15 Best Winter Vacation Spots in the Midwest

Posted on September 21, 2022 | Julie J. |

Last Updated on March 7, 2023

Planning your next winter vacation and looking for some inspiration? Whether you’re traveling with your partner and are looking for romantic getaways or as a family looking for kid-friendly destinations, discover the best winter vacation spots in the Midwest.

From hiking to frozen waterfalls to joining a winter festival to strolling through historic towns, there are plenty of things to do come winter in the Midwest. No matter the type of vacation you’re looking for, you’ll find the perfect place for an epic winter getaway in the Midwest!

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Chicago, Illinois

Chicago is definitely one of the top vacation spots in the Midwest and should be added to your winter bucket list. The city becomes a snowy wonderland and is just magical around the holidays. You’ll find plenty of outdoor activities if you’re brave enough to embrace the cold, as well as many indoor activities to warm up.

Some of the top winter activities include ice skating at the iconic ice rink in Millennium Park, sledding at Soldier Field Sledding Hill, snowshoeing on Northerly Island, visiting an indoor garden, and strolling along the frozen lake on the Lakefront Trail.

For something fun, check out the curling rink on the rooftop of The Gwen Hotel, grab hot cocoa at one of the city’s many coffee shops, and tour a few museums, before checking out a winter rooftop event or two.

When it comes to places to stay, nothing beats the Viceroy Chigaco, one of the most popular and best-rated hotels in the city with incredible amenities and the perfect location in the heart of downtown.

Indiana Dunes National Lakeshore, Indiana

Indiana Dunes National Lakeshore in winter — Picture by Tom Gill

A stunning sight to witness during winter, when Lake Michigan freezes over and shelf ice forms, Indiana Dunes National Lakeshore is a great winter destination in the Midwest for people who enjoy spending time outdoors.

The area is ideal to go winter hiking, cross-country skiing, and snowshoeing. Snowshoes and cross-country skis can be rented for free at the Paul H. Douglas Center for Environmental Education for use on the Paul H. Douglas Trail.

If you have your own equipment, you can tour part of the Glenwood Dunes Trails, interconnected loops ranging from 1 to 15 miles. Advanced skiers can challenge their skills on the 2.9-mile Tolleston Dunes Trail.

If you’re visiting with kids or are a kid at heart, there’s a sledding area near West Beach.

If you are looking to spend some time in the area, you can rent a vacation rental nearby. You can also plan a day trip from Chicago.

Covered Bridges Scenic Byway, Iowa

If you are looking for a fun winter road trip in the Midwest, you’ll enjoy driving along the 82-mile Covered Bridges Scenic Byway in Iowa for a few days, stopping by small towns full of charm, and enjoying the picturesque scenery.

Nestled in the heart of Madison county, Winterset is in the middle of the byway and will make the perfect place to base yourself. You can take your time, visiting covered bridges, historic sights, and cultural attractions. There are over 120 featured places, so enough to keep you busy for the weekend.

Some of the must-sees include the covered bridges, John Wayne Birthplace & Museum, the Iowa Quilt Museum, Madison County Courthouse & Historic District, Madison County Historical Complex, Pammel State Park and Middle River Water Trail, a couple of wineries and a cidery, and Bison ranch.

When picking a place to stay, consider some of the historic inns in the area such as the Cobblestone Inn & Suite in Winterset.

Lawrence, Kansas

Lawrence will make a great winter weekend getaway in Kansas. The historic town features many quaint shops, a charming downtown, and many interesting museums.

Outdoorsy people will love heading to Clinton State Park and either go for a winter hike or cross-country skiing. It’s also a great place for bird-watching.

Don’t miss strolling by Massachusetts Street where you’ll find hundreds of independent shops and restaurants. Make sure to grab a bite at the popular Merchants Pub & Plate, where you’ll find comfort food and many different types of tap-beers.

You can also check out Old West Lawrence with its many houses from the 19th century, all on the National Register of Historic Places.

When you need to warm up check out a museum or two. The Haskell Cultural Center and Museum, displaying student and Native American art, the KU Natural History Museum, and the Spencer Museum of Art are all great options.

