the city is beloved by many Chicagoans (including Oprah herself). One of Traverse City proper’s most popular attractions is the Village at Grand Traverse Commons: a hospital complex from the 19th century, the historic venue has since been reborn into a mixed-use space, with shops, restaurants, footpaths, and art galleries. Northwest of Traverse City is Leelanau Peninsula, which is home to the striking Sleeping Bear Dunes National Lakeshore .

Where can I go by train from Chicago?

No car? No problem. You can get virtually anywhere from Chicago by train: Memphis is 10 hours by rail; Seattle is 46. But for a weekend getaway, we’re partial to these picks:

• Indiana Dunes National Park (the South Shore Line from Chicago’s Millennium Station stops at four stations in the park )
• Milwaukee, Wisconsin (about 90 minutes by Amtrak from Chicago’s Union Station)
• Kalamazoo, Michigan (about two hours by Amtrak from Chicago’s Union Station)
• Grand Rapids, Michigan (about four hours by Amtrak from Chicago’s Union Station)

Of course, there’s plenty to do in Chicago itself before you head off; it was ranked number 2 in the best cities in the U.S. for 2023 , after all, thanks to its top restaurants , world-class museums, and abundant hotel options. On the other hand, if you’re feeling really adventurous, you could always take the ultimate epic road trip: 2,448 miles all the way to Santa Monica , California.

Happy weekending.

This article originally appeared online in 2020; it was most recently updated on August 31, 2023, to include current information.

• Destinations

20 Best Weekend Getaways from Chicago

Last Updated By VI in Illinois on November 17, 2023

Grand Geneva Resort - 1 hour 30 minutes from Chicago

Grand traverse resort - 5 hours from chicago, the abbey resort - 1 hour 40 minutes.

• Complete List & Map

Midwest Vacation Ideas: From Minneapolis , Ohio , MN , Iowa , From Detroit , Michigan --->

100 Grand Traverse Resort Village Blvd, Acme, MI 49610

269 Fontana Blvd, Fontana-On-Geneva Lake, WI 53125

Egg Harbor - The Newport Resort - 4 hours 30 minutes

7888 Church St, Egg Harbor , WI 54209

The Knickerbocker on the Lake - 1 hour 30 minute

Browse Best Beaches Near Milwaukee

The Green Tree Inn - 4 hours 25 min

15 Mill St., Elsah IL, 618-374-2821

The American Club, Kohler - 2 hours 30 minutes

East Coast Vacations: North Carolina Vacations , SC Getaways , From Atlanta , Connecticut , Rhode Island

Washington House Inn - 2 hours

More to Explore: Getaways from NYC , Maine Getaways , New Hampshire , From Boston , East Coast

Sweethaven Resort - 1 hour 20 minutes from Chicago

9517 Union Pier Rd, Union Pier, MI 49129

Hawk Valley Retreat & Cottages - 2 hours and 45 minutes

2752 W. Cording Rd., Galena IL, 888-777-6016

Mansion Hill Inn for Couples - 2 hours 30 minutes

424 N Pinckney St, Madison, WI 53703, 608-255-0172

Vrooman Mansion - 2 hours

701 East Taylor St., Bloomington IL, 309-828-8816

Oakwood Resort, Syracuse, IN

Oakwood Resort, 702 E. Lake View Road, Syracuse, IN 46567, 574-457-7100

Farmers Guest House - 2 hours 45 minutes

344 Spring St., Galena IL, 815-777-3456

Foodies can visit Crane Orchards and Cider Mill, Fenn Valley Vineyards and Winery. There are also some historic attractions you can visit including the Felt Mansion, the Old Schoolhouse History Center and the Saugatuck/Douglas History Museum. --->

Elkhart Lake

Elkhart Lake in Wisconsin is an ideal getaway destination for all nature lovers and water sport enthusiasts, boasting crystal clear lake water and an abundance of activities suitable for all ages. You can choose from a variety of accommodation options which vary from up-market resorts and vacation rentals to getting back to nature at the Broughton March Park campground, where you can pitch a tent or park your RV.

Water sports are the most popular summer activity and if you do not have your own equipment you can hire everything you need to enjoy the lake from Osthoff Resort Water Recreation Rentals or at Victorian Village Resort. You can try your hand at canoeing, kayaking, water skiing or simply enjoying the beautiful lake-side scenery on a pontoon cruise. Ecology Outfitters Guided Silent Water Tours provide equipment and lessons for beginners. The lake is famous for great fishing - Inland Waters Fishing Guide Service or Jay's Guide Service will lead the way.

Back on dry land you can explore the shores by horseback with Camp Anokjig Trailrides, do a Backroads Bike Tour (or simply rent a cycle at the Osthoff Resort) or go hiking along an abundance of trails. Speed enthusiasts can watch motorsports or enjoy various adventure programs at Road America. In winter the emphasis changes to cross-country skiing, snowshoeing and snowmobiling.

Door County

Door County in Wisconsin is situated on a peninsula which juts out into Lake Michigan and boasts over 300 miles of shoreline with beaches, bays and inlets waiting to be explored. Sun worshippers have an astounding 53 public beaches to choose from and if you would like to go boating there are 12 marinas where you can launch your own craft or charter one. Conclusion

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Weekend Getaways From Chicago

Top hotel collections.

Near Shedd Aquarium

Near The Art Institute of Chicago

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Near University of Chicago

Weekend Getaways From Chicago | Road Trips from Chicago

Here is the list of 27 weekend getaways from chicago, 1. indianapolis, indiana.

Located in Marion County in Michigan, Indianapolis is the most popular state in the U.S. The city is popularly known for its historic sites, sporting events, and several museums. With the largest collection of monuments dedicated to the soldiers/veterans of war casualties, parks, hiking and biking trails, Art and culture centres, etc. the city has a lot to offer. An abode to three Fortune 500 companies the city also hosts the world’s largest single-day sporting event called the Indianapolis 500. Other recreational activities include kayaking, bicycling, cross-country skiing, sightseeing, etc. Distance From Chicago: 185.4 miles from Chicago Best Time to Visit: May-September Popular Attractions: Indianapolis Zoo, The Children’s Museum of Indianapolis, Indiana State Museum, White River State Park, and More.

2. Woodstock, Illinois

Located 51 miles northwest of Chicago Woodstock Illinois is a suburb that was named the nation’s Distinctive Destinations in 2007. The city includes a historic town square, which is anchored by Woodstock opera house and Old McHenry County Country House. Woodstock was formerly known as Canterville because of its location at the geographic centre of McHenry County. The historic town square in Woodstock offers many shops and retail establishments that are designed in the late 19th-century Victorian style. From handcrafted jewellery stores to antiques and restaurants the town square includes all. Every year Woodstock hosts several Arts and Entertainment events, festivals, and fairs, which attract a lot of visitors. Some of the events hosted here are the Fair Didley Art Fair, Summer Band Concerts, Farmers Market, Victorian Christmas celebrations, and many more. Distance From Chicago: 61.5 Miles from Chicago Best Time to Visit: May to September Popular Attractions: Woodstock water Works, Emricson Park, Boone Creek Conservation Area, Illinois Railway Museum

3. Midewin National Tallgrass Prairie

Situated in Northern Illinois, the Midewin National Tallgrass Prairie is the largest conservational site Chicago Wilderness region. Located at the former site of Joilet Army Ammunition Plant, it was the first national tallgrass prairie ever designated in the U.S. Visitors can enjoy Hiking trails, Bird-watching, native seed-gardens, and biking along with the Midewin’s trail system. The prairie spreads across 9100 acres of land with 16 miles of hike trails, biking trails, which also facilitates horseback riding. More than a hundred bird species are present in the prairie, with a large number of Upland Sandpipers and Loggerhead Shrikes. Open throughout the year the prairie also hosts guided tours for its visitors. Distance From Chicago: 50.6 Miles from Chicago Best Time to Visit: March-June Popular Attractions: McKinley woods, Lake ChaminWood Preserve, Des Plaines State Fish and Wildlife Area, Foxford Park.

4. Beloit Wisconsin

Beloit is a small city located in south Wisconsin, which was originally named New Albany by its founder Caleb Blodgett. The city is a host to festivals including, the Beloit International Film Festival, Winterfest, Beliots Farmers’ Market, etc., which attracts a lot of visitors every year. Hikers and art lovers can also visit the art centres, savannah trails in the Beckman Hill park. Distance From Chicago: 96.8 Miles from Chicago Best Time to Visit: Mid June to Early September Popular Attractions: Wright Museum of Art, Logan Museum of Anthropology, Tefler Park, Beloit Art centre.

Top Hotels In Chicago

₽ 3,224 onwards

₽ 10,962 onwards

₽ 5,158 onwards

₽ 10,225 onwards

5. Apple River Canyon State Park

Located in Jo Daviess County, the Apple River Canyon State Park is situated near the Wisconsin Border. Stretched across a land of 1900-acres the park was built in the year 1932. The scenic canyon is a result of the Apple River switching its course. The river that once flowed eastward into the Pecatonica river started flowing southwest through an erosion gorge to the Mississippi. State Park offers hiking, fishing, hunting, campgrounds, etc. The six camping sites are available at the Canyon Ridge Campground and Walnut Youth Campground. Pine Ridge, Tower Rock, River Route, Sunset, and Primrose trails are the trails that are available within the Park. The fishing, however, is allowed only during the spring season. Distance From Chicago: 144.6 Miles from Chicago Best Time to Visit: Mid April- October End Popular Attractions : Stagecoach Trails Livery, Thriving Thistle Market, The Cove Bar/ Grill

6. Glencoe, Illinois

Located on Chicago's North shore is the village of Glencoe that is surrounded by Lake Michigan, the Cook Country Forest Preserve, and Glencoe Golf Course. The village is nestled with residential homes that are designed using the architectural styles and designs from the 1800s. Many of the homes are designed by known architects which include Llyod wright, Robert Seyfarth, Keck, and Keck, etc. The various parks, beach facilities, golf courses, etc makes it one of the attractive places along the North Shore. Surrounded to the west of the village are the Skokie Lagoons in a forest preserve and the Greenbay Trail that offer bike trails to the visitors. Visitors can enjoy golfing at the public Glencoe Golf Club, Skokie Country Club, and the Lakeshore Country Club or spend their day at the Glencoe Beach. Distance From Chicago: 24.2 Miles from Chicago Best Time to Visit: Mid June- Mid September Popular Attractions: Chicago Botanic Gardens, Skokie Lagoons, Glencoe Beach

7. Lake Mills, Wisconsin

The city of Lake Mills is located in Jefferson County, Wisconsin, and occupies the east shore of Rock Lake. In 1866, the city was named Tyranena, but a year later, it was renamed, Lake Mills. Lake Mills is picturesquely surrounded, by several wineries, restaurants, and shops. Home to the Azatalan State park, which nestles the Rock Lake, also offers hiking and biking trails along the Park. Distance From Chicago: 141. Miles from Chicago Best Time to Visit: Mid June To early September Popular Attractions: Rock lake, Aztalan State Park, Sandy Beach, Bartel’s Beach, and More

8. Fox River Valley, Illinois

Centred on the Fox River in Northern Illinois, the Fox River Valley is also commonly known as the Fox Valley. The city is a mixture of rural, suburban, and 19th-century downtowns developments. With its Fox River Trail System, Trolley Museum, Buffalo Rock State Park, Outdoor theatre, the city offers a lot to its visitors. The 32-miles fox river trail system is perfect for hiking, biking, and cross-country skiing trails. Original electric cars and trains that travel a three-mile route along the fox river, the Trolley Museum commemorates more than a century of electric trolleys. With the cheap ticket prices and the snacks, the outdoor drive-in theatre is another great place to hang out in the city. Distance From Chicago: 38.5 Miles from Chicago Best Time to Visit: Mid June To early September Popular Attractions: the Morton Arboretum, Cantigny Park, Cosley Zoo, Philips Park Zoo, and More

9. Rockford, Illinois

Located in Northern Illinois and on the banks of Rock river, Rockford is a city in Winnebago County. It is the third-largest city in Illinois. It is a cultural hub and a focal point of many monuments of historical significance. The notable outdoor recreations of the city include camping, hiking, fishing, boating, and hunting. Several golf courses can elevate the golfing experience for golfers. Distance From Chicago: 88.8 miles from Chicago Best Time to Visit: Mid June –Early September Popular Attractions: Anderson Japanese Gardens, Rock Cut State Park, Discovery Center Museum, Klehm Arboretum, and Botanic Garden, and More.

10. Cedarburg Wisconsin

Incorporated in the year 1885 and located 20 miles from Milwaukee, Cedarburg is a city in Ozaukee County, Wisconsin. The city has many German cultural associations that culminate the Lutheran churches, European-style spa, and breweries. A host to several art galleries, tourism is at its peak in the city due to Winter Festival, Strawberry Festival, German-themed October fest, Wine and Harvest Festival, as well Christmas celebrations are commemorated every year. Distance From Chicago: 112.5 Miles from Chicago Best Time to Visit: May- September Popular Attractions: Cedar Creek Winery, Ozaukee Interurban Trail, Cedarburg Art Museum, Chiselled Grape Winery, and More.

11. Mount Morris, Illinois

Mount Morris is a small village in Ogle County, Illinois. The village is built on the former site of Mount Morris College, Illinois first institute dedicated to higher learning. Dillehay Park, Maunder Park, and Zickuhr Park are some of the parks in the village that has a basketball court, playground equipment, and a skating rink. Distance From Chicago: 106 miles from Chicago Best Time to Visit: Mid-June To early September Popular Attractions: Dillehay Park, Maunder Park, Zickuhr Park, Bald Hill Prairie Preserve

12. Holland, Michigan

Located on the shores of Lake Macatawa, Holland is a city in Michigan. Found by the Dutch Americans, the city is thus known for its rich Dutch heritage. Every year the city hosts the must-visit Tulip Time festival, which is the planting of tulips. The festival started in the year 1930, and currently, there are over five million tulips all over the city. Scattered along the shorelines of lake Macatawa are several public beaches and hiking trails of the tunnel park, Holland State Park for the visitors. With over 100 swarming galleries and shops, the city upscales the shopping experience for its visitors. Distance From Chicago: 150.9 miles from Chicago Best Time to Visit: Late April or Early May Popular Attractions: Windmill Island, Nelis’ Dutch Village, Holland State Park, Lake Macatawa, and More

13. Madison, Wisconsin

Madison is the second-largest city in Wisconsin and the capital city of Wisconsin. Also known as the City of Four Lakes, Madison encircles four lakes Lake Waubesa, Lake Mendota, Lake Monona, and Lake Kegonsa. The city is a focal point of an extensive network of parks and hiking trails, museums, Several lakes, and zoos. Henry Vilas Zoo in Madison is a 28-acre zoo that has over 70000 visitors every year. Nestled in the zoo are different species of birds, fishes, mammals, reptiles from several continents. Madison Arboretum is four miles from the University of Wisconsin is a research facility that manages many conifer/deciduous forests and prairies. Hikers can also enjoy the 20 miles of hiking trails and over 3 miles of bike trails in the arboretum. Distance From Chicago: 147.3 Miles from Chicago Best Time to Visit: July, August Popular Attractions: Wisconsin State Capitol, Henry Vilas Zoo, Lake Mendota, Madison Children's Museum and More

14. Saugatuck, Michigan

Saugatuck is a city in the Allegan County of Michigan that was incorporated in the year 1868. It has a population of 960 according to the 2019 census. With the many art galleries, restaurants, paddle-wheel boats, historic churches, and other attractions, the city is sprawling with tourists during the summertime. A boon for the art and music lovers as it also hosts art and music festivals throughout the year. The Paddle-wheel boat ride is one of the best in the city, as the boat ride gives daily tours of the river Kalamazoo river and Lake Michigan. Saugatuck church is one of the oldest buildings in the city, which also contributes to a vibrant community. Distance From Chicago: 140.7 miles from Chicago Best Time to Visit: May- September Popular Attractions: Oval Beach, Saugatuck State Park, Saugatuck centre for arts, Mount Baldhead, and more.

15. Lake Geneva, Wisconsin

Lake Geneva is a city located in Walworth County, Wisconsin. Located on the shores of Geneva Lake, the city attracts many visitors from Chicago, Milwaukee, Rockford, etc., throughout the year. Camping sites, beaches, waterparks, hiking, biking, golf courses, museums, sightseeing, etc., the city has a lot to offer for its visitors. Enjoy a relaxed day at the beach, camp out in the various camping sites, or indulge in the various adventure sports, a city is a perfect place for all age groups. Their adventure activities include Zip lining, hot-air balloon rides, safari rides, skydiving, etc. Geneva lake has many beaches the Rivera Beach, Williams Bay Beach, Fontana Beach for the visitors to enjoy the Lake's pristine waters. Distance From Chicago: 83.0 Miles from Chicago Best Time to Visit: July, August Popular Attractions: Grand Geneva Way, Geneva Lake Museum, Big Foot Beach State Park, Lake Geneva Ziplines, and adventures.

