Midwest Winter Getaways: Top 10 Winter Road Trips in the Midwest

Ahhh, winter. Some love it with all the snow and sports and uniquely winter activities. Others would rather spend it indoors by the warmth of a fire. And still others just want it to go away as fast as possible. Whatever camp you’re in, one of these Midwest winter getaways is just what you need! Because there’s nothing like a winter vacation to help you savor the best parts of the season – or make it pass faster.

So, if you’re looking for a winter escape in the Midwest, we’ve got you. Below is the ultimate list of winter road trip getaways!

Want to experience winter in the city, a cabin in the woods, or experience all the fun winter activities? Then, please read on for our top ten winter road trips in the Midwest. You’re sure to find the perfect spot for your winter getaway!

Midwest Winter Getaways: Top winter road trips in the Midwest

Chicago, Illinois

No doubt about it, Chicago tops our list of Midwest winter getaways! From ice skating at Millennium Park to sledding at Soldier Field, there are heaps of fun activities in the heart of Chicago. That’s not to mention all the excellent accommodations and food.

Did we mention the fantastic food? The unique eateries are worth the trip – and it’s not just because of the excellent food; the ambiance is unmatched. Several rooftops have igloos, heated patios, and firepits with views of the city skyline.

While there, see the indoor botanical gardens and world-class museums, and take a winter walk on the shores of Lake Michigan.

See the Choose Chicago website for more winter things to do in Chicago.

Brainerd, Minnesota

Brainerd is the ideal place for all sorts of outdoor winter adventures! And if you’re looking for indoor fun, there are many great things to do (including three area waterparks)!

The Brainerd and Baxter area is a treasure trove of fun winter outdoor opportunities. Popular activities include snowmobiling, skiing, tubing, snowshoeing, fat tire biking, ice skating, and ice fishing. And Brainerd Lake hosts the world’s largest ice fishing competition!

Several area hotels have pools and water parks, which offer winter fun for all ages! But if you’re looking for a cozy winter retreat, there are also some private cabins and cottages.

The great thing is, there’s even more to do in Minneapolis-St. Paul, a short two-hour drive south of Brainerd.

Door County, Wisconsin

The sunrises and sunsets in Door County are as beautiful as ever (or even more so) in the winter. But the sunsets are just the beginning.

From all the winter sports and activities to cozy accommodations and local food and brews, Door County has a lot to offer on a winter vacation.

Explore area trails via cross-country skis, snowshoes, or winter hiking & biking. Or take your snowmobile for over 250 miles of trails. Ice fishing is another favorite winter activity (consider a charter fishing tour).

If you prefer to stay indoors, tour museums, spend a day at the spa or shopping, or relax by a cozy fire.

A range of overnight accommodations are available, from hotels and resorts to cabins and B&Bs. And the local restaurants, breweries, and wineries offer a variety of culinary experiences!

Lake Michigan winter — Lake Michigan (photo credit: Pixabay)

Council Bluffs, Iowa & Omaha, Nebraska

From unique art and shops to amazing winter hikes—plus one of the world’s best zoos—you can’t go wrong with a winter getaway to the Council Bluffs and Omaha area.

On the Iowa side, you can go skiing at the Mt. Crescent Ski area. And visit Hitchcock Nature Center to rent snowshoes to explore the Loess Hills.

Head to Omaha to see the Henry Doorly Zoo & Aquarium, Lauritzen Gardens, and the Children’s Museum. And stop by the Old Market for art galleries, quaint shops, and 45+ restaurants.

Downtown Omaha offers an excellent selection of hotels, including the historic Magnolia Hotel. You can also find hotels on the Iowa side, including two casino hotels. If Airbnb is more your style, there are some excellent options.

Black Hills, South Dakota

Looking for snowy fun? You’ll find it in the Black Hills! The average snowfall is 150 inches yearly. This makes it an ideal spot for a winter getaway full of skiing, snowshoeing, snowmobiling, and much more!

The Black Hills are a perfect place to experience the winter woods in an exciting (and beautiful) new way! Miles and miles of trails are great for snowshoeing, skiing, and snowmobiling. And if downhill skiing (or snow tubing) is your thing, put Terry Peak Ski Area on your list.

