Niagara Falls frozen during deep winter.

15 Best Winter Road Trips from Chicago

Chicago is a fantastic city, known for its stunning lakeside location, the Magnificent Mile, and its world-class museums and galleries. However, it's also famous for its harsh winters, so there might be times you want to head out of the city during the coldest months of the year.

Whether you want to enjoy the winter weather or escape from it, a winter road trip from Chicago can mean hitting the slopes at a ski resort, viewing iconic landmarks, taking a festive shopping trip or relaxing in the winter sun in the Southern states.

Whatever kind of winter road trip you're interested in, we've put together some of the key facts for a whole host of fabulous destinations. Keep reading to find out where you could go, how to get there, and our pick of what's waiting for you when you arrive.

Best winter road trips from Chicago: a quick overview

Single-day trips (under 3 hours each way).

Snow in the city often isn't much fun, so head out to one of the mountains or lakes for a one-day road trip that lets you enjoy the winter weather at its best.

If you're thinking of setting off on a road trip from Chicago in another season, check out our ultimate guide for Best Road Trips from Chicago for ideas and inspiration.

1. Lake Geneva, Wisconsin

1 hour 50 mins from Chicago (80 miles)

Why you should visit: The shortest trip on the list, Lake Geneva makes a great weekend getaway due to the short driving time, plus the area is perfectly set up for visitors to enjoy the winter weather.

There's a real variety of activities to enjoy here – take to the snow for an active day outside, then relax at a beautiful spa. This popular vacation town is also less crowded in winter compared to the summer months.

Spectacular ice formations made out of delicate icicles in Lake Geneva, Wisconsin.

How to get there: Head north on I-90 out of Chicago then join I-94. After around an hour, exit at Kenosha and pick up WI-50 west which will take you to Geneva.

Our highlights: Roll back 100 years and one of the biggest draws of Lake Geneva, WI, wasn't its snow, but the ice! Lake ice was harvested and taken to nearby towns and cities - it was big business here as late as the 1940s.

Through the rest of the season, winter sports fans will love to ski at Wilmot Mountain, a popular ski resort with over 20 ski runs suitable for a wide range of abilities. Or explore the wintery wilderness of Kishwauketoe Nature Conservancy - you can rent snowshoes if you don't have your own.

Back in town, the Ice Castles at Geneva National Resort & Club are a must-see. Ice sculptors spend nearly 2 months creating spectacular icy towers and turrets which are especially beautiful when they're illuminated at night.

Bonus: Early in February Lake Geneva's Winterfest bursts into action, with an ice sculpting competition and snow races!

Our travel tips: Book in advance if you're visiting Winterfest, as the town gets really busy.

2. Madison, Wisconsin

2 hours 40 minutes from Chicago (150 miles)

Why you should visit: Wisconsin's state capital has all the cultural and foodie delights that you'd expect in a big city, with added snow that opens up a whole range of other activities to enjoy.

Within a short distance of the city you can ski, skate, snow tube and sled, sometimes with beautiful views across Lake Mendota.

Exterior of the Wisconsin State Capitol building in the Winter.

How to get there: This is a really simple trip – just follow I-90 all the way from Chicago.

Our highlights: Just outside the city at Cascade Mountain and Devils Head Resort you'll find some exhilarating downhill skiing as well as snowtubing and sledding. It's the perfect way to enjoy the snowy conditions, and there are ski runs here to suit many different abilities.

When it's time to warm up, head back into town to Old Sugar Distillery, a small local spirits producer, for a warming taster.

While you're in town you can take a magical snowy hike through the trees at Madison Arboretum, then round off your day with outdoor dining - several Madison restaurants have heated outdoor domes so you can enjoy snowy views while dining al fresco.

Bonus: After Christmas, a free maze is built on the lake shore out of the branches of discarded Christmas trees, a custom that has become firmly cemented in Madison's holiday traditions now.

Our travel tips: Check ahead for dates of candle-lit snowshoe trails across the city. They don't run every day, but when they do they're really magical.

3. Elkhart Lake, Wisconsin

2 hours 50 minutes from Chicago (150 miles)

Why you should visit: This beautiful little lakeside town hosts a magical Christmas market every year. It's also a great place to enjoy fabulous snow-based activities - the temperature usually sits around freezing and the area experiences heavy snowfall, so conditions are perfect.

Ornament shop at a Christmas Market.

How to get there: Follow I-90/I-94 north out of Chicago, then continue north on I-94 when the interstate divides. In Milwaukee, switch onto I-43 and continue north, before leaving the interstate just after Saukville. Then, follow WI-57 towards Plymouth, from where you'll pick up WI-67 to Elkhart Lake.

Our highlights: For many visitors, the main draw is the Olde World Christmas Market, a 10-day festive spectacular bringing together Czech, German and Russian Christmas traditions. It's a great way to spend time with friends, get into the festive mood, as well as to find some unique Christmas gifts.

If you're visiting at other times during the winter, there's still plenty to do in Elkhart Lake. The lake freezes over right through the winter, so you can head out with a guide for a unique ice-fishing experience.

Also, although this isn't a ski destination like some of the other trips, you can still enjoy some winter sports in Elkhart Lake. Go snowshoeing at Quit Qui Oc golf course or ice skate at June Vollrath Park.

Alternatively, if you'd prefer to just relax and unwind, maybe after a tour round the Christmas market or some time on the ice rink, head to the luxurious Aspira Spa to round off your trip.

If you're wondering how the town got its name, it's as simple as it sounds – it's because the lake is shaped like an Elk's heart.

Our travel tips: The town will be extremely busy while the Christmas market is running, so book accommodation and any special activities well in advance.

4. Grand Rapids, Michigan

2 hours 50 minutes from Chicago (180 miles)

Why you should visit: From January to March the town hosts the World of Winter Festival, which sees dozens of huge ice sculptures on display and special events held across the town.

The World of Winter Festival is the perfect post-holiday pick-me-up - the ideal way to brighten up the dark, cold months after Christmas. Or if you're here a little earlier in winter, you can get yourself into the holiday spirit with a snowy visit to the Sculpture Gardens or enjoy some exhilarating winter sports.

Winter River Sunset. Snow and ice float down the Grand River in Grand Rapids, Michigan, USA.

How to get there: Head east out of Chicago on I-90, keeping Lake Michigan on your left, then continue on I-94 as far as Lake Joseph. From here, follow I-196 further around the lake shore. It eventually turns inland to take you right to Grand Rapids.

Our highlights: The World of Winter Festival usually starts in the first week of January, and as well as ice sculptures you can see interactive installations from artists all over the world, with walking tours taking you through some of the outdoor art highlights.

The festival also hosts many fun events. These change year on year, but in the past have included things like silent disco, outdoor musical performances, and storytelling to mark Native American traditions or Chinese New Year.

If you're in Grand Rapids earlier in the season, you can enjoy some great skiing at Cannonsburg Ski Area. It will satisfy a wide range of abilities, and you can also try out snow tubing and snowshoeing here.

If your time is limited, take your sled and enjoy a free downhill ride at one of the several hilly public parks in the city.

For a more magical festive feel, head to Frederick Meijer Sculpture Gardens. This park is illuminated with amazing twinkling lights all through the holiday period and is a really popular local attraction. Then, for a unique and romantic end to your trip, you can even take a horse-drawn sleigh ride through the city.

Bonus: As well as being known for its winter sports, Grand Rapids is famous for its many craft breweries - in fact, it's been given the title of Beer City USA! So if time allows on your trip, you might like to tour a brewery or two or try some of the locally produced beers.

Our travel tips: You don't have to have your own equipment to enjoy skating, snowshoeing or skiing – it's available to rent at many of the attractions.

If you're coming for the World of Winter Festival, remember to wrap up warm. Many of the events and installations are outdoors, so, this being Michigan, chances are you'll be enjoying them in the snow.

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Weekend trips (3-6 hours each way)

As you'd expect, with much of the Midwest sitting under snow through the winter, the weekend trips you can take from Chicago all have a winter sports element to them.

So, pack up your skis and look out for your skates - but don't worry if you're not the biggest fan of the slopes, since you'll also find great restaurants, beautiful views and stunning spas at these weekend destinations.

5. Muskegon, Michigan

3 hours 20 minutes from Chicago (190 miles)

Why you should visit: As you'd expect in a town that sees significant snowfall from December to February, you can enjoy a range of winter sports. A particular highlight in Muskegon is its Luge track, which is open to the public.

There are only 3 other Luge tracks in the whole of the United States, so if you've always fancied trying out this exhilarating sport, this is probably your best chance.

Lighthouse at the end of Muskegon Pier, overlooking Lake Michigan in winter during sunset.

How to get there: Similar to the Grand Rapids trip, follow I-90 then I-94 east out of Chicago as far as St Joseph. Then join I-196 and follow it north along the lake shore until you reach Holland. From here, turn onto Route 31 which takes you on to Muskegon.

Our highlights: As you'd expect, the main draw of Muskegon in winter is Muskegon Luge Adventure Sports Park. As well as sliding the high-speed downhill ice track, you can enjoy cross-country and downhill skiing, snowshoeing, and ice skating at the park.

Back in town you'll get beautiful winter views over icy Lake Michigan. Wrap up warm and walk out towards Muskegon South Breakwater Lighthouse – a really stunning sight – or take a walk on the lake's frozen beaches. If you're feeling active, there are places where you can sled on the frozen sand dunes.

Staying by the lake, seeing as the water freezes over, you can go ice fishing here with a guide, who can provide all the equipment you need if you don't have your own.

It's not all about the outdoors though. Muskegon Farmers Market operates indoors on Saturdays through the winter so you can warm up and stock up on some fabulous local produce.

Olympian Mark Grimmette trained on the Luge track here when he was young and went on to compete at five Winter Olympic Games, winning medals at two of them. The track is open to kids as young as 8 so bring the whole family and see if any of them catch the sliding bug.

Our travel tips: Visit the Luge in the evenings and you can warm up by a bonfire after your slide down the track. We'd recommend booking ahead to guarantee your entry, especially if you're visiting at busy times,.

You won't need any previous experience or equipment, as your entrance to the track includes a lesson and all the equipment you'll need to enjoy your visit safely.

6. Granite Peak Ski Area, Wisconsin

4 hours 30 minutes from Chicago (280 miles)

Why you should visit: As its name suggests, Granite Peak is a fabulous and long-established ski destination with some top-class runs and luxurious resort choices.

The biggest ski area in the state is perfectly set up for skiers, with fast lifts and dozens of trails to follow. You can easily fill a weekend here with fun and varied runs.

Locals of the city of Wausau and Marathon County, Wisconsin. Came out to ski down on Granite Peak Ski Area for Badger State Winter Games public event.

How to get there: Follow I-90 west out of Chicago, passing Rockford and Madison. Then, shortly after crossing the Wisconsin River, turn onto I-39 and follow it north to Granite Peak Ski Area.

Our highlights: Granite Mountain is one of the oldest ski resorts in the United States, and it's been at the forefront of innovation in the skiing industry. It was an early adopter of snowmaking technology in the 1950s.

Two different types of ski lifts were invented here - so when you ski here in modern times you'll be following the lead of some of the country's ski pioneers.

With fast lifts, extensive ski runs and stunning views, you'll probably want to spend most of your time here on the slopes. Rib Mountain, part of the ski area here, is Wisconsin's tallest mountain so you'll find plenty of downhill runs here to suit all abilities.

In Wasau, the nearest town to Granite Peak, there are some great food and drink options for the essential apres-ski part of the day! Visit in early February when the Winter Carnival comes to town and you can see firework displays or catch a fun ride on one of the resort's snow groomers.

When you're ready to head into the warm, make your way to Leigh Yawkey Woodson Art Museum. This award-winning, community-focused gallery always has something new to see, and with sculptures and exhibits inspired by nature, it makes the perfect complement to a day enjoying the views out on the mountain.

Our travel tips: This is a really popular ski area, and lift passes can sell out during the busiest periods. It makes sense to book ahead if you're planning on visiting between Christmas day and New Year, or weekends during January and February.

7. Boyne Mountain Resort, Michigan

5 hours 40 minutes from Chicago (350 miles)

Why you should visit: This is a year-round resort, but with 140 inches of snow, it comes into its own during winter. The extensive and varied ski slopes here are great for a wide range of skiing abilities.

This is the place to come for a great resort experience, with lodges, bars and of course, slopes, all in one place.

Skiers on the Boyneland Lift at Boyne Mountain in Northern Michigan.

How to get there: Follow the interstate east out of Chicago and then continue north, keeping Lake Michigan on your left. After Grand Rapids, turn onto Route 131 and continue north past Big Rapids and Cadillac, until you reach Boyne Mountain.

Our highlights: Boyne Mountain is primarily a ski resort, so take to the slopes and explore more than 415 acres of ski runs. You can also snowshoe, tube or skate if you want a break from the slopes.

If you want to strike out a little further and explore, you can go horseback riding or cross-country skiing through the woodlands or try out snow biking for something new.

For a really exhilarating ride, fly right above the snow on one of the 9 ziplines. These will carry you up to a quarter of a mile across the resort's valleys, giving you a bird's eye view of your stunning surroundings.

For the perfect post-ski wind down, visit the Spa at Boyne Mountain before you head home. Book a fantastic treatment or simply hang out in the sauna, steam room or heated outdoor pool to enjoy the mountain vibes from a different angle.

Our travel tips: Equipment can be rented at this resort but arrive early on weekends or holidays as it's first come, first served. It's a popular place to visit, so book lift passes in advance if you know when you're traveling. If you're able to visit mid-week, you'll probably find the slopes are quieter.

Longer trips (Over 6 hours each way)

Whether you're looking for a festive shopping experience to ease you into the holiday mood, or a snowbird heading south for the winter, there are plenty of fabulous longer road trips that start out from Chicago.

8. Niagara Falls and Niagara-on-the-Lake, New York

8 hours 20 minutes from Chicago (550 miles)

Why you should visit: Seeing the famous falls cascading through the snowy ground is a truly magical experience – and one that's different from any other trip you might take.

Head across the border on this road trip to see the falls from a different perspective, or visit the fabulous wineries of Niagara-on-the-Lake. Canada produces a significant proportion of the world's Icewine, a dessert wine created from grapes left on the vine to freeze before being harvested.

Seeing the falls in winter is a magical experience, with massive icicles and undulating snow drifts surrounding the famous vistas. As well as being beautiful, the crowds that flock to Niagara Falls are slightly less during winter.

Niagara Falls during winter season with lots of snow.

How to get there: Head east out of Chicago and join Interstate 90, then just keep going! The same road takes you right across Indiana and Ohio then along the whole length of Lake Erie, before you finally turn onto NY-5 through Buffalo around 5 miles before you reach your destination.

If you want to head across the border to visit Niagara-on-the-Lake make sure to pack the required travel documentation, and allow extra time to make the border crossing, especially if you're heading across Rainbow International Bridge.

Our highlights: The highlight of most people's visit to Niagara Falls is to see the mighty waterfalls up close, but if you visit in winter you can also marvel at the massive icicles that form right by the viewing platform on the Journey Behind the Falls. For amazing views of the snow-covered landscape, head up the Skylon Tower.

At night, you can see the falls lit up in spectacular illuminations as part of the Winter Festival of Lights. Then head quickly back into the warmth of your hotel to warm up. Several of the hotels in town have excellent in-house spas, so you can treat yourself to some relaxation time during your trip.

If you're crossing over the Canadian border to visit Niagara-on-the-Lake, the Icewine vineyards and wineries are probably the first thing that will get your attention. The long rows of vines stand out proudly in the snow and make a beautiful backdrop while you're learning about Icewine production or, more importantly, tasting a glass or two.

NOTL is also a really charming little town, and while you're here you might like to take a horse-drawn carriage ride through its historic streets - a wonderfully atmospheric way to travel through the snow-covered streets.

Bonus: Right through January you can enjoy the Icewine Festival, which celebrates this delicious local tipple. There's a real art to making Icewine and the conditions have to be just right to freeze the grapes for long enough on the vine.

This means you probably won't see the grape harvest unless you're out in the vineyards at night - pickers tend to work by hand to make sure of the most perfect harvest possible. All things considered, it's easy to see why Niagara-on-the-Lake's Icewine is such a special product to try during your visit.

Our travel tips: Some of the outdoor activities that Niagara Falls is famous for, notably the Maid of the Mist boat cruise, do not operate in winter, but as we've identified, there are plenty of other ways to enjoy views out across the falls.

Note that to enjoy all the attractions Niagara Falls has to offer, you might need to factor in crossing the US/Canada border so make sure you have any paperwork you need (dependent on nationality).

READ MORE - Road Trip from Chicago to Niagara Falls

9. Toronto, Canada

8 hours 40 minutes from Chicago (530 miles)

Why you should visit: With festive lights, winter markets, a good chance of snow, and plenty of big city attractions, Toronto is a picture-perfect winter city trip . Located right by Lake Ontario, you can enjoy frosty views out across the water, then head back into the city to indulge yourself in some culture or plain old festive cheer.

It's the perfect place for a romantic getaway - wrap up warm and enjoy snowy views over the beautiful city and lake before warming up with a hot chocolate and a loop or two around an outdoor ice rink.

Toronto downtown Christmas City Hall skating.

How to get there: Follow I-90 out of the city then pick up I-94 and head east towards Detroit.

After crossing the border into Canada, the road becomes ON-401. It runs parallel to Lake Erie, so if you have a little longer to make your trip then you might like to pause along the way to admire views across the lake.

Just after London, the road merges with ON-403, which will take you right into the center of Toronto.

Our highlights: Toronto is a vibrant cultural melting pot, so when you spend time in the city you'll be able to enjoy influences on food, art and recreation from all over the world.

Less than half of Toronto's residents were born in Canada, making for a varied and welcoming city that's the perfect place to head to on a road trip.

For added romantic charm, put your skates on and have laps on one of the city's many ice rinks - there are over 50 to choose from. The rinks are super-festive in the run up to the holidays, and you can relax with a hot chocolate or a local craft beer afterwards.

