The best Midwest winter getaways for families

Travel time: 2.5 hours by car

Blending small-town charm with cozy, kid-friendly adventures, Holland is the ideal winter getaway for families. Spend the day sledding, admiring frozen windmills or bravely enduring the elements before retreating downtown to thaw out. A stop at DeBoer Bakkerij for Dutch pastries is a must, followed by a visit to Lemonjello’s Coffee—because nothing says “family bonding” quite like a hot cocoa and the shared realization that winter is best experienced from the heated side of a window.

When the crowds thin and Lake Michigan transforms into a living snowglobe, the city’s charm truly shines. Wander through local favorites like the Apothecary Gift Shop to snag whimsical treasures. With quieter streets, affordable lodging and cozy corners abound, Holland offers a peaceful winter escape that stays warm long after the sun goes down.

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 ($225 full day/$125 half-day), stocked with food and drinks (at an additional cost) as well as 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. Reservations start at $204 per night, and include four waterpark wristbands.

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 can take.

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 (rooms start at $200 per night), where the kids can enjoy the heated, indoor pool to warm up after a day exploring the dunes.

Travel time: 1.5 hours 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 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.

Travel time: 1.5 hours by car 

Attention, adrenaline seekers: If you’re looking to take your indoor or warm-weather climbing to the next level, try this. Chicago’s favorite hiking destination Starved Rock State Park is famed for its dramatic waterfalls and deep, curving gorges, and as the temperatures plummet, the frozen water becomes your next summit. Bring your own equipment and test your strength at any of the park’s four approved ice climbing canyons ranging from 20–90+ feet. As you reach the top, take in the dramatic snow-covered forest and rolling hills. Little ones can enjoy playing in the snow or hiking as the adults climb. Make it a day trip or relax for the weekend at one of the rustic log cabins or wood-paneled rooms at Starved Rock Lodge. Need gear? Several Chicagoland stores like REI rent equipment. 

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–$84), 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 indoor water park that always stays between 84 and 87 degrees.

Travel time: 1 hour by car 

Just south of the Wisconsin border, Illinois Beach State Park is one of the best places for camping near Chicago. Most adventurers enjoy the nearly seven miles of shoreline in the summer, wading in the clear water and hiking the prairie landscape, but winter offers breathtaking views of the lake from the comfort of Illinois Beach Hotel, Illinois’s only lakefront hotel. Go full staycation mode under the covers as you watch the pink-hued sunrise over the frozen water through your lake-facing balcony and stay local with a meal at the on-site restaurant, Nolan’s. Visit nearby Shiloh Park around the holidays for a trail of over 100,000 lights, or venture through the state park for family activities like hiking, cross country skiing, winter birdwatching and more.

Travel time: 4.5 hours by car

Door County might be a classic Midwestern summertime destination, but the peninsula still has plenty of unique activities during the winter. 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 featuring a fiddle contest, plenty of soup and hot chocolate, candle-lit hikes and more.

Travel time: 2.5 hours by car

Put the adage “there’s no bad weather, only bad clothing” to the test and soak up some much needed Vitamin D as you glide—or stumble, depending on your skills—across the ice at one of Madison’s five lakes. In the chillier months, these summer hotspots transform into fun-filled playgrounds for all ages. For a more relaxed experience—and a hot chocolate in hand—head to The Edgewater Hotel’s outdoor ice rink overlooking the shores of Lake Mendota. Ice skating is free at some Madison parks and rentals are available at Tenney, Vilas and Elver Parks. 

Travel time: 2.5 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 5–10 provides a three-hour class focusing on proper snowboarding and skiing technique and safety. If you simply want to have fun in the snow, try tubing down a 900-foot chute instead. The Comfort Suites-Portage is also free for children under 18 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.

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. Rent a cabin nearby, or bring the entire family (yes, we mean your pets) to stay at Dog Friendly Hocking Hills. Each of the dog-friendly cabins can accommodate any dog—there are no restrictions on size or breed.

