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A portion of the Milwaukee skyline and Lake Michigan in winter
Photograph: Courtesy of Visit Milwaukee

The best family winter vacation ideas in the Midwest

Beat cabin fever with these winter vacation ideas for families, all just a short drive away

Erin Yarnall
Written by
Samantha Lande
&
Erin Yarnall
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Don’t believe the hate. Despite oftentimes brutally cold weather, there are plenty of fun activities to do in Chicago all winter long. But if you’ve already hit Christkindlmarket, the city’s best ice rinks and all of the nearby sledding hills, it might be time to branch out a little bit. Why not look outside of the city for some winter excitement? The Midwest is home to plenty of great getaways, with several big cities and countless small towns that make for perfect wintertime family destinations. From sledding on dunes to visiting ice caves in the Great Lakes, here are some of the best family-friendly winter vacation destinations.

RECOMMENDED: The best day trips from Chicago 

Winter getaways for families

Blue Harbor Resort in Sheboygan, Wisconsin
Photograph: Blue Harbor Resort

Blue Harbor Resort in Sheboygan, Wisconsin

Travel time: 2.5 hours by car

Right on the shores of Lake Michigan, the Blue Harbor Resort is a great summer destination, but its indoor water park, Breaker Bay, makes it a top-notch winter attraction, too. Kids will love the giant interactive water fort with squirt guns, cargo nets, suspension bridges and tipping water. One of the most exciting attractions is the Riptide double surf simulator, where the daring can ride the waves indoors. Families can also rent cabanas ($175 full day/$99 half-day) stocked with food and drink (at an additional cost) and other amenities to have a place to relax between water adventures. After dinner, play a round of indoor glow-in-the-dark mini-golf. There are two themed suites available for family booking—the KidAquarium suite or Boathouse suite—complete with bunk beds in a fort area and a queen bed in a separate area for the adults ($210/night and up).

Milwaukee, Wisconsin
Photograph: Courtesy of Visit Milwaukee

Milwaukee, Wisconsin

Travel time: 90 minutes by car

If you’re looking for a big-city trip without the big-city trappings of Chicago, Milwaukee’s a great spot for a winter vacation. With many of the same amenities as Chicago, Milwaukee is a more subdued version of the Second City. Check out a Milwaukee Bucks game at Fiserv Forum, or stop at the Milwaukee Art Museum to see more than 30,000  different works. Want some outdoor activities? Go  ice skating at the city’s Humboldt Park, or try your hand at snowshoeing in the city’s Havenwoods State Forest, where snowshoes are available to borrow from the forest’s nature center. Don’t forget to pick up a warm drink from Colectivo when you’re done having fun outdoors.

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Boyne Mountain in Boyne Falls, Michigan
Photograph: Brian Walters

Boyne Mountain in Boyne Falls, Michigan

Travel time: Less than 5.5 hours by car

If a wintry, scenic drive to northern Michigan sounds fun, then Boyne Mountain is worth the trek. Take snowboard or ski lessons for the whole family and, for something fun and different, check out the Zipline Adventure ($79-85), a three-hour tour above the mountains (note that participants must weigh at least 60 pounds). Once the weather gets too frigid, warm up in the always-84-degree indoor water park.

Indiana Dunes National Park
Photograph: Courtesy of Indiana Dunes National Park

Indiana Dunes National Park

Travel time: 45 minutes by car

It doesn’t seem like winter would be an ideal time to stop by the beach, but it’s a unique opportunity to see the lakefront and surrounding sand dunes at Indiana Dunes National Park ($25 per car or $15 per person for walk-in/bike-in/boat in). Follow some of the dune trails, which extend for 15 miles down the shoreline, or go sledding at West Beach. Conveniently, the park is only 45 minutes from Chicago, so it’s by far the closest national park trip you could take. But if you want to make an overnight trip out of the visit, you can stay at the Marina Grand Resort in nearby New Buffalo, Michigan ($205 per night), where the kids can enjoy the heated, indoor pool to warm up after a day exploring the dunes.