If you're not planning a trip until after Christmas, you'll be able to visit the Toronto Light Festival, when fabulous installations brighten up the city through the cold winter nights. Check ahead to find details of live performances and special events that are taking place.

If it's your first time in Toronto, you'll probably want to see some of the city's sights while you're in town too. Head up the CN Tower for great views of the city and Lake Ontario, which is particularly stunning when it starts to freeze over through the winter.

Then warm up in one of the city's fantastic museums, including the Royal Ontario Museum where you'll find a fascinating and diverse collection.

Bonus: If you're here before the holidays, get into the festive spirit at the Distillery District Christmas Market, which runs from mid-November until New Year. It's a great way to experience this historic part of the city, full of character.

Our travel tips: Although temperatures are at or below freezing through most of the winter, you're not always guaranteed snow in Toronto, so be prepared that you might miss out on the insta-perfect images of this particular winter road trip.

As you can see, there are still plenty of wintery attractions to enjoy in the city, just wrap up warm and see where your trip takes you.

READ MORE - Road Trip from Chicago to Toronto

10. Washington, DC

11 hours 10 minutes from Chicago (700 miles)

Why you should visit: You can see the Nation's Christmas Tree, a century-old tradition in the city - it's illuminated from early December in a popular ceremony that for many marks the start of the holiday season.

You can also enjoy a number of holiday markets, to really get you into the festive spirit. You have a few to choose from, including the outdoor Downtown DC Holiday Market, the Swedish Christmas Bazaar in Georgetown, and the Heurich House Museum Christkindlmarkt.

As well as all the holiday attractions and the chance to see some of the world-famous monuments beautifully surrounded by snow, the crowds at the city's museums are likely to be quieter during the winter.

United States Capitol Building and Christmas tree at night.

How to get there: Follow I-90 out of Chicago and east towards Cleveland. Then, join I-80 and follow it around the south of Cleveland before switching onto I-76 and continuing southeast past Pittsburgh.

After passing New Baltimore and Everett, change onto I-70 and continue on through the Appalachians before joining I-270 at Frederick and following it right into the center of Washington DC.

Our highlights: The nation's capital is a fantastic place to visit during the holiday period. As well as the festive markets that take place across the city, where you can admire beautiful decorations and gifts or enjoy some fabulous food and drink, you can take in a carol concert at the National Cathedral.

Afterwards, take some time to admire the cathedral's architecture - and see if you can spot the Darth Vader gargoyle.

Back outdoors, visit DC's largest outdoor ice rink at Washington Harbor, for views out across the waterfront, or see the Holiday Boat Parade, which includes fireworks and live music as well as festively decorated boats parading down the Potomac River.

If you're visiting later in the season, check out Winter Restaurant Week. The event runs in late Jan or early Feb, and hundreds of the city's restaurants showcase their best meals at reasonable prices - the perfect way to brighten up a long, cold winter.

Don't forget to check out some of the Smithsonian museums too – they're free to enter so you can visit one or many, and enjoy some of the more popular sites without the crowds, especially if you're visiting after the holiday period.

Bonus: The capital hosts a fabulous Lunar New Year Parade in January or February depending on when the new year begins. The parade brings together dragons and lions dancing through DC's streets, as well as drummers, dance troupes and firecrackers - it's a real feast for the senses.

Our travel tips: Don't go to DC expecting reliable snowfall – daytime temperatures are milder than the more northern destinations (in the mid-40 degrees Fahrenheit and above), though it still gets pretty cold at night, and snow is likely but not guaranteed in January and February.

The key message is to wrap up warm and be prepared for whatever weather the city throws at you - pretty standard for DC!

READ MORE - Road Trip from Chicago to Washington DC

11. Philadelphia, Pennsylvania

11 hours 50 minutes from Chicago (760 miles)

Why you should visit: Pennsylvania combines the kind of winter fun you might expect, like sledding and skating, with some unique winter traditions.

Visitors and locals alike flock to the Macy's Light Show, running for over half a century, and the charming Dickens Village, also found at the store.

Plus, you can fill yourself with festive cheer with a visit to the traditional market at Love Park's Christmas Village, or a stroll through streets filled with fabulous Christmas lights.

Philadelphia Museum of Art in the winter.

How to get there: Follow I-90 east towards Cleveland, switching onto I-80 just before you reach the city. This leads you south to join I-76, which you'll then follow past Pittsburgh, all the way across Pennsylvania. The same road takes you right into Philadelphia

Our highlights: You can see all the historic gems of Philly decked out with lights and trees for the holiday season, and the city's beautiful riverside setting just adds to the magic.

As you make your way from Chicago to Philadelphia , make sure to fit in a visit to Bethlehem, PA, too. The whole town gets decked out in style for the holidays. Take a magical horse-drawn carriage ride, check out entries for the Gingerbread House competition, and enjoy endless festive lights.

Once you've arrived in Philadelphia, you can ice skate beside the Delaware River at Winterfest, then warm up with a hot chocolate - or something stronger - with a view out across Benjamin Franklin Bridge.

Then, check out the Christmas Village or the Made in Philadelphia Holiday Market. If you're looking for unique and often hand-made gifts for family and friends, you'll find plenty of choice here.

The city's popular Longwood Gardens is transformed with amazing lights and live music, so it makes a great place to spend some time after the sun goes down (which happens early in winter!)

If you're in Philadelphia towards the end of the holiday season, you'll be able to watch the Mummers' Parade on New Year's Day. Thousands of people in absolutely dazzling costumes parade through the city in a historic tradition.

Bonus: Macy's Christmas Light Show – another of the city's festive traditions – is a record breaker! It features more than 100,000 lights and is the largest pipe organ in the world.

Our travel tips: Timed tickets are needed for some of Philadelphia's winter attractions, including Longwood Gardens and Dickens Village.

READ MORE - Road Trip from Chicago to Philadelphia

12. New York, NY

12 hours 40 minutes from Chicago (800 miles)

Why you should visit: New York City puts on an amazing holiday display – from festive lights to Christmas trees and fabulous window displays throughout the city, all with a thick covering of snow. This road trip from Chicago to New York is truly nothing short of magical!

Plus, if you're in the market for some Christmas shopping you can take your pick of fabulous department stores, designer brands and boutique sellers.

Get into the festive spirit and enjoy the iconic holiday views of the city - if it feels familiar, it's probably because they've featured in so many films and TV shows over the years. You should definitely visit New York in winter so you can say you've experienced them all first-hand.

Rockefeller Center all decorated surrounding the newly lit Christmas tree on December 5, 2013.

How to get there: Follow I-90 east across Indiana. Just before Cleveland, merge onto I-80 and follow this all the way across Ohio, Pennsylvania and New Jersey before crossing into Manhattan via George Washington Bridge.

Our highlights: There are so many memorable festive moments to fit into a winter trip to New York City that it's hard to know where to begin. Skate beneath the massive Christmas tree at the famous Rockefeller Ice Rink, before heading up to the Top of the Rock to take in the view of New York in the snow.

Take a carriage ride through Central Park, which is even more magical when there's snow on the ground. Or if you're feeling more active, there are sledding slopes in the park, too.

Of course, NYC is famous for its shops, so leave some space in your case for whatever gifts and treats you might pick up while you're in town. Head to Macy's, Bloomingdale's or Saks Fifth Avenue for wall-to-wall shopping opportunities, or take a walk along Fifth Avenue to indulge in designer brands.

Further afield, the city is packed full of other shopping districts, including the West Village, Bleeker Street, Union Square and the Meatpacking District to name just a few. Or if you're in town with romantic intentions, a stroll through the Diamond District might go down well.

For a different experience of New York in winter, skip the crowds and visit in January to enjoy the NYC Winter Jazz Fest or NYC Restaurant Week, where restaurants put on their best fare at affordable prices.

If you're traveling at this time of the year, you can also stop off at New Hope, PA, as you make your way from Chicago to New York City. Here you can join in with the 9-day Winter Festival (late January).

Galleries, restaurants, and local businesses come together to bring some warmth and cheer to the new year, with a legendary chili cook-off, Soup-A-Thon, and ice sculptures dotted around town.

Bonus: These days, you usually need to take a ferry across from Manhattan to Staten Island, but back in 1780, the entire harbor froze so hard that it was possible to walk all the way across the river.

Our travel tips: Parts of the city get extremely crowded in December, and accommodation prices rise accordingly. The first week of December is particularly busy, but many travelers report that the crowds and prices calm down a little mid-month.

If you'd like to learn more about the best areas to stay in NYC before you plan your trip, you can find our detailed area-by-area guide here .

READ MORE - Road Trip from Chicago to New York City

13. New Orleans, Louisiana

13 hours 40 minutes from Chicago (925 miles)

Why you should visit: Mild weather and weeks of flamboyant parades makes New Orleans the perfect contrast to snowy Chicago. The city is famous for Mardi Gras, which takes place in late February, but warm-up events actually start in January, so you can enjoy week after week of enjoyment.

As well as Mardi Gras, New Orleans is also a vibrant city where you can enjoy live music, fabulous food and warm winter weather - perhaps the closest you can get to a trip overseas without needing a passport!

Holiday decor of red bows, Garden District, New Orleans.

How to get there: On this road trip , join I-57 and follow it south all the way to Cairo, on the Illinois/Missouri border. Then, soon after crossing the Mississippi River, change onto I-55 and follow it south.

As far as Nashville, I-55 runs parallel to the Mississippi before passing through Jackson. Continue along the interstate then, after skirting the west side of Lake Pontchartrain, merge onto I-10, which takes you into the center of New Orleans.

Our highlights: From Thanksgiving onwards, enjoy a Reveillon Dinner – a local tradition that now sees restaurants across the city offering seasonal Creole-inspired food all through December.

Also running from Thanksgiving right up to New Year's Day is Celebration in the Oaks. This after-dark spectacle sees City Park lit up with more than a million lights. Given the city's mild winter climate, it's the perfect place to end the day with a romantic stroll.

If you're in the city for Christmas itself, head out along River Road on Christmas Eve, where you'll see bonfires lit on the night of the 24th so that Papa Noel can find his way from Baton Rouge to New Orleans.

Once Christmas and New Year are behind you, the party season in New Orleans really gets going. From mid-January, you can see parades and events starting up, then the main event, Mardi Gras, starts on Shrove Tuesday and carries on for two weeks. Expect fabulous parades, live music and all-night parties.

You'll have seen pictures of the beautiful and elaborate masks that are such a feature of the Mardi Gras parades. But did you know that every single participant has to wear one?

That way, current and future visitors will be guaranteed the same fabulous experience of NOLA's longstanding and unique traditions.

Our travel tips: Although average temperatures sit around 60 degrees Fahrenheit in winter, they can drop much lower or rise as high as 80, so it's wise to pack for three seasons to be prepared for a winter trip here!

READ MORE - Road Trip from Chicago to New Orleans

14. Savannah, Georgia

15 hours 10 minutes from Chicago (960 miles)

Why you should visit: The weather stays mild all year round in Savannah, so it's a great place to come and escape the Midwest chill. You can enjoy spending time outside, take a walk along the river, or just relax in one of Savannah's beautiful squares - the polar opposite of a Chicago winter.

Don't worry about missing out on too much of that winter snow either - your drive will take you through the Appalachians so you can take in some stunning views as you make your way south to Georgia.

Savannah is a great place to visit all year round but come in winter to enjoy this fabulous city without the summer crowds or humidity.

Savannah, Georgia, USA at Forsyth Park Fountain.

How to get there: After heading east out of Chicago on I-90, turn south onto I-65 and continue through Indianapolis and Louisville.

At Louisville, change onto I-64 and follow it towards Lexington onto I-75 which takes you across into Tennessee. Then, take I-40 from Knoxville to Asheville then join I-26 south passing Spartanburg and Columbia.

This leads you eventually onto I-95, which you'll follow south to Savannah.

Our highlights: There might not be snow and ice on the ground, but Savannah manages to fill the holiday season with its very own brand of festive charm.

At Coastal Georgia Botanical Gardens, you can follow the beautiful light trail through the magical gardens, for example, or take a holiday trolley tour or boat trip to see the city decked out in festive finery while enjoying a wonderful warm cider.

Then, follow the Christmas Parade, which makes its way through the city's streets and squares in early December.

All through the winter, you can also enjoy the shops and restaurants on fabulous River Street, the perfect place to spend some time whether you're looking for gifts to take home or just something special for yourself.

The city was offered up to President Lincoln as a Christmas Gift during the Civil War. As Christmas gifts go, a whole city is one we wouldn't mind receiving!

Our travel tips: Winter weather in Savannah is changeable, but the year-round humidity can make even warm days feel chilly when you're outdoors for a while.

READ MORE - Road Trip from Chicago to Savannah

15. Orlando, Florida

17 hours 30 minutes from Chicago (1,130 miles)

Why you should visit: Orlando is known as a winter sun favorite – so pack your sun cream and enjoy some time outdoors.

The theme parks of Orlando are popular year-round, but during the winter you get to experience them all dressed up for the holiday season, and without the heat and humidity that can be a feature at other times of the year.

Partial view of Christmas tree and palm tree at Seaworld 2.

How to get there: Follow I-90 out of Chicago then merge onto US-41 at the southern tip of Lake Michigan and continue south past Terre Haute and Vincennes.

Just after crossing the Ohio River at Evansville, turn onto I-69, continuing south on I-169 where the interstates divide. After Hopkinsville, join I-24 and follow it through Nashville to Chattanooga, where you'll switch onto I-75 which runs all the way to Florida.

After Gainesville, join the Florida Turnpike which takes you the last stretch of the drive into Orlando.

Our highlights: Florida is the warmest part of the continental US through the winter - perfect for escaping the sub-zero temperatures of the Midwest on this road trip from Chicago to Orlando !

Visit the theme parks in their holiday finest – whether your first choice is Walt Disney World, Universal Orlando, SeaWorld or Legoland Florida, each one will be suitably festive with parades and events to match.

You can see Cinderella's Castle made even more magical at Walt Disney World, or visit EPCOT's International Festival of the Holidays to take a whistle-stop tour around the world's traditions.

One that stands out for its festive themes is the Grinch-mas Who-liday Special at Universal Islands of Adventure. And of course, the Wizarding World of Harry Potter comes into its own during the winter.

If you have time to head out of town, make your way to Tampa to see Christmas Town at Busch Gardens. You'll find yourself in a warm weather wonderland with trees, lights, skating and fireworks.

Outside of the theme parks, you can enjoy the Winter Park Christmas Parade, a long-standing Florida tradition, with dozens of troupes followed by Santa.

And if you're missing that traditional winter vibe, visit Now Snowing in Celebration, where frosty views meet the Florida sun – including hourly snow flurries.

Our travel tips: Pack layers, as even Florida can experience cooler days, but rest assured that with heated pools and plenty of daytime sunshine, you can enjoy yourself outdoors right through the winter.

READ MORE - Road Trip from Chicago to Orlando

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Fall rushes in to Colorado in the form of snow and frost at sunrise along Kebler Pass in Crested Butte as East Beckwith Mountain is covered in a fresh dusting.

weekend trip from chicago winter

7 Winter Weekend Getaways From Chicago To Visit This Frosty Season

Grab your winter puffer and wool hate, winter is officially headed our way—which means you'll need a winter getaway asap!

Tori Levy

As the temperatures drop and the polar vortex begins to take over the city, Chicagoans will brave the frigid temperatures in their trusty black puffer coats while the unbearable wind slaps across their face. On the bright side, there’s endless fun to be had in the wintertime to combat those winter blues , from igloo dining to heading to an enclosed rooftop bar . However, if fleeing the city is more up your alley, we know a thing or two about the best winter weekend getaways from Chicago.

1. Lake Geneva, Wisconsin

People enjoying the annual icy winter playland attraction at the ice castles

Located an hour north of Chicago at the Illinois-Wisconsin border, it awaits a landscape of rolling hills and immaculate views . One of our favorite winter weekend getaways from Chicago, Lake Geneva, is lucky to have not one but two noteworthy skill hills to check out for skiing , snowboarding, and snow tubing .

You can also explore the magical Winter Realm, an open-air experience where you can explore ice volcanoes, igloos, tubing activities, mesmerizing ice sculpture s, ice slides, and ice thrones. So, whether you want to explore the winter magic, need a spa, or want to hit the slopes, there’s something for everyone!

📍 Distance from Chicago : 92.6 miles

🕐 Time from Chicago : 1 hr 35 min

2. Elkhart Lake, Wisconsin

Elkhart Lake Station on a cold spring day, Wisconsin, USA.

Elkhart Lake is the perfect winter weekend getaway from Chicago. You can i ndulge in seasonal favorites at one of the many taverns and escape the cold with a spa day at Aspira Spa .

If you’re looking for an offbeat activity, l et the Captain take you out on the ice for five hours of ice fishing with all the necessary equipment. This includes heated shanties , poles, tackle, and bait—warm clothes and a Fishing License is all you need, which you can get there.

📍 Distance from Chicago : 149.8 miles

🕐 Time from Chicago : 2 hr 29 min

3. Grand Rapids, Michigan

The winter landscape of Ada Park in Grand Rapids, Michigan

Grand Rapids has everything from skiing and snowshoeing to stage shows and festivals. The Christkindl Markt at the Grand Rapids Downtown Market is a European-style Christmas Village lined with artisan gift and food vendors, live holiday entertainment, and festive family fun. It’s bound to become another of your family’s favorite winter traditions.

You can also experience and enjoy winter in a new way during the World of Winter Festival in downtown Grand Rapids. For free, you can see large-scale outdoor art installations and amazing ice sculptures, enjoy musical performances, play games, stroll the city, and more.

📍 Distance from Chicago : 177.6 miles

🕐 Time from Chicago : 2 hr 47 min

4. Toronto, Canada

Toronto seen from Wards Island on a freezing day

How about a little trip outside the country? In Toronto, you can experience the magic of the holiday season with the much-loved Cavalcade of Lights at Nathan Phillips Square. Inspired by international lanterns, fire, light festivals, and winter solstice celebrations, Cavalcade of Lights is a free event that transforms City Hall and its surroundings into a dazzling wonderland.

