1. Wilmot Mountain Ski Resort
Location: Wilmot, WI
Recommended For: Midwest skiers, snowboarders, families, beginners, and weekenders from Chicago.
What I Love: ♥ "It’s close, it’s classic, and it’s surprisingly full of energy. The revamped base lodge, night skiing, and convenient access from Chicago make it a winter favorite."
- Carve down 23 runs across 120 acres, from gentle beginner slopes to exciting terrain parks.
- Learn at the full ski and snowboard school—ideal for first-timers and returning riders alike.
- Enjoy après-ski comfort in the upgraded Base Lodge with dining, rentals, and cozy rest spots.
Cost: Lift ticket prices vary by age, date, and season; check the official site for current rates.
Best time to visit: December through February for peak snow and race events; midweek visits offer shorter lift lines.
Local tips: Arrive early on weekends to secure parking and rentals. Night skiing is great for avoiding crowds.
Distance: About 1.5 hours from Chicago; 50 minutes from Milwaukee.
How to Get to Wilmot Mountain: From I-94, take WI-50 west, then follow County Highway W south to Fox River Road and look for the resort signs.
Address: 11931 Fox River Rd, Wilmot, WI 53192
Phone: 262-862-2301
Review:★★★★★ "I had an amazing time at Wilmot Mountain Ski Resort! The slopes were fantastic, offering runs for all skill levels. I really enjoyed the snowboarding trails, which had the perfect mix of chalenge and fun. The staff was friendly and helpful, and the views from the top were breathtaking. Can't wait to return next season!"
2. Alpine Valley Resort
Location: Elkhorn, WI
Recommended For: Skiers of all levels, families, weekenders from Chicago, and winter resort lovers.
What I Love: ♥ "From the tree-lined runs to the cozy lodge with a pool, it’s the Midwest's full-service winter escape. That 3,000-foot trail? A total adrenaline stretch with big-mountain feel."
- Shred 20 ski runs across 90 acres, served by 12 lifts—including five magic carpets for easy access.
- Challenge yourself on the 3,000-foot-long advanced run or take a lesson at the ski school for beginners.
- Relax après-ski with on-site lodging, bistro dining, and a heated indoor swimming pool.
Cost: Lift ticket and lodging rates vary by day and season—check the resort site for current pricing.
Best time to visit: December to early March for ideal snow conditions and family-friendly winter events.
Local tips: Book accommodations early for weekends. The resort is busiest Saturday afternoons—go early for shorter lift lines.
Distance: About 2 hours from Chicago; 1 hour from Milwaukee or Madison.
How to Get to Alpine Valley Resort: From I-43, take the exit for WI-20 west, then follow signs for County Road D and the resort entrance.
Address: W2501 Co Rd D, Elkhorn, WI 53121
Phone: 262-642-7374
Family-friendly Skiing Near Chicago:
3. The Mountain Top at Grand Geneva - 90 minutes from Chicago
Location: Lake Geneva, WI
Recommended For: Families, beginner to intermediate skiers, luxury resort seekers, and weekend travelers from Chicago.
What I Love: ♥ "It’s the only ski hill where you can glide by day and unwind in a full spa by night. The blend of slopes, sledding, and elegance makes it feel like a winter retreat with perks."
- Ski 20 well-groomed runs with a large terrain park, ideal for all skill levels.
- Enjoy additional activities like sledding, snowboarding, and ice skating for a full winter itinerary.
- Stay in style with upscale lodges, multiple dining options, and spa access at Grand Geneva Resort.
Cost: Lift ticket prices vary by day and age; check resort site for seasonal rates and ski packages.
Best time to visit: Mid-December through February for skiing and snow play; January offers peak snow conditions.
Local tips: Arrive midweek for shorter lines and spa specials. Book lodging early for holiday weekends and winter breaks.
Distance: About 90 minutes from Chicago; 50 minutes from Milwaukee.
How to Get to The Mountain Top: From I-43, take Highway 12 to Lake Geneva. Follow signs to Grand Geneva Resort and The Mountain Top entrance.
Address: 7036 Grand Geneva Way, Lake Geneva, WI 53147
Phone: 262-249-4726
4. Devil’s Head Resort
Location: Merrimac, WI
Recommended For: Skiers of all levels, families, budget travelers, and those seeking scenic mountain views.
What I Love: ♥ "Affordable, expansive, and surrounded by jaw-dropping views—Devil’s Head is the Midwest’s under-the-radar gem. Great for both ski weekends and off-season golf getaways."
- Ski 30 diverse runs with a perfect blend of beginner, intermediate, and advanced terrain.
- Learn at the certified ski school or take advantage of nine lifts for smooth access to the slopes.
- Stay on budget with value-friendly lift tickets, rentals, and convenient on-site amenities.
Cost: Admission and rentals are known for being budget-friendly; check the resort website for seasonal pricing.
Best time to visit: January to early March for peak snow; fall is also stunning for golf and foliage views.
Local tips: Midweek visits mean fewer crowds and better slope conditions. Don’t skip the scenic drive in—it's part of the experience.
Distance: About 3 hours from Chicago; 45 minutes from Madison, WI.
How to Get to Devil’s Head Resort: Take I-90 to WI-33 west, then follow Bluff Road signs to the resort in Merrimac.
Address: S6330 Bluff Rd, Merrimac, WI 53561
Phone: 608-493-2251
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