Winter is approaching Chicago—gusty wind and all. And with the snow officially falling, it’s time to assimilate into outdoorsy activities. You may consider Chicago and the greater midwest area flatland with rows of cornfields. However, the Midwest has a myriad of trails and hills that make it the ultimate place for skiing, snowboarding, and snow tubing. All just a short drive, these are the best ski resorts near Chicago.
1. Devil’s Head Resort
Head to Devil’s Head for the ultimate ski trip this winter. The full-service ski resort is nestled in the heart of the glacier-formed Baraboo Bluffs in South Central Wisconsin. There are over 30 gentle, long, wide, and steep runs. The longest is 1 ½ miles—perfect for long carving turns.
Address: S6330 Bluff Rd, Merrimac, WI 53561
2. Boyne Mountain Resort
One of our favorite places for a winter getaway from Chicago. Boyne Falls is the ultimate playground for all seasons. You can let loose at the Boyne Mountain Resort, which has 415 skiable acres and the Midwest’s first eight-place chairlift.
Address: 1 Boyne Mountain Rd, Boyne Falls, MI 49713
3. The Highlands at Harbor Springs
Michigan’s premiere all-season resort is one of the must-visit ski resorts near Chicago. The highlands offer an idyllic setting near the charming town of Harbor Springs, Michigan. The Highlands Resort is a family-owned destination providing the ultimate northern Michigan experience.
Address: 600 Highland Pike Rd, Harbor Springs, MI 49740
4. Sundown Mountain Resort
If you thought Iowa was just miles of cornfields, think again. Located just a few miles from where “Field of Dreams” was filmed, Sundown Mountain offers various challenging skiing and snowboarding terrain amid the Iowa farmland. A 475-foot vertical drop with terrain cut out of an old cedar forest spread over 45 acres. The most beautiful part is seeing three states and the Mississippi River valley from the top of the scenic ski hill.
Address: 16991 Asbury Rd, Dubuque, IA 52002
5. Wilmot Mountain
Whether you’re an expert or a beginner, there is enough that will satisfy your skillset. There are nearly 120 skiable acres, 23 trails, seven lifts, two magic carpets, and terrain parks with a double high-speed rope tow, day or night. For those not up to skiing or snowboarding, there is always a delightful day waiting just down the road at the tubing area with 22 lanes and two magic carpets to take you back to the top.
Address: 11931 Fox River Rd, Wilmot, WI 53192