Chicago Ski Resorts 〈2026〉

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

These resorts offer more varied terrain and are better suited for full-weekend trips. 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. Known for reliable snow and high-quality grooming, this

Known for being family-friendly, Cascade offers 48 trails and a 460-foot vertical drop. A major draw for families is that kids 12 and under ski free with a paying adult. 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)