Even more? Custer State Park’s Creekside Lodge is open year-round and offers a cozy spot to stay. And plenty of other excellent cabins, hotels, and resorts are nearby.

See the Travel South Dakota website for more information on a winter getaway to the Black Hills.

Branson, Missouri

If shopping, restaurants, shows, spas, and museums—plus cozy accommodations and miles of hiking trails—sound good, consider Branson for your list of midwest winter getaways.

Branson is on the southern edge of the Midwest and has mild winter temps and infrequent snow. So, outdoor winter sports aren’t a great reason to go. But you can still get outdoors (without getting too cold) to hike the trails, play golf, or go fishing!

And with plenty of other fun things to do, plus fewer crowds and reasonable winter rates, it makes an excellent winter vacation spot.

See the Explore Branson website for more information and things to do!

Marquette, Michigan (Michigan’s Upper Peninsula)

The whole UP is a winter wonderland! And Marquette is a splendid spot for a winter adventure. See frozen waterfalls and beautiful wintery views of Lake Superior, and get your fill of outdoor fun!

Favorite winter activities are downhill and x-country skiing, fat tire biking, and snowshoeing. Snowmobiling is another popular activity (and there are rentals nearby).

Also, enjoy a day indoors at the local museums, shops, coffee shops, breweries, and more! And there are several hotels and Airbnbs so you can rest well at the end of an adventurous day.

For more on visiting Marquette and the Upper Penninsula, see TravelMarquette.com and uptravel.com.

Michigan lighthouse — Photo credit: Pixabay

Lake Geneva, Wisconsin

Lake Geneva has a little bit of everything when it comes to winter fun! There’s something for everyone, from outdoor winter activities (including ziplining!) to waterparks, spas, and theaters.

Of course, there’s skiing (downhill and x-country), ice skating, snowshoeing, and hiking! But there’s also ziplining, sledding, and ice fishing too.

And any winter trip to Lake Geneva must include the Ice Castles! This unique attraction is sculpted ice caverns and tunnels, with slides, chandeliers, characters – and sleigh rides!

After a fun-filled day, slow it down and see a show, relax at the spa, or savor a fabulous dinner.

And top off the day at the Timber Ridge Waterpark or another hotel, resort, or B&B.

For more on visiting Lake Geneva, see visitlakegeneva.com.

Des Moines, Iowa

Des Moines might be one of the most overlooked Midwest winter getaways! But it has more to offer than you can imagine. A thriving downtown and East Village make it the perfect winter escape in the Midwest!

Excellent food, museums, nightlife, and fun activities make Des Moines a perfect getaway! See Pappajohn Sculpture Park and Des Moines Botanical Garden, and stop by the many (many!) unique shops and eateries in the East Village.

Also, there’s nothing like ice skating under the night sky at Brenton Skating Plaza. And local trails offer winter hiking, x-country skiing, and snowshoeing.

While you’re there, drive north of Des Moines to Seven Oaks Recreation for a day of skiing and snow tubing! Or go to Big Creek State Park for popular snowmobile trails. And be sure to go south to Winterset, Iowa, and check out the covered Bridges of Madison County.

Women of Achievement Bridge Winter Des Moines — Des Moines, Iowa

Cleveland, Ohio

Cleveland is a great place to spend a winter getaway! It’s home to Ohio’s only National Park, where hiking trails are open year-round, and snowshoeing is a popular winter activity. Visitors also enjoy train rides on the Cuyahoga Valley Scenic Railroad.

Cleveland also has many places to go ice skating, and you can go skiing and snow tubing at a few area ski resorts. Or head to the toboggan chutes at Mill Stream Run Reservation.

But that’s not all! The area has many museums, including the Cleveland Aquarium and the Rock n Roll Hall of Fame.

Cleveland is home to the Christmas Story House from the 1983 movie, A Christmas Story. Also, there’s a dedicated museum across the street from the house.

For more on visiting Cleveland, see thisiscleveland.com.