Travel time: 3 hours by car 

Stay warm and experience the lesser-known culinary and literary kid-friendly treasures of the Midwest, just three hours southeast of Chicago. The stunning 1920s-era Bottleworks Hotel puts you within a short distance of inviting bookstores, dimly lit cocktail bars and award-winning restaurants. Start your visit at the Kurt Vonnegut Museum and Library, a three-story exploration of both Indy’s most famous former residents and the ongoing fight for freedom of expression through art, particularly storytelling. Afterwards, celebrate contemporary Indianapolis writers and other diverse works for the whole family at bookstores like Loudmouth Indy and The Whispering Shelf. If you’ve left the little ones at home, choose from one of the hundreds of whiskey options at Massachusetts Avenue’s stately bar, The Exchange, before heading to the Kurt Vonnegut-themed, James Beard Award semi-finalist Bluebeard. Sip on literary-inspired cocktails like the San Lorenzan (gin with artichoke amaro and citrus flavors) and indulge in the decadent roasted bone marrow or yuzu trout roe linguini.

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 isles located just off the coast of Wisconsin in Lake Superior. The largest of the Great Lakes freezes over 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.

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 ($100 for 90 minutes) while their parents hit the more advanced slopes. Make a special visit for New Year's 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.

Travel time: 6.5 hours by cars

Feeling brave? “Yoopers,” or residents of Michigan’s Upper Peninsula, often joke about why anyone continues to live—and love living—in such an inhospitable place. Venture “up north” to the shores of Lake Superior to Marquette, MI, for a charming city of 19th Century-built buildings, repurposed theaters, breweries—all on the doorstep of thrilling winter adventures.

Skiing, snowboarding, snowshoeing, fat biking and snowmobiling (equipment rentals available at various sports outfitter stores in Marquette) are all popular activities, but stick around for the annual UP200, an Iditarod qualifier covering 228 miles of challenging terrain from Marquette to Grand Marais and back. Cheer on the sled dog racers in downtown Marquette as they catapult through snowy streets.

Travel time: 8.5 hours by car

Bluefin Bay (varying rates, starts at $234 per night for four people) might be a lengthy drive from Chicago, but it’s worth the effort. The resort, located in the seriously tiny community of Tofte, MN (with a population of just over 200), sits along the shore of Lake Superior, and while it offers stunning lakeside views, there’s also so much more. There’s an extensive series of snowshoeing trails near the resort’s property, and guests can join guided tours or venture out on their own.

Not feeling outdoorsy? Warm up in the indoor pool or take part in one of Bluefin Bay’s crafting classes. The resort offers both painting and wood burning classes, so you can leave with your own piece of art. There are also nightly bonfires near the lakeshore, and complimentary s’mores kits are available at the resort.

Travel time: 2.5 hours by car

Snow is wet and cold, which leads some people to stay inside once it starts to fall. For others, it’s the perfect opportunity to enjoy the outdoors. One of the most fun, family-friendly activities to do in the snow is sledding, and there are few better places to do just that than Pokagon State Park in northeastern Indiana. The park is home to a toboggan run that drops riders more than 90 feet on a quick and exciting ride. The best part? You don’t even need to wait for the snow to fall to enjoy it. The run is situated along a refrigerated track, so while snow might make the views a bit more scenic, it’s not necessary for the operation. Stay at the waterfront Potawatomi Inn and Cabins (rates start at $99 per night), a hotel located inside the park that sits along the shore of Lake James. The hotel has an indoor pool and hot tub to help you and the family warm up after a fun day outdoors.

Travel time: 5 hours by car

It’s up for debate where the true birthplace of rock and roll is, but there’s no arguing where it’s best celebrated—the Rock & Roll Hall of Fame in Cleveland, OH. No matter what genre of music your family likes the most, there will be something there that interests them. From Taylor Swift’s costumes to handwritten lyrics by The Beatles to Kurt Cobain’s guitar, the hall of fame serves as a museum and a place to showcase your own talents. Stop by The Garage exhibit, where you can take part in your own garage band experience by playing real instruments. When you’re done with the hall of fame, attend a sporting event. If the Cavaliers aren’t in town, check out a Cleveland Monsters ice hockey game—the team plays in the American Hockey League, where you can see future NHL stars before they make it big.

