The 15 Best Ski Destinations Within Driving Distance of Chicago
From dedicated trails to mountainside resorts stocked with winter fun, here are the Midwest’s best ski trip destinations.
We may not have the same dizzying, ear-popping altitudes as Utah’s Snowbird or Colorado’s Vail, but us Midwesterners still have plenty of ski-worthy slopes at our fingertips. And once you and your (vaccinated, boosted, and masked) buddies throw on those extra layers, it won’t take long to drive out to a place where you can cruise atop pristine white powder. If you’re a newbie and need some motivation, skiing is not only unbelievably exhilarating, it’s also an awesome substitute for your boring winter workout routine, improving coordination, strength, and flexibility. From bunny hills to Black Diamonds, here are 15 standout ski resorts within driving distance of Chicago sure to put an end to those mid-winter blues.
Harbor Springs Michigan
Distance from Chicago: 370 miles; 6-hour drive
Since you’re already driving all the way up to Michigan, you might as well scout out a place where you can not only ski, but sleep, shop, and eat all in one place. The Highlands Springs Resort offers Michigan’s longest ski run, 10 lifts, 53 groomed runs, and, for the more advanced shredders in the group, four terrain parks. As if that wasn’t enough, the resort also accommodates snow tubing, snowshoeing, winter ziplining, and bonfires where s’mores are highly encouraged. When you’re ready to hit the hay, take advantage of the resort's luxe lodging options which span condos, traditional hotel rooms, cottages, and entire homes for rent.
Distance from Chicago: 188 miles; 3.5-hour drive
As the name suggests, Sundown Mountain Resort lets you glide down their cedar-lined slopes far past bedtime. The resort sports 21 trails catering to all levels, and when you’re ready to take a break, head over to one of their onsite lodges. Ben’s Den warms weary skiers by the campfire with s’mores and hot cocoa, while The Barn, located right off the slopes, provides drinks and bonfires. South Lodge’s Bottoms Up will get you fed while taking in sprawling views of the runs, and Northern Lodge is your spot to sip adult beverages and caro-load on pizza and sandwiches courtesy of Tips Up Food and Spirit. Clearly this place understands how to strike a fine balance between adventure and leisure.
Distance from Chicago: 283 miles; 4.5-hour drive
This 30-run resort features steep slopes, two peaks, five aerial lifts, and plenty of backcountry terrain if you're in the market for a snowy path less traveled. Come for the day or kick back at the Mackenzie Lodge, conveniently stashed just below all the trails, where an outdoor heated pool, hot tub, and roaring fire pits offer many opportunities to get warm. And if inclines and declines aren't really your thing, the Mckenzie Cross-Country Trail also offers Nordic Skiing over 10 miles of all-level trails traversing Huron-Manistee National Forest.
Distance from Chicago: 66 miles; 1 hour, 15 minute drive
Wilmot used to be in the same class as suburban resorts that don’t amount to much more than a few slushy bunny hills, but the little mountain just across the Wisconsin border has seen some significant upgrades since Vail Resorts purchased the property in 2016 and cashed in $13 million worth of renovations. Featuring 120 skiable acres, 25 trails, 11 lifts, four terrain parks, and a 22-lane tubing hill, Wilmot 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.
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, however, it’s the closest thing Chicagoland has to a respectable ski establishment. With a top elevation of 1,040 feet and a vertical drop of 388 feet, the 90 acres of skiable terrain is situated in a rolling forested area about 20 minutes north of Lake Geneva. It might be basic, but it’s definitely a thrill, providing a diverse ski experience for all ages with 12 lifts, three terrain parks, night skiing, and ski-in, ski-out accommodations, to boot.
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. Saddle up, cowboy.
Distance from Chicago: 177 miles; 2.5-hour drive
With 47 runs, 11 lifts, and a peak elevation of 1,280 feet, Cascade officially enters the next level of Chicago-area ski experiences, complete with plenty of opportunities to go full Shaun White on big-air jumps spanning four terrain parks. Getting down the mountain via one of 15 snow tubing lanes also provides a fun alternative to the traditional wedge-and-scoot.
Distance from Chicago: 162 miles; 2.5-hour drive
Others on the list may have more snow and better runs, but few nearby ski destinations are this damn fun. Chestnut’s location in Galena (one of our top Midwest winter 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, three terrain parks, 10 lifts, and an impressive-by-Midwestern-standards 475-foot vertical drop.
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 crowded confines of popular alternatives like Cascade along with Wisconsin’s highest vertical drop measuring 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, dating to 1937, is also one of the oldest in North America.
Distance from Chicago: 312 miles; 4.5-hour drive
Instead of being crammed into some broken down old lodge, you can rent badass private homes or high-end condos and throw your own socially distant après ski party at this Thompsonville stunner. With 58 runs spread out across 80 acres of skiable terrain plus a sizable backcountry and heaps 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. Shhh.
Iron River, Michigan
Distance from Chicago: 339 miles; 5.5-hour drive
Often the first to open and the last to close each season, this sweet Michigan hideaway is a nice alternative to the megaresorts that often lay claim to the Midwest’s top runs. They have a few terrain parks, naturally, but how many resorts do you know that also house a full-on tubing park? We’re guessing just this one. With 17 runs and 12 lifts across 150 skiable acres, 30% of the runs are Black or Double Black Diamond—so it helps if you know what the hell you’re doing.
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-friendly vibe to this day. With 53 runs scattered across 248 skiable acres with nine lifts and a 427-foot vertical drop, it’s nestled in one of the most picturesque parts of northern Michigan, just 30 minutes south of the launch point to lakefront oasis Mackinac Island.
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 getaway 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 tears, check out the Cannonball or Blunder trails for some of the most delightfully challenging terrain in the region.
Boyne Falls, Michigan
Distance from Chicago: 358 miles; 5.5-hour drive
Stretching across a massive 415 skiable acres near the northern tip of Michigan, the Midwest’s most famous ski resort is tough to beat. The sheer shredability across such a dizzying array of well-groomed runs 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 find at this iconic resort is boredom. When it comes to skiing in the Midwest, this is about as good as it gets.
Distance from Chicago: 401 miles; 6-hour drive
Formed in 2014 after a merger between two of the Midwest’s premier resorts—Indianhead and Blackjack—this monstrous destination offers everything you need for a Midwestern ski weekend at its best. 56 trails and 15 lifts punctuate a combined 400 acres of skiable terrain, with Indianhead being the mountain of choice thanks to a 638-foot vertical drop and some of the finest trails in the region.
Jay Gentile is an award-winning freelance journalist specializing in travel, food & drink, culture, events and entertainment stories. In addition to Thrillist, you can find his work in The Washington Post, The Guardian, CNN Travel, Chicago Tribune, Lonely Planet, VICE, Outside Magazine and more. Follow @thejaygentile