Last Updated on September 21, 2023

There’s no escaping the fact that the Midwest experiences pretty cold winter temperatures and most people’s reactions is to escape and fly south for some much needed winter sun!  However, despite the cold and snow, some great winter adventures can be had in the Midwest!

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Midwest Winter Getaways

I called on some of my Midwest travel blogger friends to share some of their favourite Midwest winter getaways!  Whether you’re looking to enjoy the outdoors, or keep warm with fun indoor attractions, I think we’ve got you covered!

Illinois | Iowa | Missouri | Minnesota | Wisconsin

ILLINOIS

Chicago, Illinois

Suggested by Kirsten from Kids Are A Trip

Winter is the perfect time to visit Chicago. Festivities kick off right after Thanksgiving and everyone embraces the cold wintry weather. From the Christkindlmarket to the Museum of Science and Industry, the city gets decked out in its holiday finest, and puts on quite a show.

There are places to go ice skating (both public and private), but don’t miss the skating ribbon at Maggie Daley Park in the heart of downtown. Skates are available for rent and you can’t beat the location in the shadow of the city’s skyscrapers.

Warm up afterwards with hot cocoa from Ghiradelli’s chocolate shop or pop into the world’s largest Starbucks. If you prefer a more formal experience, take afternoon tea at one of the local hotels, such as The Drake or The Peninsula.

Theatre is always a good option in Chicago with a multitude of Broadway and local productions to choose from. Around the holidays there are performances of It’s A Wonderful Life, The Nutcracker, and A Christmas Carol.

If you visit in early February, take advantage of Theatre Week and get discounted tickets to some of the best performances.

Midwest Winter Travel Tip: If you’re traveling through Chicago’s O’Hare airport in winter, know that delays are quite possible. I recommend taking the first flight of the day if possible to reduce your risk of an extended stay, but know if you have to stay longer, that isn’t a bad thing.

🏨Where To Stay: Central Loop Hotel (Downtown)

IOWA

Clear Lake, Iowa

Suggested by Sara from Travel With Sara

Clear Lake, Iowa is a bustling lake town all year around. Spectators flock to Clear Lake, each year, to see the beautiful kites flying over the frozen lake in February. The Color The Wind Kite Festival is held annually and folks come from all over the world to see a frozen lake come to life.

Kites of all shapes and sizes are flown high above the lake. It’s truly a majestic experience, as spectators can walk right next to the person flying the kite and even ask a question or two. Most importantly, look up and enjoy the beauty of a flying kite and a frozen lake!

Dress accordingly as winter is cold in Iowa and visitors will want to enjoy the kites for a period of time. Hot chocolate and warm treats are available for purchase near the lake, as well as in the local restaurants and shops. My recommendation: Swing into Cookies Etc. and grab a hot chocolate and a freshly baked cookie to go.

There’s nothing like standing out on a frozen lake with a cup of hot chocolate and a cookie from Cookies, Etc. This is an Iowa classic and something everyone deserves to enjoy.

🏨Where To Stay: Best Western Holiday Lodge

Dubuque, Iowa

One of the best things to do in Dubuque during the winter season is to go skiing or snowboarding at Sundown Mountain Resort!  If possible, I’d recommend visiting during the day in the week as the slopes are emptier, it can get a little crowded in the evenings and during the weekend.

The National Mississippi River Museum and Aquarium hold an annual ‘Ice Fest’ during January or for the adults, Dubuque On Ice Brewfest is held in February, featuring a whole host of local breweries!

Winter is also a great time to see bald eagles along the Mississippi River!

Midwest Winter Travel Tip: I like to carry a frost sheet in my car, especially if I’m having to park outside. Simply lay it over the windshield and shut the tabs in the doors.  It stops frost and ice from forming on the window, so you don’t have to scrape it or wait for it to clear!

🏨Where To Stay: The Hotel Julien Dubuque and the Grand Harbor Resort are some good options for Downtown hotels. Check out this post for full reviews: 7 Best Hotels In Dubuque Iowa USA

Winterset, Iowa

Suggested by Michelle from Simplify Live Love

Winter is the perfect time to explore Winterset in Madison County and Iowa’s new Covered Bridges Scenic Byway. The six famous Covered Bridges of Madison County are beautiful in any weather, but winter adds a magical element that only snow can provide. Choose a snowy weekend and head out to explore Madison County!

