Chicago Ski Resorts May 2026

These resorts offer more varied terrain and are better suited for full-weekend trips.

While Chicago is known for its flat terrain, several ski resorts and "hills" are accessible within a few hours' drive, primarily in southern Wisconsin, Michigan, and northern Illinois. chicago ski resorts

Located about 65 miles north of Chicago, this resort was acquired by Vail Resorts and features 25 runs and a 230-foot vertical drop. It offers modern amenities including high-speed lifts and a large tubing hill. These resorts offer more varied terrain and are

Known for reliable snow and high-quality grooming, this resort offers a diverse range of winter activities about 5 hours from the city. It offers modern amenities including high-speed lifts and

A favorite for many Chicagoans, this resort is roughly a 1.5 to 2-hour drive away. It features 20 runs, a 388-foot vertical drop, and some of the only ski-in/ski-out lodging in southern Wisconsin. Weekend Getaways (2.5 - 4 Hours)

This full-service resort features 30 runs snaking down a 500-foot bluff. It is known for its long, impeccably groomed cruiser trails and slopeside lodging. Larger Regional Resorts (4+ Hours)