Don’t forget to celebrate the holidays in a way that’s only possible in Cleveland—stopping by the home from the 1983 holiday film A Christmas Story. The house has been restored to look just like it did in the movie (yes, it has a leg lamp in the window), and is open year-round for tours. Dedicated fans can even stay overnight, but be sure to make reservations well in advance. 

Travel time: 4 hours by car

It can be pretty difficult to access some national parks during the winter, but that’s never the case at Gateway Arch National Park, one of the standout monuments in St. Louis, MO. Take a ride up to the top of the arch, and then walk across the street to take in some history at the Old Courthouse—where Dred Scott v. Sandford was tried. When you’ve had enough fun exploring the arch and learning about the city’s history at the courthouse, take the kids to the Steinberg Skating Rink in the city’s Forest Park. The rink is the largest outdoor ice skating rink in the Midwest, at more than 27,600 square feet, and offers skate rentals and lessons.

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 45 minutes south of Traverse City—in fact, you don’t even have to have any equipment. Crystal Mountain rents ski and snowboard equipment for $65 a day, and the resort has ski lessons for kids as young as three years old ($95–$115), but beginners of all ages can learn the ropes as well. If it gets too cold, head inside and let the kids enjoy the heated indoor pool, which comes with a family play area, while you 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 ($160–$330, depending on service) or a massage ($160–$220, depending on service).

Travel time: 3.5 hours by car

If you're looking for a quaint spot with coffee shops, cafes and shopping, head to Galena. The winter brings about many activities, like ice skating, snowshoeing and cross-country skiing. You can even go on a bald eagle–spotting tour on select dates. For downhill skiing, visit Chestnut Mountain, where kids can take half-day ski lessons or even learn to snowboard.

Travel time: 45 minutes by car

You don’t have to travel far for some serious family fun this winter. Great Wolf Lodge, in suburban Gurnee, is only 45 minutes from the city by car, but feels like an escape from winter once you enter. The water park has seven waterslides, a lazy river and a wave pool. While the water park might be the resort’s main attraction, there’s much more to do at Great Wolf Lodge than swim: There’s fun for all ages at the resort’s indoor mini-golf course, plus seasonally-themed events like the Frosty Fest Family Dance Party and the Snowland Scavenger Hunt.

For accommodations, the resort has both standard suites and themed suites, including the Wolf Den, which has an in-suite, cave-themed sleeping area with bunk beds for the kids.

Travel time: 3 hours by car

If spending time outdoors in the winter isn’t the right fit for your family, the Dells is a great option. The “water park capital” of the Midwest offers up wet and wild fun for everyone. Kalahari is one of the best, with water attractions for toddlers to teens. It also offers a variety of indoor  “dry” activities, like laser tag, mini golf and go-carts. The less adventurous can take home a new best friend from the Build-A-Bear workshop, and there's a full-scale spa for the adults. Rooms are available to accommodate families of all sizes, with regular guest rooms to as large as 12-bedroom suites.

Travel time: 5.5 hours by car

It may not be the titular prairie Laura Ingalls Wilder described in Little House on the Prairie, but fans know her story actually began years earlier near Pepin, Wisconsin. This small village, home to just over 800 residents, serves as the setting for Wilder’s first book, Little House in the Big Woods. The author’s birthplace, and family home, is open for tours, and only $25 for a family of two adults and two children.

Even if you’re not a fan of the famous book series, there’s plenty to do in Pepin during the winter. The village is a utopia for any families who love the outdoors, with places to go snowshoeing, plenty of snowmobiling trails and its location on the Mississippi River makes it a great spot for ice fishing.