Toronto’s award-winning winter art exhibit, Window Wonderland, returns to the Junction for its fourth consecutive year. The magical urban art walk will transform the Junction into a free outd oor art gallery.

📍 Distance from Chicago : 515.1 miles

🕐 Time from Chicago : 8 hr 15 min

5. Mackinac Island, Michigan

Mackinac Point Lighthouse from Mackinac Island

Known as a unique vacation spot with an old-timey atmosphere. Mackinac Island is a national treasure, home to historic Fort Mackinac , world-famous Mackinac Island fudge, and car-free streets full of horse-drawn carriages.

This ideal vacation spot and winter getaway from Chicago is a paradise of exploration with incredible natural landmarks, awe-inspiring sunrises, and unforgettable sunsets. In winter, you can head on the Mackinac Island Turtle Trek, a beautiful lantern-lit ski and snowshoeing trek . You’ll head through some of Mackinac Island’s natural winter wonderland.

📍 Distance from Chicago : 415 miles

🕐 Time from Chicago : 6 hr 30 min

6. Saugatuck, Michigan

Winter landscape of beach grasses and the iced shoreline of Lake Michigan near sunset, Saugatuck Dunes State Park, Michigan, USA

Gaze in wonder at the ice-kissed lakeshore. Experience relaxation while exploring their tranquil woods and snow-covered dunes . Peruse the warmly lit boutiques and inspiring galleries next to their snowy sidewalks. Or capture the joy and spirit of the season with nostalgic activities like a horse-drawn sleigh ride.

📍 Distance from Chicago : 141.9 miles

🕐 Time from Chicago : 2 hr 13 min

7. Boyne Falls, Michigan

Skiers on the Boyneland Lift at Boyne Mountain in Northern Michigan.

The small village of Boyne Falls is named for the falls on th e nearby Boyne River . Take a walk on the wild side of the “World’s Longest Timber-Towered Suspension Bridge” and take in the views from this architectural masterpiece. This is one of the ideal winter weekend getaways from Chicago because it has the ultimate playground for skiers. Head to the Boyne Falls Mountain Resort, where you can let loose across 415 skiable acres.

📍 Distance from Chicago : 346.5 miles

🕐 Time from Chicago: 5 hr 16 min

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Best Weekend Getaways From Chicago

By Nina Kokotas Hahn

One of the Kohler Lake Cabins

All products featured on Condé Nast Traveler are independently selected by our editors. However, when you buy something through our retail links, we may earn an affiliate commission.

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

Lake Forest Illinois Deer Path Inn

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

Indiana Dunes National Lakeshore

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

Harbor County MI

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

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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

Historic town of Galena IL on the Mississippi River

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

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

Boyne Mountain Resort

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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24 Top Weekend Getaways From Chicago

From beaches to ballparks and trails to rails, explore top breaks from the Windy City.

A weathered wooden walkway on the Empire Bluffs Trail in Sleeping Bear Dunes.

Getty Images

Hike along Michigan's Sleeping Bear Dunes National Seashore on your next weekend getaway from Chicago.

Known as the birthplace of the skyscraper, Chicago is home to award-winning restaurants , top sports teams and prized cultural treasures. But when you need a break from the excitement of the nation's third largest city, there are countless getaways within easy driving distance. You can explore rural Illinois or enjoy neighboring Indiana, Wisconsin, Iowa or Michigan all within a weekend. Whether you're planning a romantic getaway to a small-town bed-and-breakfast or a family-friendly trip to a water park resort, these nearby Midwest destinations will relieve the stress of big city life.

(Note: Some of the following activities, attractions and locations may be affected by the COVID-19 pandemic. New policies may be in place, including capacity restrictions, reservation requirements or mask mandates. Check with the Centers for Disease Control and Prevention, the U.S. Department of State and local tourism boards before traveling.)

Best Weekend Getaways from Chicago:

About two hours or less:, fox river valley, illinois, harbor country, michigan, st. joseph, michigan, milwaukee, wisconsin, south haven, michigan, starved rock state park, illinois, gurnee, illinois, wilmot mountain, wisconsin, lake geneva, wisconsin, grand geneva resort & spa, wisconsin, about three hours or less:, turkey run state park, indiana, the american club resort hotel, kohler, wisconsin, whistling straits golf course, sheboygan, wisconsin, saugatuck, michigan, wisconsin dells, wisconsin, about four hours or less:, parke county, indiana, galena, illinois, dubuque, iowa, and the field of dreams, ann arbor, michigan, madison, wisconsin, about five hours or less:, traverse city, michigan, louisville, kentucky, st. louis, missouri, a quick flight:, minneapolis – st. paul, minnesota.

Fox River on a sunny day in Illinois.

Located along the picturesque Fox River on the western outskirts of Chicago lie the small towns that make up Illinois' Fox River Valley. Stretching from the village of Antioch in the north to Ottawa – the gateway to Starved Rock State Park – in the south, this area is an ideal daytrip from the Windy City. Go biking, hiking and cross-country skiing along the 32-mile Fox River Trail or rent a kayak for paddling on the Fox River. In addition to outdoor pursuits, unique cultural attractions abound, including Broadway productions and musical events in Aurora's historic and beautifully restored Paramount Theatre. Visitors rave about its exquisite decor and top-notch performances, applauding the Paramount for offering Broadway-caliber performances at Main Street prices. If you choose to overnight in the Fox River Valley, the Herrington Inn & Spa , which overlooks the Fox River in the small town of Geneva, would make for a romantic getaway.

New York has the Hamptons; Boston has Cape Cod . The summer playground for Chicagoans consists of eight glistening lakeshore towns dotting the coastline of southwest Michigan, collectively known as Harbor Country. Here you'll find beaches, orchards and plenty of outdoor activities. At the southern end of Harbor Country, just over the Michigan-Indiana state line and about 70 miles from Chicago's downtown loop, New Buffalo lures Chicagoans with its casual beach vibe and proximity. Families line up for burgers at The Stray Dog, but only adults can head up to the rooftop bar and patio. Patrons praise The Neighborhood Hotel Grand Beach for its modern design combined with cozy common areas, fire pits, ping pong tables and board games; they also appreciate the short walk to the beach and the heated pool.

[Read: The Top Things to Do in Michigan .]

Families will want to make the scenic 25-mile drive from New Buffalo north through the Harbor Country towns of Union Pier and Lakeside, past grand lakefront estates and bucolic farms, to St. Joseph, commonly called St. Joe's. The family-friendly Silver Beach Pizza is housed in St. Joe's former train depot, with diners saying it's well worth what can be a half hour wait for the amazing pizza. Across the street is the restored 1910 Silver Beach Carousel, a great option for passing the time while waiting for your table if you've got kids along. St. Joe's offers visitors the chance to step back in time with a beach, pedestrian-friendly downtown, boutiques and old-fashioned chocolate shops. One of St. Joe's more unique shops is Third Coast Surf, where you can rent a surfboard and sign up for surfing or sandboarding lessons. Not expecting a surf shop in the Midwest? Visitors are often surprised when they first see Lake Michigan, known to Midwesterners as the Third Coast: It resembles an ocean more than a lake.

Downtown Milwaukee skyline at sunset with Lake Michigan shore.

Located about 80 miles north of Chicago on Lake Michigan is the Brew City of Milwaukee , which boasts more than 200 breweries, museums, festivals and the Harley-Davidson Museum . As this city is home of the Milwaukee Brewers baseball team, no trip is complete without getting a taste for Milwaukee's beer heritage. Visitors give Lakefront Brewery tours high marks for entertaining guides, extensive selection, riverfront views and its popular Beer Hall restaurant with live music on Fridays. Families will enjoy the lakefront museum campus, which includes the Discovery World science museum and Betty Brinn Children's Museum, while culture lovers can visit the architecturally stunning Milwaukee Art Museum when the building's "wings" open and close several times a day. Motorcycle enthusiasts will be in hog heaven at the modern steel-and-glass Harley Davidson Museum, which celebrates the machine invented in Milwaukee that's come to symbolize the freedom of America and the open road.

Winters are harsh, so summer is one endless celebration, with a multitude of neighborhood festivals, outdoor concerts and ethnic celebrations – check out German Fest at the end of July, honoring the city's largest immigrant group. Summer excitement reaches a crescendo at the end of June with Summerfest, the world's largest music festival. After a day of sightseeing or revelry, a top lodging choice is Milwaukee's stately grand dame, the historic Pfister Hotel , offering Gilded Age elegance alongside 21st-century amenities like a pool with panoramic city views and a popular top-floor cocktail bar.

[See more of Milwaukee:  Things to Do  | Hotels  |  Photos ]

South Haven is a fun-loving beach town with a population that swells in the summer – especially in August for the National Blueberry Festival, since this Michigan destination claims to be the blueberry capital of the U.S. About 110 miles from Chicago, you'll hear a lot of Jimmy Buffett playing in the bars and restaurants of this laid-back boating town where the harbors take center stage. Kick off your visit by learning about the area's rich Great Lakes boating history at the Michigan Maritime Museum.

Along with its seven public beaches – some of the best beaches in Michigan – and iconic red lighthouse, South Haven also has a pedestrian-friendly downtown filled with unique shops and restaurants. Climb aboard the stationary Idler Riverboat, where casual dining combines with world-class waterfront views. Clementine's is another local favorite, as is Captain Lou's, which serves fresh perch and live music on the weekends. For a romantic getaway, consider Inn at the Park, a bed-and-breakfast one block from Lake Michigan: Guests praise the beautiful decor and sumptuous breakfasts, using locally grown blueberries. Travelers also love Yelton Manor Boutique Hotel for its manicured gardens, spectacular sunset views of Lake Michigan and proximity to town.

Cascade after the morning summer rain in St. Louis Canyon at Starved Rock State Park, Illinois.

Looking for an active adventure? Only about 100 miles southwest of Chicago, this wilderness known for its deep sandstone canyons and waterfalls is perfect for daytrips – though with 18 canyons to hike, there's plenty to keep you busy for a whole weekend. Walking along bluffs that lead to scenic lookouts over the Illinois River makes visitors feel immediately transported out of the flat Midwest heartland. Starved Rock State Park can be a weekend escape any time of year, but spectacular fall foliage makes it a favorite getaway for autumn in particular.

Starved Rock State Park has its own historic lodge with top-notch cabins , but kids may prefer going across the street to the family-friendly Grizzly Jack's Grand Bear Resort, with its massive water park, mini-golf, indoor arcade and Northwoods decor. Camp Aramoni is a great choice for a romantic getaway, with luxury glamping in safari tents outfitted with hardwood floors, air conditioning and heating, and full bathrooms with showers. Nightly stays include chef-prepared farm-to-table dinner and breakfast using produce grown in on-site gardens that guests are welcome to visit. End your day at Camp Aramoni's repurposed Airstream trailer that's been turned into a bar.

Looking for high-adrenaline family fun? About 35 miles north of Chicago, just south of the Wisconsin border, lies the village of Gurnee, home to the Six Flags Great America amusement park . Thrill-seekers will love the 17 heart-stopping roller coasters, but dozens of other rides mean you'll also find plenty for younger kids. Reluctant riders who want to steer away from high-speed coasters and intense drop rides can also enjoy the park's shows and other entertainment. On a hot day, plunge down steep waterslides or splash around the wave pool at Six Flags' 20-acre Hurricane Harbor water park. When it gets cold, a favorite local pastime is a stroll around Gurnee Mills, an outlet mall housing more than 170 stores.

Continue your Gurnee adventure with a stay at the Northwoods-themed Great Wolf Lodge, the most family-friendly hotel option in this destination. Guests say this water park resort makes even adults feel like kids again and rave about the endless family-friendly amenities, which include bowling, mini-golf, a ropes course and arcade – and, of course, the massive water park.

Since 1938 Wilmot Mountain has drawn visitors seeking wintertime leisure in the Midwest. About 25 miles northwest of Gurnee, just over Wisconsin's state line, Wilmot Mountain Ski Resort makes for a great cold-weather attraction when Six Flags is closed. The big-name Vail Resorts purchased Wisconsin's little ski hill in 2016 and rolled out plenty of upgrades, from improving terrain parks and snowmaking to adding chairlifts and elevating the dining experience. Enjoy winter sports over a variety of terrain at this alpine destination, whether you're looking to ski, snowboard or snow tube. There's no on-site lodging, but Gurnee's Great Wolf Lodge is still a relatively short drive away.

[Read: The Top Things to Do in Wisconsin .]

A stunning summer sunset in Lake Geneva, Wisconsin.

This Wisconsin resort city makes for an idyllic weekend or daytrip. About 70 miles northwest of Chicago, Lake Geneva is described as the " Newport of the Midwest" because of its opulent lakefront mansions. You can come surprisingly close to these impressive residences by ambling along the Geneva Lakeshore Path, a rustic 25-mile walkway that encircles the lake, cutting right through the backyards of magnificent mansions and second homes. Amazingly, there aren't any "No Trespassing" signs to scare away walkers; just beware the path is not intended for strollers, roller blades or bikes, since you'll have to maneuver past steps and other obstructions. When you've finished your stroll, a lakefront cruise is another fun way to enjoy this city. Visitors give Lake Geneva Cruise Line excellent reviews for being informative and entertaining. A variety of daily cruises are offered, but one of the most unique is the mail delivery cruise. As Lake Geneva is one of the few remaining places in the U.S. where mail is still delivered by boat, about 75 lakefront homes receive their U.S. mail service via boat – and passengers are invited to come along for the ride.

Consider a stay at the Abbey Resort, the only full-service resort directly on the shores of Lake Geneva, during a summer visit. This lodging option offers complimentary adult and kids bikes, ideal for use on the Lake Geneva Bike Path, which connects many of the resort town's amenities. The trail has five unique, color-coded segments, making it easy to find your way around. Things quiet down a bit in the fall, when the vibrant autumn colors set a serene scene.

[Read: The Best Midwest Vacations for Families .]

Tourists descend on Lake Geneva's charming downtown shops and restaurants in the summer, but the town has plenty to do year-round. One of the best winter attractions in this city is the Grand Geneva Resort & Spa , whose modest ski hill has three chair lifts, 20 runs and a terrain park. Grand Geneva Resort also has access to 5 miles of wooded trails for cross-country skiing and offers a limited number of ski rentals. Kids will love overnighting at Grand Geneva's family-friendly Timber Ridge Lodge and Waterpark for indoor aquatic fun while adults relax at the spa. Time your winter visit to coincide with Lake Geneva's Winterfest so you can observe one of the country's biggest snow sculpting competitions.

Turkey Run State Park is the crown jewel of Parke County and one of the Hoosier State's oldest and most popular state parks. Eleven trails ranging from a half-mile to 2 miles wind through rugged ravines surrounded by the park's signature sandstone cliffs – providing Midwest hiking at its best. Turkey Run Inn, a popular lodging option situated within the park, is appreciated by guests for its friendly staff and cozy atmosphere. There's an indoor pool and plenty of public sitting areas with fireplaces, whether you want to play a board game or read a book. Choose from rooms within the historic lodge or the adjacent cabins. Even if you don't stay at Turkey Run Inn, you can still enjoy its restaurant, The Narrows, which diners recommend for the catfish dinners as well as the fried biscuits and hot apple butter.

Most have never heard of this tiny town 140 miles north of Chicago, but Kohler is home to Wisconsin's only hotel to receive AAA's highest five diamond rating. The American Club Resort Hotel – part of the Destination Kohler Resort – is still owned by the family who built it: The Kohlers are best known for high-end plumbing and bathroom fixtures. The American Club's luxurious Kohler Waters Spa specializes in hydrotherapy, giving guests a chance to experience all the legendary bath and shower products Kohler is known for. Should you want to recreate that luxury spa experience in your own bathroom at home, a few steps away from the spa is the sleek, multistory Kohler Design Center, filled with model bathrooms and design ideas sure to give most of us bathroom envy. Amid your self-care ventures in Kohler, enjoy plenty of outdoor activities. Fall brings a boisterous bounty of color to this rural area, while winter experiences at The American Club include ice skating, curling, snowshoeing and cross-country skiing across miles of trails that wind through woodlands and meadows.

Ten miles from American Club Resort Hotel sits the Kohler-owned Whistling Straits Golf Course, which some golfers describe as reminiscent of the legendary Pebble Beach . Whistling Straits ranks among the top public courses in the country and has hosted 2021's Ryder Cup and three PGA championships. The two Pete Dye-designed courses at Whistling Straits offer stunning views of Lake Michigan or rolling green hills. Golfers will feel transported to Ireland's tranquil grassland or its rugged coastline as this course winds its way along the bluffs and dunes overlooking Lake Michigan.

Nautical scene with fall leaf colors in Saugatuck, Michigan.

It's easy to see why Saugatuck is one of the best places to visit in Michigan . Nicknamed the Art Coast of Michigan, this hip resort town about 130 miles from Chicago is stocked with galleries, boutiques, excellent dining and beaches. Perhaps surprisingly for a town of less than a thousand people, Saugatuck is also known for its lively nightlife and for being an LGBTQ-friendly destination. Take a seat at the counter of the century-old Saugatuck Drug Store and you'll get a taste of the town's more traditional side, served up via a classic malt or ice cream soda. Visitors are in for another nostalgia trip when you board the chain ferry: Operating since 1838, it claims to be the only remaining chain-driven ferry in the U.S., transporting passengers across the Kalamazoo River between downtown and Oval Beach. After disembarking on Oval Beach, active beachgoers love climbing the 302 steps to the top of Mount Baldhead – known as Mt. Baldy – and getting a bird's eye view of the area. Overlooking Lake Michigan, Saugatuck's Lake Shore Resort is applauded by patrons for its breathtaking views and many complimentary amenities, including bikes, kayaks, yoga and a heated pool.