16. Grand Rapids, Michigan

Located on the Grand River and east of Lake Michigan, Grand Rapids is the second-largest city in Michigan. Encompassed in the city are the Van Andel Museum Centre, the Heritage Hill, Frederik Meijer Gardens, and Sculpture Park, etc., which makes it a popular tourist attraction. Found in 1854, the Van Andel Museum Centre is one of the oldest museums in the city. The Heritage Hill, the largest urban historic district, is a home of more than 1300 homes that are designed in more than 60 architectural styles. Spread across 125 acres of land is also the Frederik Meijer Gardens and Sculpture Park, which nestles a world-class botanical garden artwork from American/French artists. Dedicated to the art lovers are also various music concert venues that organize concerts every year. Outdoor recreation activities include Skiing, snowboarding, Ice fishing, etc. Distance From Chicago: 177.6 miles from Chicago Best Time to Visit: April-October Popular Attractions: John Ball Zoo, Grand Rapids Museum, Millennium Park, Rosa Parks Circle, and More.

17. South Bend Indiana

Situated on the long tributary of Lake Michigan, St Josephs River, the South Bend City is located in Indiana. The city is a cultural hub and the fourth largest city in Indiana. Not only is the city a centre of arts and culture but, also hosts several music festivals every year. The great outdoors, sports venues, museums are some of the attractions that the city offers to its visitors. Distance From Chicago: 95.7 miles from Chicago Best Time to Visit: April-September Popular Attractions: Studebaker National Museum, Potawatomi Zoo, Nore Dam Golden Dome, The History Museum, and More.

18. Shawnee National forest, Illinois

Located in Southern Illinois, the Shawnee National Forest is situated between the Ohio and Mississippi river. With a plethora of flora and fauna, the forest is the perfect place for outdoor recreation and sightseeing. Some of the available recreational activities are camping, fishing, Hiking, Hunting, Bicycling, water activities, and much more. The camping experiences range from primitive backpacking to partial hookups camping sites. Swimming, water skiing, boating, etc., are some of the water activities offered to visitors. Distance From Chicago: 338.6 miles from Chicago Best Time to Visit: March-June Popular Attractions: Giant City State Park, Garden of the Gods, Kinkaid Lake, Tunnel Hill State Trail, and More.

19. Traverse City, Michigan

Traverse City is the largest city in the Northern Michigan region. With a large production of Tart Cherries in the city, it also hosts the National Cherry Festival every year. Some of its other attractions include freshwater beaches, forests, skiing areas, camping sites, arts and culture centres, etc. Campers can enjoy camping at the 250 camping sites, art lovers can visit the Dennos Museum, which hosts a collection of art by the Arctic people. Kayaking, Swimming, fishing, surrounding wineries are some other recreational activities that are presented at Lake Michigan. Distance From Chicago: 319.6 miles from Chicago Best Time to Visit: June- August Popular Attractions:  City Opera House, Clinch Park, East Front Street, Mari Vineyards, and More. "

20. Galena Illinois

Located in Jo Daviess County, Galena is a small town in Illinois known for its 19th-century architectural style buildings. From the many historic sites, local cuisine to a plethora of boutiques and shops, the city has a lot to offer. With a ride in the hot air balloons, hiking, golfing, biking, etc., the city hosts several outdoor adventures along the Mississippi River. Distance From Chicago:  163.7 miles from Chicago Best Time to Visit: May- October Popular Attractions: Galena Grant Park, Belvedere Mansion, Old Blacksmith Shop, and More

21. Elkhart Lake Wisconsin

Elkhart Lake is a village in Sheboygan County in Wisconsin. Located within the Town Rhine the village was popularly known to host road races in the 1900s’. Located a few miles away from the village is a race track called Road America. The village has several historical figures like the Victorian Village theatre, which is a 100-year theatre where still cultural programs are performed. There are two parks called the Broughton Sheboygan Marsh Park and Fireman's Park, which offer campsites, picnicking, fishing, and trails for its visitors. The recreational activities in the village are hosted every Summer, Winter, and Spring Season. Distance From Chicago: 149.4 Miles from Chicago Best Time to Visit: June- August Popular Attractions: Road America, Two Fish Gallery, Crystal Lake, Wade House Historic Sites, and More.

22. Starved Rock State Park, Illinois

The Starved Rock State Park on the Illinois River is a wilderness area in the state of Illinois that offers several recreational activities for the visitors. The park is spread across 2630 acres of land and has waterfalls, 18 sandstone canyons, 13 miles of wooded trails, and diverse wildlife. Established in the year 1911, it attracts a lot of visitors every year. Among other recreational activities, the park offers camping, fishing, boating, horseback riding trails, ice skating, scenic views from the Eagle Cliff Overlook and Beehive Overlook. Distance From Chicago: 98.9 miles from Chicago Best Time to Visit: September- December Popular Attractions: Ottawa Canyon, LaSalle Canyon, Grand Bear Falls Indoor Waterpark, French Canyon, and More

23. Milwaukee, Wisconsin

Located on the western shore of Lake Michigan, Milwaukee is the largest city in Wisconsin. The city is known for its breweries, summer fest, and cultural attraction. With Over 140 well-developed parks that facilitate picnic spots, golfing, ice skating, the parks are spread across 15000 acres. The 2 km Monarch Trail highlights the migration of the milkweed butterflies. Nearby local markets and farmers markets sell the produce of local business, which includes seafood, gourmet, plants, and vegetables. Distance From Chicago: 92.4 miles from Chicago Best Time to Visit: June - September Popular Attractions: Milwaukee Art Museum, Harley Davidson Museum, Discovery World, Milwaukee County Zoo, and More.

24. Mineral Point, Wisconsin

Mineral Point is a city in Iowa County and the third oldest city in Wisconsin. The city’s historical significance and lead/ Zinc mining centres makes it a popular tourist attraction. Mineral Point is the endpoint of the 76-km Cheese country Trail in Southern Wisconsin. A historic district with many cottages and businesses that were crafted by the Cornish settlers. The restaurants in Mineral Point serve Cornish Foods following the Cornish heritage of the city. Distance From Chicago: 167 Miles from Chicago Best Time to Visit: June, July, August Popular Attractions: The Walker House, Orchard Lawn, Merry Christmas Hill, Pendarvis

25. Lake Forest, Illinois

Founded in the 1900s, lake Forest is a city along the shores of Lake Michigan located in Lake County, Illinois. With the Citadel theatre, the Wildlife Discover Centre, and the Lake Forest Symphony, the city is a cultural hub for visitors. Distance From Chicago: 32.7 miles from Chicago Best Time to Visit : Mid-June to Mid-September Popular Attractions: Wildlife Discovery Centre, Fort Sheridan Forest Preserve, Chicago Botanic Garden, Sunrise Park, and More

26. Ann Arbor, Michigan

Founded in 1824, Ann Arbour is a city in Michigan that is the focal point of art, natural history, and sciences. Home of the University of Michigan and a sprawling tech-hub, the city draws several companies due to the research programs by the university. The local cuisine, outdoor activities, unique shopping, renowned arts, and culture, etc., are some of the recreations that the city offers. Seasonal sports like kayaking, canoeing, paddleboarding on the River Huron, ice skating, skiing, and snowshoeing are offered during different months of the year. Hikers can enjoy the best biking trails in the nearby state parks. Art lovers can visit the University of Michigan Museum, which displays century-old arts from all over the world. Distance From Chicago: 241.4 miles from Chicago Best Time to Visit: March-September Popular Attractions: Ann-Arbor Hands-on Museum, Matthaei Botanical Gardens & Nichols, University of Michigan Nichols Arboretum, Gallup Park, and More

27. Indiana Dunes State Park, Indiana

Established in the year 1925 and located in Porter County, Indiana, the Indiana Dunes State Park is a few miles away from Chicago. The park is spread across 1530 acres of land and is an abode to several hiking trails and dune landscape. With the several hiking trails, picnic shelters, hiking tours, etc., there are several activities in this state park that the visitors can indulge themselves in. Their hiking trails extend over 16 miles, a bird observation tower for bird watching, swimming in the small portion of Lake Michigan shoreline, around 140 campsites with 50 amp electric hook-ups, and picnicking are some of the recreational adventures that attract a lot of visitors. Distance From Chicago: 50.1 miles from Chicago Best Time to Visit: Any time of the year Popular Attractions: Taltree Arboretum and Gardens, Chapel of the Resurrection, Portage Lakefront and Riverwalk and More

We hope you enjoyed our list of Weekend Getaways from Chicago. Drop your feedback in the comments section below.

This post was published by Akshita Dhiman

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10 Best Weekend Road Trips From Chicago, Illinois

Posted by Brittany Varano June 01, 2021 Updated May 21, 2024

Sometimes you need a change of scenery, and these weekend road trips from Chicago make it easy to get away from the bustle of the Windy City.

Perfectly perched within reach to four different states, Chicago conveniently sits at the crossroads to destinations in Wisconsin, Michigan, Indiana, Iowa, as well as the rest of Illinois.

Its prime location means endless weekend road trips that range from city escapes to small-town excursions and outdoor getaways. And you’ll have your choice of several sandy beach towns lining the shores of neighboring Lake Michigan.

Below, you’ll find a diverse list of the best weekend road trips from Chicago to inspire your next adventure out of the city.

Related Read: The 10 Best Illinois Glamping Rentals

1. Milwaukee, Wisconsin

Milwaukee is an easy weekend trip just north of Chicago over the Wisconsin border. Known for its craft breweries and local eats, there’s a lot to do and see in this smaller midwestern city. If you’re interested in learning about the local history, make time to visit Milwaukee’s beloved museums like the historic art museum or the Harley Davidson Museum to marvel at one of Elvis Presley’s classic motorcycles.

If you’re a sports fan, make time to catch a Milwaukee Bucks basketball game or tailgate outside of Miller Park before watching the Brewers play ball. The end of summer is also a fantastic time to visit Milwaukee as Summerfest is in full swing. Summerfest is a music festival held along the picturesque shores of Lake Michigan in downtown Milwaukee and brings notable acts each year.

Distance from Chicago: 93 miles (approx. 1 hour and 30 minutes)

Related Read: 11 Best Cabin Rentals in Illinois For an Outdoor Getaway

2. Starved Rock State Park

If peace in nature is what you’re seeking, Illinois’ Starved Rock State Park is a beautiful outdoor getaway known for scenic sandstone canyons, numerous waterfalls, and miles of hiking trails. The park’s top sights include Lover’s Leap Overlook (a lookout point offering clear views of the Starved Rock Dam) as well as the Wildcat, French, and St. Louis canyons.

Summertime is the best time to visit, bringing sunshine and warm weather. Winter is also not a bad time to visit, when the canyon falls freeze over in a spectacular show of ice and snow. Many visitors opt to camp out in the state campground, where reservations can be made up to six months in advance. The park is on the Illinois River southwest of Chicago.

Distance from Chicago: 94 miles (approx. 1 hour and 30 minutes)

Related Read:   9 Fabulously Unique Places to Stay in Illinois

3. Indianapolis, Indiana

Indianapolis is an excellent weekend road trip from Chicago for city dwellers and racing fans. Home to the world-famous Indy 500 and the Indianapolis Motor Speedway Museum , car lovers can cheer on their favorite drivers and learn a bit about the sport’s history.

No visit to Indy is complete without sampling some local cuisine, including local specialities like pork tenderloin sandwiches and shrimp cocktail. The city was named as an ‘Underrated Food City in America’ by Condé Nast Traveler for its rich and diverse restaurants and dishes. Other popular things to do in Indianapolis include walking the eight-mile Indianapolis Cultural Trail that stretches through downtown or visiting the iconic Monument Circle.

Distance from Chicago: 184 miles (approx. 3 hours)

Related Read:   10 Romantic Getaways Near Chicago, Illinois

4. Galena, Illinois

For a taste of small-town living, look to Galena, Illinois . The city has consistently been ranked as one of America’s most livable cities and offers a lovely weekend trip from the big city. Galena is known for its quaint main street lined with historic brick buildings dating to the 1800s.

Visitors can tour the former home of Ulysses S. Grant and visit the beautiful grounds of the Dowling House, the oldest home in the city. Rolling hills and Native American effigy mounds surround Galena, such as the Horseshoe Mound, a nature preserve boasting views of three nearby states. The best way to experience Galena is to stay in a charming bed and breakfast or a local vacation rental.

Distance from Chicago: 164 miles (approx. 2 hours and 45 minutes)

5. Indiana Dunes National Park

Boasting the shortest distance of all the road trips from Chicago, the Indiana Dunes National Park is a convenient road trip from Chicago to northwestern Indiana. The park protects over 15,000 acres of diverse landscapes that include sunny beaches, sand dunes, wetlands, and forests.

The park is a four-season destination offering wildflowers in the spring, water fun in the summer, fiery colors as the leave change in the fall (and sunsets are great), and cross-country skiing in the winter.

Most people opt to camp out in the national park campground or stay in nearby vacation rentals. Besides the outdoor adventures inside the park, make time to shop at the Saturday European Market in Chesterton, visit the Old Lighthouse Museum , and indulge in Indiana comfort food.

Distance from Chicago: 49 miles (approx. 56 minutes)

6. Grand Rapids, Michigan

Get a feel for Michigan city life with a weekend in Grand Rapids . About three hours north of Chicago, the city was once a hub for furniture manufacturing, securing the nickname “Furniture City.” Today, locals and visitors alike enjoy strolling the downtown riverwalk along the Grand River, eating out at hip restaurants like Divani and Stella’s Lounge,  and shopping at the Grand Rapids Downtown Market.

The Frederik Meijer Gardens & Sculpture Park is another must-see stop, with walking trails meandering through nearly 160 acres of colorful gardens and sculptures. In the evening, sip cocktails as the sun sets at the New Hotel Marten’s hip rooftop.

Distance from Chicago: 177 miles (approx. 3 hours)

7. Madison, Wisconsin

Home to the majestic Wisconsin state capitol building, Madison is a charming city best known for its location on an isthmus surrounded by four scenic lakes. The University of Wisconsin Madison campus sprawls through the downtown area, bringing with it a vibrant artistic atmosphere as well as hip bars and restaurants. Along the pedestrian friendly State Street, boutique shops and charming cafes lead the way to the capitol building.

One of the best things to do in Madison includes visiting the Saturday farmers market, where 150 vendors line the capital square selling locally sourced produce, flowers, and sweet treats. Grabbing a pitcher of beer at the Union Terrace along Lake Mendota and visiting the admission-free Henry Vilas Zoo are also popular things to do. That said, Madison is a very outdoorsy city, so you’ll find plenty of options for everything from paddling to hiking, biking, and outdoor movies and festivals.

Distance from Chicago: 147 miles (approx. 2 hours and 20 minutes)

8. Lake Geneva, Wisconsin

Lake Geneva is a four-season resort destination in south-central Wisconsin. The city is named after the large 5400-acre Geneva Lake that attracts fishing and boating enthusiasts. The city’s Big Foot Beach State Park is one of the best places to go for swimming, sun tanning, and kayaking. If you enjoy casual walks, take a stroll along the Geneva Lake Shore Path that circles the lake for 21 miles.

While summer is an ideal time to make the most of the lake and surrounding beaches, winter also offers a unique weekend getaway. Every year, the Geneva National Resort and Club hosts the award-winning Ice Castles festival, where ice sculptures and structures amaze winter visitors. Prices and hotels cross into a variety of budget and lux options, but in general, it’s one of the cheaper towns for a summer getaway near Chicago.

Distance from Chicago: 83 miles (approx. 1 hour and 30 minutes)

Related Read:   13 Exciting Things to Do in Lake Geneva, Wisconsin

9. Saugatuck, Michigan

Saugatuck, Michigan , is an artsy beach destination best enjoyed in the summer. This small town is on Lake Michigan and Kalamazoo Lake, offering fantastic water fun like fishing, swimming, and boating. The area is also famous for its idyllic grassy dunes, Mount Baldhead Park hiking, river cruises, and the Dutch windmills and gardens in nearby Holland, MI.

The city’s center features Butler Street, where visitors can enjoy up-and-coming gourmet restaurants and boutique shops. Don’t forget to pack your swimsuit for a trip to Oval Beach. For the best experience, opt for a cozy B&B along the water or in the downtown area, but be sure to plan ahead as lodging fills fast in the summer.

