Visiting the Midwest in winter is not for the faint of heart, or at least not for those who don’t own snow boots. When I moved to Cleveland for college and my Clevelander cousin told me I needed knee-high snow boots, I thought she was exaggerating. She wasn’t.
Despite the cold, these midwest destinations are still a perfect place to worth a visit for winter vacation. In fact, if you summon your courage and visit the snow-covered cities of the Midwest for a winter vacation in winter, you’ll find that the snow and winter weather actually make these destinations more magical!
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The best Midwest winter getaways for families are Wisconsin Dells for indoor waterparks, Door County for snowshoeing and small-town charm, Minneapolis for the Mall of America and city sledding, Cleveland and Detroit for world-class museums, and Keystone, South Dakota, for a nearly empty, snow-dusted Mount Rushmore. Pittsburgh, just east of the Midwest, is a bonus pick for holiday lights at Kennywood.
Midwest Winter Getaways at a Glance
| Destination | Best for | Indoor or outdoor | Drive from Chicago | Where we’d stay |
|---|---|---|---|---|
| Wisconsin Dells, WI | Indoor waterparks, younger kids | Indoor | ~3 hrs | Great Wolf Lodge |
| Door County, WI | Snowshoeing, winter festivals | Outdoor | ~4.5 hrs | The Landing Resort |
| Minneapolis, MN | Mall of America, sledding and skating | Both | ~6.5 hrs | JW Marriott Mall of America |
| Cleveland, OH | Rock Hall, A Christmas Story House | Indoor | ~5 hrs | Metropolitan at The 9 |
| Detroit, MI | Henry Ford Museum, Motown history | Indoor | ~4.5 hrs | TownePlace Suites Dearborn |
| Keystone, SD | Crowd-free Mount Rushmore, wildlife | Outdoor | Fly to Rapid City | K Bar Lodge |
| Pittsburgh, PA (bonus) | Holiday lights, inclines, Mister Rogers | Both | ~7 hrs | Sheraton Station Square |
Cleveland, Ohio
I have to start with Cleveland, my home away from home. Cleveland is one of the best places because of the quality and quantity of museums there: a perfect winter activity!
Cleveland is famous for being home to the Rock and Roll Hall of Fame. At the Rock Hall you can pay your respects to legends like Prince, the Beatles, and more. Your kids will like the current music section, where they will find memorabilia from today’s artists. The whole family will enjoy the Power of Rock experience, featuring music from induction ceremonies and plenty of fog machines.
Get your DISCOUNT Rock and Roll Hall of Fame ticket here!
The Cleveland Art Museum is world-class and FREE. It has an extensive Asian art collection, an Impressionist collection, and many other works.
While you’re in town, stop by the Christmas Story House! Tour Ralphie’s bedroom, get a chance to hide in the kitchen cabinets, and try your hand against Black Bart (or at least pretend to). Just don’t curse or you’ll end up trying Lifebuoy soap.
The house is open for tours daily, with extended hours in December.
Want to pretend to be a VIP while in Cleveland? Stay at The 9. That’s where all the professional sports teams stay when they are in town, so you might get to rub elbows with Joe Burrow if you time it right.
Don’t Miss! Most Awesome Things to Do in Cleveland with Kids
Detroit, Michigan
Detroit also makes the list for its awesome museums in the United States! Detroit is home to the Henry Ford Museum, a HUGE museum dedicated to, well, just about everything. Plan a full day here. Maybe more than one day. Henry Ford also gets exceptional seasonal exhibits, so make sure you check their schedule! Don’t miss the Rosa Parks bus, an important educational opportunity for your entire family kids.
While you’re in town, stop by the Motown Museum! It’s a small museum but definitely a great option; an afternoon is plenty of time, but it’s still worth a stop! The exhibits upstairs rotate but always feature Motown’s most famous artists. You’ll finish your tour with a visit to the recording studio downstairs. (Accessibility note: the Motown Museum does not have an elevator).
Make it a two-day December trip to Dearborn. Next door to the museum, Holiday Nights in Greenfield Village fills the historic village with carolers, free ice skating, Model T and horse-drawn wagon rides, and a fireworks finale with a sing-along. It runs Dec 3–6, 10–13, 17–23 and 26–28, 2026, from 6:30 to 10 p.m. Public tickets ($39–$48, kids 4 and under free) go on sale Nov 4 and often sell out, so book early. Read our family guide to Greenfield Village.
When we were in town, my family stayed at the Towneplace Suites in Dearborn because of its proximity to the Henry Ford Museum.
The Motown Museum and the famous recording studio in the basement are must-sees on your vacation itinerary.
