15 Ski Resorts Near Chicago to Visit This Winter

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Skiing in Chicago is impossible without a lot of imagination, but skiing near Chicago is very possible. As long as you’re willing to take a bit of a road trip, you have plenty of good options. Here are 15 ski resorts near Chicago to visit this winter.

15 Ski Resorts Near Chicago to Visit This Winter

1. Chestnut Mountain Resort

Distance from Chicago: 162 miles | 2hr 40min

Located near Galena, IL on the border of Illinois and Iowa, Chestnut Mountain is one of the closest slopes to Chicago that has more than just bunny hills. With 19 ski runs and a 7-acre terrain park, there’s something here for skiers of all skill levels. Don’t get confused when you drive up and can’t find the mountain – it’s actually a valley where the parking lot, restaurants, and amenities are all located at ground level, and you ski down into a basin.

2. Boyne Mountain Resort

Distance from Chicago: 351 miles | 5hr 20min

If you’re willing to drive a bit further, Boyne is the best place to go skiing near Chicago. It’s been around since the 1940s and continues to entertain visitors with all the amenities you could ask for at a ski resort. The 60 ski runs are split pretty evenly beginner, intermediate, and expert skill level, so everyone can have a fun time there.

3. Crystal Mountain

Distance from Chicago: 305 miles | 4hr 40min

With 58 ski runs, Crystal Mountain is pretty comparable to Boyne Mountain. It’s really a toss up between which mountain skiers like better. Nearly 50% of the ski runs at Crystal are “blue,” or intermediate trails. Crystal Mountain also has three terrain parks, over 15 miles of cross country skiing, and night skiing.

15 Ski Resorts Near Chicago to Visit This Winter

4. Alpine Valley Resort

Distance from Chicago: 92 miles | 1hr 30min

Just across the border in Wisconsin is Alpine Valley, one of the closest and most easily accessible ski resorts near Chicago. If you’re just learning how to ski or snowboard, or it’s been a few years since you’ve skied, Alpine Valley is an excellent option. For more advanced skiers, there are also plenty of blues and blacks to choose from, as well as three terrain parks to practice some new tricks. With 21 ski runs in total, Alpine Valley is much smaller than Boyne or Crystal, but it’s also much closer to Chicago.

5. Cascade Mountain

Distance from Chicago: 177 miles | 2hr 40min

There’s not a lot to do at Cascade Mountain when it comes to apres ski activities, but its 47 ski runs and four terrain parks can easily keep you occupied all day. For non-skiers, or if you get tired of skiing earlier in the day, there’s snow tubing as well. Even though Cascade is on the farther side for a day trip, if you can get out of Chicago early and don’t mind driving back after a day of skiing, a day trip to Cascade is your best option.

6. Devil’s Head

Distance from Chicago: 184 miles | 2hr 50min

Devil’s Head is a lot of fun if you’re an intermediate or advanced skier. There’s only one long green run here, so it’s usually pretty crowded. Nearly half the mountain consists of black runs, so if you’re comfortable skiing Midwest black diamonds, you’ll have a great time here. There’s also a 3.5 mile cross country loop and several terrain parks.

7. Granite Peak

Distance from Chicago: 280 miles | 4hr 10min

Granite Peak is higher and has more ski runs than Indianhead, Cascade, Alpine Valley, Tyrol Basin, and Wilmot. In fact, it’s the tallest and largest ski resort in Wisconsin. There are hotels, restaurants, spas, and even theaters and museums in the ski town, so it’s a great place to spend the entire weekend with family or friends. The 68 runs at Granite Peak are split pretty evenly between all skill levels, making it a fun ski resort for everyone.

8. Indianhead at Big Snow Resort

Distance from Chicago: 401 miles | 6hr 10min

Indianhead and Blackjack were two separate ski resorts that merged into one in 2014. Today, the two are part of Big Snow Resort in Michigan’s Upper Peninsula. Together, there are 56 ski runs, 410 skiable acres, and three terrain parks. Thanks to its location and the resulting lake effect, both Indianhead and Blackjack consistently receive a large amount of snow – which means lots of fresh powder.

