Ski Resorts near Chicago

The Windy City may be known for its cold and snowy winters, but its flat terrain means that skiers and snowboarders will have to venture out of the city to hit the powder. Luckily, a number of top-rate slopes are within easy driving distance of Chicago, ideal for long weekends with options for skiers and snowboarders of all skill levels.

Chestnut Mountain Resort (Galena, IL; 3 hours west of Chicago)

With a 120-room resort lodge nestled on a bluff overlooking the Mississippi River, Chestnut Mountain offers plenty of activities (including a sauna and indoor pool) to keep you entertained in between ski runs. Skiing and snowboarding, however, are Chestnut Mountain’s true draws. With a 475-foot drop running for 3,500 feet across 19 slopes, Chestnut Mountain offers runs appropriate for beginners through black diamond-level skiers. Weekend tickets cost $52 with equipment rentals available for $35.

Cascade Mountain (Portage, WI; 3 hours northwest of Chicago)

Snowboarders in particular will find thrills at Cascade Mountain, with four terrain parks featuring obstacle courses, a half-pipe and a superpipe. Younger and less-experienced family members of skilled snowboarders will still find lots to do; a snow-tubing park and beginner-level slopes with a small 460-foot hill are well-suited to entertain newer snow bunnies. Eight-hour tickets cost $50 with equipment rentals from $25 to $44.

Bittersweet Ski Resort (Otsego, MI; 2.5 hours northeast of Chicago)

For skiers and snowboarders just learning the ropes, Bittersweet offers 20 runs with seven lifts. The resort features a ski school that caters to beginning and intermediate skiers alike, helping attendees learn the fundamentals. For true beginning skiers and snowboarders, the beginner hill’s Wonder Carpet lift makes it easy to get the hang of getting to the top of the hill.