Door County, Wisconsin
Another not to miss midwest winter getaway for families is Door County, Wisconsin. Door County is a string of small towns on a peninsula bordering Lake Michigan and Green Bay. It’s mostly a summer and spring tourist hotspot but even in the winter, there are plenty of fun family activities. Take a naturalist-led guided hike, with snowshoes if you’re lucky, through the Ridges Sanctuary, the most biologically diverse spot in all of Wisconsin. Another great place for outdoor activities is Peninsula State Park. Climb the all-abilities accessible Eagle Tower through its ramps or 95 steps. Eagle Tower is 60 feet high and provides a carpet view of the trees covering Peninsula State Park and a clear shot to Horseshoe Island. Then enjoy the roughly two-hour Eagle Trail that takes adventurers past caves and ominous-looking cliffs. Don’t forget your waterproof pants because Peninsula State Park is also the place for cross-country skiing, snowshoeing, ice fishing, snowmobiling, sledding, and tubing!
If you go in February, check out Fish Creek’s Winter Festival, Feb 6–7, 2027: free, in a heated tent on Green Bay, with the Stumpf Fiddle contest, games and live music. There’s live entertainment, a Fruit-Loop run, a chili cook-off, and cherries, of course.
Stay at the Landing Resort with a kitchen and rooms that feel more like apartments than hotels. Our room had a back patio with a verdant lawn leading to a small grove of trees. There is also an indoor pool and breakfast included.
Icy Calm Photo by Dominik Dombrowski on Unsplash
Wisconsin Dells
Who says you can’t enjoy the water in the dead of winter? Not innovative Wisconsinites! Wisconsin Dells is considered the “waterpark capital of the world.” There are more than 200 waterslides in Wisconsin Dells and 16 million gallons of water push family travelers through the Dells’ favorite heated spots. Seventy acres of waterslides, including one that loops, and a lazy river makes Noah’s Ark America’s largest outdoor waterpark. However, sadly this outdoor park is only open in summer…so next time!
The Wilderness Resort is America’s largest indoor-outdoor combination waterpark. It has a 180-foot-long slide, bumper boats, a wave pool, spa, and golf course. There is also the Kalahari Resort, Wisconsin’s largest indoor waterpark. Thrillseekers will love its 250-foot-long slide and the wave simulator for indoor bodyboarding and surfing. There is also a Great Wolf Lodge there with a whole Snowland program for winter fun. Snowland runs late November to early January, with Santa visits on select days, a Snowfall Celebration, scavenger hunts and crafts included with your stay.
We also recommend your family stay at The Great Wolf Lodge. There are quests and arcades and so many fun indoor experiences that you’ll forget there’s a tundra right outside!
Just like the real thing…only safer! © Rina Nehdar
Minneapolis, Minnesota
The Mall of America puts Minneapolis on the map, at least a shopping map. Do your holiday shopping at the biggest mall ever, which is similar to many theme parks! Kids will love the Nickelodeon-themed rides, and it is a perfect family vacation. Good luck getting them out of that place! They’re building an indoor waterpark with hot tubs and indoor pools slated to open in 2029!
Get your DISCOUNT ride tickets here!
For immediate waterslide action, book Great Wolf Lodge Bloomington minutes from the mall. I’m convinced they built a huge mall in Minnesota because it’s so cold there most of the year, making you want to hide inside! If you’re stuck inside, what better to do than shop?
Want to try your hands at some winter sports? Visit Theodore Wirth Park and try out cross-country skiing, snowshoeing, sledding, tubing, ice skating and more outdoor adventures! You can avoid overweight/oversize baggage charges by renting your gear from the park.
I recommend the JW Marriott because it’s connected to the Mall of America. You can drop off your new goods at your room when your arms get tired.
If you can’t find it at the biggest mall in the world, it probably doesn’t exist. Photo Courtesy of Farragutful, via Wikimedia Commons.
Keystone, South Dakota
If you’ve never heard of Keystone, South Dakota, I don’t blame you. Just 250 people live there as of the last census. But Keystone has an important purpose: it’s the gateway to Mount Rushmore National Memorial and the Black Hills. Why visit Mount Rushmore in the winter? Well, low crowds for one. Most people don’t venture to an outdoor attraction in the winter. Plus you’ll have a chance to see Mount Rushmore covered in snow, a beautiful sight to behold during your winter vacation. Additionally, you can enjoy yourself while ice fishing in Lake Horsethief, which is only 4 miles away from this historic monument!
The Mount Rushmore grounds are open year-round, but the Iron Mountain Road and Needles Highway usually close in winter.
Get your private Mt. Rushmore tour tickets here!
While you’re in town, take your kids to see the ongoing construction at the Crazy Horse Memorial. Once it’s completed, it will be the second-tallest statue in the world! It’s also a great opportunity to learn about Native American history.