One unique feature about Indianhead is that the “base” of the ski hill is actually at the top. Most runs pick up speed as you get deeper into the bowl, so don’t let the easy starts fool you. As the larger of the two resorts, Indianhead also offers wider trails and a much larger beginner ski area than the neighboring Blackjack.

Source: https://www.bigsnow.com/big-snow-trail-map

9. Blackjack at Big Snow Resort

Distance from Chicago: 401 miles | 6hr 10min

While Indianhead has a lot of wide open areas and a huge beginner area, Blackjack is more suited for intermediate and advanced skiers. Blackjack is the smaller of the two mountains and also offers much more limited lodging, so if you want to visit both resorts, I would definitely recommend staying overnight at Indianhead.

10. Big Powderhorn

Distance from Chicago: 407 miles | 6hr 20min

Big Powderhorn is right next to the two Big Snow Resorts, and you can get passes to all three resorts. So, while Big Snow and Big Powderhorn are quite a long drive away, they probably offer the best skiing and most variety if you have a long weekend and want to ski a different mountain every day. Big Powderhorn is the largest of the three and offers the best lodging options, including a number of ski in/ski out cabins carved into the side of the mountain. With 45 ski runs divided pretty evenly between all skill levels, Big Powderhorn offers something for everyone.

Out of all 15 ski resorts near Chicago to visit this winter, if you’ve got the time, the three Big Snow Country resorts should be at the very top of your list.

11. Nub’s Nob Ski Resort

Distance from Chicago: 370 miles | 5hr 55min

Nub’s Nob in northern Michigan has been around since 1959, so you know it’s a well oiled machine. As one of the largest ski resorts in the Midwest, Nub’s Nob has 53 ski runs, with about half rated as intermediate, and the longest ski run at over seven miles long. It has a great ski town vibe, and you shouldn’t have a hard time finding lodging with the nearly 60 lodges, condos, and hotels on site.

15 Ski Resorts Near Chicago to Visit This Winter

12. Wilmot Mountain

Distance from Chicago: 67 miles | 1hr 10min

Wilmot is pretty much what you’d expect to find in the suburbs of Chicago (read: not much), but it may be worth checking out this season after all the improvements they made earlier this year. They have brand new lifts, a new terrain park, and a completely transformed base area, to name a few. If you’re desperate to get out on the snow and don’t have time for more than a day trip, then consider checking out the new and improved Wilmot Mountain.

13. Tyrol Basin

Distance from Chicago: 172 miles | 2hr 40min

Like most ski hills in the Midwest, Tyrol Basin has shorter runs but offers fun challenges with its intermediate and advanced trails. This is a great place to go if you have a group of friends of all skill levels because you can take the same chair lift for beginner and advanced runs. Its diverse runs make it a solid Midwest ski hill, especially considering its proximity to Chicago.

14. Ski Brule

Distance from Chicago: 343 miles | 5hr 30min

Ski Brule advertises itself as a family friendly ski spot, and it’s no wonder because there’s something here for everyone. In addition to skiing and snowboarding, you can also go snow tubing, cross country skiing, snow shoeing, and even ride on sleighs. If you’re trying to plan a trip for a group of friends with varied interests and/or young children, you should definitely consider Ski Brule.

15. Mount Bohemia

Distance from Chicago: 455 miles | 7hr 30min

WARNING: Mount Bohemia is NOT for the average skier. With almost exclusively black diamond and double black diamond runs, Mount Bohemia is an extreme skier’s paradise. There are plenty of backcountry runs and even snowcat skiing (if you don’t know what that is, you probably shouldn’t be doing it!), Mount Bohemia is THE most extreme ski resort in the Midwest. If you just moved out here from Colorado or Washington and think you can’t find any good skiing in the Midwest, check out Mount Bohemia, and let me know what you think then.

With these 15 ski resorts near Chicago to visit this winter, you should be able to keep a pretty busy ski schedule even if you’re unable to make a trip out west. Let us know where you end up skiing this winter, and which ski resort near Chicago is your favorite!

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