Distance from Chicago: 141 miles (approx. 2 hours and 15 minutes)

10. The Wisconsin Dells

Known as the waterpark capital of the world, the Wisconsin Dells is a resort town with 20 different indoor and outdoor water parks and resorts. It’s a perfect weekend road trio from Chicago for families looking for something fun but family-friendly – and the area offers more to do than just waterparks. Take a tour along the Wisconsin River and surrounding forests on a Wisconsin Duck, an amphibious truck that dates back to WWII.

Be sure to check out other popular activities such as local winery tours, the hiking trails through nearby Devil’s Lake State Park, and the vibrant nightlife of downtown. When visiting, there are plenty of cozy Wisconsin Dells cabins to stay at if resort living isn’t for you.

Distance from Chicago: 195 miles (approx. 3 hours)

Explore More in the Midwest

10 Best Lake Camping Destinations in Wisconsin

11 Peacefully Secluded Cabin Rentals in Wisconsin

10 Awesome Glamping Getaways in Michigan

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Seen in: Illinois , Midwest , Road Trips

Posted by Brittany Varano

Brittany is a freelance travel writer and avid photographer with a love of hiking and nature. Originally from Wisconsin, she fell in love with travel blogging after living and teaching English in South Korea. She’s now location independent and enjoys slow travel to new and exciting places.

9 Fabulously Unique Places to Stay in Illinois

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9 easy must-do weekend trips from Chicago

Chicago is blessed with world-class museums, an amazing food scene, some of the best breweries in the country, and everything else you’d ever want to do. But even the most passionate Chicagoans need to escape the city every now and then. Luckily, there are dozens of superb weekend getaway destinations, all within a few hours’ drive of the Windy City. 

There are miles upon miles of Lake Michigan coastline to explore, there are national and state parks with gorgeous nature, and there are charming cities and towns all over the Great Lakes region where you can find a little bit of quaint comfort. Planning will go a long way to ensure a successful weekend trip. So research where to go, find luggage storage in Chicago if you need to drop the bags off, book lodging, plan where to eat and what to do, and hit the road. 

Here are the best weekend getaways from Chicago: 

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Dubuque, Iowa 

Located on the banks of the Mississippi River, Dubuque is the ideal weekend getaway for history buffs and older tourists. Baseball fans will want to visit the famous “ Field of Dreams ” ballpark, which is now the home of special events hosted by Major League Baseball. 

The town itself has been revitalized somewhat in recent years, with art galleries, breweries, murals, and restaurants opening in downtown Dubuque. Dubuque is heavy on the small-town charm and well worth a visit. 

Distance from Chicago 

It takes just under three hours to reach Dubuque from Chicago. Driving is the only option for transit. 

Our activity recommendations

This historic town is a delightful change from downtown Chicago, with a picturesque old-school Main street with many pre-Civil War buildings, like the Black Horse Inn. There’s also the Febekon Place Elevator, which is a scenic railway that overlooks the city and provides a spectacular aerial view. 

Best season to visit

Summer, fall, and spring are the best times of year to visit Dubuque. 

Holland, Michigan 

Western Michigan has a ton of delightful towns for weekend getaways, and Holland is one of the best family-friendly options. Located less than a mile from the stunning Lake Michigan coastline, Holland is famous for its large Dutch immigrant population and its furniture-making industry. 

Distance from Chicago

You’ll have to drive south and east for about two and a half hours to get to Holland. Driving really is the best way to get there, although Amtrak runs a train as well. 

Explore Holland’s (aptly-named) Dutch heritage by exploring delightfully kitschy attractions like Nelis’ Dutch Village, De Klomp Wooden Shoe, and the Windmill Island Gardens . 

In proper Dutch fashion, Holland (Michigan) celebrates the annual blooming of tulips every springtime. With millions of tulips planted across the area, it’s a gorgeous time of year to visit. Summer is also ideal, with the Lake Michigan shore and beaches only a mile away from town and gorgeous Lake Macatawa providing plenty of outdoor recreation. 

Grand Rapids, Michigan 

While far from the largest city in the country, Grand Rapids has a massive beer scene. Since the industry’s boom in the past two decades, Grand Rapids has quickly become one of the craft beer meccas, drawing thousands of beer nerds to its taprooms and breweries. 

It’s a three-hour drive from Chicago to Grand Rapids, probably less if you miss Friday traffic. Amtrak also runs a service from Union Station directly into downtown Grand Rapids, the train ride is about four hours. 

Beer truly is the main draw for visitors, with companies like Founders, Brewery Vivant, Saugatuck Brewing, and Grand Rapids Brewing all operating popular taprooms. The food isn’t bad at all either, with local favorites Forty Acres Soul Kitchen and Terra GR being high-end dining options.

When you’re not drinking, renting kayaks or bikes to enjoy the riverfront are great ways to stay active. Lake Michigan is less than 30 minutes away by car too.

Summer and fall are perfect for enjoying some time outdoors, especially if you’re looking at kayaking and swimming along the river or Lake Michigan. Winter is also a great time to do a long weekend because you can hit the slopes at the nearby Cannonsburg Ski Resort. Also, the many Grand Rapids breweries are great for a cozy pint to warm up.

Indiana Dunes National Park, Indiana

The sandy dunes overlooking Lake Michigan have finally gotten their due and were made into a national park. Indiana Dunes National Park is the closest conservation and recreation area of its kind to Chicago and the perfect weekend getaway (or day trip) for outdoor enthusiasts.  

It’s only about 90 minutes by car (which is the most convenient way to get there) from downtown Chicago. Unless you want to explore the whole area and stay in a cabin, Indiana Dunes National Park is one of the best day trips from Chicago. The South Shore Line will also take you to the Indiana Dunes, but driving is easier and more flexible. 

There are over 15 miles of beautiful Lake Michigan shoreline to explore and enjoy. You can enjoy the beach, go for a swim, hike the trails along the dunes, and even go horseback riding. 

Summer and fall are the best times to go. Visiting during winter is absolutely inadvisable because of lake effect weather. Spring is better, but the weather brings frequent rain that impacts the hiking trails and terrain.

Kohler, Wisconsin 

Located north of Milwaukee along Lake Michigan, Kohler is famous for its resorts and golf courses. The American Club is a bucket-list course for golfers, and there are a number of spas and restaurants that make Kohler a relaxing destination. 

Kohler is a two-and-a-half-hour drive from Chicago. A great way to break up the trip is to stop in Milwaukee for lunch.

Our activity recommendations 

The upscale resorts and golf courses are the main draw at Kohler, which makes them frequent weekend getaway destinations for older travelers. The Kohler Waters Spa is the perfect place to unwind, and the American Club boasts one of the best golf courses in the country. 

For weekend getaways based around golf, summer and fall are the best times of year to head up to Kohler. Kohler is also a wonderful destination for spas and resorts during the winter. 

Lake Geneva, Wisconsin 

Of all the weekend getaways from Chicago, this one has to be the most popular. Lake Geneva is Chicago’s equivalent of The Hamptons. Basically, everyone knows someone with a house up there. This makes sense, given it’s only a 90-minute drive from Chicago, just over the Wisconsin border. There are plenty of hotels, like The Abbey and Grand Geneva Resort . Multiple golf courses surround the lake as well. But the main reason to head to Lake Geneva is to appreciate the natural beauty with friends and family. 

Lake Geneva is about as close to Illinois as you get, and it only takes about 90 minutes to get there from Chicago by car, which is the only real way to get there. 

All the best activities in Lake Geneva are based around the water. Renting a boat from one of the marinas is a great way to get the family out on the water. There are multiple public beaches as well. 

During the winter, there is a village of ice castles made by expert sculptors that’s worth checking out. Alpine Valley Ski resort is nearby, which also hosts concerts during the summer. 

Summer is the best time to take a weekend trip to Lake Geneva, but it does get busy during this time of year. During the fall, Lake Geneva gets a boost when the leaves change color, despite it being too cold for boating and swimming. 

Madison, Wisconsin 

Wisconsin’s capital city is one of the most popular weekend getaways from Chicago. All the best Wisconsin culture is represented in Madison, which mostly consists of beer, brats, and Badger Football. The University of Wisconsin’s gorgeous campus is located right in Madison, which gives the city energy when students are on campus. But there’s a nice variety of outdoor activities and culture in the city as well. 

Madison is a three-hour drive from Chicago. There are also bus routes between downtown and Madison that take about three hours and 30 minutes. 

For such a small city, there’s plenty to do in Madison. Snowshoeing in the winter, hiking in the summer, appreciating the leaves in the fall, and drinking all year long. 

Just outside of Madison is the Wisconsin Dells area, which has indoor and outdoor water parks and other outdoor activities. It’s a great excursion from Madison and less than an hour’s drive from the capital. 

Summer and fall are the best times to visit, especially when the leaves change and the University is in full swing.

Milwaukee, Wisconsin

Chicago’s neighbor to the north is an obvious choice for weekend getaways. There is culture, there’s beer (and plenty of it), there are several pro sports teams, and there’s a lot of character. Milwaukee has all the amenities of a larger city, just without all the inconvenience of getting around a place like Chicago. 

If you’re driving up to Door County or Kohler, it’s well worth it to stop in Milwaukee for lunch. 

There is a train from Union Station that lands you right in downtown Milwaukee. This takes less than two hours and can save you some traffic headaches. The drive up to Beer City only takes about 90 minutes. 

There are a number of amazing museums to visit, including the Milwaukee Art Museum, which is a gorgeous modern building along the lakefront. There’s also the Harley Davidson museum which details the story of how Milwaukee became the largest builder of motorcycles in the world. 

Outside of that, there are world-class breweries, restaurants, and bars. Definitely make sure to try a famous Bloody Mary dressed up Wisconsin-style. 

The Milwaukee lakefront is incredible, and there are frequent festivals and events going on, so summer is an amazing time for a weekend trip. But there is enough culture that visiting Milwaukee is fun year-round. If you’re free during the first few weeks of July, hit up Milwaukee Summerfest , which is the largest music festival in the world. 

Starved Rock State Park, Illinois

As far as outdoor activities go, Chicago is hardly the best city in the world. But the area’s best hiking area is absolutely worth visiting. Starved Rock State Park, with waterfalls and topography (rare in a painfully flat state like Illinois), makes for a perfect weekend getaway for outdoorsy types.  

It’s only a two-hour drive from Chicago, but you’ll want to leave early to beat traffic and have a head start on the other hikers. Leaving yourself a full day to explore the nooks and crannies of this park is the best way to go. 

Essentially, there’s really only one thing to do at Starved Rock, and that’s hiking. With 13 miles of trails winding through glacier-carved canyons and terrain, it’s the best hiking Illinois has to offer. There are gorgeous waterfalls and winding streams to take a dip in if you’re hiking during the sweltering Illinois summer. 

Late spring, summer, and early fall are the best times of year to explore Starved Rock. Winter is basically out of the question. Early spring and late fall are entirely weather-dependent.

It’s hard for locals and transplants to find a place they love more than Chicago because there is a lot to love. But getting out of the city for a weekend getaway is a necessary way to recharge and reset. You’ll be more in tune with nature, you’ll feel a little more relaxed after taking a break from traffic, and you’ll have a new appreciation for the gorgeous region surrounding Chicago. If you’re short on time, you can always opt for a fun day trip from Chicago as well, and if you only have a limited time in the city itself, check out our guide on how to spend 3 days in Chicago to maximize your itinerary.

Planning one of the many fun weekend getaways from Chicago is a great way to find a new appreciation for not only the Midwest but also Chicago. Because you can only stay away from that deep dish for so long… 

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30 Delightful Road Trips from Chicago

If you’re looking to get away from the city, here are the best destinations for day trips and weekend road trips from Chicago.

Chicago’s location makes it an ideal place to get in the car and go, whether you live in the city or you make it your home base for some Midwestern exploration.

I’ve lived in Chicago and its suburbs for twenty years, and in the Midwest my entire life (except for a brief four years in my early twenties).

Let’s just say I’ve been to a LOT of towns, villages, cities, parks, etc., that are within easy driving distance from the Windy City.

And while I love Chicago (I even wrote a book about it ) and The Local Tourist began as a guide to the city’s River North neighborhood, sometimes even I just need to get away.

I’ve hand-picked some of my favorite Midwest road trips from Chicago. If you’re looking for delightful towns with delicious food and drink, boutiques and artisan shops, intriguing history, outdoor adventures, natural beauty, and so much more, you’re sure to find your perfect road trip from Chicago.

Road trips are the equivalent of human wings. Ask me to go on one, anywhere. We’ll stop in every small town and learn the history and stories, feel the ground and capture the spirit. Then we’ll turn it into our own story that will live inside our history. Victoria Erickson

Love travel quotes? Here you go!

There may be affiliate links in this post, which means we may get a small commission if you make a purchase. It’s at no extra cost to you and helps keep TLT free. Everybody wins!

Road Trips from Chicago

How to choose the best road trips from chicago.

How far will you drive for a weekend trip?

I asked that question of members of The Local Tourist Facebook group and their answers surprised me. The winning time was five hours, and second place was four hours.

Several of these road trippers would even drive eight hours for a weekend vacation!

Based on their input, and my own obsession with road trips, I’ve included some destinations that require a few hours behind the wheel.

I’ve also included places that are much closer. In fact, there are a few towns and cities that are technically suburbs of Chicago. Depending on your starting point, these destinations may provide more of a staycation than a vacation.

But hey – that’s what being a Local Tourist is all about, right?

I’m only including destinations that I’ve personally visited and enjoyed. Clearly, I need to spend more time in Ohio and Michigan.

For each road trip destination, I’ve included driving time. This assumes you’ll be driving interstates and won’t be avoiding toll roads. It also assumes no traffic.

Depending on when you leave for your weekend road trips from Chicago, traffic could increase times by at least an hour, so check Google maps or Waze before you go.

I’ve also included suggestions for places to stay, as well as links to each destination’s official Convention and Visitors Bureau, or CVB. These local resources are my travel planning not-so-secret weapon .

Ready to plan your road trips from Chicago? Let’s go!

Related: before you go, check out all my tips for planning a road trip .

10 Day Trips from Chicago

If you’re looking for a quick getaway or even a day trip, these locations are short road trips from Chicago and all within two hours of the Windy City.

Elgin, Illinois

Driving time: 1 hour

Known as the City in the Suburbs, Elgin, Illinois, is a relatively quick drive or an easy train ride from downtown Chicago. Its proximity makes it perfect for a day trip, but there’s enough to do that you’ll want to make a weekend of it.

A good place to start is downtown Elgin. Located right on the Fox River, it’s filled with public art and historic buildings.

Get the history of the area at the Elgin History Museum (pictured above).

You can also take a free self-guided walking tour of the Elgin Historic District.

Since that walking will make you hungry, grab a sandwich at Blue Box Café or head up to West Dundee for a burger and a pint at Emmett’s Brewing Co., an award-winning brewery.

Another one of the great things to do in Elgin is visit Lords Park and Zoo. On its grounds is the Elgin Public Museum, the only natural history museum in the Fox Valley.

Where to stay in Elgin, Illinois: Most of the hotels in Elgin are along the I-90 corridor. The Holiday Inn & Suites is one of the most highly rated accommodations near Elgin.

CVB: Explore Elgin Area, exploreelginarea.com

Indiana Dunes National Park, Indiana

One of our newest national parks is a short drive or train ride from Chicago. Established in 2019 , Indiana Dunes National Park is 15,000 acres along the southern shores of Lake Michigan.

There are over fifty miles of trails, making hiking Indiana Dunes National Park one of its top attractions. Hikers can traverse dunes, wetlands, prairies, rivers, and forests, all in one park.

There’s a fee to access the park: $15 per person (up to $25 per family group) and $25 per carload.

You could spend the entire weekend at the park. However, if you want a break, drive a little further east to Michigan City.

While the town is known for Lighthouse Place Premium Outlets, it’s also home to several museums, including the Old Lighthouse Museum.

Where to stay near Indiana Dunes State Park: Camping is available within the park itself, and there are several hotel chains in Michigan City .

CVA: South Shore Indiana, southshorecva.com

Harbor Country, Michigan

Driving time: 1 hour 15 minutes

Just across the border from Michigan City, Indiana, is Harbor Country.

The Red Arrow Highway takes you through eight small towns, each unique, each charming in its own away. Think boutique instead of big box, locally owned versus chain.

Outdoor enthusiasts will find everything from kayaking and paddle boating to fishing, surfing, and golf. Of course, you can also spend the day at the beach.

One of the biggest attractions is the number of Southwest Michigan wineries and breweries. The climate is very similar to Napa Valley, and the area’s known for its award-winning wines.

Where to stay in Harbor Country: You can find inexpensive hotels as well as private homes in New Buffalo, Michigan .