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Cascade Mountain in Portage, Wisconsin
Photograph: Cascade Mountain

Cascade Mountain in Portage, Wisconsin

Travel time: Less than 3.5 hours by car

This ski resort close to the Wisconsin Dells offers free admission for skiers under 12 with a paid adult. The Cascade kids' learning program for ages 4–10 ($120) provides a three-hour class focusing on proper snowboarding and skiing technique and safety. The Comfort Suites-Portage is also free for kids under 12 and includes breakfast. Kids will love the 54-foot-long indoor pool as well. If you're looking for more water fun, head a little farther to the Chula Vista Resort in the Dells to splash around in the indoor water park, which has plenty of waterslides.

Hocking Hills, Ohio
Photograph: Courtesy of Hocking Hills Tourism Association

Hocking Hills, Ohio

Travel time: 6.5 hours by car

The caves in Hocking Hills State Park are a popular destination in the summer, but they’re even more dramatic, and beautiful, in the winter, when the park’s waterfalls are frozen over and icicles hang off of the rock walls and cliffs. Stop by for the park’s Christmas in Ash Cave event and enjoy holiday refreshments, a visit with Santa and Christmas tree decorating activities, all within the natural cavern. Stay the night at nearby Glenlaurel, a Scottish-themed inn with separate cabins on the property ($240 per night), and continue to explore the outdoors on the inn’s 140 acres of property.

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Bayfield, Wisconsin
Photograph: Courtesy of Grandon Harris

Bayfield, Wisconsin

Travel time: 7.5 hours by car

Bayfield is a charming Hallmark-esque town in northern Wisconsin, but most visitors make the trek up to check out the Apostle Islands, a group of islands located just off the coast of Wisconsin in Lake Superior. The largest of the Great Lakes freezes over near the islands during the winter, making it easy to walk around the islands instead of traveling by boat. Don’t forget to stop by the Ice Caves (parking ranges from $5-10 per day) at the Apostle Islands National Lakeshore to see the uniquely beautiful icicle formations and caves.

Devil's Head Resort in Merrimac, Wisconsin
Photograph: Devil's Head Resort

Devil's Head Resort in Merrimac, Wisconsin

Travel time: 3 hours by car

For families who love to ski—downhill or cross-country—Devil's Head is the perfect place to go. Kids can take beginner skiing lessons ($80 for 90 minutes) while their parents hit the more advanced slopes. Make a special visit for New Years Eve and catch the resort’s festivities, including a fireworks display, torchlit parade and DJ sets. There are plenty of packages available for skiers and non-skiers alike that include meals, lift tickets and activities, and non-package rates are also available.

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Door County, Wisconsin
Photograph: Fish Creek

Door County, Wisconsin

Travel time: Less than 4.5 hours by car

Door County has plenty of unique winter activities. Ice fishing is a favorite and, during the holiday season, you can even ride along in horse-drawn carriages. Art galleries and cute shops are open year-round, and you can plan your visit around the various winter festivals in the area, including the February Fish Creek Winterfest with a fiddle contest, plenty of soup and hot chocolate, candle-lit hikes and more.

Crystal Mountain in Thompsonville, Michigan
Photograph: Courtesy of Crystal Mountain

Crystal Mountain in Thompsonville, Michigan

Travel time: 4.5 hours by car

You don’t have to be an expert at skiing or snowboarding to have fun at this Michigan resort located just south of Traverse City—in fact, you don’t even have to have any equipment. Crystal Mountain rents ski and snowboard equipment for $60 a day, and the resort has ski lessons for kids as young as three years old ($75), but beginners of all ages can learn the ropes as well. If you get too cold, head inside and let the kids enjoy the heated, indoor pool which comes with a family play area, and take a dip in the hot tub to warm back up. Or spend a day getting pampered at the resort’s spa where you can relax with a rejuvenating facial ($145-315, depending on service) or a massage ($135-300, depending on service).

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