Family-Friendly Ski Resorts Near Chicago for Your Next Getaway

These fun-filled winter wonderlands just a drive away.

No matter if you’re a family of powder hounds or just starting out on the bunny hills, you don’t have to go far from home to ski or snowboard. Here are three ski resorts within driving distance to get in your winter shredding. 

Book private or group lessons and learn a new sport together or give the kids the gift of confidence in an activity they can enjoy for years to come.

Wilmot Mountain Ski Resort

Wilmot, Wisconsin; 1 hour from Chicago

So close to home that you don’t even need to stay overnight, Wilmot Mountain is a smaller, affordable ski hill, which is easier to learn on. With 120 acres, 25 trails, 10 chairlifts and three terrain parks, there’s reason to come back several times a season. Adult, child, private and group lessons are available to help you get comfortable or to up your game. And if you forget goggles or other gear, the retail shop will make sure you’re set.

Wilmot also features a 22-lane tubing area, each offering 1,000 feet of giggle-inducing sliding in the snow. Warm up at the lodge with a brat and tots or other Wisconsin favorites, like a Spotted Cow beer, Kringle pastry or Friday night Fish Fry. If you have Epic Passes, you can also use them at nine other Midwest resorts or at Vail, Breckenridge and Park City.

Chestnut Mountain Resort

Galena; 2.5 hours from Chicago

With 19 different runs from beginner bunny hills to daredevil black diamonds, Chestnut Mountain Resort offers skiers of all levels fun for their skill set. Located in picturesque Galena overlooking the Mississippi River, the resort offers a breathtaking backdrop on a sunny winter day and a 475-foot vertical drop, which is uncommon in the Midwest. Older kids and more confident skiers will be stoked for the seven-acre Far Side Terrain Park. Stocked with a quarter-pipe, two half-pipes and its own triple lift, this 25-trail terrain park will slather smiles across the faces of adrenaline-seekers. 

Children’s ski programs help little ones learn the basics like snowplow stops and turns. There’s even a Powder Playcare for toddlers to rest while parents hit the slopes. Afterwards, splash around in the indoor pool and enjoy appetizers, pizzas and sandwiches at the restaurant. 

Cascade Mountain

Portage, Wisconsin; 2.5 hours from Chicago

Twenty minutes from Wisconsin Dells, you’ll find tons of outdoor winter fun at Cascade Mountain, where you can ski, snowboard and tube until 10 p.m. most Fridays and Saturdays and 8 p.m. Sundays through Thursdays. Of the 48 trails available for skiing and snowboarding, 37% are beginner runs, 40% are intermediate and 23% are advanced, so everyone should be able to find trails that are their speed. Kids 12 and under can ski free, with up to five free child lift tickets per paying adult.

Lessons are available for first-timers and those who want to race. If rails, jumps and jibs are your jam, Mountain Top Park has them all. Cottontail Park contains smaller features for practicing the basics of freestyle skiing and riding. If you’re an expert, J.J. Terrain Park is where you’ll want to hang.

Snow tubing is another super fun way to enjoy a day in the powder. Link your tubes and slide down together. Then take the magic carpet back up for another joy ride down. No worries if it hasn’t actually snowed — Cascade Mountain has snow-making capabilities. Warm up and grab food at the café or snack bar. Just remember that they’ve gone cashless, so credit cards and Apple Pay are some of the ways to pay. 

Stay in nearby Wisconsin Dells to add water park fun to your winter adventures.

Mt. Brighton 

Brighton, Michigan; 4 hours from Chicago

Brighten your winter day at Mt. Brighton Ski Resort, where you can learn to ski or snowboard or tear it up on a terrain park. Or brighten your night by skiing or riding under the lights. Twenty-five trails and five lifts on more than 130 skiable acres make for an uplifting snow sports scene. Close to home, this ski resort is one of the highest points in Livingston County. Take a sunset ride on chair 2 or 3 to drink in the views. 

You may even remember this 60-year-old ski resort from its cameo in the cult classic movie, “Aspen Extreme.” 

Brighton events are the best way to beat winter blues. Build a sled out of cardboard and duct tape and enter the Duct Tape Derby. Toast up Sunday S’mores for a sweet treat around a crackling fire pit. Slush Cup is a memorable way to end the season. If you have Epic Passes, you can also use them at nine other Midwest resorts, or at Vail, Breckenridge and Park City.

Crystal Mountain 

Thompsonville, Michigan; less than 5 hours from Chicago

Celebrate winter at Crystal Mountain, a family-owned resort not far from Traverse City and Sleeping Bear Dunes National Lakeshore. New snow guns help ensure there’s always ample snow for optimal skiing and snowboarding conditions. Kids and parents can feel more confident when little ones are learning the slopes with new GPS tags that track students’ progress on the slopes, increasing peace of mind. Plus, use the data to know which runs kids are comfortable with and where to return on their next lesson.

After your day on the mountain, dine in cozy 12-foot outdoor igloos at the Wild Tomato. Up to eight people can enjoy beverages, small plates and treats like s’mores roasted over mini tabletop fire pits. Snuggle up in a blanket while overlooking Barr Park or watch the kids glide around the ice skating rink. Take a winter walk around Michigan Legacy Art Park, which is home to more than 50 sculptures and installations, including “Gateway to Black Eden” by Detroit artist M. Saffell Gardner.

Boyne Mountain Resort

Boyne Falls, Michigan; 5.5 hours from Chicago

Boyne Mountain boasts 415 skiable acres in the lower peninsula of Michigan with all sorts of upgrades for the season, including new conveyors, runs and LED music and lighting for tubing. The resort’s 75th anniversary will be a big celebration. 

SnowSports School lessons are available for all ages, in groups or one-on-one for individual attention. Take a sunrise or sunset on-slope guided tour on an electric MoonBike. Or go tubing, snowshoeing or ice skating.

There’s plenty to do, even for those who prefer not to ski or snowboard. Splash the day away at Michigan’s largest indoor water park or indulge in a spa experience. Winter ziplining and horseback riding can be exhilarating. SkyBridge Michigan, the world’s longest timber towered suspension bridge, is aglow with a winter light experience. Sleep well at your choice of lodges, cabins or villas. 

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Cortney Fries
Cortney Fries
An award-winning travel journalist, Cortney Fries (pronounced "freeze") has been writing about family travel for over a decade. She knows that parents planning trips are looking for all members to have fun and make lasting memories. Cortney believes that you should definitely try anything that makes you slightly nervous.


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