You can book a room at the well-rated SpringHill Suites by Marriott Lawrence Downtown, offering free parking, complimentary breakfast, and an indoor pool. You’ll also find plenty of comfortable vacation homes around town.

Marquette, Michigan

The Upper Peninsula turns into a winter wonderland where you’ll find plenty of trails, ice caves, mountains, cultural activities, and winter events. Marquette makes a perfect Midwest winter getaway and a good base to explore all the things Michigan has to offer during the winter.

Thrill-seekers can challenge their skills by climbing one of the 70 frozen waterfalls in the area. The most popular ones for ice climbing include the blue ice curtains at Sand Point, the 40-foot column at Miners Falls in the Pictured Rocks National Lakeshore, or the Eben Ice Caves which are the closest ones.

For winter sports head to Marquette Mountain Resort where you’ll find plenty of skiing and snowboarding slopes and trails. Cross-country skiers can head to Forestville Trails & Campground instead. You’ll also find many winter trails for hiking and snowshoeing in the area.

A fun thing to try is fat-tire biking, bikes with special tires that can go on snow!

For something indoors, check out some of the museums in town. The Marquette Maritime Museum & Lighthouse, the Upper Peninsula Children’s Museum, the DeVos Art Museum, the Shiras Planetarium, and the Michigan Iron Industry Museum are all highly recommended.

Don’t forget to check out the town’s event calendar as they organize many fun winter festivals!

You’ll find plenty of accommodation options for all budgets in Marquette. A good idea could be to book a vacation rental, especially if you’re traveling with friends or family.

Grand Marais, Minnesota

Winter Sunset at Grand Portage State Park, Minnesota — Picture by Shaun Cupp

Located along Minnesota’s north shore of Lake Superior, Grand Marais will make a perfect winter vacation spot if you want to see frozen waterfalls and go winter hiking.

The best places to go hiking to frozen waterfalls are High Falls at Grand Portage State Park, Devil’s Kettle Falls at Judge C.R. Magney State Park, and Cascade Falls at Cascade River State Park.

For scenic views over Lake Superior, hike or snowshoe the 3.8-mile out and back trail to Pincushion Mountain Overlook. On that same mountain, you’ll find an extensive cross-country ski trail system. You can also hike the 2.3-mile Oberg Mountain Loop Trail for views of the lake.

In town, sample some donuts at World’s Best Donut, get breakfast at Java Moose, enjoy dinner at Angry Trout Cafe, and grab a bite and a brew at Voyageur Brewing Company. You’ll also find plenty of cute independent stores to shop for souvenirs.

You can rent one of the many vacation rentals in town or on the lake’s shore. Otherwise, book a stay at Aspen Lodge where you’ll find rooms that can accommodate up to 6 people, some with lake views and/or a jet bath.

Voyageurs National Park, Minnesota

While you might see the Northern lights year-round in Voyageurs National Park, chances are higher during winter, making winter the best time of the year to visit.

It’s hard to predict if the Northern lights will show or not, to maximize chances you can check the Alaska Geophysical Institute’s Aurora Forecast up to a month in advance. Plus, the sky will need to be clear.

If you’re feeling adventurous, you can camp at the park, or book a vacation rental nearby for more comfort. You can also book a hotel room in the closest town to the park, International Falls.

In winter, you can explore the park with a snowmobile, on cross-country skis, in an auto on the ice road, or on snowshoes. At the Rainy Lake Visitor Center, adult and child-sized skis, snowshoes, boots, and poles are available free of charge. There’s also a sledding hill inside the park.

If you are there in January, check you the fun events held in the towns near the park during the “Icebox Days“.

Defiance, Missouri

The gateway to historic Missouri Wine Country, Defiance is a fun place to visit during winter. You’ll find plenty of recreational facilities to enjoy the snow, quaint shops and cozy cafes to warm up.

For winter sports, you can head to the Hidden Valley Ski Resort, offering trails for all levels and the largest tubing hill in the state.

You can also go for a winter hike at the Katy Trail State Park passing through bluffs, quaint towns, and incredible scenery, or at Babler State Park, known for its bird-watching opportunities. Another great place to see wildlife is the Howell Island Conservation Area, but the road there is not always open, so check beforehand.

