best ski trips near chicago

Are you looking for a ski destination close to Illinois? Aspen Colorado may not be an option, but there are plenty of “day trip & short weekend” ski resorts closer than you may realize! 

Check it out:

Wilmot Mountain

Wilmot, Wisconsin
Distance from Chicago: 66 miles

120 skiable acres, 25 trails, 11 lifts, four terrain parks, and a 22-lane tubing hill. Wilmot still is not exactly the same as Vail’s signature properties, but it can provide for nice practice runs about as close to home as you can get.

Alpine Valley Resort

Elkhorn, Wisconsin
Distance from Chicago: 90 miles

You probably know Alpine Valley as that place where you saw your favorite concert back in high school. In winter, it’s the closest thing Chicago has to a respectable ski establishment. With a top elevation of 1,040 feet and a vertical drop of 388 feet, its 90 acres of skiable terrain located in a rolling forested area about 20 minutes north of Lake Geneva is basic but still fun—providing a diverse ski experience for all ages with 12 lifts, three terrain parks, night skiing, and ski-in/ski-out accommodations.

Bittersweet Ski Resort

Otsego, Michigan
Distance from Chicago: 159 miles

12 lifts, 20 runs, two terrain parks, and 100 acres of skiable terrain topping out at 850 feet with a 300-foot vertical drop. Bittersweet is one of the small resorts in southwest Michigan. These also include Swiss Valley and Timber Ridge.

Chestnut Mountain

Galena, Illinois
Distance from Chicago: 162 miles

Other resorts on this list may have more snow/better runs, but this one is loads of fun. Chestnut’s location in Galena is high on a bluff overlooking the Mississippi River. It provides a unique environment to survey your surroundings before tackling the resort’s 19 runs with three terrain parks, 10 lifts, and an impressive-by-Midwestern-standards 475-foot vertical drop.

Cascade Mountain

Portage, Wisconsin
Distance from Chicago: 177 miles

47 runs, 11 lifts, and a top elevation of 1,280 feet, Cascade kicks things up a notch into the next level of Chicago-area ski experiences! Getting down the mountain via one of 15 snow tubing lanes also provides a fun alternative to the traditional.

Granite Peak

Wausau, Wisconsin
Distance from Chicago: 275 miles

This overlooks the highest point in Wisconsin and offers more room to roam than the more crowded confines of popular alternatives like Cascade or Devil’s Head. It also brags Wisconsin’s highest vertical drop at 700 feet. With 74 runs plus six terrain parks and one of the highest elevations in the Midwest at 1,942 feet, this resort which opened in 1937 is also one of the oldest in North America.

ski trips near chicago

Crystal Mountain

Thompsonville, Michigan
Distance from Chicago: 312 miles

58 runs spread out across 80 acres of skiable terrain with a sizable backcountry and plenty of well-groomed cross-country trail. This family-owned resort overlooks the scenic Betsie Valley about 30 miles southwest of Traverse City.

Ski Brule

Iron River, Michigan
Distance from Chicago: 339 miles

This resort is often the first to open and the last to close each ski season. It’s a fun resort. and a nice alternative to the mega resorts that often lay claim to the Midwest’s best runs. They have a few terrain parks, naturally, but they also have a tubing park. 17 runs and 12 lifts across 150 skiable acres, 30 percent of the runs are black or double-black diamond!

Boyne Mountain

Boyne Falls, Michigan
Distance from Chicago: 358 miles

415 skiable acres near the northern tip of Michigan – this is the Midwest’s most famous ski resort. With 60 trails, 12 lifts, and 7 terrain parks, you definitely won’t be bored. When it comes to skiing in the Midwest, this is about as good as it gets.

Nub’s Nob

Harbor Springs, Michigan
Distance from Chicago: 376 miles

This resort, named after founder Nubby Sarns, opened in 1958 and continues its family-run to this day. With 53 runs scattered across 248 skiable acres with 9 lifts and a 427-foot vertical drop, it is nestled in one of the most picturesque parts of northern Michigan. It’s 30 minutes south of the launching point to the popular resort community of Mackinac Island.

Big Snow Resort

Wakefield, Michigan
Distance from Chicago: 401 miles

This mega-resort offers everything you need for a fun Midwestern ski weekend. With 56 trails and 15 lifts across a combined 400 acres of skiable terrain, Indianhead is the mountain of choice here with a 638-foot vertical drop and some of the finest skiing in all of the Midwest.

Big Powderhorn

Bessemer, Michigan
Distance from Chicago: 408 miles

253 skiable acres features one of the largest vertical drops in the Midwest, Big Powderhorn has a wide variety of terrain across 45 trails and three terrain parks. With 9 lifts and one-third of the resort dedicated to black or double black diamond runs, check out the Cannonball or Blunder trails for some of the most challenging terrain in the region.




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