CVB: Harbor Country Chamber of Commerce, harborcountry.org

Kenosha, Wisconsin

Driving time: 1 hour 20 minutes

Kenosha is the fourth largest metro area in Wisconsin, as well as the fourth-largest city on the shores of Lake Michigan, and there are TONS of things to do.

It’s the home of the oldest operating velodrome in the country, a free dinosaur museum, historic restaurants, not one but two lighthouses, and you can still ride an electric trolley.

Start your visit at the Kenosha History Center for an overview of the area’s past. Then don’t miss the Dinosaur Discovery Museum or Kenosha Public Museum, both of which are free.

The Civil War Museum is an impressive look at Wisconsin’s role in the war.

A must-visit restaurant is House of Gerhard, featuring traditional German specialties. Another favorite is Franks Diner. Guy Fieri featured it on  Diners, Drive-ins, and Dives and it serves up tasty American cuisine with a side of sass.

Check out more reasons you should visit Kenosha, Wisconsin .

Where to stay in Kenosha: you can stay in Kenosha hotels that are conveniently located off I-94, or you can choose an historic inn like The Stella Hotel and Ballroom. For a great view, check out Wyndham Garden Kenosha, right on the harbor.

CVB: Visit Kenosha Wisconsin, visitkenosha.com

McHenry County, Illinois

Driving time: 1 hour 30 minutes

I lived in McHenry County, whose northern border is shared with Wisconsin, for five years and still found new things to do.

One of the most surprising aspects of the area is the sheer number of parks. The McHenry County Conservation District manages more than thirty conservation areas, and most of them have hiking trails.

There are also city and village parks, as well as two state parks within the county.

Another great thing about the area is the food. Oh, the food! There’s farm-to-table at 1776 Restaurant and Duke’s Alehouse and Kitchen, incredible Italian at 750° Cucina Rustica, rich encased meats at Richmond Brathaus, and the best custard anywhere at Julie Ann’s Frozen Custard.

All are local; all are family-owned; all are delicious.

McHenry County’s county seat is Woodstock, which you might recognize. It’s where Groundhog Day was filmed, and the town celebrates with their very own groundhog, Woodstock Willie.

You can even stay in the same bed and breakfast where Bill Murray’s character woke up again, and again, and again.

With the mouthwatering breakfasts served each morning at Cherry Tree Inn Bed and Breakfast, though, you won’t mind if the same thing happens to you.

Read more about why I love being a Local Tourist in McHenry County , and you will, too!

Where to stay in McHenry County: Cherry Tree Inn Bed and Breakfast , of course! Since there are only four rooms, if they’re full, you can find hotels in Crystal Lake , the largest town in the county.

CVB: Visit McHenry County, visitmchenrycounty.com

Starved Rock State Park

Head to Starved Rock State Park for a day of fresh air, physical fun, and outdoor adventure.

Located just 94 miles southwest of Chicago, the landscape is an unexpected tableau of bluffs, steep trails, and waterfalls. Since it’s on the Illinois River, there’s also fishing and boating.

You can bring a lunch to enjoy at the waterfront picnic area, or grab a bite to eat at the historic lodge.

Nearby Ottawa is a charming town with lots of creative chefs, so you can have the best of both worlds.

Where to stay in Starved Rock State Park: There’s a lodge at the park itself, but I personally prefer camping. Starved Rock has one of the best campgrounds in the Midwest .

Janesville, Wisconsin

Driving time: 1 hour 45 minutes

Located right off I-90, Janesville is an ideal weekend road trip from Chicago, especially if you like the great outdoors, art, and history.

The town’s tagline is “Wisconsin’s Great Outside,” and there are thirty miles of trails in Janesville, including a portion of Wisconsin’s Ice Age Trail. One of the most scenic treks is the mile and a half hike to Devil’s Staircase.

The Rotary Botanical Gardens is a non-profit garden covering twenty acres. You won’t want to miss their Holiday Light Show.

From Thanksgiving weekend through December, the gardens become a magical winter wonderland strewn with hundreds of thousands of lights.

History buffs will get a kick out of exploring Janesville’s thirteen historic districts. One of the highlights of any visit to Janesville would be the Lincoln-Tallman House.

Built in 1857, it’s been a museum since 1951. Eighty-five percent of the furnishings in the house are original, including the bed that Lincoln slept in when he was a guest.

Janesville’s dining scene is relatively new, but with restaurants like Genisa Wine Bar and the Sandwich Bar, it’s gaining steam and there are enough unique spots to keep your palate happy.

I definitely recommend bellying up to the 1933 Art Deco bar at O’Riley and Conway’s Irish Pub for some Scotch eggs.

Combine history and beer at Gray Brewing Co. They’ve been brewing beer since 1856, except during that pesky Prohibition when they turned to sodas. It’s one of the oldest family-owned breweries, not just in Wisconsin, but in the United States.

When you visit Janesville, make sure you’ve got your walking shoes and plenty of room on your SD card, because the town is filled with vibrant and colorful murals.

Where to stay in Janesville, Wisconsin: Renovated in 2019, the Hampton Inn provides comfortable rooms with modern décor. Breakfast is included, and it’s one of the better spreads I’ve seen.

When I stayed, the hot items were frequently replenished and there were several options including both waffles and mini-waffles.

CVB: Janesville Area Convention and Visitors Bureau, janesvillecvb.com

Lake Geneva, Wisconsin

Located just 75 miles northwest of Chicago on the other side of the Wisconsin border, Lake Geneva provides a year-round escape from hectic city life and is a short day trip from Chicago or great weekend destination.

One attraction with a direct tie to Chicago is the Yerkes Observatory (pictured above).

Yerkes is considered the birthplace of modern astrophysics and was funded by Charles Yerkes, who had a huge role in developing Chicago’s public transportation.

Lake Geneva has long been a playground for Chicagoans. In the late 1800s and early 1900s, it seemed that every wealthy Chicagoan built a mansion on the shores of the lake. Today, many of those mansions still stand.

The best way to see them is to take a boat tour, especially if you can ride along when they’re delivering the mail. Lake Geneva is one of the few places left in the country where mail is delivered by boat.

Another way to see the mansions is to walk the path that surrounds the lake. Like Chicago’s lakefront with its public beaches, Geneva Lake is surrounded by a trail that’s open to everyone.

The lakefront path is one of the most popular things to do in Lake Geneva .

One place you can only visit from a boat, unless you have physical limitations and can’t climb the many stairs from the dock, is Black Point Estate. This historic mansion has many ties to Chicago, including Jane Addams .

For something completely different, feed an ostrich. Safari Lake Geneva is a drive-through experience that allows you to feed giraffes, alpacas, elands, and emus.

An experience that’s both fun and tasty is taking a class at Lake Geneva Cooking School. Chef John teaches you how to make dishes you might never attempt on your own, and he pairs them with stellar wines.

Like many, during lockdowns he pivoted and fulfilled his dream of publishing a cookbook . I’ve made several recipes from it, and highly recommend it.

Golf is one of Lake Geneva’s biggest draws. During the winter months, you can ski, snowboard, snowshoe, and ice fish.

Where to stay in Lake Geneva: Technically located in Fontana on the west side of Geneva Lake, The Abbey Resort is a sprawling complex with beautiful rooms overlooking a marina.

They also have multiple pools and there’s often live music, either in the bar or outside during the summer.

CVB: Visit Lake Geneva, visitlakegeneva.com

Milwaukee, Wisconsin

Milwaukee, Wisconsin, is an urban getaway filled with culture and outdoor fun.

The instantly recognizable Milwaukee Art Museum is definitely worth visiting, and after you’ve browsed its collections you can take a walk along the lakefront.

For more art, book a room at Saint Kate The Arts Hotel . This astounding hotel is like staying in a work of art – because you are. It’s right downtown, providing easy access to the river walk.

Beer lovers will have a blast exploring Milwaukee’s breweries. Lakefront Brewery is known for its fun tours. Milwaukee Brewing Company and Mobcraft are also great places to visit.

There’s no beer at the Pabst Mansion, but you’ll still want to see Captain Frederick Pabst’s house, built in 1892. It’s a gorgeous Flemish Renaissance Revival mansion that’s on the National Register of Historic Places.

Fun fact: Captain Pabst earned his stripes with the Goodrich Line of steamships, which was based out of Chicago.

Another nautical stop is North Point Lighthouse. Built in 1888 high on a bluff, Frederick Law Olmsted himself designed the grounds. Chicagoans will recognize the famous landscaper’s name from the 1893 World’s Columbian Exposition and the University of Chicago, among others.

Olmsted also landscaped Lake Geneva’s Yerkes Observatory, which was part of the University until recently.

The Harley-Davidson Museum is another must-stop and be sure to dine at Motor, the on-site restaurant.

During the summer there are festivals just about every weekend, so check Visit Milwaukee’s events calendar to find out what’s happening.

And of course, make sure you have some cheese curds, brats, and beer.

Where to stay in Milwaukee: Saint Kate The Arts Hotel for a modern art experience, The Pfister Hotel for a dose of history, and Iron Horse for more industrial décor and easy access to the Harley-Davidson Museum.

CVB: Visit Milwaukee, visitmilwaukee.org

Lafayette, Indiana

Driving time: 2 hours

My grandparents lived in West Lafayette, Indiana, so I grew up visiting. However, it wasn’t until a few years ago that I actually explored the town. Boy, had I been missing out on a lot.

Known as the home of Purdue University, West Lafayette, and its sister city Lafayette, have history, art, culture, delicious food and drink, and a vital sense of community.

There are several places that make this a great place for a road trip from Chicago. One is the Haan Mansion Museum of American Art.

The mansion was originally built for the 1904 World’s Fair in Saint Louis. Now it’s in West Lafayette and is filled with impressionist paintings and historic furniture.

Another is SAMARA. Designed inside and out by Frank Lloyd Wright for Dr. John and Catherine Christian, it’s a nearly perfectly preserved example of Wright’s Usonian architecture.

Another fascinating spot is Prophetstown State Park, combining a landscape that’s distinctly Indiana with the history of the Native Americans who fought the settlers’ encroachment, and the farmers who eventually tilled the land. While there, visit the nearby Tippecanoe Battlefield.

I’ve got even more places to visit in Lafayette. These include not only places I’ve been, but also spots recommended by students at Purdue University. I’ve partnered with a 400-level travel-writing class since 2018, and many of their submissions are local to the college town.

See why you should visit Lafayette and West Lafayette Indiana

Where to stay in Lafayette, Indiana: Mr. TLT and I loved the cozy intimacy of Black Blanket Farms Bed and Breakfast . If they’re booked, Lafayette has a gazillion hotel options since it’s a college town.

CVB: Visit Lafayette-West Lafayette, homeofpurdue.com

9 Weekend Road Trips from Chicago between 2 and 3 hours

Shipshewana, indiana.

Driving time: 2 hours 15 minutes

If you’re looking for a slower pace, yet still want plenty to do, add Shipshewana to your weekend adventures.

Shipshewana is in LaGrange County, also known as Indiana Amish Country. You’ll know when you get close because you’ll start seeing horse-drawn buggies and bicyclists everywhere.

With the third largest Amish population in the world, this area is a definite departure from the hustle and bustle of city life. Instead, it’s antiques and hand-crafted furniture, delicious food, and fun entertainment.

One of Shipshewana’s most well-known attractions is the Shipshewana Flea Market . Begun in 1922 with a livestock auction, this family-owned business is the largest flea market in the Midwest.

Learn what it’s like to attend the Shipshewana Misc & Antique Auction .

You also don’t want to miss the Davis Mercantile . Another family affair, it’s a destination for dining, shopping, and riding the carousel.

If you plan your trip in advance, you might be able to dine in an Amish home, which is a real treat (and the best mashed potatoes ever). If it’s a last-minute getaway, The Blue Gate Restaurant is always a favorite. After dinner, head upstairs for a show at the theater.

Other fun things to do in Shipshewana include touring Cook’s Bison Ranch, exploring one of the many county parks, having dinner in an Amish home , canoeing or kayaking on the Pigeon River, and taking a driving tour on a hunt for barn quilts.

Where to stay in Shipshewana: The Blue Gate Garden Inn is a comfortable hotel that’s filled with amenities, including outdoor fire pits and an ice cream shop.

CVB: Visit Shipshewana, visitshipshewana.com

Sheboygan, Wisconsin

Driving time: 2 hours 30 minutes

When people ask me the destination that surprised me the most, Sheboygan, Wisconsin, tops the list.

I visited in August 2021, and it was my first press trip post-cancer. It was exactly the experience I needed: waves, beaches, amazing food, brilliant art, and a community that preserves its past.

Your first stop should be the Sheboygan Visitor Center. It is absolutely the coolest visitor center I’ve ever seen – and I’ve been to a lot.

Sheboygan’s known as the Malibu of the Midwest, so of course I had to get out on the water. One of my favorite things to do was take a first sailing lesson in Lake Michigan. That’s right – you can learn how to sail on a weekend trip to Sheboygan.

The Kohler name is prominent in the area. In addition to the manufacturing company and a nearby resort, there’s also the Kohler Arts Center and the Kohler Art Preserve, which opened in 2021.

Kohler also manages the James Tellen Woodland Sculpture Garden, one of several artist-built environments throughout the state.

History geeks will want to stop at Sheboygan Indian Mound Park and the Sheboygan County Historical Society and Museum.

For dining, don’t miss Black Pig, Il Ritrovo, and BoMallies. Breakfast should absolutely begin at Paradigm Coffee and Music. Best. bagel. sandwich. ever.

Check out my piece about this surprising place, and I’ve even included the perfect 3-day Sheboygan itinerary .

Where to stay in Sheboygan: Blue Harbor Resort offers gorgeous rooms and an even better view. They’ve also got a whole water park, on-site dining, and easy access to the beach.

CVB: Visit Sheboygan, visitsheboygan.com

Elkhart Lake, Wisconsin

About twenty minutes from Sheboygan is another delightful road trip from Chicago.

Elkhart Lake has all the feelings of a resort town. There are historic accommodations, unique boutiques, and delicious dining.

The eponymous lake is gorgeous, with crystal clear water. You can take a pontoon boat ride, or go kayaking or paddle boarding.

The village is also right by the Ice Age Scenic Trail and Kettle Moraine State Forest – Northern Unit, providing lots of opportunity for outdoor activities.

Racing fans won’t want to miss Road America. This four-mile road course is considered the best in the United States and one of the top in the world.

Not only can you watch racing, you can also take a spin around the track yourself. They offer both motorcycle and automobile driving schools.

Where to stay in Elkhart Lake, Wisconsin: Osthoff Resort is an historic inn that offers a variety of room options, including suites and villas, and features amenities such as an indoor and outdoor pool, spa, and fitness center.

The resort also has several dining options on-site, including a fine-dining restaurant and a casual bistro.

CVB: Elkhart Lake, visit website

Galena, Illinois

Driving time: 3 hours

Galena, Illinois, is located near the Mississippi River on the opposite side of the state from Chicago. Surrounded by the rolling hills and bluffs of the Driftless Region, it’s an area dotted with wineries and golf courses.

There are many reasons nearly a million people visit the former mining mecca each year. From shopping along its historic main street to the many wineries in the area, it’s a great spot for a romantic weekend or a girls getaway.

A stroll down Main Street feels like a step back in time. Be sure to stop into Galena Canning Company for a taste of salsas and jams, and Galena Brewing Company offers a lineup of tasty beers.

Thrill-seekers will love a visit to Long Hollow Canopy Tours , a zipline adventure through the woods.

Nature lovers can explore trails along the nearby Mississippi River, and golfers will love a few rounds at Eagle Ridge Resort & Spa.

There are also several historic buildings, and the Ulysses S. Grant Home is one of the most popular places to visit for a look into the past.

Where to stay in Galena, Illinois: While there are hotels that are closer to Galena’s historic Main Street, two of my favorites are a short drive from downtown. Goldmoor Inn Bed and Breakfast is an elegant getaway overlooking the Mississippi River.

Eagle Ridge Resort and Spa is my home away from home when I’m in Galena. I’ve stayed there at least five times. I love the variety of accommodations, activities, and the delicious food.

CVB: Visit Galena, visitgalena.org

Hendricks County, Indiana

My first visit to Hendricks County, Indiana, was in 2017, and since then I’ve returned four? five? times. You might say I like it. I even taught the first writing workshop for Midwest Travel Network (I’ve now taught three) at Natural Valley Ranch, a cabin with that private pond out its back door.

There are also horses, that you can ride. Squeee!

It’s a large county comprised of several towns. Some are large, like Plainfield and Avon, and others are small, like the tiny Lizton, which is home to the best barbecue – and pecan pie – in Indiana (and possibly the Midwest).