In town, don’t miss touring the Historic Daniel Boone Home at Lindenwood Park to learn more about his past. If you like wine, make sure to visit a winery or two and go wine tasting. The award-winning Chandler Hill Vineyards is a must-see, check out their event calendar, they always organize fun things.

You’ll find a couple of cozy inns and charming bed and breakfasts set in historic houses around town. The Merry House Inn is a great option, with an ideal location. Otherwise, book a vacation home.

Omaha, Nebraska

Lauritzen Gardens Kenefick Park, Omaha, NE

If you are looking for a winter city break, Omaha makes the perfect winter destination in the Midwest as it offers the perfect blend of cultural activities, artsy vibes, an innovative food scene, and entertainment. It’s also a great family-friendly destination with plenty of fun things to do with kids.

Stroll around the Dundee–Happy Hollow Historic District where you’ll find several parks, historic buildings, restaurants, and independent shops. Eat at Pitch Pizzeria for some of the best pizzas in town or try something new at the trendy Lalibela Restaurant, serving Ethiopian food.

If you like beer, a fun thing to do is to take a ride on a Omaha’s Brew Bus which will take you on a tour of local breweries, sampling local brews.

You’ll also find many museums around town. If you are traveling with kids, don’t miss Omaha’s Children Museum and its hands-on exhibits that are fun and educational. The Durham Museum is great to learn more about the region’s past and is set in an old train station. Nearby, don’t miss the iconic Bob Kerrey Pedestrian Bridge.

There are many historic places to tour as well like the General Crook House, the Rails West Railroad Museum, the Squirrel Cage Jail, and Joslyn Castle.

If the weather is nice you can take a stroll in one of the city’s many parks and gardens. Look at the sculptures at Pioneer Courage Park, enjoy nature at the OPPD Arboretum, or discover local flora at the Lauritzen Gardens/Kenefick Park.

The Farnam is a great place to stay at, conveniently located within walking distance of most of the city’s attractions. You can also check out some of the many great vacation rentals available around town.

Medora, North Dakota

theodore roosevelt national park, north dakota

Surrounded by the Little Missouri National Grassland and Theodore Roosevelt National Park, the tiny town of Medora will make an awesome winter vacation spot in the Midwest for true outdoor lovers.

In winter, you’ll find many miles of cross-country skiing and snowshoeing trails at Theodore Roosevelt National Park. It’s a great time to see wildlife, especially bison and wild horses. You can also plan a scenic drive through the park to take in the stunning winter scenery.

In town, you can tour the Chateau de Mores, a 26-room summer home built in 1883, and the Maltese Cross Cabin, where President Theodore Roosevelt stayed in the late 1800s. Don’t miss the fun North Dakota Cowboy Hall of Fame as well.

The first weekend of December, the town organizes the Medora’s Old Fashioned Cowboy Christmas with plenty of fun events for everyone to enjoy.

Note that winter is the off-season so many businesses in town might be closed when you visit.

You’ll find a couple of cabins available for rent in and around town. Or you can book a stay at the comfy AmericInn by Wyndham Medora offering an indoor pool and a complimentary breakfast.

Hocking Hills, Ohio

Hocking Hills is usually popular during the warmer months, but visiting during winter will allow you to escape the crowds and see the area turned into a freezing wonderland. There are actually quite a few things you can do there come winter, from hiking in the snow to pampering yourself with a spa day.

With miles of hiking trails passing by caves, gorges, and waterfalls, you’ll find plenty of opportunities from easy strolls to strenuous hikes. Some of the best places to check out during winter include Ash Cave, Old Man’s Cave, Cedar Falls, and Rock House.

Book a cabin with a fireplace and hot tub so you can warm up after a day spent outdoors. Take it up a notch by booking a spa treatment or massage at the Inn & Spa at Cedar Falls. You can check out their glamping options as well, they offer luxurious yurts and geodome.

In the evening, head to Hocking Hills Winery where you can sample some local wine while enjoying the live weekend entertainment. If beer is more your thing, head to Brewery 33 instead.

