The 12 Best Ski Trips Near Chicago
The mountains are calling.
When one thinks of Chicago, one rarely thinks of skiing. And rightly so. But while the ski terrain in the Midwest is admittedly a far cry from the far more famous (and more famously crowded) slopes of the West, that doesn’t mean you still can’t have a decent ski weekend. From short practice runs close to home to full-size resorts that will have you reconsidering that flight to Colorado, here are 12 great ski trips within driving distance of Chicago. Remember: This ain’t Aspen, so pack some patience and an open mind.
Distance from Chicago: 66 miles; 1 hour, 15 minute drive
Wilmot used to be in the same class as suburban joke “resorts” like Villa Olivia or Four Lakes, but the little mountain just across the Wisconsin border has seen some significant upgrades since Vail Resorts purchased the property in 2016 and sunk in $13 million worth of renovations. Featuring 120 skiable acres, 25 trails, 11 lifts, four terrain parks, and a 22-lane tubing hill, Wilmot still is nowhere near being in the same conversation as Vail’s signature properties out West. But it does provide for some nice practice runs about as close to home as you can get.
Find Airbnb nearby: Search Wilmot area
Distance from Chicago: 90 miles; 1.5-hour drive
You probably know Alpine Valley as that place where you saw Dave Matthews that one time 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.
Find Airbnb nearby: Search Elkhorn area
Distance from Chicago: 159 miles; 2.5-hour drive
With 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 typical of the small cluster of resorts in southwest Michigan that also includes Swiss Valley and Timber Ridge. They certainly won’t blow you away, but they won’t totally bore you either.
Find Airbnb nearby: Search Otsego area
Distance from Chicago: 177 miles; 2.5-hour drive
Finally, we’re starting to get into some decent terrain. With 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 with plenty of opportunities to go all Shaun White with big-air jumps at four terrain parks. Getting down the mountain via one of 15 snow tubing lanes also provides a fun alternative to the traditional.
Find Airbnb nearby: Search Portage area
Distance from Chicago: 162 miles; 2.5-hour drive
Others on the list may have more snow/better runs, but few are this fun. Chestnut’s location in Galena (one of our top Midwest vacation spots) perched high on a bluff overlooking the Mississippi River provides a unique environment from which 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.
Find Airbnb nearby: Search Galena area
Distance from Chicago: 275 miles; 4-hour drive
Located within the chilled-out Rib Mountain State Park overlooking the highest point in Wisconsin, this resort offers more room to roam than the more crowded confines of popular alternatives such as Cascade or Devil’s Head—along with Wisconsin’s highest vertical drop at 700 feet. With a whopping 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.
Find Airbnb nearby: Search Wausau area
Distance from Chicago: 312 miles; 4.5-hour drive
Instead of being crammed into some run-down old lodge, you can rent badass private homes or high-end condos to throw your own socially distant après ski party. With 58 runs spread out across 80 acres of skiable terrain with a sizable backcountry and plenty of well-groomed cross-country trails, this family-owned resort overlooking the scenic Betsie Valley about 30 miles southwest of Traverse City might just be one of the Midwest’s best-kept secrets.
Find Airbnb nearby: Search Thompsonville area
Boyne Falls, Michigan
Distance from Chicago: 358 miles; 5.5-hour drive
Sprawling out across a massive 415 skiable acres near the northern tip of Michigan, the Midwest’s most famous ski resort is tough to beat. The skiing across a dizzying array of well-groomed runs of course is first-rate, but then again, so is the snow biking, horseback riding, and ziplining. With 60 trails, 12 lifts, and seven terrain parks, one thing you won’t be at this iconic resort is bored. When it comes to skiing in the Midwest, this is about as good as it gets.
Find Airbnb nearby: Search Boyne Falls area
Iron River, Michigan
Distance from Chicago: 339 miles; 5.5-hour drive
Often the first to open and the last to close each ski season, this fun little resort is a nice alternative to the megaresorts that often lay claim to the Midwest’s best runs. They have a few terrain parks, naturally, but how many resorts do you know that also have a tubing park? We’re guessing just this one. With 17 runs and 12 lifts across 150 skiable acres, 30 percent of the runs are black or double-black diamond—so it helps if you know what the hell you’re doing.
Find Airbnb nearby: Search Iron River area
Harbor Springs, Michigan
Distance from Chicago: 376 miles; 6-hour drive
This loveable little resort named after founder Nubby Sarns opened in 1958 and continues its affable family-run vibe to this day. With 53 runs scattered across 248 skiable acres with nine lifts and a 427-foot vertical drop, it is nestled in one of the most picturesque parts of northern Michigan just 30 minutes south of the launching point to the popular resort community of Mackinac Island.
Find Airbnb nearby: Search Harbor Springs area
Distance from Chicago: 408 miles; 6-hour drive
With 253 skiable acres featuring one of the largest vertical drops in the Midwest, Big Powderhorn is a classic Upper Peninsula resort offering a wide variety of terrain across 45 trails and three terrain parks. With nine 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 delightfully challenging terrain in the region.
Find Airbnb nearby: Search Bessemer area
Distance from Chicago: 401 miles; 6-hour drive
Formed in 2014 after the merging of two of the Midwest’s premier resorts—Indianhead and Blackjack—this mega-resort offers everything you need for a fun Midwestern ski weekend at its best. 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.
Find Airbnb nearby: Search Wakefield area