Race fans not only have easy access to the Indianapolis Motor Speedway, they can also see the NHRA Finals at the Lucas Oil Raceway within Hendricks County.

The only Doctor Who Museum and Store is in Hendricks County, as is the Tie-Dye Lab, where you can make your own tie-dye apparel. Beasley’s Orchard has the best apple cider. Oasis Diner is the only diner on the National Road and it’s got one of the best pork tenderloin sandwiches anywhere.

Basically, go to Hendricks County . There’s so much to do I bet you’ll want to go back again and again, just like I do.

Where to stay in Hendricks County: Natural Valley Ranch is great if there’s a big group of you exploring the area. If not, then I’m a fan of Staybridge Suites . Each room includes a kitchenette, plus they offer free breakfast and weekday happy hours.

CVB: Visit Hendricks County, visithendrickscounty.com

More Road Trips from Chicago between 2 and 3 hours

• Madison, Wisconsin; 2 hours 45 minutes
• New Glarus, Wisconsin; 2 hours 45 minutes
• Indianapolis, Indiana; 3 hours
• Quad Cities, Illinois/Iowa; 3 hours

11 Weekend Road Trips from Chicago between 3 and 5 hours

Fort wayne, indiana.

Driving time: 3 hours 10 minutes

When you go to Fort Wayne, go hungry. And thirsty. This northeastern Indiana town has a thriving food and beer scene that will have you coming back for more.

This All-American City is located at the confluence of three rivers, and that riparian location has fed its personality since it was founded when General “Mad” Anthony Wayne built a fort there in 1794. That fort didn’t last long, and by 1815 the town was on its third fort, built by Major John Whistler.

Chicagoans might recognize that name: he built Fort Dearborn when he was a Captain. You can visit a replica of Whistler’s fort, and they often have events.

One of the best things to do in Fort Wayne is visit the YLNI Farmers Market. This bustling marketplace features everything from handmade chocolates to hot sauces that’ll blow your top off to candles that smell like Fort Wayne (and Montana, Chicago, and everywhere else Simple Nature‘s creative creator has been). 

But what about that food, you ask? A few favorites include Club Soda, for white tablecloth dining with a side of live music, Birdie’s for shared plates in an airy rooftop, and Hall’s Prime Rib for down-home diner cooking.

Beer fans will want to belly up at Junk Ditch, The Hoppy Gnome, and Hop River Brewing Company.

Where to stay in Fort Wayne, Indiana: Courtyard Fort Wayne Downtown at Grand Wayne Convention Center is in a great location; across from the convention center and in between Parkview Field and Embassy Theatre.

CVB: Visit Fort Wayne, visitfortwayne.com

Green Bay, Wisconsin

Driving time: 3 hours 15 minutes

While it may seem blasphemous to some to suggest driving to the home of the Packers from the home of the Bears, I guarantee there’s a lot more going on than gridiron battles.

Auto enthusiasts will love The Automobile Gallery. Opened in 2016, this collection of pristine vehicles span over a century of automotive history.

From the iconic 1908 Cadillac Model T to the sleek 1960 Chevrolet Corvette, every car enthusiast will find something to admire.

The museum also features a rotating selection of vehicles, ensuring that there is always something new and exciting to discover.

For transportation of another kind, visit the National Railroad Museum. The museum began in 1956 and now covers a sprawling 33-acre campus.

Not only can you see locomotives like the iconic “Big Boy” No. 4017, you can step inside a Pullman sleeper car and learn about the porters who worked America’s rail lines.

Ready for a drink? From Captain’s Walk Winery to Zambaldi Beer, you’ll find something to whet your whistle.

And if you’re hungry, Green Bay will keep you fat and happy. (Speaking from experience here.) Don’t miss the authentic kringles at Uncle Mike’s Bake Shoppe or a cup of Booyah, a hearty Belgium chicken stew.

Where to stay in Green Bay, Wisconsin: Stay in the heart of Green Bay at the historic Hotel Northland . The hotel’s especially great for a romantic getaway.

CVB: Discover Green Bay, website

Dubuque, Iowa

Driving time: 3 hours 20 minutes

You’ll be glad Dubuque Iowa is one of these easy road trips from Chicago, because there’s so much to do you’ll want to return again and again.

Dubuque’s location on the Mississippi means it’s filled with river lore. Begin your visit at the Mines of Spain, a National Historic Landmark and Iowa State Recreation Area. It’s named for the mines that Julien Dubuque, the town’s founder, worked with permission from first the Mesquakie and then the Spanish. The Julien Dubuque Monument resembles a rook and overlooks the Mississippi; Dubuque is buried on the site.

Get an in-depth introduction to the river and the region at the National Mississippi River Museum and Aquarium, then go on the river itself. You can take a steamboat tour or an American Lady River Cruise aboard a yacht.

Like Janesville, Dubuque’s downtown is also covered with murals, and it’s a fun afternoon to walk the streets and find your favorite.

Dubuque’s most unusual attraction is the Fenelon Place Elevator. It’s the shortest, steepest railroad and a ride to the top provides some of the best views in the city.

Another spot for great views is Eagle Point Park. You’ll get a birds eye view of Lock and Dam #11 and can see into both Wisconsin and Illinois.

One of the most famous attractions is in nearby Dyer. The Field of Dreams Movie Site is surprisingly moving, especially now that you can tour the house. Inside you’ll discover stories behind the filming of this beloved classic.

I think the food scene in Dubuque will surprise you. It certainly surprised me to discover several innovative chefs serving quality cuisine. Make reservations for both Brazen Open Kitchen and Pepper Sprout and you’ll be one happy diner.

Where to stay in Dubuque, Iowa: since it’s right downtown, you can’t get much more convenient than Hotel Julien Dubuque . Plus, it’s a gorgeous hotel with oodles of history, including stories about Mr. and Mrs. Lincoln and a certain gangster from Chicago.

CVB: Travel Dubuque, traveldubuque.com

Brown County, Indiana

Driving time: 4 hours

Brown County, Indiana, is known for its beauty when the leaves change colors, but that doesn’t mean you can only visit in the fall. The rolling hills are beautiful year round.

While the area is easy to get to now, that wasn’t always the case. Its relative isolation fostered a vibrant artists community, which thrives to this day.

Visit Brown County and you can see the home and studio of one of the founding artists T.C. Steele. He was one of the five members of the acclaimed Hoosier Group. In the late 1800s, that group put Indiana’s art scene on the map, and Brown County in particular.

Browse the galleries of Nashville, Indiana, and you’ll see works of art from those early painters as well as artists of today.

Get a two-for-one cultural experience at Country Heritage Winery. Not only can you taste wines, when you take a weekend road trip from Chicago, you can do so while listening to live music.

Another favorite is Hard Truth Hills. Inspired by Sierra Nevada’s set-up in Asheville, North Carolina, this is a multi-purpose destination with a brewery, a distillery, a restaurant, and an outdoor stage. Pro tip: get the to-die-for pulled pork nachos.

Brown County is one of those places where you can choose to go-go-go, or you can kick back and relax. Either way, it’s definitely worth the drive.

Learn more about Brown County and how it became the tourist destination it is today.

Where to stay in Brown County: Abe Martin Lodge is located within Brown County State Park. Bring the kids and your swimsuits; they’ve got an indoors water park. Want something more secluded? There are cabins, too.

CVB: Brown County, browncounty.com

Sandusky, Ohio

Driving time: 4 hours 45 minutes

Sandusky is most famous for being the home of Cedar Point amusement park, but this city on the shores of Lake Erie is much more than roller coasters and funnel cakes.

A fun way to get an overview is to take a Segway tour. Sandusky Segwave offers guided tours through the historic downtown. Perched atop your personal transporter, you’ll glide past historic sites, through city parks, along the lakefront, and past the Merry-Go-Round Museum. You’ll learn about the town’s very beginnings, as well as its role in the Underground Railroad.

Another reason to visit Sandusky is Kelleys Island. Take a high-speed ferry to the largest American island in Lake Erie for a day of art, shopping, and wine.

While you’re on the island, don’t miss Glacial Grooves State Memorial. This National Natural Landmark protects the largest easily accessible grooves in the world. To see them is to witness the power of the glaciers that shaped North America.

Before you go back to Sandusky, get a scoop of Lake Erie Cookie Island Monster. It’s the official ice cream of Ohio’s Lake Erie Shores and Islands , Sandusky’s visitors bureau.

Warning: it will turn your tongue blue!

Check out my guide to see many more things to do on Kelleys Island .

Where to stay in Sandusky, Ohio: Hotel Kilbourne . This place puts the boutique in boutique hotel. In addition to being the only Sandusky hotel that’s on the water, it’s also got a rooftop bar and an on-site restaurant.

CVB: Ohio’s Lake Erie Shores and Islands, shoresandislands.com

Driving time: 5 hours, or as long as you’d like!

Route 66 epitomizes the freedom of the open road, and it begins in Chicago. The route became official in 1926, providing many small towns access to significant national roadways for the first time. Although it was decertified in 1985, the Mother Road lives on.

This scenic byway changed course over the years, and these alignments are well marked in Illinois. If you’re short on time, I-55 will take you from one attraction to the next, but the fun of driving one of the country’s most historic byways is in following its original path.

Some of the most popular roadside attractions include Buckingham Fountain (not technically on Route 66, but you’re so close!), the Gemini Giant, Bunyon’s Statue, and Carlinville’s Million Dollar Courthouse.

Route 66 in Illinois is only 301 miles, but it’s nearly a century of Illinois history, so take your time.

More road trips from Chicago between 3 and 5 hours:

• Iowa City, Iowa; 3 hours 45 minutes
• Door County, Wisconsin ; 3 hours 50 minutes
• Bloomington, Indiana ; 4 hours
• Spencer, Indiana : 4 hours
• Collinsville, Illinois and Cahokia Mounds State Historic Site : 4 hours 45 minutes
• Traverse City, Michigan; 4 hours 55 minutes

Want an epic trip from Chicago but don’t feel like driving? Consider a train to Seattle – here’s what it’s really like to ride the Amtrak Empire Builder !

Map of Road Trips from Chicago

I hope these delightful road trips from Chicago will help you find someplace wonderful to visit for your weekend getaways. Each place is special and offers unique experiences. When you go, I’d love it if you’d share your photos in our Facebook group .

Oh, and be sure to bookmark this page, because I’ve got more destinations to add!

Protect Your Trip »

29 top cheap weekend getaways in the u.s..

Weekend getaways are often cheaper by default – especially in these destinations.

Top Cheap Weekend Getaways

Jason Tarr | Courtesy of ExploreAsheville.com

Asheville, North Carolina, is one of the best places for an affordable weekend escape.

Sometimes you just need to escape from your everyday routine – but you may not have weeks (or funds) on end to spend away from home. For those seeking a quick, affordable trip, we've compiled a variety of cheap weekend getaways across the U.S., organized by region so you can find something within driving distance to keep costs low (or further afield if you're up for the journey).

Top Regional Destinations:

Burlington, vermont.

Getty Images

You don't have to spend a lot of money to enjoy Burlington, Vermont – especially since the best ways to experience it are low-cost or free. Rent bikes and go for a ride on the Burlington Bike Path, which later becomes the Island Line Trail – a stunning pathway over Lake Champlain. You can also stroll Church Street Marketplace, where the Burlington Farmers Market is hosted on Saturdays; sample sweets at Lake Champlain Chocolates; and enjoy a craft beer tasting or two.

Niagara Falls, New York

There's no cost to visit this iconic landmark , and if you want to get up close, you'll find several affordable tours of Niagara Falls – namely boat rides that'll get you up close to the roaring waters. A visit to Niagara Falls, New York, also omits the cost (and hassle) of getting or renewing a passport . Free and low-cost things to do in Niagara Falls include hiking state parks and sampling vinos along the Niagara Wine Trail.

Atlantic City, New Jersey

You can enjoy an affordable weekend in Atlantic City – provided you steer clear of (or don't spend too much time at) the casinos. Instead, explore the beach and boardwalk, whose roots date back to 1870. Other budget-friendly things to do in Atlantic City including visiting Absecon Lighthouse (the tallest in New Jersey) and Lucy the Elephant. If you come here for a romantic getaway , treat yourself and your partner to dinner on the waterfront.

The Poconos, Pennsylvania

Spend as much or as little as you like in the Pocono Mountains. Located in northeastern Pennsylvania, the region's terrain affords a variety of free and low-cost activities amid beautiful scenery, from hiking and biking to fishing and boating. Lake Wallenpaupack, Hickory Run State Park and Lehigh Gorge State Park offer some of the best camping for those who'd like to keep lodging costs low, though you can also find affordable vacation rentals in the area.

Gettysburg, Pennsylvania

Courtesy of Destination Gettysburg

Gettysburg National Military Park (which also comprises the Gettysburg Museum and Visitor Center) is free to visit, and there's no cost to explore the Civil War battlefields with a national park ranger. Gettysburg ghost tours – a must for anyone who's interested in the area's haunted history – are relatively affordable, too, as are local hotels , which include options under $200 and $100 per night.

Farm Sanctuary: Watkins Glen, New York

Courtesy of Farm Sanctuary

Farm Sanctuary in the Finger Lakes region of New York is part animal sanctuary, part country retreat – and an ideal location for a weekend escape from New York City . Travelers eager for a break can book a tiny home or cabin and spend time with more than 500 rescued farm animals in Watkins Glen. Nightly rentals start at $250 per night (plus a $25 membership fee) for up to two people in May through December, and include a special tour each morning of your stay. Sample the region's signature rieslings and chardonnays at some of the top wineries in the Finger Lakes during your visit, or hike to waterfalls at Watkins Glen State Park .

Address: 3150 Aikens Road, Watkins Glen, NY 14891

Black Hills National Forest and Badlands National Park, South Dakota

This area of the U.S. is home to Mount Rushmore, Custer State Park and the fascinating caverns of Wind Cave, making it easy to see several iconic attractions in one jaunt. To save on entry fees, consider the America the Beautiful National Park Pass. Priced at $80, it provides access to all national parks and federally protected lands in the U.S., so you'll likely be able to use it for another trip down the road, too.

Read: The Top Things to Do in South Dakota

Holiday World & Splashin' Safari: Santa Claus, Indiana

Courtesy of Holiday World & Splashin' Safari

Holiday World & Splashin' Safari ranks among the most affordable amusement parks in the U.S., in part because of its free parking and modest lodging costs. The amusement park also offers complimentary family-friendly perks with admission, including sunscreen and soft drinks.

Address: 452 E. Christmas Blvd., Santa Claus, IN 47579

Wisconsin Dells, Wisconsin

Courtesy of Wisconsin Dells Visitor & Convention Bureau

Wisconsin Dells is home to myriad water park resorts – many of which combine water park admission and overnight lodging in one rate. Other attractions in Wisconsin Dells include a Ripley's Believe It Or Not museum, a bustling downtown and plenty of gorgeous scenery marked by unique rock formations. You can frequently find hotel and attraction discounts on the Wisconsin Dells tourism bureau's website ; keep in mind for any family trips that the best prices are typically available when kids are in school.

Branson, Missouri

Courtesy of Explore Branson

Table Rock Lake State Park, where you can swim, canoe, kayak, fish, hike and bike, as well as Branson Landing, which features a spectacular fountain show at night, are among the free attractions in Branson, Missouri . You can also ride a free trolley around town from March to December. The most expensive activity in Branson might be a visit to Silver Dollar City, though you can often find deals on tickets, like discounted evening rates in the fall. For affordable lodging in Branson , try the Thousand Hills Resort Hotel , which often lists rates around $100 per night.

Indianapolis, Indiana

Courtesy of Visit Indy

There are a variety of free things to do in Indianapolis , including the Monon Trail, which connects downtown Indy to the Carmel area, with shops and restaurants along the way; the 250-acre White River State Park, perfect for a picnic lunch; and the Indianapolis Cultural Trail, which connects the city's public spaces. On the first Thursday of every month, the Newfields Art Museum offers free admission (and whether or not you go to the museum, the grounds alone are worth a visit). In the summer, Concerts on the Canal brings free entertainment to the area – just bring your own blanket or lawn chair.

No matter your budget, a visit to the Indianapolis Children's Museum is worth the splurge if traveling with kids – it is the largest children's museum in the world.

Cedar Point: Sandusky, Ohio

Courtesy of Cedar Point

Not only is Cedar Point one of the best amusement parks in the U.S. – and the self-proclaimed Roller Coaster Capital of the World – but a visit here is also relatively cheap when you factor in the affordability of hotels in Sandusky . The Comfort Inn Sandusky , for example, offers free breakfast with rates starting at less than $100 per night. Keep in mind that, as a seasonal attraction, Cedar Point is typically closed from November to early May.