Make sure to explore Winterset’s downtown square too. Named “Outstanding Retail Experience” at the 2019 Iowa Tourism Conference, the square features many fun, independently owned shops with something for everyone!

If you’re a John Wayne fan, you won’t want to miss the John Wayne Museum, the only museum in the world dedicated to this celebrity. Warm up with a Pammel Park Coffee Company coffee at The Cellar and grab a delicious lunch at the famous Northside Café.

Head over here to learn more about the Madison county bridges and what to do while you’re in Winterset, Iowa.

Midwest Winter Travel Tip: Explore the 82-mile scenic byway safely by stocking your car with emergency essentials like wool blankets, snacks, water, and a full tank of gas. Take it slow if roads are icy, remember not to use cruise control on slippery roads, and take care when driving on gravel.

🏨Where To Stay: Cobblestone Inn & Suites

MISSOURI

Defiance, Missouri

Suggested by Kay from Happy Trails Hiking

Nestled in Missouri Wine Country is a slice of National history in the form of The Historic Daniel Boone Home. Each December, this reconstructed 1800’s frontier village comes to life for Christmas! Visitors step back in time at the Christmas Candlelight Walk.  

These walks take place on Fridays and Saturdays in December and sell out quickly. You can get your tickets through the Boone Home’s Facebook page.

We recommend making a full day tour of wine country stopping at Montelle Winery for the BEST views from a Missouri Winery as well as Defiance Gardens and vineyard for a wonderful afternoon snack.

Taking a walk at Klondike Park around the Lakeside Loop is a relaxing way to enjoy mid-afternoon, as well. Ending your day at the candlelight walk to really get you in the holiday spirit.

Even if you find yourself at the Boone Home during the week, you can still get a tour of this Historic Home and the village.

Park hours for home tours are 8:30 a.m.–5 p.m. Monday–Saturday; 11:30 a.m.–5 p.m. Sunday through December 16th. Then, Winter hours are 9 a.m.–5 p.m. Saturday; 12–5 p.m. Sunday.  The outdoor spaces are open for you to look around during the week all year long.  Find out more at Happy Trails Hiking.

🏨Where To Stay: TownePlace Suites by Marriott St. Louis Chesterfield (7 miles from Defiance)

MINNESOTA

Maple Grove, Minnesota

Suggested by Nicky from Little Family Adventure

Just minutes from downtown Minneapolis is the city of Maple Grove, home to Elm Creek Park Reserve. This regional park is an outdoor treasure that few people know about.

During the winter months, come out and enjoy tubing, Nordic skiing, snowshoeing, dog sledding, and snowboarding. Best of all, the prices are extremely reasonable! Lessons start at $24 and an annual ski pass is just $75.

If snow isn’t in the forecast, manmade snow ensures a full winter of fun. The opening of ski season is a huge event in the area. The parks hosts an annual 8k ski race, ski expo, and more the first Saturday in December. Visit their website for more information.

In addition to outdoor fun, the area has a thriving shopping and entertainment area. Visit the Shoppes at Arbor Lakes for local retailers and restaurants like Grey Duck Games & Toys and Patrick’s Bakery Cafe.

If you’ve never played Whirlyball, then a visit to Whirlyball Twin Cities is a must too! So whether you are looking for indoor or outdoor winter fun, you’ll find plenty just outside Minneapolis. Discover 11 more things to do in the northwest Minneapolis suburbs.

Midwest Winter Travel Tip: There’s an old Nordic saying, “There’s no such thing as bad weather, such the wrong clothes.” This is so true and wearing the “right” clothes means wearing layers. Invest in quality base layers to keep you warm and wick away moisture. Favorite brands include Fjällraven and Smartwool. Next add comfortable mid layers and finally great outerwear/coat.

🏨Where To Stay: Hampton Inn Brooklyn Park (4.5 miles from Elm Creek Park Reserve)

Mall of America – Bloomington, Minnesota

The Mall of America is a great place to escape the cold Midwestern winters!  There’s so much to do for all the family.  Not only are there hundreds of stores, you’ll find a huge indoor theme park, complete with a high ropes climbing course and zip lines, not one but TWO mini golf courses, an escape room, an aquarium, go kart tracks and plenty of different restaurants and food outlets to choose from!