About 190 miles northwest of Chicago is the ultimate Midwest family getaway: the "Waterpark Capital of the World." If traveling with kids to Wisconsin Dells, stay at one of the immensely popular water park resorts , such as the flagship property of Great Wolf Lodge. Guests appreciate the original Great Wolf Lodge for its signature Northwoods decor, endless amenities and the feeling of being in a tropical paradise year-round.

Beyond its myriad indoor and outdoor water parks, Wisconsin Dells boasts a wide variety of kid-friendly entertainment options, from zip lines to animal parks. Catch a performance at the Palace Theater, which offers everything from concerts to comedy shows to children's plays and Broadway-style productions; some theatergoers swear there isn't a bad seat in the house. More fun for the whole family can be found at the Rick Wilcox Magic Theater shows, which wow audiences with both humor and illusions that keep you guessing. Want to escape the indoor attractions for a natural one? Head over to Mirror Lake State Park for a scenic hike along a tranquil, no-wake lake set among sandstone bluffs. Pontoon boats, kayaks and stand-up paddleboards are available to rent here.

[Read: The Top Things to Do in Wisconsin Dells .]

Billing itself as the covered bridge capital of the world, Parke County, Indiana – about 160 miles south of Chicago – maintains 31 of these Instagram-worthy symbols of a bygone era. Visitors descend on the area every October for the Parke County Covered Bridges Festival, Indiana's largest annual festival. The popular biker bar Thirty Six Saloon is a family-friendly roadhouse in Rockville, the town where the popular fall festival is headquartered. Kids may be mesmerized by Thirty Six Saloon's vast collection of taxidermy, with animals from the region mounted throughout the restaurant. Diners compliment everything from the burgers and ribs to the fish sandwiches and unique decor. Another popular culinary option is the tenderloin sandwich at the Mecca Tavern in Mecca. Parke County's oldest tavern overlooks Mecca's historic schoolhouse and covered bridge. Locals and visitors alike say stopping by Wheelhouse Donuts is another must: This adorable bakery lets you design your own doughnut.

About 150 miles west of Chicago, in the northwest corner of Illinois, the charming Mississippi River town of Galena regularly makes national lists of best small towns . Its elegant dining, historic sites, quaint shops and bounty of bed-and-breakfasts make Galena an excellent choice for a romantic getaway. Because the glaciers that flattened most of the Midwest didn't reach here, the pastoral farmland is hillier, perfect for a Sunday drive. The 19th-century buildings in this old mining town have been painstakingly preserved, with 85% on the National Register of Historic Places – including the Ulysses S. Grant Home State Historic Site, a residence gifted to the nation's soon-to-be 18th president in 1865 by Galena citizens.

One memorable overnight option would be a stay at the former county jailhouse – now the luxurious Jail Hill Inn. For a more romantic atmosphere, the Goldmoor Inn is beloved by guests for its stunning views of the Mississippi River, in-room fireplaces and two-person hot tubs. Galena is gorgeous any time of year, with plenty of travelers drawn here during harvest time for apple and pumpkin picking amid the abundance of fall colors. Winter brings its own charm with shops along Main Street resembling something out of a Norman Rockwell painting. The small town also houses a popular old-school ski resort: Guests say Chestnut Mountain Resort's decor and amenities are a bit dated, but its 19 ski runs provide scenic views of the river below.

Long exposure image of downtown Dubuque, Iowa, taken from the top of the Fourth Street Elevator.

Head 170 hundred miles west of Chicago, cross the Mississippi River, and you'll be in Dubuque, Iowa. Get a feel for how important the river is here by visiting the National Mississippi River Museum and Aquarium, or take a ride on a riverboat for another scenic way to experience the Mississippi. Visitors give the Celebration Belle river cruise high marks for being fun, informative and affordable. Another must-see attraction is Fenelon Place Elevator, a steep funicular railway providing fabulous views of the surrounding area. History lives on at the elegant Hotel Julien Dubuque, which guests compliment for its charm and friendly service. Baseball fans will want to make the additional 25-mile drive west to the town of Dyersville to explore the Field of Dreams, one of the best tourist attractions in the U.S. Play on the baseball diamond and tour the home where the movie "Field of Dreams" was filmed.

About 230 miles northeast of Chicago, Ann Arbor is a quintessential college town, filled with independent bookstores and great live music. University of Michigan alumni are a proud bunch – and not just on game days, when they march clad in blue and yellow to what's known as The Big House, the largest sports stadium in the country. Ann Arbor also scores an A when it comes to food and culture. The world-class University of Michigan Museum of Art displays works by Picasso, Monet and Warhol. A few blocks away on Liberty Street is the edgier public art canvas known as Graffiti Alley, just steps from the historic Michigan Theater and State Theatre, which delight visitors with film screenings, festivals and live music throughout the year (as long as you follow the theaters' COVID-19 regulations ). A pastrami sandwich at Zingerman's Deli is a 40-year tradition, but if you're hungry for a more budget-friendly option head to Frita Batidos and take a seat at one of the communal tables for Cuban-inspired street food. Hit the books at Literati, a beloved independent bookstore. A fun hotel choice is Graduate Ann Arbor with its University of Michigan-themed decor.

[See more of Ann Arbor: Things to Do | Hotels | When to Visit | Photos ]

About 140 miles northwest of Chicago, Madison is more than just a cool college town: It's also the capital of Wisconsin. No trip here is complete without visiting the beautiful, white-domed Wisconsin state Capitol building; free tours are given throughout the day. Madison's isthmus location on a narrow strip of land between two lakes means waterfront biking and hiking trails abound. Foodies will also get their fill at Fromagination, a cheese lover's paradise popular with Wisconsin cheeseheads as well as out-of-town visitors. Located across from the Capitol, this delightful cheese shop features dozens of one-of-a-kind artisanal Wisconsin varieties. If visiting Madison between April and November, head to Capitol Square on Saturday morning for the Dane County Farmers' Market, the country's largest producer-only farmers market. The 72-room, collegiate-themed Graduate Madison hotel is an easy walk to campus, dining, shopping and nightlife. Decorated in the University of Wisconsin colors of red and white, the hotel gets high marks from guests for its nostalgic decor and artwork, including collages of political buttons, a nod to the town's legacy of social activism.

[See more of Madison: Things to Do | Hotels | When to Visit | Photos ]

Cars parked watching the sunrise over the coast of Lake Michigan in downtown Traverse City, Michigan.

Those who have more time could leave the bright lights of Chicago for the serenity of Michigan's Traverse City to visit Sleeping Bear Dunes National Lakeshore and its 64 miles of pristine coastline and mountains of sand dunes. Traverse City is about 300 miles from Chicago, but you'll be rewarded with breathtaking beaches, peaceful hikes, top-notch cuisine and the added perk of what's considered the " Napa Valley of the Midwest": the 24 wineries of the Leelanau Peninsula Wine Trail. When the temperatures drop and the snow arrives, a great winter weekend getaway involves cross-country skiing in Pere Marquette State Forest or the Leelanau Trail, which runs from Traverse City to Suttons Bay. Traverse City and northern Michigan are also filled with summer lake resorts: Top options include Lake Leelanau's Fountain Point Resort, the upscale Homestead Resort and the all-inclusive White Birch Lodge in nearby Elk Rapids. With White Birch known for its water sports program, teens and tweens will love water-skiing, tubing and ending the day swapping adventures with new friends around a beach bonfire.

[See more of Traverse City: Things to Do | Hotels | Tours | When to Visit | Photos ]

Best known as the location of the Kentucky Derby, Louisville sits 300 miles south of Chicago and has a whole lot more going on than just horse racing. About 95 percent of the world's bourbon is made in Kentucky ; for a taste of the state's signature liquor, head to downtown Louisville's historic Whiskey Row. Here you'll find distilleries, unique restaurants and live music. Topping any sports lover's itinerary should be a visit to the Louisville Slugger Museum and the Muhammad Ali Center , which visitors applaud for honoring the boxer's life, faith and humanitarian service. Art lovers would enjoy staying at the 21C Museum Hotel Louisville , which houses its own contemporary art museum.

[See more of Louisville: Things to Do | Hotels | Photos ]

About 300 miles southwest of Chicago, just over the Illinois border along the Mississippi River, sits this Missouri city. St. Louis is well worth a weekend trip for its plethora of restaurants, breweries and cultural treasures. Nicknamed the Gateway City for its iconic Gateway Arch , St. Louis gives travelers the chance to take a tram ride to the top of this engineering marvel. After getting a bird's-eye view of the surrounding area, head over to the nearly 1,300-acre Forest Park , site of the 1904 World's Fair, now home to the Saint Louis Zoo and several museums. Music lovers can't miss the National Blues Museum, which sings the praises of that melancholy American music form. If you find yourself in need of more music lessons, make your way to the Scott Joplin House State Historic Site, where the king of Ragtime lived. After a busy day sightseeing, Drury Plaza Hotel St. Louis at the Arch makes a good place to rest. Guests rave about the unbeatable value of the hotel's free breakfast and happy hour with complimentary hot food and drinks.

[See more of St. Louis: Things to Do | Hotels | When to Visit | Photos ]

Minneapolis aerial with Downtown Minneapolis skyline in the background and Loring Park with Loring Pond in the foreground, during early autumn.

The Twin Cities of Minneapolis − St. Paul straddle the Mississippi River, about 450 miles northwest of Chicago, with Minneapolis as Minnesota's most populous city and St. Paul as the state capital. Minneapolis is known as a city of lakes, but visitors also like to walk along the riverfront, taking in the magnificent Mississippi. Groundbreaking pop musician Prince was born in Minneapolis; now his legacy lives on at Paisley Park, a sprawling complex in the nearby town of Chanhassen that was once the artist's studio and home. Millions more travel here to visit the largest mall in the Western hemisphere, Mall of America , located in the nearby suburb of Bloomington. As much an entertainment complex as a retail center, this mall houses the indoor amusement park Nickelodeon Universe, a highlight for kids. Guests give Minneapolis' Hewing Hotel stellar reviews for its character, charm and stunning views from the rooftop lounge.

[See more of Minneapolis − St. Paul: Things to Do | Hotels | When to Visit | Photos ]

You might also be interested in:

  • The Best Weekend Getaways
  • The Top Romantic Getaways in Illinois
  • The Top Romantic Getaways in Wisconsin
  • The Top Romantic Getaways in Michigan
  • The Top Romantic Getaways in Ohio
  • The Top Fall Weekend Getaways
  • The Top Travel Neck Pillows
  • The Top Travel Backpacks
  • The Top Duffel Bags

Tags: Travel , Midwest Vacations , US Vacations

World's Best Places To Visit

  • # 1 South Island, New Zealand
  • # 4 Bora Bora

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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.

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.

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.

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

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.

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.

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.

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.

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 university

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

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 .

Fall colors in Traverse City

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.

A woman laying in a super bloom of golden California poppies in Antelope Valley

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10 Best Weekend Getaways From Chicago

Waterfalls, wildlife, and lots of small-town charm await.

Elizabeth Rhodes is a special projects editor at Travel + Leisure , covering everything from luxury hotels to theme parks to must-pack travel products. Originally from South Carolina, Elizabeth moved to New York City from London, where she started her career as a travel blogger and writer.

weekend trip from chicago winter

With fascinating architecture, great museums, and plenty of delicious local eateries (deep dish pizza, anyone?), Chicago has a lot to offer tourists and residents alike. That said, we could all use an escape from the hustle and bustle of the Windy City every so often, so we've rounded up the best weekend getaways from Chicago. Whether you're looking for beautiful landscapes or small-town charm, these quick trips are sure to please every type of traveler.

Here are our top 10 weekend getaways from Chicago.

Starved Rock State Park, Illinois

Wander through towering trees to find waterfalls and wildlife at Starved Rock State Park . This park, located on the Illinois River, is situated about an hour and a half from Chicago, making it the perfect choice when you want to trade skyscrapers for the great outdoors for the weekend. In the spring, the waterfalls are especially active, thanks to heavy rains, and in the fall, the leaves turn beautiful shades of orange, red, and yellow. Stay within the state park at the Starved Rock Lodge , or opt to spend the night in nearby Ottawa, a charming little town with restaurants, shops, and more.

Indianapolis, Indiana

Just a three-hour drive from Chicago, Indianapolis, affectionately referred to as "Indy" by locals, offers plenty to do. Kids will love the Children's Museum of Indianapolis and the Indianapolis Zoo , while sports fans will want to check out the iconic Indianapolis Motor Speedway . The Broad Ripple neighborhood has nightlife, dining, shopping, and more, and the Massachusetts Avenue Arts District offers theaters, galleries, and independent boutiques. History lovers should book a stay in one of the 1920s Pullman train car rooms at the Crowne Plaza Indianapolis Downtown-Union Station .

Saugatuck, Michigan

Summer is the perfect time to visit this lakeside town, located just under two and a half hours from Chicago. Lounge on the sandy shores of Oval Beach or Saugatuck Dunes State Park , rent a boat and explore the lake, browse the art galleries, or check out the local breweries. After a day enjoying Lake Michigan's most pristine beaches, rest your head at one of the adorable inns or bed-and-breakfasts in town.

Lake Geneva, Wisconsin

For another nearby waterfront escape, head to beautiful Lake Geneva , located just an hour and a half from Chicago. During the summer, you can get out on the lake, sunbathe on its beaches, or go zip lining, along with other outdoor activities. During the winter, check out the Ice Castles , an awe-inspiring display of icicles.

Milwaukee, Wisconsin

An hour and a half north of Chicago on Lake Michigan, you'll find Milwaukee, a city teeming with great museums and better beer. Milwaukee has played a major role in U.S. beer production, with Pabst Brewing Company and Miller Brewing Company calling this city home. Today, you can toast to the city's beer heritage by trying these classics or visiting one of the many local craft breweries. The Milwaukee Public Museum is a must-visit — it's home to fossils, a European village, a full-size display recreating the streets of Milwaukee in the late 19th and early 20th centuries, a butterfly garden, and more. Other sites worth visiting include the Milwaukee Art Museum , the Harley-Davidson Museum , and the Mitchell Park Horticultural Conservatory, also known as The Domes .

Indiana Dunes National Park, Indiana

Just under an hour from Chicago, Indiana Dunes National Park makes the perfect quick weekend getaway from Chicago. You can even squeeze it in for a day trip if you're short on time (it's accessible from the South Shore Line, so you don't even have to drive). This national park covers 15 miles of Lake Michigan's shoreline, making it ideal for a relaxing weekend away from the city. Go for a hike along the dunes, fly a kite on the beach, enjoy horseback riding, or check out the historic 1933 World's Fair Century of Progress Homes .

Madison, Wisconsin

Wisconsin's capital city is just over two and a half hours from Chicago, and it offers something for every type of traveler. Food-loving folks will want to visit the National Mustard Museum and try fresh ice cream at the Sassy Cow Creamery, located 20 miles from Madison. Meanwhile, outdoorsy types will love kayaking or taking a cruise around the lake during the summer and snowshoeing in the winter. Families will want to check out the Madison Children's Museum and the Children's Theater of Madison for kid-friendly entertainment.

Holland, Michigan

Holland, Michigan is a unique weekend getaway destination, located under three hours from Chicago. Taking its name from the region of the Netherlands, the city's Dutch heritage is evident in its famous attractions like the Windmill Island Gardens , De Klomp Wooden Shoe and Delft Factory , and Nelis' Dutch Village . The yearly Tulip Time Festival is another great reason to visit Holland — millions of tulips are planted across Holland, so visit in spring to see the beautiful flowers in bloom.

Wisconsin Dells, Wisconsin

For a family-friendly getaway, opt for a weekend trip to Wisconsin Dells , located about a three-hour drive from Chicago. This area, known as the "water park capital of the world," is packed with attractions kids will love, like Noah's Ark Water Park , the largest water park in the United States. To relax, take a scenic boat ride through the Dells or visit one of the local wineries and breweries.

Geneva, Illinois

Just an hour outside of Chicago, you'll find Geneva, Illinois , a destination perfect for people looking for a small-town getaway. Wander the city, check out the murals and outdoor sculptures, take a stroll through the Fabyan Forest Preserve , and browse local, independent shops selling coffee, tea, chocolate, gelato, ice cream, popcorn, baked goods, and more.

chicago 101

weekend trip from chicago winter

From the Editor

Midwest travel.

My name is Christine Zwolinski and I'm your mom friend around town. I live in chicago with my husband manny and two children, Noah and Mila!

weekend trip from chicago winter

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The Best Winter Midwest Getaways from Chicago

October 20, 2023.

Chicago winters are long and brutal. It’s this time of the year we need to get out. But when hopping on a plane from ORD to LAX isn’t in the cards, try these 6 places to escape the daily grind. All of these getaways are five hours or less.

Lake Geneva, Wisconsin

Located in the southeastern part of Wisconsin, Lake Geneva is a beautiful destination that is filled with fun and adventure. We always stay at the Grand Geneva Resort & Spa and take the kids to the Moose Mountain Falls Waterpark at Timber Ridge Lodge, which is a part of the Grand Geneva. It’s nice because once you are at the hotel, it has everything you need and you don’t need to leave. If you can sneak away for some adult time, I love their spa too. It’s located in a separate building tucked away.

If you’re looking for a more relaxed weekend, you can take a leisurely tour of the local wineries or book yourself a spa appointment. Afterward, take a walk around the charming downtown area of Lake Geneva and explore the historic architecture and shops. It’s probably one of my favorite, easiest getaways from the city.

weekend trip from chicago winter

Galena, Illinois

One of our favorite getaways is Galena! It’s an easy drive – just a little over 3 hours from Chicago with lots to do and see. We have stayed at an Airbnb or the townhomes at Eagle Ridge Resort, which is then a short drive to downtown. Indoor pool, spa, and beautiful grounds. They also have townhomes to rent on the property, great for families! See my babymoon blog post about Eagle Ridge here.

