10 Ski Resorts within Driving Distance of Chicago 

The summer is the star of the show in Chicago. We all collectively wait for the three months of perfect weather in the summer and complain the rest of the year about the cold. Chicago winters are harsh, but this year, I have vowed not to let the snow and ice stop me from getting outdoors. Unfortunately I am one of the unlucky children that were born during one of the coldest months of the year.

The summer is the star of the show in Chicago. We all collectively wait for the three months of perfect weather in the summer and complain about the cold the rest of the year. Chicago winters are harsh, but this year, I have vowed not to let the snow and ice stop me from getting outdoors.

Unfortunately, I am one of the unlucky children born during one of the coldest months of the year. Growing up, I always loved my birthday because my family went away skiing. Since moving to Chicago, having a winter birthday has been a drag. Nobody wants to head downtown to a restaurant, club, or karaoke bar when the wind chill is below zero. I decided to change it up this year and reconcile with being a winter baby by skiing. There are several ski resorts within driving distance from Chicago. Here are several ski resorts you should check out this winter.

Villa Olivia 

Distance: 1 hour 
Total Trails:
Total Lifts: 7
Summit Elevation: 1500′

Villa Olivia is a golf course that offers winter sports during the off-season. Villa Olivia is one of the closest ski resorts near Chicago and is ideal for getting a short day of skiing in.

Wilmot 

Distance: 1 hour 
Total Trails: 21
Total Lifts: 10
Summit Elevation: 958′

A short drive from Chicago Wilmot Resort is perfect for a snowy day trip, especially for beginners. Wilmot has slopes ranging from green to black, but there are slopes specifically for ski school students. If you are new to the sport or have children you want to introduce to skiing, Wilmont is an excellent place to start. For the advanced skiers the black diamond runs will be a fun challenge. The slopes are short but so are the lines, so don’t be surprised if you get to tackle one slope several times throughout your experience.

ski resorts near Chicago
Ski resorts near Chicago- Wilmot Mountain
Ski resorts near Chicago- Wilmot Mountain

Alpine Valley 

Distance: 2 hours 
Total Trails: 21
Total Lifts: 12
Summit Elevation: 1403′

Alpine Valley is a short two hour drive from Chicago and has a slope for everyone. Aside from the runs one of the most fun parts about Alpine Valley is their terrian park. It’s a great option for those who want to get a few jumps in or those who are skiing for the first time.

Swiss Valley 

Distance: 2 hours 
Total Trails: 12 
Total Lifts:
Rope Tows: 4 
Vertical Drop: 225′

Swiss Valley Ski Resort near Chicago is known for being Michigan’s #1 Learn to Ski Resort. It’s an excellent place for beginners skiers and snowboarders to become experts before hitting more advanced slopes. Learn to ski or relax in the fireside room for a fun winter day.

Trail map- for ski resort in Chicago

Timber Ridge

Distance: 2.5 hours 
Total Trails: 20 
Total Lifts: 10
Summit Elevation: 850′
Vertical Drop: 250′

Timber Ridge is a family-owned and operated ski resort near Chicago, stretching fifty acres. They have various ski slopes, from numerous green slopes to a double black diamond and terrain park; Timber Ridge has a ski slope for all ski levels. While the slopes are short, the ski lift lines are too so you can ride your favorite runs over and over again.

Timber Ridge- Ski Resort Near Chicago

Devil’s Head 

Distance: 3 hours 
Total Trails: 30 
Total Lifts: 8
Summit Elevation: 995′
Vertical Drop: 500′

Devil’s Head might be hell for beginners, but heaven for the advanced skier. Devils Head ski resort is known for it’s steep black runs, a fun challenge for the advanced and daring skier.

Chestnut Mountain 

Distance: 3 hours 
Total Trails: 19 
Total Lifts: 9
Summit Elevation: 1020′
Vertical Drop: 476′

Chestnut Mountain is near the beloved getaway town of Galena. Galena is known for its 19th-century buildings and charm. Rich in history, restaurants, and culture, Galena is an excellent destination for Chicagoans to get out of town. Chestnut Mountain Ski Resort has something for everyone. Enjoy Galena and a weekend skiing at Chestnut Mountain.