You can also plan to spend a few hours visiting Nelsonville and its charming historic downtown filled with independent stores, coffee shops, and restaurants.

Black Hills, South Dakota

Outdoor lovers will love visiting the Black Hills during winter. The stunning landscape and the many activities and entertainment options make it a top winter getaway destination in the Midwest. You could easily spend 2 weeks there and find new things to do every day.

Start your winter adventure with a 19-mile scenic drive along the Spearfish Canyon Scenic Byway, stopping along the way to gaze at Roughlock Falls, Bridal Veil Falls, and Spearfish Falls. Advanced hikers and ice climbers will enjoy the uphill trails to Community Caves and Baker’s Cave.

If you want to see wildlife head to Jewel Cave National Monument and Wind Cave National Park where you’ll find hiking trails and scenic drives. Badlands National Park is also a must-see in the area.

Skiers and snowboarders of all levels will enjoy the 80 trails at Terry Peak. Full equipment rental and ski lessons are available at the resort as well as an onsite restaurant. If snowshoeing is more your thing, head to Custer State Park where you can rent equipment and enjoy endless miles of groomed trails.

In the northern Black Hills, all the way through Deerfield, you’ll find an extensive interconnected trail system, where you can go on a snowmobile tour through forested mountains and valleys.

Another incredible thing to experience during winter is to watch the sunrise over Mount Rushmore National Memorial.

The communities of Lead, Deadwood, Spearfish, Sturgis, Belle Fourche, and Hulet are great places to grab a bite, have drinks, and sleep. You’ll find many cabins in the area with easy access to trails.

Door County, Wisconsin

Lighthouse in Door County during winter, United States

Door County turns into a winter wonderland with the first flakes of snow, book a cabin, sip on hot cocoa warming up by the fireplace, and enjoy some of the best winter activities in the state.

With over 50 miles of trails to explore in the county, you’ll be spoiled for choice. Whether you want to go winter hiking, snowshoeing, or cross-country skiing, add one or two local state parks to your itinerary. Peninsula State Park is a great option.

Even in winter, you should go for a stroll on one of the many local beaches to admire the frozen landscape.

For something to do indoors, you can visit a couple of local breweries like Starboard Brewing Company, Shipwrecked Brewery, and Door County Brewery, or sample some cider at Island Orchard Cider.

There are a couple of wine-tasting opportunities as well in the area. Check out Harbor Ridge Winery, Stone’s Throw Winery, and Door Peninsula Winery.

No matter when you visit, you’ll find plenty of events and festivals going on, so make sure to check out if there’s anything happening during your vacation.

The Wanderlust Hotel is a great place to stay in Sturgeon Bay for couples (adult-only). Families will enjoy the Open Hearth Lodge with its family rooms, free breakfast, and indoor pool. You can also book a vacation rental, many feature great views over the lake.

Lake Geneva, Wisconsin

By Patti from The Savvy Globetrotter

Lake Geneva is one of the best places to visit in the Midwest for a winter vacation. Located in southeastern Wisconsin, this picturesque lakeside resort city becomes a winter wonderland when it snows. Fun outdoor winter activities in the area include skiing, snowboarding, sledding, snowshoeing, cross-country skiing, and ice skating.

One of the most unique winter attractions in Lake Geneva are the ice castles, a man-made frozen attraction that can be found in only five cities in North America.

The castles are built using hundreds of thousands of icicles, hand-placed by professional ice artists and include sculptures, thrones, slides, ice-carved tunnels, and more. The ice castles are the most beautiful at night when they are lit by LED lights in various colors.

A popular winter event is the annual Winterfest celebration, the highlight of which is the U.S. National Snow Sculpting Championship where teams of snow sculptors and artists compete for a national title.

Lake Geneva is easy to reach – it is located less than 90 minutes from Chicago and about an hour away from Milwaukee.

The Grand Geneva Resort & Spa is the most convenient place to stay for visitors interested in skiing, snowboarding, and sledding. In addition to its ski hills, this AAA Four-Diamond resort offers many indoor amenities for those looking to stay warm including several restaurants, a spa, and an indoor pool.

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