Address: 1 Cedar Point Drive, Sandusky, OH 44870

Read: The Top Water Parks in Ohio

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Washington, D.C.

Courtesy of Washington.org

With 22 free Smithsonian museums including the National Zoo, Washington, D.C. is an obvious choice for a cheap weekend getway. And while many hotels in D.C. are expensive, you can still find affordable accommodations on rental sites like Airbnb and Vrbo.

Gulf Shores, Alabama

Gulf Shores boasts more than 30 miles of white sand beaches , making it one of the best beaches on the Gulf Coast . You don't have to visit during the summer to experience the area's best weather, though: Spring and fall bring temperatures that are still comfortable for sunbathing, swimming and strolling on the sand.

Budget-friendly things to do in Gulf Shores include bike riding at Gulf State Park; casting a line at Gulf State Park Fishing and Education Pier; exploring The Wharf, an entertainment and shopping venue; and visiting the Orange Beach History Museum and the Gulf Shores Museum, both of which are free. At local hotels like the Staybridge Suites Gulf Shores , nightly rates for apartment-style accommodations and free breakfast currently hover around $100 a night.

Massanutten Resort: Massanutten, Virginia

An ideal weekend getaway from Washington, D.C. , Massanutten Resort offers four-season fun, from winter sports like skiing and snowboarding to golf, mountain biking and water park action during warmer months. A la carte fees for many activities allow you to spend as much or as little as you'd like, and while there's a nightly resort fee, it covers access to the indoor and outdoor pools, playgrounds, sports courts (including pickleball), hiking trails and more. Plus, the resort fee doesn't seem so bad when you consider that townhomes and guest rooms are available for less than $150 a night.

Address: 1822 Resort Drive, Massanutten, VA 22840

Asheville, North Carolina

Krista Rossow | Courtesy of ExploreAsheville.com

Situated within the Blue Ridge Mountains, Asheville is known for its mix of history (Biltmore Estate), nature (the Blue Ridge Mountains) and food (from craft breweries to a flourishing dining scene). Travelers can tackle a number of hikes in Asheville for some scenic – and low-cost – fun. You can also stroll along the 1.7-mile Asheville Urban Trail to learn about the city's unique past, go for a drive along the Blue Ridge Parkway and explore downtown, where you're bound to come across some of the tiny city's famous street performers. Great Smoky Mountains National Park is an easy and relatively affordable day trip from Asheville, too.

Bahia Honda Key, Florida

You don't have to visit Key West – or break the bank – to experience the best of the Florida Keys; in fact, the best beaches in the Florida Keys are not even in Key West. At Bahia Honda State Park, for example, you can swim, rent kayaks and snorkeling gear, or even hop on a boat to snorkel in the Looe Key marine sanctuary reef. Entry fees at Bahia Honda State Park are $8 per vehicle with two to eight passengers. Plus, you can camp here for just $36 per night (not including tax and the utility and reservation fees). Renting a cabin costs about $120 per night plus fees from May through October, and slightly more in the cooler months.

Read: The Best Places for Camping in Florida

Myrtle Beach, South Carolina

One of the most affordable beach destinations in the U.S., Myrtle Beach is known for its roster of low-cost or free activities that appeal to travelers of all ages. Explore the mile-long Myrtle Beach Boardwalk (home to the iconic Skywheel) as well as Broadway at the Beach (an entertainment complex), both of which offer live entertainment including music performances and fireworks shows. Vereen Memorial Gardens, just north of the city, is also free to visit. When it comes to Myrtle Beach accommodations , there are affordable options aplenty; the Crown Reef Resort, for example, offers an on-site, year-round water park and rates as low as $92 per night for a family of four.

Polk County, Florida

Courtesy of Visit Central Florida

A vacation in Orlando has its time and place, but if you're on the hunt for a cheap weekend getaway, head to Polk County instead. Here, you can explore stunning (and free) parks and nature preserves such as Bok Tower Gardens, a National Historic Landmark, as well as Bonnet Springs Park. The park connects several attractions, including a kids treehouse, a rooftop bar, a butterfly house, The Florida Children's Museum, botanical gardens and more. Legoland Florida Resort and Peppa Pig Theme Park are close by if you decide to splurge on a theme park visit.

New Orleans

There are more things to do in New Orleans than you could ever accomplish in a weekend, but you can still enjoy a short and cheap trip to The Big Easy. Ogle the historic houses in the Garden District, stroll along iconic Magazine Street, wander through the French Quarter (where you're bound to see street performers), or stop in a local eatery for a famous po'boy sandwich or beignet. For affordable accommodations in New Orleans , look outside of the French Quarter.

South Padre Island, Texas

Courtesy of South Padre Island CVB

Not only does South Padre Island offer 34 miles of coastline and the cleanest beach water in Texas, but it's also ultra-affordable. Low-cost attractions include Sea Turtle, Inc., which is currently building the world's largest sea turtle hospital, and South Padre Island Birding and Nature Center. There are also plenty of places to enjoy fishing, one of the island's most popular activities. A visit to the Port Isabel Lighthouse State Historic Site – the last Texas lighthouse open to the public – costs just $5 per adult ($3 for kids). Sandcastle Days, the island's beloved festival that is hosted every October, is also free.

Joshua Tree National Park, California

One of the most beautiful national parks in California , Joshua Tree National Park is also fairly affordable thanks to campgrounds like Jumbo Rocks, where you can enjoy the seclusion of the deserted wilderness. There are more than 100 primitive campsites available here, with reservations required in the busy season from September to May; a maximum of six people can occupy a campsite for just $20 per night (on top of fees to enter the park).

San Luis Obispo, California

Courtesy of Visit SLO CAL

Combining small-town charm with beautiful weather, San Luis Obispo is an ideal weekend getaway from Los Angeles (about 190 miles from the city). With the plethora of outdoor activities here, visitors can enjoy budget-friendly fun like hiking the area's trails, surfing in the ocean, zip lining or horseback riding. For local flavor, visit the Thursday evening farmers market or dine alfresco at one of many downtown patios. The town's free Concerts in the Plaza series features performances by the area's top artists. Beaches await those seeking relaxation in SLO, while wine lovers can explore the region's Edna Valley wineries.

A glitzy getaway in Las Vegas can be yours – and it may be less expensive than you initially imagined. Hotels in Vegas can cost as little as $50 per night on weekdays (plus resort fees), and local attractions like Bellagio Fountains, the Fremont Street Experience, the Las Vegas Sign and Seven Magic Mountains (just outside the city) are all free to visit. This might just mean you'll have some room in your budget for a casino visit, tickets to one of the city's spectacular shows , and/or a tour of the Grand Canyon .

Sedona, Arizona

Courtesy of Sedona Chamber of Commerce & Tourism Bureau

It won't cost you a penny to visit most attractions in Sedona , including Cathedral Rock, Devil's Bridge and Fay Canyon. And while Sedona's spa and wellness resorts are undoubtedly pricey, you can find lodging for less in off-peak months (summer and winter), as well as a variety of vacation rentals year-round.

Read: The Top Things to Do in Arizona

Gros Ventre Wilderness, Wyoming

The Gros Ventre Wilderness, which is part of the greater Yellowstone ecosystem, is another natural wonder worth visiting. Plan a weekend here to discover rolling rivers, abundant wildlife, and amazing geological features such as rock formations and natural slides. As for accommodations, travelers can rent the cozy Hoback Guard Station cabin for $80 per night for a party of up to six guests from May to October.

Olympic National Park, Washington

Olympic National Park is well worth a weekend visit, whether you want to hike, stargaze or explore its more than 70 miles of untouched Pacific Coast shoreline – which include dog-friendly beaches , if your furry friend wants to come along. While here, visit the famous Hoh Rain Forest, Lake Crescent and Rialto Beach. You can even camp within the park for as little as $40 per night for up to 10 people sharing a campsite. Note that you'll have to pay a fee to enter the park.

Read: The Best Weekend Getaways from Seattle

Albuquerque, New Mexico

Courtesy of Visit Albuquerque

Albuquerque is quirky and fun, with an Old Town that features cobblestone streets and adobe-style buildings and is free to explore. Plan a visit during spring or fall for the best weather, then take advantage of local, low-cost festivals: May brings the New Mexico Wine Festival ($25 or less per ticket) to town, or come autumn, you can stop by the famous Albuquerque International Balloon Fiesta (around $15 per person) to witness one of the best hot air balloon festivals in the U.S. Other things to do in Albuquerque include visiting the Petroglyph National Monument, which is free of charge. Opt for a vacation rental rather than a hotel to save some coin.

San Antonio, Texas

San Antonio is an affordable Texas destination brimming with cultural flair, historical significance and free activities. There's no cost to visit iconic attractions like the Alamo or the San Antonio Missions National Historical Park, and you won't pay anything to stroll the famous River Walk (though dining at least once here is a must). Another popular activity, narrated river cruises are also cheap, with tickets for less than $15 per person via local operator GO RIO Cruises.

You might also be interested in:

• The Best Cheap Family Vacations
• The Best Cheap Spring Break Destinations
• The Best Presidents Day Weekend Getaways
• The Best Places to Go for the Fourth of July
• The Cheapest Travel Insurance Companies

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Tags: Travel , Budget Travel , US Vacations

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• # 1 South Island, New Zealand
• # 4 Bora Bora

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• 9 Ideal Illinois Destinations for a 3-Day Weekend in 2024

While Chicago is undeniably the most famous destination in Illinois, drawing in millions of tourists annually, the state offers countless lower-profile getaways showcasing a rare side of the Prairie State. Beyond the hustle of the big city lies a range of distinct communities and locales perfect for mini-breaks to escape bustling crowds. 2024 encourages opportunities to veer off the major highways and uncover the true heart of Illinois during a relaxed weekend trip in the overlooked backcountry.

From historic settlements saturated in Americana to pastoral prairies blanketing millennia-old scenic views, these ideal Illinois destinations guarantee immersion in authentic Midwest charms. Over three unforgettable days, exploring off-the-beaten-path routes presents a unique glimpse of the state at a relaxing pace. Those who appreciate quality over quantity should consider venturing along picturesque backroads to recharge in these intimate countryside delights.

Spend a fabulous weekend surrounded by picturesque natural beauty and small-town charm in this adorable village of LaSalle County. Oglesby is the famous home of Starved Rock State Park, one of Illinois's most unique wilderness areas. Straddling the Illinois River , it boasts wooded trails, sandstone canyons, and seasonal waterfalls that promise adventurers endless recreational opportunities. Enthusiasts come from across the state to hike, camp, fish, kayak, and watch wildlife across its 2,600-acre territory. The town further offers Matthiessen State Park, which offers additional space for outdoor adventures and a great alternative if you want to escape the crowding in Starved Rock State Park.

After a fulfilling adventure in the great outdoors, guests can relax and unwind with a cocktail while listening to music in the cozy atmosphere of Lizzie's Lounge. Afterwards, they can sleep a comforting night and experience delightful accommodation that won't break the bank.

A rich mix of attractions in this bustling college town in McDonough County promises tourists a jam-packed long weekend in the fringes of Illinois. Home to Western Illinois University, this harbors a lively art scene that welcomes newcomers for a unique visual art experience at the WIU Art Gallery. The recognized exhibits diverse works by regional and national artists featuring various art forms. History lovers get insight into the town's past by touring the Western Illinois Museum. Inside, a diverse artifact collection with archives and memorabilia paints a vivid picture of McDonough County's colorful history.

A wide array of nature spaces ensure outdoorsy travelers are spoilt for choice when stepping into the open. The Malcomb Park District enriches the tourist experience with acres of recreation opportunities. Options remain just as abundant when it comes to accommodation, although the Hampton Inn is definitely among the best local hotels.

From its popular annual festivals to its charming historic district and its beautiful outdoor spots, Woodstock has something for everyone. A weekend escape during the Woodstock Folk Festival is the perfect way to experience the rich cultural vibes in this adorable McHenry County community. However, there is plenty of fun for those visiting outside the festival period. Woodstock boasts a quaint historic district with an incredible display of old-world architecture, perfect for exploring at a snail's pace. Strolling down its quiet streets reveals iconic landmarks like the Woodstock Opera House. The historic venue is housed in an 1880s building and provides moving live art performances for the public's amusement.

Meanwhile, one of the best times to be downtown is during the Woodstock Farmers Market. The atmosphere is consistently energetic on Tuesdays and Saturdays as vendors bring out their fresh produce and traditional crafts. For accommodation, consider staying at the Quality Inn & Suites.

A small town with a "big" profile, this quiet community boasts a fair share of Guinness Book of World records that never fail to delight first-timers. These constitute quirky roadside attractions that stand out for their extraordinary size, including the 46,000-pound World's Largest Rocking Chair and the 12-meter-long World's Largest Wind Chime. Collectively, they are charismatic landmarks enticing tourists with fantastic photo opportunities. When not checking off the list of "World's Biggest" attractions in Casey, you can revel in its serene natural scenery at Fairview Park. This riverfront oasis encourages tourists to enjoy the ultimate outdoor experience with its multiple campsites.

While discovering the different points of interest lining the downtown corridors, remember to stop by Wildflour Bakery & Candy Co. to indulge your sweet tooth with delicious chocolates, gourmet candy, and novelty baked goods. With this, staying at Eighteen-Ninety Sleepover keeps you at a central location in the town for easy exploration.

Rich history naturally blends with bustling arts in this lovely town along the Pecatonica River in Stephenson County. Freeport hosts a fair share of historical markers, notably the actual site of the second Lincoln-Douglas debate. You can witness the landmark location at the Lincoln-Douglas Debate Square. The site features lush park surroundings, with the focal point being life-size statues of the two great men of history. Furthermore, there is even more detailed history to uncover at Silver Creek Museum. This magnificent facility harbors diverse artifacts that hint at the town's and country's heritage.

Freeport is renowned for its lively arts community, and newcomers can join locals inside the Winneshiek Playhouse to enjoy entertaining and family-friendly performances. Additionally, you can book a room at the Country Inn & Suites by Radisson for luxurious accommodation without compromising your budget.

If you are up for an immersive trip down memory lane during your weekend retreat, Galena is one of the ideal Illinois destinations for this. Boasting a heritage dating back to the 1820s, the town's rustic charm shines through a classic display of old-world architecture throughout its historic downtown district. You can discover some of its most treasured gems through taking the narrated Galena Trolley Tours, which highlights the individual landmarks in the site-rich neighborhood. Consider touring the U.S. Grant Home State Historic Site to uncover rich American history. The storied legacy of the 18th president of the United States comes alive in the modest Italianate building.

You will also want to check out the bustling craft brewery and distillery scene in Galena, where you can taste freshly crafted beers and spirits at establishments like the Galena Brewing Company. Finally, cap off your day with a unique, yet comfortable, accommodation experience at the historic DeSoto House Hotel.

This isolated community in the Shawnee National Forest promises tourists a laid-back short vacation where they can revel in Mother Nature's majesty. Pomona presents plenty of natural wonders perfect for exploration, notably the Pomona Natural Bridge. This hidden treasure stretches around 30 meters and is the ideal hiking trail for adventurers who prefer quiet and secluded routes. The Little Grand Canyon is another scenic hiking opportunity, spoiling tourists with dramatic canyon vistas along the Big Muddy River.

Pomona lies in the Shawnee Hills wine country region and houses several wineries where oenophiles can sample tasty local crafts. Tourists have the chance to visit establishments like Pomona Winery and Hickory Ridge Vineyard and Winery along the Shawnee Hills Wine Trail. While there aren't many B&Bs in Pomona, you can find decent accommodation in nearby small towns, such as Makanda Inn, which is about 20 minutes away.

Located south of Springfield, this south-central Illinois gem is a major highway stop that welcomes many in-transit visitors. Litchfield is enveloped by lush landscapes offering a pleasant outdoor escape, with access to a lovely swimming lake. Milnot is popular during the summer, with locals and tourists flocking to its sandy shores to enjoy a cool dip and sunbathe. Those who enjoy good-natured social encounters will love the atmosphere at Litchfield Pickers Market. Bustling with spirited vendors and buyers, it is a hub for souvenir hunters with various antiques, primitives, and collectibles.

However, historically inclined travelers may gravitate towards the Litchfield Museum and Route 66 Welcome Center. This fantastic facility preserves the community's historic artifacts in a premier venue along Route 66. Multiple hotels and inns, including Baymont by Wyndham Litchfield, provide lodging services to the many people passing through Litchfield.

