The Best Midwestern Ski Destinations Within Driving Distance of Chicago

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.

Wilmot, Wisconsin
Distance from Chicago: 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, night skiing on select dates through February, 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. And in true Wisco form, Friday Fish Frys are served weekly at Walt’s Tavern.

Elkhorn, Wisconsin
Distance from Chicago: 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, 20 runs (the longest of which is 3,000 feet), three terrain parks, night skiing, and ski-in, ski-out accommodations, to boot.

Otsego, Michigan
Distance from Chicago: 2.5-hour drive
With six lifts, 20 runs, two terrain parks, and 100 acres of skiable terrain topping out at 850 feet with a 350-foot vertical drop, Bittersweet is typical of the small cluster of resorts in southwest Michigan that also includes Swiss Valley and Timber Ridge. You certainly won’t confuse it for Vail, but it won’t bore you either. Saddle up, cowboy.

Portage, Wisconsin
Distance from Chicago: 2.5-hour drive
With 47 runs, 11 lifts, a peak elevation of 1,280 feet, and an immense amount of snowy turf, 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 the wooded runs, be it an easy route or a Black Diamond, provides a veritable choose-your-own-adventure of winter fun, while 15 snow tubing lanes also provide a fun alternative to the traditional wedge-and-scoot.

Galena, Illinois
Distance from Chicago: 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. Finish up at The Summit Food & Spirits, where the menu ticks all the comfort food boxes, from walleye strips to white cheddar cheese curds.
 

Merrimac, Wisconsin
Distance from Chicago: 3-hour drive
When one thinks of glacier-carved mountains, Wisconsin probably isn’t the first state that comes to mind. But smack dab in the middle of it, amidst the Baraboo Bluffs, roadtrippers will find some of the tallest, snow-capped peaks in Wisconsin—sprawled across 300 acres of powdered terrain, making it among the largest ski resorts in the Midwest. Several lifts service even more runs, from easier slopes like Pete’s Dragon and Devil’s Playground, to Black Diamond plummets, like Cyclops and the unnervingly named Revenge. When you’re done, enjoy an après drink at The Devil’s Den, a cozy sports bar that turns into a nightclub, Devil’s Head, later.

Dubuque, Iowa
Distance from Chicago: 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, across 85 acres, 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 carbo-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.

Wausau, Wisconsin
Distance from Chicago: 4-hour drive
Granite Peak is as close to the western mountain ski resorts as you’re gonna get in the Midwest. Located within the chilled-out Rib Mountain State Park overlooking the highest point in Wisconsin, the oldest ski resort in the state 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, including some off-slope runs through the trees, plus three 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.

Cadillac Michigan
Distance from Chicago: 4.5-hour drive
This 27-run resort features steep slopes, three 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. Indoors, Beatie’s Bar & Grill offers cozy respite with craft beer, Bloody Marys, and après-ski chicken tenders. 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.

Thompsonville, Michigan
Distance from Chicago: 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 après-ski party at this Thompsonville stunner. With 59 runs spread out across 100+ acres of skiable terrain plus a sizable backcountry, three terrain parks, 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.

Harbor Springs Michigan
Distance from Chicago: 6-hour drive
Since you’re already driving all the way up to Michigan, about as far north as you can get without entering the Upper Peninsula, 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 horseback riding, and bonfires where s’mores are highly encouraged. New this season is Camelot 6, the first—and fastest—bubble chairlift in the Midwest. 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. At the Main Lodge, there’s an outdoor heated pool and hot tub that are both open year round.

Boyne Falls, Michigan
Distance from Chicago: 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 basically the Aspen of Michigan. 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. There’s even plenty of pool action, from the year round heated outdoor pool at Clock Tower Lodge, to the largest indoor waterpark in the Midwest, Avalanche Bay. When it comes to skiing in the Midwest, this is about as good as it gets.

Iron River, Michigan
Distance from Chicago: 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, and the longest run clocks in at an impressive one mile, 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 11 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.

Bessemer, Michigan
Distance from Chicago: 6-hour drive
With 253 skiable acres featuring one of the largest vertical drops in the Midwest, and plenty of natural lake-effect snow from Lake Superior to keep things fluffy, 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.

Harbor Springs, Michigan
Distance from Chicago: 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 and three peaks, 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.