Grab a coffee and take the trolley (check their winter hours) on a scenic, historic tour of Galena where you’ll see many of the original early nineteenth-century buildings. You can take a hike with goats with Hoof It Goat Treks , and then shop the small boutiques & cafes that line the main streets. I love Bread and Vine or Otto’s (it’s rumored to be haunted!) for breakfast, brunch, or lunch, Isabella Ltd for gifts and home decor, Bloody Mary’s at Fried Green Tomatoes, and Poopsies for toys and gifts.

weekend trip from chicago winter

New Buffalo, Michigan

Many people think that New Buffalo is only a summer destination, but we actually love it during the winter because it’s empty! We love to go to David’s Deli for brunch, have Italian dinner at Brewster’s, and head to Sawyer for Sawyer’s Market which is next to Greenbush Brewing! For coffee, Whistle Stop is cute with great bagel sandwiches, and stopping by the Swedish bakery on Red Arrow Highway is a must! We also like taking a hike at Galien River County Park.

We usually get an Airbnb (here are two of the homes we have rented, home 1 and home 2 – both highly recommended for families and both are walkable to town. We have also stayed at the Marina Grand Resort a few times and love it! It’s crazy expensive in the summer, but prices are much better in the winter. They have an indoor pool, a very small game, room, suites that come with kitchens, and an on-site restaurant! It’s right on the water. It’s beautiful!

weekend trip from chicago winter

Kenosha, Wisconsin

If you want to go skiing, we went to Wilmot Mountain which is about 50 miles outside Chicago. It’s an easy drive! You could easily do it in one day, but we decided to stay overnight in Kenosha, which is about 20 minutes from Wilmot.

We stayed at the Apis Hotel, a small boutique hotel and restaurant. It’s new and gorgeous! Walkable to downtown coffee shops like the Buzz Cafe and restaurants. Sazzy B is a good bar/restaurant! There’s a pretty path along the lake and a Kenosha public museum close by.

As for skiing, we loved Wilmot! Highly recommend a ski lesson if you’re a beginner like me.

weekend trip from chicago winter

Des Moines, Iowa

Des Moines, Iowa is such a cute little town. It’s family-friendly with also plenty to do if you want to make it a girl’s getaway or romantic weekend. Stroll the super cool Pappajohn Sculpture Park and then have dinner at the festive Exile Brewing (reservations recommended). The Science Center of Iowa is an interactive museum that is great for kids! Des Moines offers lots of holiday light shows, like the Jolly Holiday Lights at Adventureland Park and Gingerbread Lane , a neighborhood where 31 homes participate in telling an original Gingerbread story. Another favorite restaurant is Lachele’s Fine Foods !

weekend trip from chicago winter

Indianapolis, Indiana

Indianapolis, Indiana is about a 3-hour drive and it’s great for kids! The Children’s Museum of Indianapolis is phenomenal and can keep those kids busy all day. If the weather isn’t too frightful, visit 100 Acres: The Virginia B. Fairbanks Art and Nature Park for hiking, playing, and exploring. The Garden at Newfields has a Winterlight Show and for dining, I recommend: Almost Famous tapas bar, Festiva for Mexican cuisine, and Big Bear Biscuits for brunch!

weekend trip from chicago winter

Hopefully, some of these have inspired you to get outta town this winter season! If you need other winter or Chicago staycation things to do, check out my winter holiday hotel guide HERE .

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If you desperately want to go somewhere but have only a couple of days to spare, try one of these seven getaways — all within a three-hour drive.

As the pandemic continues to evolve, please check with venues before you go and stay up to date on current COVID-19 protocols.

An Artisan Shopping Trip

Bottleworks Hotel

Indianapolis • Drive time: 3 hours ■   ■   ■ When the swanky Bottleworks Hotel (from $249; bottleworkshotel.com ) opened last December in Indy’s old Coca-Cola plant, it sparked a boom in its 12-acre Bottleworks District . Make a beeline to Good Neighbor for stylish and responsibly made clothing brands, Pumkinfish for stocking stuffers, and Woodhouse Day Spa for its salt therapy room. Later, sip an Old Pretender with fig-infused Scotch at the new apothecary-themed Sundry and Vice before an indie flick at the eight-screen Living Room Theaters .

Extra: Continue on Indy’s buzzy Massachusetts Avenue for more options, including FortyFive Degrees , a sushi bar with a window made for people-watching, and College Avenue’s Penn & Beech Candle Co.

A Romantic Culinary Affair

Illustration by Kate Pullen

Galena, Illinois • Drive time: 3 hours ■   ■   ■   ■   ■   ■ Once upon a time, beef Wellington was the reason to dine at the Goldmoor Inn (from $305; goldmoor.com ), an elegant B&B overlooking the Mississippi River. Now there’s another: new executive chef Brandon Veitch (formerly of the Lobby at the Peninsula Chicago), who’s whipping up dishes like slow-braised short ribs with shaved black truffles. Afterward, get comfy in your choice of 13 suites, three cottages, and two log cabins (one that’s pet friendly). The cabins are especially secluded and winning in wintertime, if only for the breakfast delivered to your door.

Extra: December in Galena is a festive affair, so take in any number of cheery events, including Classical Blast’s Dark Side of the Yule concert (December 10); Night of the Luminaria, featuring a candlelit classical music concert (December 11); and the Goldmoor’s seven-course New Year’s Eve menu.

A Woodland Retreat for Grownups

A Kohler cabin

Kohler, Wisconsin • Drive time: 2 hours 25 minutes ■   ■   ■   ■   ■ You’ve heard about the resort’s over-the-top spa and championship golf courses, but recent additions are turning Destination Kohler ( destinationkohler.com ) into an unexpected all-seasons gem. Hotel accommodations include the American Club (from $191), but a dreamy itinerary for couples or adult groups starts with one of four super-luxe two- to four-bedroom cabins in the woods — or on a pond or Lake Michigan — each outfitted to the nines with full kitchens (from $1,029). From there, plan on ice bowling and snowshoeing at the 500-acre River Wildlife, a proper spa day (duh), and private dome dining at the Taverne on Woodlake.

Extra: Meander the free new Art Preserve near Kohler. The museum’s exterior is a striking mix of concrete and soaring timbers; the unique artist-built environments inside were all created using found objects.

A Sleepaway Camp With Your Dog

Lake Delton, Wisconsin • Drive time: 3 hours ■   ■   ■   ■ The perfect holiday gift for you and your pooch: winter camp at Camp Dogwood (January 7–9, $495 per human for up to two dogs, campdogwood.com ), a lakefront camp set on 700 acres. The price includes your own room and bathroom, all meals, and a slew of indoor and outdoor events geared toward both newbies and pros in the world of organized dog activities. Each day, choose from barn hunts, canine circus school, sheep herding, pet projects (read: arts and crafts), pack walks through the woods, and as many naps as you like. At night, guitar music and a big campfire are the backdrop for a Champagne toast under the stars.

Extra: Not a dry eye will be found when dog sledding begins and every pup — from blind dogs to tiny Cavaliers — has its day.

A Snow-Packed Family Adventure

Lake Geneva, Wisconsin • Drive time: 1 hour 30 minutes ■   ■   ■   ■   ■ Give in to the first snowfalls of the season with a spontaneous trip to Grand Geneva Resort & Spa ( grandgeneva.com ). Take your pick of anything from skating and sledding to snowshoeing to a perfect 20-run hill for ski and snowboard lessons. Sip hot chocolate inside the new club lounge while warming your bum by the fire, or go for a jaunt to the nearby Timber Ridge Lodge & Waterpark.

Extra: You could have groceries delivered and make dinner in your modern villa (from $50), but then you couldn’t stuff your face in a private igloo with a well-earned dry-aged steak from Geneva ChopHouse , which has a new heated patio.

An Instant Escape at a Luxe Inn

Deer Path Inn

Lake Forest, Illinois • Drive time: 35 minutes ■   ■   ■   ■ Expect to be enamored with the 57-room Deer Path Inn ( thedeerpathinn.com ), a hop-skip from the city but seemingly worlds away. Step up to a wooden reception desk backed by a wall of room keys, and the high-touch service will whisk you to posh rooms with Frette linens and massive suites with tubs filled by a ceiling waterfall. Then warm up with a glass of Cabernet by the fireplace, all part of the charm of this English manor–inspired hotel. Dinner reservations are coveted, so get yours in advance for the Bar, English Room, and brunch on the heated courtyard patio (a beauty even in winter). Steps away, find bougie boutiques.

Extra: The Deer Path Inn is as fancy as it is playful. Think private mixology classes in a cellar, outrageous holiday cocktails, festive packages for grandparents, and one of the most entertaining, binge-worthy hotel Instagram feeds we’ve seen ( @deerpathinn ).

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  • Activities for Kids

Winter Escapes a Road Trip Away from Chicago

weekend trip from chicago winter

Get out of the house this winter and discover three amazing winter getaway destinations

Staycations are great , but being away is sometimes just what we need. Kids dig hotel stays for the chance to sprint down long hallways and jump like monkeys on the bed. Parents love vacation for the squad-bonding opportunity, replacing the same ole for a new scene and having someone else make the bed for a change. Find great winter destinations that allow for time in the great outdoors and lots of memory-making.

The American Club - Kohler, WI

weekend trip from chicago winter

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Buckle the kids in for a drive 145 miles north of Chicago to the city best known as home to the Kohler company, recognized for its high-quality faucets and bathroom products. But you don’t need to come for the potty talk, folks. Sit back and enjoy all this town has to offer.

For a romantic couples getaway or girlfriends' retreat to the spa, the five-star The American Club and the contemporary The Carriage House guest rooms are your go-to spots. The adults-only atmosphere provides a nice break from any school-year chaos and you and your travel mates will be treated to complimentary yoga, indoor cycling, a Himalayan salt stone lamp, Peloton stationary bikes are provided in select suites and a Wellness Concierge helps to maximize your time and experience.

Families will be more comfortable in the private cabins with gorgeous views, or at the Inn on Woodlake , which features boutique-style guest rooms as well as multi-bedroom suites. They even have a limited number of dog-friendly rooms, so the family pet can tag along.

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Kids stay happily entertained with oodles of family activities that include zombie dodgeball, TopGolf swing simulator, indoor tennis lessons, ice skating, hiking, snowshoeing, sledding, and fat tire biking. If you're in need of time in the kid-free zone, register for the Saturday evening Kidz Dinner and Movie. Kids will enjoy a night of food, movies, and games, while you dine, explore the onsite spa or just catch some much-needed zzz’s. As a bonus, when receiving services at the spa, you can utilize the childcare for at Kids Core at the Sports Core Health & Racquet Club just minutes away.

Add a little culture to your itinerary and visit the John Michael Kohler Arts Center located just five minutes away. With the Art Center's help, stay outside, by taking The Sheboygan Project Walking Tour , which brings the street art movement to Sheboygan. The urban landscape and available wall space is the canvas for works that reflect the city's people and culture.

French Lick Resort - French Lick, IN

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Peace. Quiet. Relaxation. You might have forgotten the meaning of the words, but you’ll quickly recall them at the French Lick Resort in this quiet town snuggled aside a sulfur spring in the southern Indiana woodlands.

This sprawling getaway spot is known for KidsFest , an indoor-outdoor area dedicated to little travelers. Activities include bike rentals, bowling, an arcade, arts and crafts projects, cooking classes, horseback riding, and video games. There’s also an indoor pool, footgolf, horse-drawn carriage rides, and several family-friendly restaurants onsite.

If you find yourself with kid-free time and can resist the urge to nap, bathe in the rejuvenating mineral springs, leave your stress at the spa, shop the Promenade or play the odds at the casino.

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You can easily spend days without leaving the hotel, but it’s worth exploring the area. Nearby Hoosier National Forest has miles of hiking, biking, and horseback riding trails;  Patoka Lake  is a pretty place for anglers-in-training to cast a rod; and  Morengo Cave is full of gems that you can mine for and take home.

For western-style fun, check out a working cattle ranch and go ziplining, ATV-riding, see a drive-thru lights show, and experience a Drive-Thru Safari Park to see more than 40 species of animals at Wilstem Ranch . Even if the weather isn’t cooperating, you can put on your swimsuit and dive into 40,000 square feet of slides, drops, lazy rivers, and wave pools at Big Splash Adventure Indoor Water Park .

Lake Lawn Resort - Delavan, WI

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This getaway spot has a history that is 130 years rich and is situated in tranquil woods 90 miles northwest of Chicago in Delavan, Wisconsin. Evidence of the land’s Native American beginnings can be seen in the property’s 40 remaining effigy mounds, the largest collection in southern Wisconsin. It was also once the longtime headquarters of the largest traveling circus of its day, Mabie Brothers US Olympic Circus.

A great time to plan a Lake Lawn Resort adventure is in the winter for all of their winter fun activities. Take the kids sledding down the Rudy Lange Sledding Hill or go explore a historic site or museum and learn something new.

No matter when you make your way north, there are plenty of activities to keep this vacation from heading south. With four restaurants (ranging from fine dining to classic bar and grill), an arcade to display your Dance Dance Revolution prowess, and a spa to massage any twerking injuries, you never need to leave. Go for a swim in the heated indoor pool, make a craft in the Kids Zone, or go cross-country skiing, ice skating, or snowshoeing.

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You could easily hole the family up in the resort and never leave, but The Dancing Horses Theatre located nearby is worth venturing away from the cozy fire. Trainers treat guests to a parade of equestrian showmanship, followed by the mischievous antics of an exotic bird show that will leave the kids in a fit of giggles.

Nearby Lake Geneva hosts the U.S. National Snow Sculpting Competition during the village’s annual Winterfest , Feb. 1-5. Festival-goers are treated to the intrigue of snow sculpting as well as music, helicopter rides, laser tag, s'mores, bonfires, and dog sled races.

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9 easy must-do weekend trips from Chicago

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: 

Weekend trip to Dubuque from Chicago

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. 

Chicago weekend trip to Grand Rapids, MI

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.

Weekend trips from Chicago to Lake Geneva

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. 

Trip for the weekend from Chicago to Madison

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 weekend trips from Chicago

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.

Easy weekend trips from Chicago

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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BEST Weekend Getaways From Chicago in 2023 (From a Local)

The best weekend getaways from Chicago in 2023 whether you love nature, beaches, cities or small towns. From romantic getaways for couples to fun vacations for friends or families, there is something for everyone on this list.

Best Weekend Getaways From Chicago

Looking for the best weekend trip from Chicago? Fortunately there are many places in the United States (and even Canada) that are a short drive or flight away. You will love these weekend getaways from Chicago – from amazing places in the Midwest that you can easily drive to from Chicago to a few incredible cities that are only a short flight away.

(And make sure to check out my  essential road trip packing list (with free printable pdf) if you are driving or my carry on packing list  to make sure you have all your travel essentials before you go!) Disclaimer: This article contains affiliate links. I may make a small commission if you make a booking using my links at no extra cost to you. As an Amazon Associate I earn from qualifying purchases.

Lake Geneva, Wisconsin

Lake Geneva Wisconsin is one of the best weekend getaways from Chicago

Lake Geneva, a resort city on the shore of Geneva Lake is a popular vacation destination from Chicago. In fact, wealthy Chicagoans built their mansions here during the Gilded Age. Visitors can still get an up close view of these beautiful homes by walking the 20 mile Geneva Lake Shore Path around the lake.

If being in the water is more your thing, you can rent just about anything (speedboats, jetskis, kayaks, pontoons, etc) for an adventurous day. While Lake Geneva is a great place for some beach fun, visitors can also enjoy zip-lining, a waterpark, golf, a petting zoo, spas and more.

Lake Geneva is also a great destination for a winter weekend getaway as visitors can go skiing and snowboarding or visit the ice castles .

Read about the best things to do in Lake Geneva here .

Stay: Grand Geneva Resort & Spa

Getting There: By Car: Lake Geneva is only 83 miles from Chicago

Elkhart Lake, Wisconsin

Elkhart Lake is a less known weekend getaway from Chicago

Elkhart Lake is a quaint town where visitors can really experience an authentic summer lake getaway but also enjoy the year-round offerings. Take a dip in the crystal clear waters, experience the various watersports (paddleboarding, kayaking, jet skiing), go fishing or just lounge around on a pool float.

While the lake is a big draw, there is so much more to the area. From hiking the picturesque Kettles, The Ice Age Trail or along the shore of Lake Michigan, there is no shortage of beautiful hiking spots. Golf enthusiasts will appreciate the top golf destinations located less than 30 minutes away. Motorsports lovers and thrill seekers will want to check out Road America Racetrack , North America’s longest natural road racing facility.

The fun doesn’t end when summer is over. Dog sledding, snowshoeing, skiing and carriage rides are available for winter time fun.

Stay: The Osthoff Resort

Getting There: By Car: Elkhart Lake is 150 miles from Chicago (about 2.5 hour drive)

Galena, Illinois

Galena Illinois is one of the best weekend getaways from Chicago

Galena is short road trip from Chicago but it is a great place for a weekend getaway whether on a romantic trip or traveling with kids. Galena is a charming and historic small town. A large portion of the city is listed on the National Register of Historic Places and there are many historical sights to explore including the Ulysses S. Grant Home, the Elihu B. Washburne House, Dowling House and the Old Market House.

Some things to do in Galena including shopping downtown at the many boutiques and antique stores, eating at local restaurants and wine tasting at local vineyards or exploring the lush rivers and hiking trails dotted throughout the area. Galena is close to Apple River Canyon State Park , an Illinois state park, where you can go hiking, fishing and more.

Stay: Country Inn & Suites by Radisson

Getting There: By Car: 164 miles driving distance from Chicago

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Dubuque, Iowa

Dubuque, Iowa’s oldest town, is located across the Mississippi River about 20 minutes from Galena, Illinois. With its historic architecture and hilly landscape, Dubuque is worth visiting year round.

Some of the best things to do in Dubuque including visiting the 14-acre National Mississippi River Museum & Aquarium and enjoyng spectacular views of the river from Eagle Point Park .