This Mississippi River town near the Iowa border delights tourists with 19th-century charm and relaxed rural scenery. Outdoors enthusiasts can look forward to exciting adventures in Savanna thanks to Mississippi Palisades State Park. Covering over 2,500 acres, this recreation hub beckons campers, picnickers, hikers, and bird watchers to discover its spellbinding river bluffs and dramatic rock formations. Besides the beautiful outdoors, Savanna interests the indoor inclined at the Savanna Museum and Heritage Center. Inside, a vast collection of archives, artifacts, and relics tell the unique story of Savanna through the years.

Alternatively, visitors can catch the latest Hollywood installations at Savanna Times Theater. The family-friendly venue screens classic and new movies at very reasonably priced tickets. You don't have to search too long for a hotel in Savanna, with top options like Savanna Inn & Suites available.

Wrapping Up

Illinois' unbeatable charms come from the authentic experiences in its lesser-known small towns. From the historic riverfront settlement of Freeport to the dynamic communities of Macomb, these hidden gems offer a genuine taste of prairie living. Whether simply relaxing on picturesque courthouse squares, hiking diverse trails, or enjoying parades and festivals with locals, visitors gain notable insight into the true heartland character shaping the state outside its large cities. For those seeking to fill limited time with quality cultural immersion, any of the above ideal Illinois destinations will be an excellent choice.

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The best day trips from Chicago for an exciting adventure

Explore small-town breweries, bakeries and artisan shops when you embark on these easy day trips.

Photograph: Shutterstock

Sometimes, you just want a little escape from the city. If a weekend getaway isn't possible but you're still looking for new scenery and an adventure, there are plenty of options for a day trip within a few hours’ drive of Chicago. Spend an afternoon soaking up the rays on beaches along Lake Michigan, go  hiking near Chicago  in a state park or sample a variety of beers and cheeses up north in Wisconsin. The attractions are endless, ranging from amusement parks and Japanese gardens to museums and historic lighthouses.  And the best part? Many of these destinations are also accessible by  Metra . So get to planning with our guide to the best day trips from Chicago.

RECOMMENDED: The most unique day trips from Chicago

Been there, done that? Think again, my friend.

Top day trips from Chicago

1.  milwaukee, wi.

Driving time from Chicago: One and a half hours

Getting to the Cream City requires a painless drive, but if you plan to fully indulge, ditch the car and hop on the BYOB-friendly Amtrak, which will deposit you in the heart of the city in an hour and a half. Start your day with a stack of Johnny cakes and a round of mimosas at Uncle Wolfie's Breakfast Tavern . Meander around the Historic Third Ward and hop into home decor shops like The Home Market or fun specialty shops like MOD GEN . Seek refuge and treats at the Milwaukee Public Market , where you’ll find a hodgepodge of the city’s best vendors, including blends from The Spice House , seafood from St. Paul Fish Company , hand-dipped chocolate from Kehr’s Candies and vino from Thief Wine Shop & Bar . Before catching a train home, walk off the day with a trek along to Lakeshore State Park , a unique 22-acre urban oasis that juts out from the

2.  Madison, WI

Driving time from Chicago:  Two and a half hours

Located on an isthmus between two lakes, Madison is a city that’s filled with beautiful sights—in addition to all the cheese and beer you’ve heard so much about. Begin your visit with a scenic tour of the college town on two wheels. You can rent a bike from dozens of BCycle stations , allowing you to make 30-minute trips. The Capital City trail winds around Lake Monona (the smaller of the two lakes) and provides plenty of picturesque stops for an Instagram snapshot of the skyline. Now, onto that cheese and beer: To drink like a local, head for The Malt House , a “craft beer oasis” that dates back to the Civil War era and boasts taps from local brewers like New Glarus and Central Waters. Head for Capitol Square to visit Fromagination , where you’ll find artisanal Wisconsin cheeses and knowledgeable cheesemongers to help you make a decision. Take an evening to visit the Memorial Union   Terrace , a lakefront space on the University of Wisconsin campus where you can enjoy brats, beer and live music during the summer months. 

3.  New Buffalo, MI

Driving time from Chicago:  One and a half hours

A charming beach town in Harbor Country, New Buffalo is popular during the warmest months. Escape the crowded Chicago lakefront and head for the sandy shores of the Mitten State, where the water’s warmer and clearer. Soak up some rays and then stroll down Whittaker Street to peruse cute shops and art galleries. Book a spa treatment at The Harbor Grand Hotel for a re-energizing experience; adventurers can rent a kayak or paddleboard from Third Coast Paddling and go exploring on the Galien River. When you need to refuel, grab a seat on The Stray Dog Bar & Grill’s bustling patio or sink your teeth into a big, juicy burger from Redamak’s . But make sure to save room for unique ice cream flavors, like Mackinac Island Fudge and Jacked Up Tennessee Toffee, at Oink’s Dutch Treat .

4.  South Bend, IN

Driving time from Chicago: One hour and 45 minutes

There’s more to South Bend than Fighting Irish football. Check out the city’s cultured side with an afternoon visit to the History Museum , a stately Victorian mansion that was once home to the family of local industrialist and inventor James Oliver. From there, browse the local bounty at the South Bend Farmers' Market , where you can shop everything from artisan breads and doughnuts to farm-fresh fruits and veggies. When hunger strikes, head to Café Navarre , an upscale dining spot housed in a repurposed '20s-era bank. 

5.  St. Joseph, MI

Golden, sandy beaches and a picturesque shoreline attract visitors to St. Joseph and its twin city Benton Harbor. You can spend an entire day out on the water with a rental from Blue Water Boat Rentals , or walk over to the St. Joseph Lighthouses — guided tours are available. If you’re hungry, you won’t have to wander far for good grub, as Silver Beach Pizza —located inside a century-old train depot—slings dependable tavern-style pies. Oenophiles, hit up a variety of vineyards and tasting rooms on the Lake Michigan Shore Wine Trail for some fine Midwestern pours.

6.  Lake Geneva, WI

Lake Geneva has long been an accessible weekend destination for wealthy suburban Chicago families. But no matter your budget, a quick retreat to this idyllic vacation town is sure to be a blast. The town rests on Geneva Lake, an 8-square-mile body of water made for summertime fun. First things first: Get out on the water. Rent a kayak or paddleboard from Clear Water Outdoor , or take a wake surfing private lesson at Gage Marine . If you can’t get your sea legs, trek a portion of Lake Geneva’s 21-mile circumference on the Geneva Lake Shore Path and gawk at the century-old mansions that rest on the shore. When you’re hungry, Egg Harbor Café and Simple Cafe , both in the town center, offer delicious, no-fuss diner eats. If you’re feeling spendy, Baker House , a 19-century mansion-turned-hotel, offers a popular Champagne brunch with waterfront views.

7.  Harbor Country, MI

Just across the Indiana border, Michigan’s lakeside “Harbor Country” is only an hour and a half drive from downtown Chicago. Start at the north end, in Sawyer, where you can visit the original taproom of Greenbush Brewing Co. Pair a pour of Star Chicken Shotgun IPA with some barbecue or Cajun fare. Up next, take the Red Arrow Highway down the lakeshore for great shopping, like hunting through the Harbert Antique Mall . Head back inland to the artsy community of Three Oaks to finish your day at Journeyman Distillery . A $15 tour and tasting nets you samples of 12 different spirits made in the converted corset factory. Plan to sit down for a meal at the distillery’s Staymaker restaurant afterward; you’ll need some food before getting back on the road to Chicago.

8.  Fennville, MI

Driving time from Chicago: Two hours and 20 minutes

Many Chicagoans wait until fall to venture up to western Michigan’s fruit belt. But there’s a compelling argument to be made for hitting the area a couple of months earlier, when the countryside is tranquil and stone fruits like peaches and cherries are ripe for picking. The petite town of Fennville is a great base for tasting the region’s sweet bounty in a host of iterations. Start off with a slice or two of the good stuff at local favorite Crane’s Pie Pantry , a bakery, restaurant and winery housed in a 150-year-old barn. From here, a five-minute drive will deliver you to Virtue Cider , founded by former Goose Island brewmaster Greg Hall. Reserve a spot for a guided trail tour that includes a glass of cider. Finally, make your way to Salt of the Earth for wood-fired pizza and seasonal dishes made from scratch with local and sustainable ingredients.

9.  Gurnee, IL

Driving time from Chicago: One hour

Located right off I-94, the village of Gurnee is a shopping and entertaining hub that draws 23 million visitors each year—including plenty of nearby Chicagoans. Start your day with a sweet treat at Gurnee Donuts , where you can grab ube donuts on weekends . Spend some time digesting while you stroll around Gurnee Mills , which hosts more than 160 stores selling everything from sporting goods to home decor. Thrill seekers won’t want to miss Six Flags Great America , where you’ll find high-speed roller coasters and intense drop rides. On a hot day, you’ll want to plunge down the water slides and splash around the wave pool at Hurricane Harbor. If you can resist indulging in funnel cakes or turkey legs at the park, save your appetite for Primo Italian American Cuisine , where the dinner menu features black truffle ravioli and a tomahawk ribeye. Those visiting on a Friday can end the night with live music in The Parlor, Primo’s speakeasy-style lounge.

10.  Grand Rapids, MI

Driving time from Chicago: Three hours

Summer and fall are peak seasons to visit Grand Rapids, but you’d do best to plan ahead and book your visit during ArtPrize , an international art competition in September and October when art is displayed in museums, bars, public parks and hotels. Regardless of when you go, Grand Rapids has you covered on the beer front with dozens of breweries—so be sure to bring a designated driver. First stop: Brewery Vivant for poutine and a German- or Belgian-style beer. A quick 10-minute drive will put you in the middle of downtown, where you should find parking and hoof it a while. Stop at Madcap Coffee for a post-beer pick me up before heading to City Built Brewing for creole bites and a range of beers for every palate. Finally, grab your car and head to Butcher's Union for a dinner complete with prime cuts of beef and pours of whiskey.

11.  Holland, MI

Driving time from Chicago: Two and a half hours

Once a stronghold of Calvinist separatists who arrived here from the Netherlands in the mid-19th century, the town of Holland continues to celebrate its Dutch heritage. To go Dutch for the day, start off with a breakfast of flaky, almond paste-filled bankets and house-roasted coffee at deBoer Bakkerij . Afterward, head across town to Veldheer Tulip Gardens , where five million of the eponymous flowers explode into bloom each spring. When hunger hits, make your way downtown for lunch and a beer at New Holland Brewing , one of the Midwest’s best-loved brewpubs. (Not sure what to sip on? Look for limited-release variations on brewery fave Dragon’s Milk, a bourbon barrel-aged stout, enriched with ingredients like cocoa nibs and peanut butter.) Wrap up your trip with a leisurely stroll around Windmill Island Gardens , a picturesque park centered around a 250-year-old Dutch windmill purchased by Holland residents in the 1960s.

12.  Galena, IL

While this city on the Mississippi River might be best known for its resorts, you don’t need to stay the night to enjoy its mix of historical sites and outdoor activities. Start your day with brunch at Otto’s Place  and  enjoy breakfast burritos with a Bloody Mary or mimosa. Head across the Galena River to Nuts Outdoors and rent an electric bike to ride along the trails and into town. Take a tour of the city’s proudest attraction, the Ulysses S. Grant Home , which was gifted to the 18th president when he returned from fighting in the Civil War. If you want to learn more, you can visit the Galena & U.S. Grant Museum , which also features an offsite working blacksmith shop. That history is also on display at Galena Brewing Company , where you can sip Uly’s Dark Chocolate Oatmeal Stout while listening to live music and feasting on a bison burger or a giant pretzel with beer cheese and house mustard.

13.  New Glarus, WI

Chances are you’ve already heard of New Glarus thanks to the town’s eponymous brewery —which offers self-guided tours Monday through Friday and a lovely beer garden—but there are plenty of reasons to visit “America’s Little Switzerland” other than beer. This charming, walkable town features a variety of tempting shops, hearty restaurants and themed events celebrating the town’s Swiss history and culture like the Heidi Folk Play Festival in June. Be sure to grab a nut horn at the New Glarus Bakery , and get your fondue fix at the Chalet Landhaus restaurant. If you visit between May and October, don’t miss the seasonally-open Swissland mini golf course, featuring Alpine-themed obstacles and friendly goats.

14.  Fair Oaks, IN

Driving time from Chicago : One hour and 15 minutes

Fair Oaks, Indiana is more than just an exit on the long stretch of Indiana’s notoriously uneventful I-65. Under a beaconing silo,  Fair Oaks Farms offers a chance for city dwellers to learn, explore and taste the heartland’s agricultural roots. Eat lunch or dinner at farm-to-table spot  Farmhouse Restaurant or pack your own picnic and explore the grounds. While most educational attractions and activities like storytime and learning how to milk a cow are family friendly , you don’t have to be a kid to get excited about spotting cows, pigs, chickens and other livestock, and all ages will enjoy homemade ice cream and grilled cheese from the Cowfe . Whether you visit this compound on a day trip or weekend getaway—or even as a pitstop for gas and award-winning artisanal cheese on a weekend getaway , check for seasonal offerings such as you-pick apples and workshops like candle making.

Exploring the farm grounds are free and general admission for the Dairy, Pig and Crop adventures are $25 for access to all three.

15.  Rockford, IL

Driving time from Chicago: Two hours

Situated less than 100 miles northwest of Chicago, Rockford is a surprisingly plentiful road trip destination for families. If the kids are in tow, start the day with a visit to the Discovery Center Museum , which boasts more than 300 hands-on exhibits focused on everything from light and art to color and electricity. For a dose of fresh air and nature, wander through the Anderson Japanese Gardens , a breathtaking 12-acre oasis that's filled with winding pathways, koi-filled ponds, and colorful plants. Everyone in the car will find something to love at Prairie Street Brewing Company , where bar food is elevated through dishes like Baja-style shrimp tacos, Cajun mac ‘n cheese and poke bowls. Pick up a few cans of Screw City Light—with notes of fresh-baked bread—to take home and extend your day trip.

16.  Oglesby, IL

It may not be the mighty Colorado, but Oglesby’s Vermillion River offers the best rafting you’re liable to find within a quick jaunt from Chicago. A 9.5-mile run with Vermillion River Rafting will shoot you over 14 rapids, most of them class I and II. After you’ve handed over your paddle, hop in the car and head up the road to Starved Rock Lodge , where you can catch your breath and lunch on casual fare like burgers or a strawberry pecan salad at the Back Door Lounge. When you feel sufficiently refreshed, hit the hiking trails at adjacent Starved Rock State Park to spot dramatic waterfalls and explore cool glacial canyons. Unwind from your nature adventures by grabbing a nostalgic treat at The Rootbeer Stand or check out "farm to foam" at The Lone Buffalo by Tangled Roots Brewing Company in nearby Ottawa. 

17.  Kenosha, WI

Driving time from Chicago: One hour and 15 minutes

About an hour north of Chicago sits this Wisconsin town filled with a plethora of things to do. Within a mile radius of the downtown area are five museums—you can gaze at dinosaur fossils and learn about the link between the prehistoric reptiles and birds at the Dinosaur Discovery Museum , or explore how the Civil War affected people on the western front at the Civil War Museum . During spring to fall, visit the Southport Lighthouse and climb 72 steps to the top for unparalleled views of Kenosha and, on a clear day, the Chicago skyline. If it’s summertime, you must check out the Bristol Renaissance Faire , where you’ll find a recreated 16th century port city populated with fairgoers dressed as knights, maidens and much more. After you’ve worked up an appetite, head over to Frank’s Diner , an almost century-old restaurant set inside an old railway car. And don’t forget to grab some cheeses and New Glarus beers at the famed Mars Cheese Castle on the way home.

18.  Cedarburg, WI

Located just 20 miles north of Milwaukee, Cedarburg is an ideal place to wind down and take things slow. The charming small town is brimming with old-world architecture, friendly Midwesterners and culture galore. If you can, plan your trip around one of the town’s seasonal events, with options including the Wine & Harvest Festival and Oktoberfest —all of which offer ample opportunities to meet local vendors and sample their wares. When you’re not rubbing elbows with the close-knit community at a street fest, make time to walk around the Cedarburg Art Museum , which hosts exhibitions from Wisconsin artists inside a former home that was designed in 1898. If wine bars are more your scene, head to Cedar Creek Winery , where you can sip your way through a $12 wine fight or enjoy a seasonal wine and cheese tasting for $25. On your way out of town, make one last stop at Amy’s Candy Kitchen to grab a hand-crafted caramel apple for the road.

19.  Kankakee County, IL

The Kankakee River has been a treasured area for centuries, occupied by the Illini and Miami tribes in the 17th century. Kankakee River State Park surrounds the river for about 11 miles, totaling to 4,000 acres of protected land. It’s a popular spot for fishing, canoeing, hiking and bicycling. Frank Lloyd Wright fans can visit the B. Harley Bradley House , built in 1900 and billed as the architect’s first Prairie Style home. Bring the kids to Perry Farm Park , which features a children’s museum, nature trails, playground and picnic areas.

