A ski slope in your own backyard? Total pipe dream. A mountain within driving distance? Start packing up the car — each of these five wintry wonderlands is within three short hours of Chicago.
Wilmot Mountain
Wilmot, Wisconsin (Drive time from Chicago: 90 minutes)
Wilmot has been a destination for family skiing, snowboarding, and tubing since 1938 — and a recent purchase by Vail Resorts has seen a whopping $13 million in improvements, ensuring that its future is bright. New perks include three four-person chairlifts, a high-speed rope tow in the terrain park, two new lifts in the beginner’s area, an upgraded Base Lodge, and a new kids’ ski and snowboard school.
The Mountain Top at Grand Geneva Resort &Spa
Lake Geneva, Wisconsin (Drive time: 90 minutes)
There’s something for skiers of all ages and abilities at this 30-acre family-friendly ski destination at Lake Geneva’s iconic Grand Geneva Resort. Featuring three chairlifts and two carpet lifts, easy equipment rental, lessons for beginners, and night skiing, the Mountain Top is a one-stop shop for a whirlwind weekend on the slopes. For even more winter fun, try some sledding and ice skating, and be sure to warm up with a hot meal or drink by the fire at Leinenkugel’s Mountain Top Lodge.
Alpine Valley Resort
Elkhorn, Wisconsin (Drive time: 2 hours)
Park your poles here to enjoy over 90 skiable acres with 20 runs — including Big Thunder, a steep run with a vertical 388-foot drop and Alpine, the resort’s longest run at 3,000 feet. Ski school for adults and kids is available for beginners of all ages, while experts can check out the flat bar, donkey rail, and corrugated tube at the terrain park. If that’s not enough to entice you, guests at Alpine Valley Resort can enjoy on-site ski-in and ski-out rooms (120 are available, including family suites), complete with bistro dining, free weekend movie nights, and an indoor pool and hot tub. No snow? No worries — Alpine Valley will make some.
Cascade Mountain
Portage, Wisconsin (Drive time: 3 hours)
Calling all thrill-seekers! This hot spot near Wisconsin Dells boasts four terrain parks with several obstacles, a super pipe and halfpipe, and 10 black-diamond runs with steep descents and mogul fields. But you don’t have to be hardcore to appreciate the place, as the mountain is also home to plenty of beginner slopes (kids under 12 ski free!), a tubing park, and shorter runs.
Devil’s Head Resort
Merrimac, Wisconsin (Drive time: 3 hours)
Fun fact: This full-service resort — home to one of the state’s highest mountains — is located in Baraboo Bluffs, which was formed by glaciers over a billion years ago. Amenities include a large ski pro-shop, twice-daily groomed trails, long and wide runs, 500-foot vertical rise, accredited ski instructors, a terrain park with tubes and jumps, and available cross-country skiing.
Chestnut Mountain Resort
Galena, Illinois (Drive time: 3 hours)
Nestled right next to historic Galena and overlooking the Mississippi River, you’ll find 19 ski trails and a seven-acre terrain park with 25 rails and structures. Everything you need is right on site: rooms; an indoor pool, sauna and hot tub; three restaurants with contemporary cuisine and craft beer; children’s programs; and ski runs for all levels.
Wendy Altschuler is a seasoned travel and lifestyle writer with more than a decade of clips in various publications: MSN, Delta Sky, Modern Luxury, Sun-Times Media, Tribune Brand Copy, Parents Magazine, Yoga Magazine, The Daily Meal, Spafinder, Red Tricycle, Eluxe Magazine and many more. She is happiest when out exploring and adventuring or on a trail with her family and pup. Follow her on social @wendyaltschuler or visit her website: wendyaltschuler.com
Wendy is a big fan of volunteering with her kids and The Honeycomb Project, a sort of nonprofit aggregator that sets up family-friendly service projects for all ages. “We can sign up for community events around Chicago that help protect animals and the environment; fight hunger, poverty and homelessness; and offer joy and support to those in need. Doing good feels good,” Wendy says.
