While Chicago’s geographically flat landscape does not bode well for downhill skiing and snowboarding, its cold weather certainly does. Good ski resorts can be found near Chi-Town for those willing to take a drive.
Within three hours of The Windy City, there are plenty of ski resorts located in western Illinois as well as near border states like Wisconsin, Iowa, and Michigan. These resorts have great, shorter ski runs for all levels of skiers. Each ski area is accompanied by a good dose of Midwestern hospitality.
Here are ten ski resorts within 3 hours from Chicago, Illinois, in order of driving proximity:
Wilmot Mountain Ski Resort, WI – 65 miles | 1.25 hr
Wilmot Mountain Ski Resort is one of the oldest and most popular skiing, snowboarding, and tubing resorts in the Midwest. Founded in 1938, this mountain has been a winter sports paradise for generations of Midwesterners.
The resort was recently bought and renovated in 2016 by the Vail Resorts Management Company. In addition to updating the restaurant and lodge, the resort added more 4-person chairlifts and 56 new snow guns for increased snowmaking.
While the vertical drop is only 220 feet, Wilmot is a notable ski resort in the Midwest due to its origins and simplistic nature. The mountain has 4 terrain parks with multiple rails and small jumps to enjoy. The ski runs are good for beginner to moderate skiers, making this site a good place to learn the basics.
11931 Fox River Rd, Wilmot, WI 53192 (Map) | (262) 862-2301 | wilmotmountain.com
Mountain Top at Grand Geneva, WI – 85 miles | 1.5 hr
One of the most popular destinations for Chicagoans is Lake Geneva in southern Wisconsin, about 90 minutes northwest of Chicago. Boasting a resort and spa, The Mountain Top Ski & Adventure Center at Grand Geneva is sure to fill your winter sports needs.
The Mountain Top has 20 downhill ski runs and terrain adequate for all types of skiers. A perfect destination for families to enjoy a weekend adventure on the slopes, this resort also provides night options for those looking to avoid crowds. Mountain Top at Grand Geneva will satisfy your itch to get out on the slopes!
7036 Grand Geneva Way, Lake Geneva, WI 53147 (Map) | (262) 249-4726 | grandgeneva.com/ski-snow-sports
Alpine Valley Resort, WI – 93 miles | 1.5 hours
Alpine Valley Resort in Elkhorn, Wisconsin is an excellent ski resort that is well respected in the Midwest for its slopes. Boasting over 90 acres of skiable property and 20 different ski runs, with the longest being over 3,000 feet, you are sure to find one that suits your needs.
The vertical drop at Alpine measures 388 feet surrounded by mature trees and the Kettle Moraine area’s rolling terrain. The ski hill and terrain park are adequate and suitable for beginners. The steepest run at Alpine Valley Resort, Big Thunder, is a black diamond route sure to please advanced skiers looking for a challenge.
W2501 Co Rd D, Elkhorn, WI 53121 (Map) | (262) 642-7374 | alpinevalleyresort.com
Ausblick Ski Resort, WI – 114 miles | 1.75 hours
Just north of Milwaukee, Wisconsin, you will find Ausblick, a small, cozy ski resort. The goal of the resort is to provide its members with a proper ski facility for a reasonable cost and minimal congestion on the slopes.
Ausblick Ski Resort has a race ski program and snowsports school on site. It should be noted that Ausblick is a private ski resort that requires membership to join. Guests are welcome at Ausblick to ski and snowboard as long as they are accompanied by a member.
W260N6395 Mary Hill Rd, Sussex, WI 53089 (Map) | (262) 246-3090 | ausblick.org
Swiss Valley Ski Area, MI – 130 miles | 2.25 hours
Swiss Valley Ski & Snowboard Area in Jones, Michigan sits about 30 minutes northwest of South Bend, Indiana right along the southern border of Michigan. At Swiss Valley, you will find 11 different ski runs for beginner, intermediate, and advanced skiers, including a black diamond.