Nearby Custer State Park is also excellent to visit in the winter. The snow scares most visitors away, so you’ll have the park to yourself! It is one of the best state parks for wildlife viewing during this time of year! Just make sure to check a map; depending on snowfall there may be seasonal road closures. Most of the fun things to do in the park, including their famous jeep tours, are available in the winter, but call ahead to confirm availability.
I recommend the K Bar Lodge when visiting the Keystone area because of the beautiful views of the surrounding mountains.
Keystone looks like something out of a Hallmark movie. (Be careful that no one asks you to save an inn or enter the town baking contest.) Photo Courtesy of TravelingOtter, via Wikimedia Commons
Bonus: Pittsburgh, Pennsylvania
I might be cheating by including Pittsburgh. I don’t think it’s “technically” considered a Midwest weekend getaway. But I’m including it because it’s a great time and a beautiful city to visit in the winter!
Kennywood Holiday Lights runs Nov 13, 2026 – Jan 3, 2027, with rides, seasonal food, and meet-and-greets with Rudolph, Clarice, Bumble, and Sam the Snowman. (How many people can say they’ve ridden a roller coaster that’s over 100 years old?) Kiddieland and other historic rides, such as the Auto Race, which is the last of its kind, are usually open to enjoy as well.
Get your DISCOUNT Kennywood tickets here!
Don’t miss the Duquesne incline, one of the few remaining inclines of its kind. It’s a historic cable car, used to get workers up and down Mount Washington before cars were common. You can ride to the top for just a few dollars. You’ll be treated to a gorgeous view once you get to the top! Your kids will definitely be impressed by this one-of-a-kind ride. The top of Mount Washington is an incredibly popular place to propose, so be on the lookout for happy couples.
If you’re a Mister Rogers fan, be sure and stop by the Pittsburgh Children’s Museum. They have lots of exhibits that pay respect to our favorite neighbor; after all, he was a Pittsburgh native!
Don’t Miss! Best Things to Do in Kennywood for Families!
Pittsburgh also has a lot of seasonal festivals. Be sure to check out visitpittsburgh.com for the schedule!
Just outside the city is the 7 Springs Ski Resort. 7 Springs has plenty of family-friendly skiing slopes, cross country skiing, and snowboarding, but my mom and I prefer the world-class spa and hot tub during this time of year.
I recommend staying at the Sheraton at Station Square because of its easy proximity to shopping and dining.
Pittsburgh has the second-most number of bridges in the world, after Venice. It’s no wonder with 3 rivers! Photo by Emily Householder Stacey.
No matter which Midwest city you pick this winter, be sure to pack some snow boots! And trust me, a packable winter jacket is also a good investment for frequent winter travelers. If you do have to drive in the snow, just remember to pretend that your grandma is riding with you and she’s got a crock pot full of soup on her lap. Drive slowly and carefully and you’ll be just fine!
Midwest Winter Getaways: FAQ
What is the best Midwest winter getaway for families?
Wisconsin Dells is the best all-around Midwest winter getaway for families because its indoor waterparks at Kalahari, Wilderness Resort and Great Wolf Lodge stay at swimsuit temperature no matter the weather. For snow play instead, Door County and Minneapolis offer snowshoeing, sledding and skating.
What are the best Midwest winter resorts for families?
Top family resorts for a Midwest winter trip include Great Wolf Lodge and Kalahari in Wisconsin Dells, Wilderness Resort for its indoor-outdoor waterpark, the JW Marriott connected to the Mall of America in Minneapolis, and The Landing Resort in Door County, which has kitchens, an indoor pool and free breakfast.
What are good Midwest winter weekend getaways from Chicago?
Wisconsin Dells is about three hours from Chicago, which makes it the easiest winter weekend. Door County and Detroit are each about four and a half hours away, and Cleveland is about five.
Is Mount Rushmore open in winter?
Yes. Mount Rushmore National Memorial is open year-round, and winter brings few crowds and the chance to see the faces dusted with snow. Some scenic Black Hills roads, including Needles Highway and Iron Mountain Road, typically close for the season, so check road conditions before you drive.
What can families do in the Midwest in winter besides skiing?
Families can visit museums like the Henry Ford and the Rock & Roll Hall of Fame, tour A Christmas Story House in Cleveland, snowshoe with a naturalist at The Ridges Sanctuary in Door County, or go to Fish Creek’s free Winter Festival on February 6–7, 2027.
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Emily Householder Stacey is a writer, travel agent and mom based in sunny Cleveland, Ohio. Emily runs Aida’s Adventures travel agency while her son takes his afternoon nap. She has traveled throughout Australia, Asia and North America and the rest of the world is on her bucket list. Emily and her family love a good theme park. They have annual passes to 6 of them!