20.  Oak Park, IL

Drive time from Chicago:  30 minutes

You can't call yourself a Frank Lloyd Wright fanatic until you've spent the day in Oak Park, where you'll find the famed architect's home and studio as well as a smattering of other Prairie-style abodes he designed. If it's your first time, book a tour through the Frank Lloyd Wright Trust . Now that you've worked up an appetite, grab brunch or dinner at Maya del Sol , where margaritas flow like water and the ceviche is tops. Have time for one last stop? Grab a seat at Kinslahger Brewing Company , a small but mighty taproom pouring lagered brews.

21.  Zion, IL

Zion’s Illinois Beach State Park is one of the  best places for camping outside of Chicago . Outside the 4,160-acre nature haven along the Wisconsin-Illinois border, you’ll find good brews—both coffee and alcohol—and pieces of unique history. Sip coffee from a mug in the quirky collection of mismatched ware at the cozy It’s All Good Coffee in downtown Zion, and a half mile north, tour Shiloh House , a historic 1901-era mansion housing the Zion Historical Society and former residence of Zion’s founder, Dr. John Alexander Dowie. There, learn more about  Dr. Dowie, a Scottish-Australian minister who founded Zion as a planned religious utopia and committed large-scale fraud. 

Head just north of Zion to Winthrop Harbor’s North Point Marina, one of the largest along the Great Lakes. Weather permitting, rent a  kayak or stand-up paddle or stay on land for live music, good views, and craft beers at Harbor Brewing . If you want bragging rights, stand with one foot on either side of the state border at North Point Beach .

22.  Monroe, WI

If your cheese preferences embrace the pungent, you’ll find yourself in good company in charming Monroe, Wisconsin, gateway to a region teeming with cheesemakers specializing in varieties like Swiss and nostril-tingling Limburger. For some context, begin your day at the National Historic Cheesemaking Center , where you’ll get a crash course in south central Wisconsin’s cheesy history. Next, head to the Alp and Dell cheese store to browse more than 100 varieties of cheese, mostly from local producers, and all the wine, beer and sausage you’d want to pair them with. When you’re ready for lunch, make your way to the unapologetically old-school Baumgartner’s Cheese Store & Tavern on Monroe’s pleasant courthouse square and order the infamous specialty: a slab of Limburger on rye crowned with mustard and sliced red onions. For a chaser, stroll around the block to Minhas brewery.

23.  Lemont, IL

The Village of Lemont developed as part of the construction of the canal linking the Illinois River and Lake Michigan, which also led to the discovery and development of the limestone quarries used to supply materials for iconic Illinois buildings like the Chicago Water Tower. Today, you can hop on the Metra and visit the Heritage Quarries Recreation Area , where you can walk, bike or fish along the I&M Canal (just be sure to look out for the many water birds drawn to the area). If you’re hoping for a bit more excitement, visit The Forge: Lemont Quarries . The adventure park features laser tag, a zipline and ropes courses for all ages and skill levels. Afterwards, head to the village’s historic downtown area to visit Pollyanna Brewing Company and try The Full Lemonty, their signature golden ale. You can also find the brewery’s beer on tap at Wooden Paddle , where you can watch your wood-fired pizza and other small plates being prepared before they hit your table.

24.  Long Grove, IL

Driving time from Chicago: 45 minutes

Located 35 miles northwest of Chicago, Long Grove was founded in the 1800s by German farmers, and many of the town’s original homes and buildings are still standing. Try to visit Long Grove during one of its many delicious festivals such as Apple Fest or Strawberry Fest , when local chefs and other vendors flock to the historic downtown area to offer numerous versions of the spotlighted food. Stop by Buffalo Creek Brewing and have a beer in their Bavarian-style taproom or in the Biergarten, which hosts live music and food trucks during the summer. Before you hit the road, swing by Long Grove Confectionery to pick up some peanut brittle or their signature Giant Myrtle, made with roasted pecans or cashews topped with caramel and milk or dark chocolate.

25.  Evanston, IL

Driving time from Chicago: 40 minutes

If you're short on time but craving a day away from the city, hop on the Purple Line and head to Evanston. The sweet college town is located just a few miles north of Chicago, which means you can explore the day away and still be home for dinner. Start the morning at the otherworldly Baha'i House of Worship , an architectural gem located a few miles north in Wilmette. Wander the pristine grounds before stepping inside the functioning temple, one of the oldest of its kind in the world. Up next: Fill up on colorful macarons, cakes and doughnuts at Bennison's Bakery before checking out the outdoor exhibition at the Block Museum of Art and taking a free art walk to see the 16 sculptures placed in public spaces on Northwestern University’s campus. Don't get back on the train without grabbing a brew from Temperance Beer Co. If you have the time, take a $10 brewery tour that includes samples and a souvenir pint glass. 

26.  Michigan City, IN

If you’re car-less, this small city is a perfect option for a day trip from Chicago. Hop on the Amtrak at Union Station and you’ll be in Michigan City in just over an hour. Or, take the South Shore Line and you can hop off right at the Indiana Dunes National Park , 15 miles of gorgeous sand dunes on the southern shore of Lake Michigan. Michigan City proper, too, is filled with great things to do. Visit Washington Park where you can picnic on the beach or check out the lions, wolves and other animals from around the world at the Washington Park Zoo . Hungry? Walk over to Shoreline Brewery , a gem of a microbrewery with a rotating selection of beers on tap and tasty pub grub. You can also sample local flavors at Fiddlehead , which serves high-quality comfort food including fried lake perch and grass-fed beef burgers.

27.  Skokie, IL

Driving time from Chicago : 30 minutes 

Head 16 miles north by car or CTA for art, history, and nature in downtown Skokie. The village is lined with locally-owned shops and restaurants, and is home to the Illinois Holocaust Museum & Education Center . Start your day with an everything bagel with lox from Kaufman’s Bagel & Delicatessen and use the free app Otocast for a self-guided route of the area’s murals and sculptures. Mid-tour, grab coffee and a halal savory empanada or SALAMAT! Filipino cookie at Complimentary Coffee . If that wasn’t enough art, head east to the north channel of the Chicago River for the North Shore Sculpture Park , a two-mile walkway with over 60 pieces of public art. Download a self-guided tour or plan to make it to one of free guided tours Saturdays and Sundays, May through October.

28.  Fairbury, IL

Observant Chicago foodies may have noticed a couple of names popping up over and over again in the menu sourcing notes that have become de rigueur in these locavore-obsessed times: Kilgus Farmstead (for dairy) and Slagel Family Farm (for a range of meats). Turns out, our favorite chefs’ favorite suppliers sit just a three-mile hop from each other in the central Illinois town of Fairbury. On an hour-long tour of Kilgus , you’ll get acquainted with the farm’s herd of sweet, doe-eyed Jersey cows, learn the ins and outs of milking, and sample freshly spun soft-serve. Bring a cooler and hit the on-site store for Kilgus dairy and meat as well as goods like eggs and honey from nearby producers. Slagel has teamed up with chefs from notable Chicago restaurants to put on a program of farm dinners throughout the summer and fall. After an interactive tour and a butchering demo, you’ll retire to a picturesque barn for the main event, a family-style, BYOB meal prepared by the guest chef.

29.  Spring Green, WI

Driving time from Chicago: Three and a half hours

Despite boasting a population just shy of 1,700 people, this town west of Madison has a lot going on. Most visitors are here to visit one of two sprawling complexes: Taliesin , the estate and studio of legendary architect Frank Lloyd Wright, or the infinitely weirder House on the Rock , the brainchild of artist Alex Jordan where curious travelers can explore rooms on rooms of infinity mirrors, dollhouses, nostalgic cars, circus ephemera and the world’s largest indoor carousel. When you’ve had your fill of architecture or funky assorted collections, get a taste of traditional Wisconsin hospitality at Arthur’s Supper Club . Theater buffs can take in a show at the American Players Theatre .

30.  Aurora, IL

Driving time from Chicago : 50 minutes 

Aurora made headlines when Wallethub named the small city the happiest place to live in Illinois. Once you make a visit, it’s easy to see why. Easily accessible by Metra, this western Chicago suburb features a walkable downtown with music, festivals, street fairs and ample green space to get your nature fix. Grab your running shoes or bike—or  kayak  if floating is your preferred method of sightseeing—and hit the Fox River Valley Trail, an over 40-mile paved path. Finish the afternoon with coffee or craft beers at Two Brothers Roundhouse , a 1850s-era limestone building listed on the National Register of Historic Places, before heading back downtown for a Broadway show at the Paramount Theater .

31.  Joliet, IL

If there’s a place that embraces its unique and often complicated past, it’s Joliet. History is intertwined in nearly every aspect of this canal and quarry city, from the limestone facades of the castle-like Bishop Hill Winery to its recreational spots, like the  Joliet Iron Works Historic Site , once the second largest steel mill in the United States and now converted into an outdoor park. Names of many local businesses, like Prison City Vintage , even reference the past. Contextualize the city with a visit to the Joliet Area Historical Museum , a collection of over 30,000 artifacts, including memorabilia from the first Dairy Queen in the U.S. and Route 66. After, roam the 1858-constructed Old Joliet Prison , a frequent filming location and must-see for TV and movie buffs. Finish off with classic diner food at the in-theme Joliet Route 66 Diner .

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15 Things To Do In Chicago This Weekend: Pride Fest, Vegandale And A Bronzeville Bazaar

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CHICAGO — This weekend is packed with Chicago street and food festivals, including Pride Fest, Vegandale, Motoblot and the Magnificent Mile Art Festival.

There’s also the Andersonville Vintage Market, a Lakeview native plant sale, the Bernard Street Yard Sale in Logan Square, a 5K along the 312 RiverRun trail and the return of the Bronzeville Vendor Fair and Wildflower Music Festival.

And if you’re still looking for Juneteenth celebrations in the city, there are more happening this weekend and through the end of June. Find them here .

Here’s a roundup of 15 things to do in Chicago this weekend:

All Weekend

Motoblot: Motorcycle Street Rally

5 p.m.-2 a.m. Friday, noon-10 p.m. Saturday, noon-dusk Sunday

Cobra Lounge, 235 N. Ashland Ave.

This 11th annual motorcycle and hot rod show features 20 live bands, a beer hall, food trucks, a pin-up contest, a mini grand prix and more. Live performers include The Living Deads, Ichi-Bons, London Calling, Rebel Queens, Iris Marlowe, Sabbatha and more.

One-day tickets start at $18 and three-day tickets start at $45. Learn more and buy tickets here .

11 a.m.-10 p.m. Saturday-Sunday

On Halsted Street from Addison to Grace streets

Pride Fest, an annual two-day celebration of LGBTQ+ life, culture and community,  returns with more than 40 performers , 150 merchandise and food vendors, speakers, dance exhibitions, a safe space for youth and more. Headliners include JoJo Siwa, Natasha Bedingfield and Kaleena Zanders.

There is a suggested $15 donation upon entry. Learn more  here .

The Magnificent Mile Art Festival

10 a.m.-5 p.m. Saturday-Sunday

875 N. Michigan Ave.

This inaugural art fest will showcase the work of 60 juried artists from around the country, including jewelry, fashion, glass and functional art.

Admission is free. Learn more  here .

11 a.m.-8 p.m. Saturday-Sunday

Grant Park’s Butler Field, 350 E. Monroe St.

Vegandale is the largest vegan food experience in North America. The plant-based food festival returns to Chicago this weekend with over 100 global vendors, interactive art pieces and live performances by 2 Chainz, Saweetie and NLE Choppa.

Tickets start at $15 for Saturday and $60 for Sunday, which features the music performances. Learn more and buy tickets here .

21+ Night at WNDR Chicago

6 p.m. Thursday

WNDR Museum, 1130 W. Monroe St.

Dance among WNDR Museum’s multi-sensory installations at this 21-and-older after-hours event, which features local DJs spinning tunes and drinks and snacks to buy.

Tickets are $25. Learn more and buy tickets here .

View this post on Instagram A post shared by Erie Neighborhood House (@eriehouse)

Brews & Bites

6-10 p.m. Friday

Goose Island Barrel House, 603 N. Sacramento Blvd.

At this 17th annual fundraiser for Erie Neighborhood House, which provides critical services to immigrant and low-income families in Chicago, neighbors can enjoy food, drinks and hear stories from people impacted by Erie’s work.

Individual tickets are $75, and packages for groups of two or more are available. Learn more and buy tickets here .

Native Plant Sale

9 a.m. Saturday

Southport Plaza along the Lakeview Low-Line, 3410 N. Southport Ave.

Lakeview neighbors can shop over 35 species of native wildflowers, sedges and ferns at this plant sale hosted by the Southport Neighbors Association. All plants are sold as pints and cost $7-$8. Native plant gardeners will be at the event to help answer questions.

The sale will continue until the plants are sold. Shoppers are asked to bring their own box or container to carry their plants home. Learn more here .

Bernard Street Yard Sale

9 a.m.-4 p.m. Saturday

Along Bernard Street between Fullerton and Wrightwood Avenues

Logan Square neighbors are once again teaming up for a big rummage sale this weekend. In previous years , neighbors have sold clothing and a slew of household items, from kitchen gadgets and furniture to homemade pottery and books.

Walk It Out For Andrew: Family 5K Walk

10 a.m. Saturday

West Lawn Park, 4233 W. 65th St.

The 15th annual Walk It Out For Andrew is a community celebration of Andrew Smialek, who died of cancer in 2007 at 19 years old. This family 5K was founded by friends to carry on Smialek’s legacy and raise funds for the Teen Hematology and Oncology Support Groups at Advocate Children’s Hospital.

Learn more and register for $40 online .

312 RiverRun 5K

10 a.m.-noon Saturday

Clark Park, 3400 N. Rockwell St.

Run or walk through Clark, California and Horner Parks along the 312 RiverRun trail. The race is open to all levels of runners, and the course is mostly flat with one gentle incline. Each participant will receive a limited-edition bandana, snacks and water. There will be an afterparty at Burning Bush Brewery, 4104 N. Rockwell St.

Registration is $40 for adults, $25 for youth and $5 for children 5 and younger. Learn more and sign up here .

Bronzeville Vendor Fair & Wildflower Music Festival

10 a.m.-9 p.m. Saturday

3201 S. State St.

The annual Bronzeville outdoor bazaar returns this weekend to 33rd Boulevard between Michigan Avenue and State Street. There will be a lineup of local merchants, makers and artists; food trucks; a bouncy house for kids; and Bronzeville musicians and vocalists performing live.

The Wildflower Music Festival stage will feature local talents and be hosted by Senabella Gill, an awarded jazz vocalist and activist known as the Bronzeville Diva.

Admission is free. Learn more here .

Chicago History Podcast Live

11 a.m.-noon Saturday

Mary Bartelme Park, 115 S. Sangamon St.

The “Chicago History Podcast’s” Tommy Henry and West Loop historian Connie Fairbanks will broadcast live during the neighborhood’s weekly farmers market. Listeners will be able to learn and ask about the history of Mary Bartelme Park and the location before it was built.

Learn more here .

Pride Icons Drag Brunch

11 a.m. and 2 p.m. Saturday

The Walnut Room, 111 N. State St.

This annual Pride drag brunch hosted by popular Chicago drag queen Lucy Stoole pays tribute to “Pride icons” like Lady Gaga, Cher, Whitney Houston, Madonna, Beyoncé, Janet Jackson and more.

Tickets are $20 online, and all customers must buy an entree. Learn more and buy tickets here .

Dim Sum & Drag: Chan Yun

Noon Saturday

Furama, 4936 N. Broadway

At this dim sum and drag brunch, Asian drag performers will perform a parody production of “Chan Yun: China After C*nty-nism.” Alongside a buffet-style brunch, the show is filled with silk fans, choreography and comedy.

Tickets are $35. Learn more and buy tickets here .

Andersonville Vintage Market

10 a.m.-4 p.m. Sunday

1500 W. Catalpa Ave., continuing along Catalpa between Clark Street and Ashland Avenue

The fourth annual Andersonville Vintage Market returns this weekend with dozens of local retailers selling home decor, jewelry, clothing, music, body products and other bric-a-brac. Participating vendors include DMApothecary , Fad2Fresh , JANVIER , Lottie Dottie Vintage ,  Luvsick Vintage , Macramentadas , Mega Studios , Ruby Baby Vintage , Textile On Toast Vintage and more. There will also be musical entertainment, and pets are welcome.

There is a $5 suggested donation upon admission. Learn more here .

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