I planned my winter getaway to the Twin Cities area around the Hot Chocolate 5k/15k race.  These races take place in various cities around the US during the winter season.

Typically I had to run my 5k in a BLIZZARD but it was a fun experience and all participants receive a personal chocolate fondue kit and a cup of hot chocolate at the end of the race!  There are several Midwest locations including: St Louis, Chicago, (Minneapolis), Kansas City, Oklahoma City and Detroit.

Midwest Winter Travel Tip: The hotel I stayed at in Minnesota had snow shovels and equipment to help guests dig their car out of the snow!  You may have to wait and share with other people but it saves from having to travel with your own giant shovel!

🏨Where To Stay: Residence Inn by Marriott Minneapolis St Paul/Roseville

NEBRASKA

Omaha, Nebraska

Suggested by Nikki from She Saves She Travels

If you’re looking for a Midwest destination in the winter time, then Omaha is an excellent choice. Omaha is an affordable city and will surprise you with one of the top 5 zoos in the world! The Omaha Henry Doorly Zoo and Aquarium regularly competes with the San Diego Zoo as the top zoo in the US.

When in Omaha, hang out in America’s largest indoor rainforest while watching monkeys swing on branches at the Lied Jungle. Experience the depths of the ocean as sharks swim above you at the aquarium. Pet sting rays at the Sting Ray Beach, or even marvel at hundreds of butterflies at the Butterfly Pavilion.

Perhaps the best place to be in the middle of winter? The world’s largest indoor desert, which just happens to be shaped like a dome. It’s the warmest exhibit as you work your way through the zoo.

The Omaha Henry Doorly Zoo and Aquarium is one of the most Instagrammable spots in Omaha, and rightfully so! My favorite spots to grab incredible photos are the desert dome and jungle.

The Zoo is Nebraska’s largest tourist attraction. But if you go in the winter, it’s way less crowded! Pro tip – buy your tickets online in advance and skip the lines.

🏨Where To Stay: Red Roof Inn & Suites Omaha – Council Bluffs IA

WISCONSIN

Eagle River, Wisconsin

Suggested by Chelsey Knuth from The Wisconsinista

Eagle River is located in the northwoods of Wisconsin and holds the honor of being the world’s snowmobile capital. With over 500 miles of groomed trails, there is endless potential for your next winter getaway!

Pro tip: the Polaris Ride Command mobile app uses GPS to track your location on the trails, so it can be a life-saver if you get lost and don’t have cell phone reception.

If you’d rather watch the sport than hop on a sled yourself, be sure to stop by the World Championship Derby Complex on the third Sunday in January to catch the annual World Championship Snowmobile Derby and see a new world champion be crowned.

Cabin-style lodging, like the Wild Eagle Lodge, adds to the cozy ‘up north’ experience and comes highly recommended by any true Wisconsinite. Leif’s Café should be your first breakfast stop, followed by the Country Store for all your sweet treat needs and Williams’s Pine Gables Supper Club for a classic Wisconsin supper club experience.

🏨Where To Stay: Wild Eagle Lodge

Wisconsin Dells, Wisconsin

The Wilderness is the perfect Wisconsin Dells resort for a Midwest winter getaway.  There are 3 main indoor waterparks with slides that are suitable for adults as well as children. The waterparks are spread out across the complex but are connected by internal hallways, so you don’t have to worry about having to go out into the cold!

Once you’ve had your fix of water slides, the Wilderness also has games arcades, climbing walls, an indoor go kart track, 3D backlit mini golf and a paint your own pottery studio.  The outdoor zip line course is open year round too!

If you decided to head out of the hotel, the Wisconsin Dells is home to a whole range of various other attractions and restaurants as well as nearby by skiing and snow tubing.  The Tommy Bartlett Exploratory is a fun hands on science museum and the Grateful Shed Truckyard (indoor food trucks and bar) as a unique place to eat!

To save money, you could stay at a chain hotel such as the Econo Lodge, buy a day pass to the water park at the Kalahari and explore the rest of what the Wisconsin Dells has to offer!

🏨Where To Stay: Econo Lodge Inn & Suites (to avoid expensive resort costs!)

Thanks again to all my Midwestern friends for sharing their knowledge!

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