From April though November, visitors can ride Fenelon Place Elevator Company (also known as the Fourth Street Elevator), a historic cable car. This funicular railway has been called “the world’s steepest, shortest scenic railway” and has great views of downtown Dubuque, the Mississippi River and 3 states.

Winter activities include skiing and snowboarding at Sundown Mountain Resort, cross country skiing, snowshoeing and hiking.

Stay: Hotel Julien Dubuque

Getting There: By Car: Dubuque is 178 miles from Chicago (just over a 3 hour drive)

Milwaukee, Wisconsin

Milwaukee is famous for its beer -it is nationally recognized with the nickname “Brew City” due to its nearly two centuries of brewing heritage from multiple past major brewers including Miller Brewing Company, Pabst Brewing Company, and Joseph Schlitz Brewing Company. One of the best things to do in Milwaukee is to tour one of its many breweries. Another interesting attraction is the Harley-Davidson Museum.

Stay: Brewhouse Inn and Suites (boutique hotel housed in what was once the main Pabst brewery building)

Getting There: By Car:   93 miles driving distance By Train: Amtrak Hiawatha train offers frequent daily service between Milwaukee and Chicago. By Air: It probably does not make sense to fly but there are daily nonstop flights from Chicago O’Hare to Milwaukee Mitchell International Airport (MKE)

New Buffalo, Michigan

New Buffalo, Michigan is a charming beach town on the shores of Lake Michigan. The beaches face west and have beautiful sunsets.

In addition to the beaches, a must see attraction is Galien River County Park , a beautiful park with boardwalk paths through the marsh.  For those that enjoy gambling, New Buffalo is home to the Four Winds Casino Resort .

Getting There: By Car: 70 miles driving distance By Train: New Buffalo has daily Amtrak service from Chicago on the Blue Water and Wolverine lines.

South Bend, Indiana

One of the best things to see in South Bend is the Studebaker National Museum , featuring a large collection of Studebaker automobiles drawn from the history of the company, beginning with horse-drawn carriages. They also have the carriage that Abraham Lincoln took to Ford’s Theater the night he was assassinated.

For those with a sweet tooth, visit the South Bend Chocolate Company, which is home to one of the largest collections of chocolate memorabilia in the world, including a 1,300-year-old Mayan chocolate pot among the hundreds of tins, containers and chocolate boxes of all shapes and sizes.  Visitors can take a factory tour for a history lesson of chocolate and its origins, as a guide leads guests through all of the factory processes, including panning, enrobing and more, including a test sample at the end. For an extra special treat, you’ll dip a chocolate spoon, walk through the Chocolate Museum and receive 10% off your purchase that day.

South Bend is famous for being home to the University of Notre Dame. There are many attractions on the beautiful, large campus including the Golden Dome, Notre Dame Stadium, the Basilica of the Sacred Heart and the Grotto of Our Lady of Lourdes, a replica of the famous shrine.

Stay: Aloft South Bend or Morris Inn at Notre Dame (if you want to stay on-campus)

Getting There: By Car:   96 miles driving distance By Train: South Shore Line commuter rail runs multiple daily trains between Millennium Station in downtown Chicago and South Bend Airport station. By Air: United Express has multiple daily flights from Chicago O’Hare and South Bend International Airport (SBN)

Madison, Wisconsin

In addition to being the capital of Wisconsin, Madison is a fun college town full of cafes, breweries, restaurants, bookstores and other attractions. For those that enjoy being outdoors, Madison is a good base for nature-filled activities in the area including hiking, biking, fishing and boating.

Getting There: By Car: 147 miles driving distance from Chicago

Holland, Michigan

Located on the shores of Lake Michigan, the city of Holland, Michigan, which was founded by Dutch Calvinists in the late 1840s, proudly flaunts its Dutch origins, and is home to canals and a 250-year-old authentic Dutch windmill.

Holland is especially pretty in the spring when you can see colorful tulips in local gardens, parks, attractions and lining the streets. You can see millions of tulips at Veldheer Tulip Gardens . One of the mont popular times to visit is during the Tulip Time Festival , the largest tulip festival in the United States which is held every year in May.

Stay: Courtyard by Marriott Holland Downtown

Getting There: By Car: 150 miles driving distance from Chicago

Door County, Wisconsin

Door County , located in the northeast corner of Wisconsin, is a hidden gem full of charming villages and towns, lighthouses, state parks, vineyards, and outdoor attractions and activities.

Sturgeon Bay is a convenient base for exploring the area. The city is a fisherman’s mecca, with some of the best bass fishing in the world. You can also tour a restored tug, visit the Door County Maritime Museum, learn the history of Door County, stroll down historic 3rd Avenue, or enjoy nature at Potawatomi State Park on the city’s edge.

Explore one or more of several little towns located along the east and northeast coastline of Door County which full of unique shops, galleries, restaurants and breweries.

Bring your car or bike on the 30 minute ferry to Washington island, located northeast of the tip of the Door Peninsula.

Stay: Sturgeon Bay, Egg Harbor, Fish Creek, Bailey’s Harbor or Sister Bay all have good options

Getting There: By Car: 244 miles driving distance to Sturgeon Bay

Shawnee National Forest

Nestled between the Mississippi and Ohio Rivers in southern Illinois, the Shawnee National Forest is full of natural beauty, making it ideal for outdoor recreation from hiking to climbing.

The stunning Shawnee National Forest landscape features woodlands, hills, lakes, creeks, rock formations, cliffs and bluffs. You can also see wildlife such as bad eagles.

Shawnee National Forest is the best place to go hiking in Illinois with spectacular views. Trails include the long River to River Trail and the Rim Rock National Recreational Trail. The must see attraction is the Garden of the Gods wilderness area featuring ancient sandstone cliffs and formations.  Climbers should not miss the Jackson Falls climb on 60 feet of sandstone cliffs and boulders that include numerous freestanding towers.

If you enjoy wine, The Shawnee Hills Wine Trail features 11 wineries located along a 35-mile scenic drive along highway 127 and highway 51 in the Shawnee National Forest.

Stay: Riverview Mansion Hotel (a unique boutique style mansion)

Getting There: By Car: 300 miles driving distance from Chicago

Do you prefer to fly rather than drive? Here are a few cities worth visiting for the weekend that are only a short flight away.

Toronto, Canada

Canadian bucket list places to visit in canada during the summer

Although Toronto is in a different country, it is only a short flight away. You can even drive there in one day but that is long drive unless you have a long weekend.

Toronto is very similar to Chicago in that it offers great theater, shopping and restaurants. The CN Tower, the tallest freestanding structure in the Western Hemisphere is a must see attraction. If you are feeling brave, try the EdgeWalk, a walk outside on the ledge encircling the top of the CN Tower. Other must see places are St. Lawrence Market and the Distillery District.

Looking for more things to do in Toronto? Here is a 3 days in Toronto itinerary written by a local.

Stay: Fairmont Royal York (located right by Union Station)

Getting There: By Air: Several airlines offer nonstop flights between Chicago O’Hare and Toronto Pearson International Airport (YYZ) which is approximately a 1.5-2 hour flight. By Car:   523 miles (about 8.5 hour drive)

Atlanta, Georgia

Atlanta, Georgia is another great city for a weekend getaway especially if you want to indulge in some southern food.  Some must see attractions (especially for families) include Piedmont Park, Georgia Aquarium, College Football Hall of Fame and the World of Coke. Here are the best things to do with 2 days in Atlanta .

Getting There:

By Air: There are numerous flight options between Chicago and Atlanta from both Chicago O’Hare and Chicago Midway. Flight time is approximately 2 hours.

New York City

New York City is an easy city to fly to for the weekend. Here are the best things to do with 2 days in NYC .

By Air: There are numerous flight options between Chicago and New York City from both Chicago O’Hare and Chicago Midway. Flight time is approximately 2 -2.5 hours.

What are your favorite weekend getaway from Chicago ?

Related Posts

30+ BEST Things to Do in Chicago in the Summer 2023 (From a Local)

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VickyFlipFlopTravels

19 Awesome Road Trips from Chicago (with Timings)

Keeping your introduction to road trips from Chicago short and simple, let’s take a look at the summer, winter and weekend favourites!

The city of Chicago is awesome and all, but it’s also a great starting point for some great Chicago road trips. The city’s prime location acts as a portal to the Midwest – from historical cities to sprawling state parks and urban-stress-relieving beer. 

chicago road trip

Best Chicago Road Trips in Summer

If you’re looking for one of the longest Chicago road trips, how about driving from Chicago to New Orleans ? If you’re thinking a little shorter, then read on…

Do you need a rental car for your road trip? Check out the award-winning comparison site Discover Cars for the BEST DEALS the world over. Book early for the best price!

Distance: as far as you can go

No American road trip is complete without covering some part of classic Road 66 – of which, lucky for us, kicks off in Chicago!

road trips from Chicago

Snap a selfie at the official sign between East Adams and South Michigan Avenue then check-off stops such as the Gemini Giant, the Pontiac murals, Lincoln Presidential Library and more. If you can spare a month, make it all the way down to the Pacific Ocean.

best road trips USA

2. Illinois’ Great River Road

Distance: 3.5-hour drive

In a seemingly never-ending chain of historical sites and activities, the drive along Mississippi River to East Dubuque is one of the best road trips from Chicago.

Chicago road trips

Moline and Rock Island are two cool detours but you can head straight for East Dubuque for its Chicago Great Western Railway Depot Museum. John Deere Pavilion lets you hop from car to farm machines, while the city Nauvoo shows off many historic homes. 

3. Lake Michigan to South Haven

Distance: 2.5-hour drive

Escape the heat by packing your car with beach gear and setting off for a nice drive around Lake Michigan and towards South Haven.

Road adventures Lake Michigan

There are plenty of berry farms along the way so you can stain your hands with blueberries; or maybe you prefer to climb up a lighthouse?

To take your road trip even further, bring a bike! Cruise along the water front; take a dip or two. 

Do you have a favourite road trip quote? Click for the best long drive quotes to inspir e your next adventure!

4. Shawnee National Forest

Distance: 6-hour drive

One of the longest Chicago road trips on the list, it’s more than worth it to visit Shawnee National Forest. In fact, plan to camp amidst the spectacular range of landscapes for one of the best driving trips from Chicago!

Chicago days out

Local favourites include the Garden of the Gods – you’ll find super special rock formations like Anvil Rock. Little Grand Canyon and Bell Smith Springs feature moderate hikes; Inspiration Point offers panoramic views over the prairie, Mississippi River and the forest.

Not convinced? Shawnee Hills Wine Trail is a brilliant drive that links up vineyards and wineries in the area – a great stop on a road trip from Chicago.

How about driving from Chicago to Atlanta? Here’s my guide to the best stops on a Chicago to Atlanta road trip , just for you.

Best Chicago road trips in Winter

If you want the best road trips from Chicago when it’s colder and darker, then these are the best ones for you.

5. Grand Rapids

Distance: 3-hour drive

After just long enough of a drive, pull into Grand Rapids for a nice sweep of activities. The Beer City Ale Trail will keep you road-tripping on foot (or car, if you have a Designated Driver); or wander through Downtown Market for food adventures instead.

Chicago road trips

Warmed by booze, drop by the 158-acre Frederik Meijer Gardens & Sculpture Park where their installations are bright pops of colour against an all-white backdrop. 

6. Muskegon

Speaking of unusual winter activities, I’ve heard so much about Muskegon Winter Sports Complex. Just an hour from Grand Rapids, it’s a great next stop on your Chicago road trip.

Chicago road trip adventures

Their Olympian-designed ice-luge course is perfect for beginners, spanning 850 feet of forested speed racing. Muskegon is also home to USS Silversides Submarine Museum if you’re into marine vehicles, and there’s a great pier and lighthouse too.

7. Indianapolis

When temperatures are cold, cold, cold – you might opt for staying indoors. The city of Indianapolis is one of the best road trips from Chicago during winter because of its incredible indoor entertainment: museums.

Chicago road trip

From the Indianapolis Museum of Art to the Indianapolis Children’s Museum to quirky Indiana Medical History Museum, you can escape the cold all day!

Of course, drop by famous City Market for great eats and then maybe go on a catacombs tour underground too. This makes for one of the best road trips from Chicago.

8. Boyne Mountain Resort

Distance: 5-hour drive

Michigan winters are best captured with the ski resort of Boyne. Drive past snowy landscapes to reach 850 acres of skiing, snowmobiling, dogsledding and photography escapades.

Boyne Mountain Chicago

While the forested grounds offer romantic snow-covered views, don’t miss out on the epic zip lines that take you through the trees and slopes. 

If you like your road trips from Chicago with a bit of snow and ski thrown in, then this is a great option for you.

Your ESTA for the USA

Before you go to the USA make sure you have your ESTA organised. You can find help with this on this link: https://www.application-esta.co.uk/ESTA-guide . It doesn’t take long and organising it beforehand will make things go that bit smoother at the airport.

9. Apostle Islands

Distance: 7-hour drive

Does driving over ice count as going off-road?

chicago road trip

It’s an unforgettable journey to Apostle Islands National Lakeshore as winter ice freezes thickly to transform water into road, ending with stunning ice caves!

Make sure to visit the only inhabited Madeline Island as well for a cool wind sled experience and hot tub stay. 

Day Road Trips from Chicago

10. lake geneva.

Distance: 1.5-hour drive

Chicago’s number one when it comes to day trips, Lake Geneva is one of the best lake town’s in the US.

Road trips from Chicago

Downtown boasts all the food and drinks you need for the inevitable food baby; you might even land a booze cruise.

Hot air balloon rides, Lake Shore Path, ziplines and even ski slopes make it a year-round place to visit. It’s a multi-visit destination for sure!

11. Harbor Country

Distance: 1-hour drive

Wind between the towns of Michiana, Grand Beach, Three Oaks, New Buffalo, Lakeside, Union Pier, Harbert and Sawyer. This Chicago road trip will have you hopping between wineries and breweries, not to mention the beach.

Road trips through chicago

It’s so close to the city, but the sand dunes and soft grasses make it a wholly different world. 

12. Starved Rock State Park

Distance: 2-hour drive

Families and romantics will love Starved Rock State Park for reasons that include: 13 miles of hiking, 18 canyons, free entry and nature-surround lodge.

It’s a great location to unplug for a day as you hunt down natural rock pools, waterfalls and incredible moss-strewn glades. You can even visit in the winter for cross-country skiing and cuddles in front of expansive mountain views. 

13. Saugatuck 

Making up Lake Michigan’s “art coast of Michigan”, Saugatuck and its neighbours (Fennville and Douglas) are house dozens of art galleries!

weekend trip from chicago winter

Unique and LGBTQ+-friendly shops feature alongside artsy hubs to make it a super welcoming town. Of course, famous Oval Beach appeals with soft dunes and paddleboat rides too. From craft booze tours to fruit picking and corn mazes, it’s one of Chicago’s best road trips.

14. Elkhart Lake

I won’t spoil it for you but this 292-acre lake and nearby Kettle Moraine State Forest is truly a place to unwind from the crowds.

Road trip in Chicago

You can hike the epic Ice Age National Scenic Trail or bike down Old Plank Road Trail. Pumpkin patches, race-tracking and fishing are all inclusive!

Want a charming hideaway? This is it.

Road Trips 4 hours from Chicago

Want your road trips from Chicago for a special weekend? Then these Chicago road trips are only 4 hours away.

15. Ann Arbor

If you’re looking for an all-season destination, Ann Arbor is the perfect road trip from Chicago.

driving from chicago

Huron River entertains with kayaking, paddle-boarding, tubing and swimming; Matthaei Botanical Gardens and Nichols Arboretum displaying beautiful foliage. Definitely spare some time for Kerrytown Market and Shops for all their indie offerings! 

16. Door Country

Also called ‘Cape Cod of the Midwest’, Door Country is a 70-miles-long basket of fun!

You’ll never get tired of exploring its orchards, coves, lighthouses and wineries. Away from the light pollution, Newport State Park offers stunning starlit skies while Ephraim is all the small-town charm you need. Just imagine – 300 miles of coastline.

You can reach Galena under 4 hours but I recommend taking your time. Pull up through scenic rolling hills to go back in time because the Galena Historic District is made up of cobblestone streets and over 1,000 buildings from the 19 th century.

Day trips from Chicago

For those non-history buffs, Chestnut Mountain opens as a ski resort in the winter; Stagecoach Trail and Apple River Canyon State Park are open year-round. 

18. Richland County

To really escape from people, Richland County is a rural road trip destination where you can bunk for the night. But away from the isolated and lush property of Candlewood Cabins are fields and hills that keep you outdoors all day.

The Ridge Road and Pine River Recreation Trail fulfils all your adventurous needs – where else would you find wildlife while biking over abandoned railroads?

You also have three rivers and five state parks within an hour’s distance, and the lovely 100-mile Lower Wisconsin River Scenic Byway for more driving way. 

19. Huron-Manistee National Forest

Michigan really surprises us again and again!

Huron-Manistee National Forest

Along the peninsula is the expansive Huron-Manistee National Forest, one of the best road trips from Chicago if you are a nature enthusiast. A single paved road takes you through dense forest (beautiful in the fall) to parking areas so you can hike your way through the serene space or canoe on the rivers. 

Road trips from Chicago

Of course there are loads of great things to do in Chicago but visiting Chicago really opens up a world of opportunities when it comes to road trips.

VickyFlipFlop up the Skydeck

Whether you’re taking the car out for an hour-long spin or you’re willing to buckle down for a few hours, you won’t be disappointed by the scenery along your journey or the fantastic destinations ahead. 

Related Posts:

  • 7 Ways to Make the Most of Your Road Trip Budget
  • 57 Coolest Things to Do in Chicago for 2023
  • Planning a Road Trip in the USA: 13 Best Routes!
  • Christmas Things to Do in Chicago in Winter: 21+…
  • 11 Unique Stops on the Drive from Chicago to Atlanta
  • 14 Awesome Stops on a Chicago to New Orleans Road Trip

Hi, I'm Vicky! I wrote this. You can find me on all the social media @VickyFlipFlop. I love a bit of adventure, will try anything once, and have a strong passion for the local food and drink, whatever it may be. I'm here to help inspire you to travel to places a little out of your comfort zone, or at least to explore the usual destinations in a different way. Stay, have a look around, and if you have any questions – let me know below.