Terrain Park Near Chicago | Chestnut Mountain Resort

Sundown Mountain 

Distance: 3.5 hours 
Total Trails: 21 
Total Lifts: 3
Vertical Drop: 475′

Sundown Mountain, located in Dubuque, Iowa, has 21 ski runs and 2 terrain parks. The runs are considered to be intermediate terrain for Iowa, but my favorite part of the runs is the cedar trees that line the path. Sundown Mountain stretches over 45 acres and is one of the most scenic ski mountains in the midwest.

Sundown Mountain Ski Resort Area Overview - OnTheSnow

Granite Peak 

Distance: 4 hours 
Total Trails: 74
Total Lifts: 7
Vertical Drop: 700′ 

Granite Peaks is the place to do if you love tree skiing. Almost all of their runs include dodging trees along the trail. Skiing is only one aspect of the fun at this ski resort. Granite Peaks Ski Resort in Wisconsin loves a good celebration. Throughout the year, they host family-friendly festivals such as the Holiday Spirit, Mardi Gras, and Saint Patrick’s Day Festival. Additionally, Granite Peaks hosts fireworks shows throughout the year. Don’t miss the next one on February 10, 2024.

Granite Peak Review — Ski or Board There! – The Wisconsin Skier

Caberfae Peaks 

Distance: 4.5 hours 
Total Trails: 30 
Total Lifts:
Vertical Drop: 485′ 
Summit Elevation: 1545′

Caberfae Peaks is located in the lower peninsula of Michigan and is farther away from Chicago than other resorts. Don’t let the distance deter you. With three large peaks, several backcountry trail, and a relaxing lodging with a heated pool and spa, Caberfae Peaks is worth a visit. Staying at the Mackenzie Lodge is the best way to make the most out of your time. Guests of this slope-side lodge not only get easy access to the runs but also get discounts on their lift tickets when booked with the room.

Caberfae Peaks Ski Resort

Crystal Mountain 

Distance: 5 hours 
Total Trails: 59 
Total Lifts: 11
Vertical Drops: 375′
Summit Elevation: 1132′

Crystal Mountain is a ski resort and conference center just south of Traverse City. The slopes encompass over 100 acres and can occupy 12,400 skiers per hour. The best part about Crystal Mountain Ski Resort is the 59 trail runs and 27 slopes open for night skiing. You won’t get bored at Crystal Mountain. If you want to take a break from the winter weather, Crystal Mountain also offers a fitness center with group classes, a spa, a heated indoor pool, and personal training options.

Crystal Mountain, MI Ski Resort Area Overview - OnTheSnow

Boyne Mountain 

Distance: 5:5 hours 
Total Trails: 60 
Total Lifts: 11
Vertical Drop: 500′ 
Summit Elevation: 1120′ 

Boyne Mountain is one of the larger ski resorts near Chicago, with over fifty runs, including bunny, green, blue, black, and double black diamond slope options. The resort is for more than just skiers. The resort has a bar, restaurant, arcade, spa, and water park. If you have a non-skier in the group, I recommend trying the Swedish massage or one of their luxury facials for a relaxing day at the spa. Additionally, you can grab a glass of mulled wine or hot chocolate at the lodge at the top of the mountain before skiing down. Boyne is certainly worth the five hour drive from Chicago for the weekend.

Ski resort near Chicago Boyne Mountain
Boyne Mountain Resort Ski Resort Area Overview - OnTheSnow

Snowriver Mountain Ski Resort  

Distance: 6 hours 
Total Trails: 43
Total Lifts: 6
Vertical Drop: 538′
Summit Elevation: 1752′

Snowriver Mountain Ski Resort is located just off the coast of Lake Superior. If you visit during the winter season, you will likely experience a winter wonderland. The area surrounding Snowriver Mountain Resort receives, on average, 200″ of snow annually. Downhill skiing/snowboarding, cross-country skiing, and snowmobiling are all things that guests can enjoy during the winter season.


Going to any one of these ski resorts near Chicago will help mend your relationship with winter. It’s the only time I might actually hope for snow. Happy skiing.

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