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Vacation packages from Chicago

Search our inventory of vacation deals to find the best vacation packages from Chicago. Whether you’re planning luxury trips or cheap vacations from Chicago, when you bundle flights or car rentals with your hotel you can earn savings. To book a cheap vacation package from Chicago, view our current offers! A good tip to save more is to stay flexible with dates, hotel location and amenities, flight details, and car rental types and providers so you can compare multiple options and get the best deals.

Plan a friends’ getaway with one of our vacation packages to Miami or head to the Big Apple with a package trip to New York . Book one of our vacation packages to Las Vegas for a few days of winning big.

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We source amazing deals on weekend getaways from Chicago for all types of travelers. Book one of these romantic hotels in New York with your loved one, or plan a trip that the kids will love with one of our weekend family getaways from Chicago. Look out for our family-friendly filter!

During the cold months, take a quick flight south (perhaps Austin, Texas, or Miami, Florida) for warm weekend getaways from Chicago. And when you want to hit the slopes, there are various skiing and snowboard destinations nearby in Michigan for winter weekend getaways from Chicago.

Great road trips from Chicago

There are many options for good road trips from Chicago, including those to lakeshore towns in Michigan or Wisconsin. For an extended vacation, take a road trip from Chicago to New York, where you can relax after a day of exploring the city at your hotel with a spa or pool. No matter where your 2024 road trips from Chicago may take you, explore Expedia’s amazing car rental deals sourced from various providers—all at attractive prices.

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Book an all-inclusive vacation from Chicago to exciting destinations. Take quick getaways from Chicago to the beach or longer trips to mountain towns or other large cities. For inspiration, check out our deals on all inclusive resorts across the US . To save more on your trip, bundle your travel into an all-inclusive vacation package from Chicago.

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Check “Free cancellations” or “No change fees” when planning your trip for flexibility. Some package bookings for getaways from Chicago are eligible for refunds, but check your itinerary to confirm. Visit our customer service portal for assistance.

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Winter road trips

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Forget that trip to Cancún—you're too old to party with spring breakers at Señor Frog's anyway. The getaway you seek is right under your chilly nose. From catching air at a snowboard park to catching up on your sleep in a rustic log cabin, these Midwest road trips feed your need to leave the city.

College towns

College towns

Hanging out in a college town as a non-student can be a blast, especially when you're not on that ramen budget anymore.

Snow sport getaways

Snow sport getaways

You don't take your vacations sitting down. A winter getaway has to involve skis, sleds, snow and a surge of adrenaline.

Winter spa getaways

Winter spa getaways

Check out the best relaxing Midwestern resorts and hotels for a winter getaway.

Quaint and quirky winter getaways

Quaint and quirky winter getaways

Escape traffic, smog and other urban irritations for these quaint and quirky getaways.

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10 family-friendly winter weekend getaways in the US

When I'm looking for a surefire way to beat the post-holiday blues, I plan a winter weekend getaway for the family. With a couple of long weekends on the calendar in the first quarter of the year, plus the ability to create your own whenever works for you, winter is an ideal time to get a fun trip on the schedule.

Whether you want to play in the snow or escape the cold for a balmier location, there’s a winter weekend trip within an easy drive or flight from where you live. Here are 10 of my favorite ideas for a memorable and fun-filled, family-friendly long weekend trip.

WHERE TO GO: 25 best family vacation spots in the U.S.A.

1. Nashville, Tennessee

I took my teenage daughter on a winter getaway to Nashville, and it was a perfect destination for a not-too-cold long weekend. Each morning began with our own DIY coffee shop-boutique hotel tour, starting the day with breakfast, a cup of coffee, and a stroll through the lobbies at the Fairlane Hotel, Bobby Hotel, and Noelle Nashville.

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Then we set off on foot (and one day by trolley) to experience Music City at spots like the Country Music Hall of Fame and Museum, Ryman Auditorium, and the highly impressive and interactive National Museum of African American Music. 

Food’s a big draw here, and we tried as much as we could by taking a food tour with Walk Eat Nashville and eating at Assembly Food Hall, which offers food and drink from more than 30 mostly local eateries and bars.

Where to Stay in Nashville: The Countrypolitan Nashville is a stylish and well-situated home base for exploring downtown Nashville, and you just might hear the next big thing performing at the hotel’s restaurant in the evening.

2. Crystal River, Florida

Winter is an ideal time to visit this city on the west coast of Florida, about an hour north of Tampa and less than two hours west of Orlando. That’s because winter is known as Manatee Season. Between November and March, hundreds of West Indian manatees head to the warmer spring-fed waters in these parts once the water temperature in the Gulf of Mexico drops. 

OCEANSIDE FUN: 10 best family beach resorts in Florida

The “Manatee Capital of the World” is the only place in the U.S. where you can legally observe manatees while swimming alongside them (accompanied by local guides who make sure everyone behaves properly). 

If you don’t want to get in the water, you can spot the gentle creatures on a boat tour or at places like Crystal River National Wildlife Refuge , the only refuge in the U.S. specifically created to protect habitats for manatees.

Where to Stay in Crystal River: There's nothing particularly fancy about the King's Bay Lodge , but its roomy suites sleep four comfortably, its spring-fed pool is a kid favorite, and its proximity to everything you'd want to do in Crystal River is unbeatable. 

3. Long Beach Peninsula, Washington

Want to make a dramatic getaway? Head to Washington’s Long Beach Peninsula during the winter. Not far from Portland or Seattle, the area rates as a great place for storm watching during winter, thanks to the combination of seasonal king tides, stormy weather at this time of year, and the rushing water from the Columbia River. 

COAST TO COAST: 7 charming coastal towns in the U.S. perfect for a family vacation

Bring your camera to capture the moody scenery, and take it with you when you wander the area’s seven state parks and five wildlife/conservation areas, where you might spot loons, chickadees, sparrows, and hawks during the colder months. 

The region also sits along the state’s Cranberry Coast, and the Pacific Coast Cranberry Research Foundation Museum offers a self-guided tour of its cranberry bogs year-round. Winter is also a great time for oysters on the Long Beach Peninsula, which you can enjoy at restaurants like Shoalwater Seafood and The Depot.

Where to Stay on Long Beach Peninsula: Book a room at the pet-friendly Oceanview Inn at the Arch and you’ll be within walking distance of the beach and downtown Long Beach and well situated for enjoying all that the area has to offer. 

4. Montgomery, Alabama

With winter weather that’s typically on the mild side, Montgomery offers a long weekend escape with lots of options. Outdoor fun can be found at spots like the Alabama Safari Park, Montgomery Zoo, and the Lagoon Park Trail. 

GO SOMEWHERE WARM: 10 tropical destinations you can visit without a US passport

This is an amazing place for the family to learn about the city’s important role in Black history and the American Civil Rights Movement at sites like The Legacy Museum and National Memorial for Peace and Justice, Civil Rights Memorial Center, and Freedom Rides Museum . Annual events on Martin Luther King, Jr. Day include a parade down historic Dexter Avenue, where you can find the Dexter Avenue King Memorial Baptist Church where King led the congregation from 1954 to 1960. 

Refuel along the way at Chris’ Famous Hotdogs, where everyone from Franklin D. Roosevelt and Dr. King to Elvis Presley has eaten.

Where to Stay in Montgomery: Occupying a century-old building, the newish SpringHill Suites Montgomery Downtown offers suites well-suited for family getaways and a downtown location that makes it easy to explore the city.

5. Coeur d’Alene, Idaho

This northwest Idaho city not far from Spokane, Washington, boasts 109 miles of lake shoreline and snowy scenic vistas during the winter. Take a Scenic Hot Cocoa Cruise with Lake Coeur d’Alene Cruises, and you might spot bald eagles swooping overhead while sipping your sweet treat (they congregate around Lake Coeur d’Alene every year from November through February). 

SUN AND SAND: 12 best beach resorts in the U.S. for families  

Three ski resorts located within an hour of Coeur d’Alene are an easy day trip from town and offer trails and terrain for all levels of skiers and snowboarders, while Raptor Reef Indoor Water Park provides thrills of a different kind. An annual mac and cheese festival takes place in January, serving up comfort food just right for the season, and the Winter Lights outdoor art experience illuminates downtown Coeur d’Alene every evening from January 26 through February 4. 

Where to Stay: Set on the shores of Lake Coeur d’Alene, Coeur d’Alene Resort offers spacious rooms and suites (many with amazing views) plus amenities like a spa, fitness center, and indoor pool.

6. San Luis Obispo, California

Located between San Francisco and Los Angeles, San Luis Obispo (or SLO, pronounced "slow," as it’s known) offers a weekend getaway with a sustainable side. Many of its wineries are SIP-certified (sustainable in practice), and the city even uses herds of goats to clear out brush along its hillsides. Check out the area’s natural beauty while pedaling the city’s bike trails, hiking at spots like Irish Hills Natural Reserve and Reservoir Canyon, or strolling the area’s beaches. 

WORLD’S BEST: 10 best all-inclusive beach resorts in the world  

Head downtown for shops and restaurants, catch a flick at the Palm Theatre (the first solar-powered theater in the U.S.), and taste local produce and foods at the Downtown SLO Farmers’ Market that takes place every Thursday. And the kids will get a kick out of adding their own contribution to the quirky Bubblegum Alley.

Where to Stay in SLO: Tweens and teens will love the retro-modern, collegiate vibes and the on-site burger joint at The Wayfarer San Luis Obispo , located near the campus of Cal Poly San Luis Obispo.

7. Scottsdale, Arizona

Plan your escape to Scottsdale, where the sun is shining almost every day of the year and winter temperatures tend to be in the 60s and 70s. That means the weather is ideal for strolling through Old Town Scottsdale, exploring the Sonoran Desert at places like McDowell Sonoran Preserve and Pinnacle Peak Park, and frolicking at the kids’ splash pad and play area at the recently revitalized Scottsdale Civic Center. 

GO WEST: 7 West Coast vacations with something for everyone in the family

There’s always an interesting exhibit or programming to enjoy at Western Spirit: Scottsdale’s Museum of the West and Frank Lloyd Wright’s Taliesin West, and the kids will appreciate riding the train and carousel at McCormick-Stillman Railroad Park and enjoying something sweet at the 1950s-era Sugar Bowl Ice Cream Parlor & Restaurant.

Where to Stay in Scottsdale: The kids will be fans of the Sonoran Splash pool at Fairmont Scottsdale Princess , which features two waterslides and a zero-entry; the grownups will enjoy making use of the kids' club to hit the links or squeeze in a spa treatment.

8. Boston, Massachusetts

Bundle up and spend a winter weekend wandering around Boston, which is road trip distance from much of the Northeast. It’s an ideal time of year to visit the city’s many excellent museums, like the Boston Children’s Museum, Museum of Science, and Museum of Fine Arts art museum. Glide around the Frog Pond Ice Skating Rink or sled down Flagstaff Hill at Boston Common (the oldest public park in the United States), then warm up over a plate of pasta in the city’s North End. 

ATLANTIC COAST: 11 best seaside villages and coastal towns in New England  

After strolling picturesque (and potentially snow-covered) neighborhoods like Beacon Hill and the Back Bay, head indoors to browse and taste your way through spots like Boston Public Market, High Street Place, Hub Hall Boston, and the much-visited Faneuil Hall Marketplace and Quincy Market.

Where to Stay in Boston: Choose the Boston Marriott Long Wharf for your long weekend stay and you’ll enjoy views of Boston Harbor and be within walking distance of sites like the New England Aquarium, Faneuil Hall, and portions of the Freedom Trail.

9. Lake Geneva, Wisconsin

Make the most of the winter weather in Lake Geneva, which is within easy driving distance of cities like Chicago and Milwaukee. Head to spots like The Mountain Top at Grand Geneva Resort, Big Foot Beach State Park, and The Ridge Hotel for skiing, sledding, snowshoeing, hiking, and ice skating, or kick things up a notch with a winter ziplining and ropes course adventure or some ice fishing. There’s an annual snow sculpting event during the winter months, and the Winter Realms experience includes ice slides, ice sculptures, and other chilly fun. 

BRING THE KIDS: 10 best Caribbean family resorts

Where to Stay in Lake Geneva: Timber Ridge Lodge & Waterpark serves as a great all-in-one location for families, where suites offer lots of room for the whole crew and amenities include an indoor water park, mini bowling, and an arcade.

10. Washington, DC

Plan a low-cost, museum-filled winter getaway to Washington, DC. Admission is free at the city’s Smithsonian Institution museums, where the family can explore the history of flight at the National Air and Space Museum, the African American experience at the National Museum of African American History and Culture, and the natural world at the National Museum of Natural History. 

Head outdoors to admire the city’s many monuments and memorials like the Lincoln Memorial, Jefferson Memorial, and Martin Luther King Jr. Memorial (all free to visit), and take a spin around the ice skating rinks at the National Gallery of Art Sculpture Garden or at The Wharf. Then warm up over dinner at family-friendly restaurants like Old Ebbitt Grill, Boardwalk Bar & Arcade, and Tonic at Quigley’s Pharmacy. FOR OLDER KIDS: 10 best family resorts with teen clubs and activities  

Where to Stay in DC: Four Seasons Hotel Washington, DC caters to families with amenities like baby gear and strollers; games, books, and sports equipment for use; an indoor pool; and sightseeing guides geared toward children. 

10 family-friendly winter weekend getaways in the US originally appeared on FamilyVacationist.com .

More from FamilyVacationist:

  • 12 Best Hotel Booking Sites for Cheap Prices
  • 10 Best Vacation Ideas for Families with Teenagers
  • 10 Best All-Inclusive Beach Resorts in the World

The views and opinions expressed in this column are the author’s and do not necessarily reflect those of USA TODAY. FamilyVacationist.com and TourScoop.com are owned and operated by Vacationist Media LLC. Using the FamilyVacationist travel recommendation methodology , we review and select family vacation ideas , family vacation spots , all-inclusive family resorts , and classic family vacations for all ages. TourScoop covers guided group tours and tour operators , tour operator reviews , tour itinerary reviews and travel gear recommendations .

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25 Things To Do In Chicago This Weekend: Polar Plunge, Windy City Comedy Fest And A Skate Party

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weekend trip from chicago winter

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CHICAGO — Despite the cold, March is coming in hot with a jam-packed weekend of events, from the Windy City Comedy Festival to a Logan Square bar hop.

Neighbors can also take a communal plunge into the icy waters of Lake Michigan for charity, enjoy local theater productions on stage and sip hundreds of beers at a Brewsology booze fest.

Here’s a roundup of 25 things to do in Chicago this weekend:

Truth After Dark Creole Cuisine Grand Opening

5 p.m. Thursday-Saturday

Truth After Dark Creole Cuisine, 56 E. Pershing Road

A new Creole restaurant is coming to Bronzeville this weekend, serving up New Orleans-inspired dishes like Cajun dry rub wings, Louisiana style gumbo and jambalaya. Reservations are required for this special weekend. Make them online here .

weekend trip from chicago winter

Chicago Flamenco Festival

7-8:15 p.m. Thursday, 7-8:30 p.m. Sunday

Instituto Cervantes, 31 W. Ohio St.

The Chicago Flamenco Festival returns for its 22nd edition this week and runs through March 23. On Wednesday and Thursday, celebrated flamenco guitarist and Latin Grammy-winner Antonio Rey will perform new and old compositions. Tickets are $30 online . On Sunday, Spanish star María José Llergo will perform her flamenco-inspired sophomore album, “Ultrabelleza.” Tickets are $35 online .

weekend trip from chicago winter

Avery*Sunshine Live

7:30-9 p.m. Thursday-Saturday

City Winery, 1200 W. Randolph St.

Atlanta-based singer, pianist and composer Avery*Sunshine has been praised by the likes of Aretha Franklin, Patti LaBelle and other music icons. The multi-hyphenate artist is bringing her soulful R&B sound and uplifting anthems to Chicago for four shows this weekend. Tickets are $62-$75 online .

weekend trip from chicago winter

‘Mothers’ With The Gift Theatre Company

7:30 p.m. Thursday-Saturday, 3 p.m. Sunday

 Filament Theatre, 4041 N. Milwaukee Ave.

Award-winning playwright Anna Ouyang Moench’s “Mothers” closes out its month-long Chicago run this weekend. The story follows three moms, a stay-at-home dad and a nanny as they watch their kids play at a mommy-baby meetup. When catastrophe strikes, these five characters have to survive not only each, but also a war.

This dystopian production directed by Halena Keys explores “the primal heartache of raising children in a disintegrating world.” Tickets for the final Chicago shows are $35-$45 online .

YouTube video

‘Flood’ With Shattered Globe Theatre

8 p.m. Thursday-Saturday, 3 p.m. Sunday

Theater Wit, 1229 W. Belmont Ave.

A play prepared for the end of the world, “Flood” takes place in a 19th floor apartment, where Edith simply wants to have tea with her husband. While he’s preoccupied and the kids don’t call enough, outside, “the waters are rising, rising, rising.”

Written by Mashuq Mushtaq Deen and directed by Kenneth Prestininzi, the show is playing in Chicago through March 9. Buy tickets for $15-$45 here .

weekend trip from chicago winter

Greektown Restaurant Week

Kicks off Friday

Various locations around Greektown

Chicagoans can “go Greek” this week during Greektown Restaurant Week, which launched in 2021. Select restaurants will offer specials through March 7, including half-price Greek wines and beer from 9 Muses Bar & Grill, a free Saganaki dish per table at Athena Restaurant and complimentary baklava with each Mr. Greek Gyros plate purchased.

Find more information and a list of participating eateries here .

weekend trip from chicago winter

North Side Restaurant Week

Various North Side restaurants

Several North Side Chambers of Commerce groups have joined forces for this inaugural restaurant week. Diners can enjoy global flavors — from Argentinian to French to Southern comfort — across Lincoln Square, Ravenswood, Andersonville, Edgewater, North Center, Rogers Park and Uptown. Select eateries will offer special prix fixe menus through March 15.

Find more information and participating restaurants here .

weekend trip from chicago winter

‘Conjecture’ Exhibition

5-9 p.m. Friday

Oliva Gallery, 3816 W. Armitage Ave.

See sculptures by artists Mitch Clark and John Upchurch at this month-long exhibit opening Friday. Clark creates dreamlike sculptures from materials such as wire, paper and thread — “so delicate, that the tiniest wisps of air could result in them falling apart.” Photographs of his ephemeral work allow them to live on and be seen in galleries. Upchurch’s sculptures are composed of discarded materials, industrial relics and old tools, repurposing them into new, beautiful, hilarious and often anthropomorphized creations. His work represents “the hopeful notion that almost anything can become something else.” Learn more here .

weekend trip from chicago winter

First Fridays At Sunnyside Plants

6-7:30 p.m. Friday

Sunnyside Plants, 4800 N. Milwaukee Ave.

At this monthly event, Chicagoans looking to cultivate a green thumb can bring their ailing houseplants and questions to a Jefferson Park plant nursery. The Sunnyside team will be on hand to guide neighbors to gardening success. Light refreshments will be provided, or BYOB.

YouTube video

Thaddeus Tukes Quartet

7:30 and 9:30 p.m. Friday

Winter’s Jazz Club, 465 N. McClurg Court

Chicago’s own Thaddeus Tukes — an acclaimed musician known as the “world’s best vibraphonist” — is performing two Friday night shows in the city. General admission tickets are $27.75 and VIP tickets are $32.75. Buy them here .

weekend trip from chicago winter

Windy City Comedy Festival

8 p.m. Friday

Arie Crown Theater, 2301 S. DuSable Lake Shore Drive

See a lineup of world-class comedians like Sommore, Lavell Crawford, Don “DC” Curry, Special K and Teddy Carpenter at this highly anticipated festival. Tickets are $59 online .

weekend trip from chicago winter

Children’s Story Time In The Grove

10 a.m.-noon Saturday

The Shops at North Bridge, 520 N. Michigan Ave.

Enjoy a family-friendly story time with a special guest speaker in honor of National Read Across America Day. Guests can also get a photo with Clifford the Big Red Dog and make their own bookmark. Register for free online .

weekend trip from chicago winter

Women’s History Month Soul Pop-Up

10 a.m.-2 p.m. Saturday

Strugglebeard Bakery, 5221 S. Harper Court

A Hyde Park bakery is hosting Saturday Soul pop-up shops through March with a different Black woman-owned business each weekend. This Saturday features Kissed By A Bee Organics, an apothecary and urban farm by Akilah Scott-Amos, who hails from Chicago but is based in Manvel, Texas.

weekend trip from chicago winter

Afro Soca Love Marketplace

11 a.m.-6 p.m. Saturday

The Promontory, 5311 S. Lake Park Ave.

Carnival comes to Chicago this weekend for an Afro Soca Love market and party. Dress to impress, shop local and enjoy beats and bites inspired by Africa and its diaspora, from Caribbean to Afro-Latin to African American. There will be live DJs, entertainment and a photo booth. RSVP for free online . There will also be a 21-and-older afterparty 10 p.m. Tickets start at $10 here .

weekend trip from chicago winter

‘Syndey’s Big Speech’ Story Time & Signing

Noon-1:30 p.m. Saturday

Three Avenues Bookshop, 3009 N. Southport Ave.

Local author Malcolm Newsome will read and sign his latest picture book at the Lakeview bookstore. The story follows a young girl, Sydney, who wants to be a great leader but needs encouragement to overcome her fear of public speaking.

RSVP for the free event here , and pre-order the book for $19.99 here .

weekend trip from chicago winter

House Of Chelsea B Pop-Up Shop

1-5 p.m. Saturday

The Silver Room, 1506 E. 53rd St.

Englewood streetwear designer Chelsea B is hosting her first pop-up this weekend, showcasing original looks and samples from her brand House of Chelsea B. Attendees can shop garments, accessories and more “wearable art” from the brand, which has recently been worn by popular artists, including Megan Thee Stallion and Lizzo.

View this post on Instagram A post shared by BUILD Chicago (@buildchicago)

BUILD Youth Art Showcase

5-9 p.m. Saturday

BUILD Campus, 5100 W. Harrison St.

BUILD — a nationally recognized gang intervention, violence prevention and youth development group on the West Side — is hosting its seventh annual youth art showcase celebrating the potential and resilience of Chicago’s young people.

This year’s theme is “Art of Possibilities: Explore & Discover,” and the exhibit features work donated by local artists and creations by young people in BUILD programs. Art on display will be available for silent auction, and proceeds will benefit BUILD’s prevention and art programs. Tickets are $75 online .

weekend trip from chicago winter

Brewsology Beer Fest

6-11 p.m. Saturday

Museum of Science and Industry, 5700 S. Lake Shore Drive

Sample 200 beers from more than 60 breweries at the nation’s largest science museum. Museumgoers can browse exhibits, try flight simulators and more with a drink in hand. It’s a self-proclaimed “boozy hybrid of your middle school field trip.” Tickets start at $55 online .

weekend trip from chicago winter

Chicago Fire FC Vs. FC Cincinatti

7:30 p.m. Saturday

Soldier Field, 1410 S. Museum Campus Drive

The highly anticipated home opener game between soccer teams Chicago Fire FC and FC Cincinatti is on this weekend. Tickets and resale tickets start at $21 online .

View this post on Instagram A post shared by Thalia Hall (@thaliahallchicago)

Saturday Skate Party

8 p.m. Saturday through midnight

Thalia Hall, 1807 S. Allport St.

Grab your roller skates (no blades) and head to Thalia Hall for a 17-and-older party hosted by Chicago skating guru Myesha McCaskill and skate group Inspired By Favor . Tickets are $25 online .

weekend trip from chicago winter

Chicago Polar Plunge

8 a.m. Sunday

North Avenue Beach, 1600 N. DuSable Lake Shore Drive

Dive into the chilly waters of Lake Michigan while raising money for child athletes with intellectual and developmental disabilities. Thousands of Chicagoans participate in the plunge, which is returning for its 24th edition.

Sign up and donate online . Funds support Special Olympics Chicago and Special Children’s Charities.

weekend trip from chicago winter

Wicker Park Winter Market

9 a.m.-2 p.m. Sunday

The Robey Chicago, 2018 W. North Ave.

Grab a tote bag and shop local at an indoor farmers market in Wicker Park. There will be vendors selling produce, baked goods, coffee, candles, jam and more. It’s held every first and third Sunday of the month through April.

weekend trip from chicago winter

Logan Square Makers Market & Bar Hop

1-6 p.m. Sunday

Various locations

With a drink in hand, neighbors can shop from 35 local makers across three neighborhood bars. There will be vendors selling handmade goods, including candles, jewelry, artwork and knit goods.

Participating locations are Revolution Brewing at 2323 N. Milwaukee Ave., Navigator Taproom at 2211 N. Milwaukee Ave. and Pilot Project Brewing at 2140 N. Milwaukee Ave. This is a family-friendly event and free to attend.

weekend trip from chicago winter

Synth Flea Market

Marz Community Brewing, 3630 S. Iron St.

Meet up with neighbors, jam and sell and swap synthesizers and other music gear at a South Side brewery. It’s free to attend and participate.

YouTube video

Trinity Irish Dance Company

3 p.m. Sunday

Auditorium Theatre, 50 E. Ida B. Wells Drive

Founding Artistic Director Mark Howard is leading Chicago’s renowned Trinity Irish Dance Company to the stage for one upcoming show in the city.

A recent inductee in the 2023 Irish American Hall of Fame, the dance company is drawing upon American Vaudeville and its place in Irish step dance history for this “at once whimsical and fierce” performance. The group is also working with renowned choreographer Harrison McEldowney, who has come out of retirement to collaborate with Trinity on a new work called “P.O.V.” Tickets start at $25 online .

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In Chicago, It’s Summer in February

An unseasonably warm winter peaked on Tuesday with melting ice rinks and 70-degree weather. Temperatures will plummet from there, but even so, this winter without winter has left some people rattled.

Strollers and runners along a lakefront, one without a shirt.

By Julie Bosman

Reporting from Chicago

February is usually frigid perfection for the ice rink at Millennium Park in downtown Chicago, a favorite winter stop for tourists and local families that stands in the shadow of the reflective sculpture known as the Bean.

On Tuesday morning, the rink was melting.

Under an intense sun and 70-degree air temperatures, water slowly trickled out of the empty rink, flooding the surrounding concrete. Baby birds splashed happily in the pools of water. The ticket counter was abandoned, apparently closed for the day.

Winter in Chicago — or the lack of it — reached an unnerving peak on Tuesday, when the city came close to breaking a 48-year-old high-temperature record.

But forecasters said that the balmy spell was not going to last. They pointed out that the mild conditions in Chicago and around the Midwest this week were extreme, not just for the warmth but also for what would follow.

That was likely to include plunging temperatures dropping into the 20s, blustery northwest winds gusting up to 40 miles an hour and potentially dangerous storms, including tornadoes.

Still, for most of Tuesday, Chicago looked and felt like summer: Apartment windows were pushed open to catch the warm breeze. Restaurants set up tables and chairs on sidewalks for al fresco lunch service, a rare sight in a Chicago February.

The lakefront was teeming with runners, cyclists and couples strolling hand in hand.

“We expected it would be very cold,” said Ana Marchal, 41, a doctor from Cádiz, Spain, who arrived in Chicago on Monday for a vacation with her husband, Rolf Hartmann.

They had figured on spending their holiday indoors, by shopping, visiting museums or attending Blackhawks and Bulls games.

Instead, they found themselves walking on the beach, looking delighted and a little perplexed. They stopped to take a selfie by Lake Michigan, which is usually icy and forbidding this time of year.

“How beautiful,” Mr. Hartmann said. “It looks like the sea.”

“It’s colder in Spain than here,” Dr. Marchal said.

Others found the weather ominous.

Shailaja Chandrashekararao, a social worker who moved from India to Chicago last year, had just finished a 10-kilometer jog downtown. She said she would have liked to keep running.

“It was too hot,” Ms. Chandrashekararao said, tugging at the sleeve of her neon-orange workout top.

Climate change has made summers in India unbearably, dangerously brutal, she said, making Chicago something of a weather haven. But the city’s mild winter, on the heels of the warmest year on record in 2023, felt eerie and unpredictable.

“I’m not enjoying this,” she said. “It’s quite crazy, actually.”

Temperatures are also rising across the Midwest, in part because of human-caused climate change, according to the 2023 National Climate Assessment , the government’s premier compilation of scientific knowledge on the effect of human-caused warming. The report also noted that the warming posed significant economic risk to the region.

The June-like temperatures will be one factor in producing severe thunderstorms in the Chicago area Tuesday evening and overnight. Some of the storms could spawn tornadoes, forecasters said, with the most likely area stretching from Missouri across southern Illinois and northern Indiana to Michigan. Tornadoes that occur after dark can be more dangerous because so many people are asleep.

The main threat from the storm system, though, will be hail, possibly including hailstones as large or larger than hen’s eggs.

Unseasonably high temperatures across the Great Plains, along with high winds, were propelling wildfires in Nebraska and Kansas, which were still a threat on Tuesday after forcing evacuations this week. Wildfires were also raging across the Texas Panhandle.

And from Tuesday to Wednesday in Chicago, the temperature could drop by nearly 60 degrees, according to David King, a meteorologist for the National Weather Service.

“It’s remarkable,” he said, noting that the last time the city saw such a rapid temperature drop was in the 1990s. “It’s just a wild time for weather here in Chicago.”

A normal daytime high in Chicago at this time of year is about 40 degrees. According to the National Oceanic and Atmospheric Administration, only 4.3 percent of the Great Lakes’ surface is ice-covered , well below the average .

The unseasonably warm and dry winter has affected tourism in the region, especially in Michigan, Wisconsin and Minnesota, where industries that depend on snow have suffered. Gov. Tony Evers of Wisconsin announced last week that many businesses in northern Wisconsin — ski slopes, restaurants and snowmobiling tours, for example — may be eligible for a federal disaster loan program if they have incurred losses from the mild winter.

The mild day on Tuesday was already feeling familiar, said Charles Jones, who manages maintenance work for a residential building in downtown Chicago.

Mr. Jones spent his break standing outside in short sleeves, as people walked their dogs in the sunshine. He has lived in Chicago his whole life, he said, and was used to the harsh winters that the city is known for. But it was hard to remember the last winter where the cold had felt truly brutal — “a few years ago, maybe,” he shrugged.

This winter has been a lot like the one before, Mr. Jones said, without very much snow or many cold, icy days. In the last few months, he said, he has only had to salt the sidewalk twice.

“I don't trust this weather, though,” he said. “You know we’re going to get a little snow before winter is done. It’s Chicago. It can be 70 and then jump down to 30.”

Judson Jones contributed reporting.

Julie Bosman is the Chicago bureau chief for The Times, writing and reporting stories from around the Midwest. More about Julie Bosman

Explore Our Weather Coverage

Preparing Your House for the Cold:  Here are steps to take  to prepare for bitter cold, strong winds and other severe winter conditions at home.

Wind Chill Index: Even if the ambient temperature stays the same, you might feel colder when you are hit by a gust of wind. This is how meteorologists measure the feeling of cold .

On the Road:  Safety experts shared some advice  on how snow-stranded drivers caught in a snowstorm can keep warm and collected. Their top tip? Be prepared.

Is It Safe to Go Outside?:  Heat, flooding and wildfire smoke have made for treacherous conditions. Use this guide to determine when you should stay home .

Climate Change: What’s causing global warming? How can we fix it? Our F.A.Q. tackles your climate questions big and small .

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Extreme Weather Maps: Track the possibility of extreme weather in the places that are important to you .

Watch CBS News

Chicago gets warm, windy weekend weather

By Mary Kay Kleist

March 1, 2024 / 3:50 PM CST / CBS Chicago

CHICAGO (CBS) -- A warming trend sets up for the weekend.

3-panel-daypart-left-this-evening.png

Clouds may linger early Saturday and then depart by the afternoon. Temperatures should run a good 20 degrees above average. 

sat.png

It'll be windy and warm for Sunday with highs about 30 degrees above average. The gusty, dry southwest flow may elevate the risk of brush fires.

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The next front arrives late day Monday. Still warm ahead of the front with scattered storms by evening.

7-day-forecast-pm.png

TONIGHT: MOSTLY CLOUDY. NOT AS COLD. LOW 35.

SATURDAY: EARLY CLOUDS THEN CLEARING SKIES. HIGH 60.

SUNDAY: WINDY & WARM. HIGH 70.

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Meteorologist Mary Kay Kleist can be seen on CBS News Chicago and weeknights on CBS2 News at 5 p.m.

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Powerful blizzard dumps snow across Sierra Nevada with 145 mph wind gusts in biggest storm of the season

A powerful blizzard is underway in the Sierra Nevada and forecast to bring relentless snow over the next two days, with wind gusts already clocking 145 mph at the highest peaks in the Sierra and creating dangerous white-out conditions. 

This is the biggest snowstorm for the Sierra season, with blizzard warnings active for the Sierra Nevada and parts of eastern Nevada.

Heavy snow is falling, with areas forecast to pick up between five to 10 feet of snow, and localized areas up to 12 feet. 

Skiers in California

With snow falling two to four inches an hour, travel is life-threatening and impossible, and portions of the highly-traveled Interstate 80 will likely close for days. 

California Highway Patrol in Truckee , California, said Friday that “travel is highly discouraged,” noting that conditions over Donner Summit deteriorated Thursday night, causing “a traffic mess.” Trucks are now at maximum restrictions.

Adding to the wintry mix, winds are roaring. A 145 mph wind gust was reported on the high peaks west of Lake Tahoe. Strong winds gusting 50 to 100 mph will be possible this weekend for the Sierra chain and all elevated areas and mountains across California and into Utah. 

The snow and wind will taper off by Sunday. 

A worker clears snow

The UC Berkeley Central Sierra Snow Lab, based in Soda Springs, California, said Friday it received 19.1 inches of snow in the last day.

“Conditions have already deteriorated this morning with gusty winds and significantly reduced visibility. The next 24 hours will be the heaviest portion of the storm," the lab said.

Meanwhile, a backcountry avalanche watch is in effect through 5 p.m. local time Sunday for the central Sierra Nevada Mountains between Yuba Pass and Ebbetts Pass, including the Greater Lake Tahoe area with “high to extreme” avalanche danger and “large to very large avalanches expected.”

Yosemite National Park asked visitors to be out by Friday afternoon due to possibly dangerous conditions through at least noon Sunday. 

The California Governor’s Office of Emergency Services has prepositioned fire personnel and equipment in multiple counties “to be able to respond if needed” due to the winter storm. 

Nevada Gov. Joe Lombardo said Friday: “This storm is expected to bring dangerous temperatures and conditions to our state, and it’s critical that Nevada families are prepared.”

He said that the state’s department of transportation, energy and emergency management are working “to maximize preventative measures and recovery efforts.” 

Several school districts, including Northern Nevada’s Washoe County School District and Storey County Schools, and California’s Tahoe Truckee Unified School District and Lake Tahoe Unified School District, were closed Friday due to the weather. 

Large snowstorms are common in March. Sierra snowfall usually reaches its peak snowpack on April 1 before the melt season begins. 

weekend trip from chicago winter

Kathryn Prociv is a senior meteorologist and producer for NBC News. 

Breaking News Reporter

IMAGES

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  3. Chicago in Winter (Best Things to Do + 3-Day Itinerary

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  4. Best Things to Do in Chicago in the Winter

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COMMENTS

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