There are 4 rope tows, 2 quads, and a triple chair lift to quickly shepherd skiers and snowboarders up the mountain. Only providing a 225-foot vertical drop, Swiss Valley Ski Resort is a great location for novice riders.
The resort uses snow farming technology to create fresh powder for the slopes and terrain park. For those interested in night riding, Swiss Valley does not limit where you ride by keeping every run open.
13421 Mann St, Jones, MI 49061 (Map) | (269) 244-5635 | skiswissvalley.com
Bittersweet Ski Resort, MI – 150 miles | 2.5 hours
Bittersweet Ski Resort is located in Otsego, Michigan, just south of Grand Rapids. The resort contains 20 runs, 7 chair lifts, 2 wonder carpets, and 2 rope tows. The runs include multiple beginner trails as well as intermediate, and black diamond runs for everyone to enjoy.
The lodge at Bittersweet is an excellent ski lodge with all the perks including a restaurant and bar. The ski services include individual and group ski training classes with certified instructors.
600 River Rd, Otsego, MI 49078 (Map) | (269) 694-2820 | skibittersweet.com
Cascade Mountain, WI – 177 miles | 2.75 hours
Cascade Mountain is one of the premier ski resorts in Wisconsin and is located in the Wisconsin Dells area north of Milwaukee. The runs here are shorter than those of Colorado and Utah, but they are quite enjoyable given the elevation is 460 feet, larger than most ski resorts in the Midwest.
Cascade Mountain operates on 175 acres of property and offers 47 ski and snowboard trails. It is a bigger complex than most of those listed and is also one of the busiest ski resorts.
The longest trail in the resort, “Far Out”, is a beautiful beginner cruise trail where you weave through old-growth forests and even a waterfall. For the more experienced skiers, there is plenty of intermediate and black diamond runs for you to enjoy on the property.
W10441 Cascade Mountain Rd Portage, WI 53901 (Map) | 608-742-5588 | cascademountain.com
Chestnut Mountain Resort, IL – 162 miles | 2.75 hours
Chestnut Mountain Resort is located in Galena, Illinois, about 3-hours northwest of Chicago. This western Illinois ski resort is open for business during the summer and winter months.
In the winter, the resort has multiple slopes for beginners, intermediate, and professional skiers alike. The 475-foot vertical drop covers about 3,500 feet of terrain through 19 different runs ranging from novice to black diamond. The 20,000-foot ski center is home to brand-name equipment, clothing, and top-quality rental gear.
8700 W Chestnut Mountain Rd, Galena, IL 61036 (Map) | (800) 397-1320 | chestnutmtn.com
Snowstar Winter Park, IL – 187 miles | 3 hours
Located in Andalusia, Illinois in western Illinois along the Iowa border you will find Snowstar Winter Park. This park is the only ski resort in the Quad Cities area, about 3 hours from Chicago. Snowstar is a ski park and zip line facility that offers alpine skiing and snowboarding, a freestyle terrain park, and certified ski instruction.
Snowstar Winter Park is a good option for beginner skiers as the hills are not very difficult and they offer certified ski instruction.
9500 126th St W, Andalusia, IL 61232 (Map) | (800) 383-4002 | skisnowstar.com
Sundown Mountain Resort, IA – 188 miles | 3.25 hours
While Iowa is most known for cornfields and wrestling, they also have a ski resort in Dubuque, Iowa called Sundown Mountain. Sundown has 21 varied ski runs and 2 terrain parks on the property. The 475-foot vertical drop mountain has over 150 snow guns and the runs are groomed daily.
Additionally, they have a fully lit resort meaning night skiing is an option for those who are up for it!
What’s unique about Sundown is that they have two mountaintop lodges compared to most resorts whose lodges are at the bottom of the mountain. Guests are encouraged to eat and drink while taking in incredible views of the entire property!
16991 Asbury Rd, Dubuque, IA 52002 (Map) | (563) 556-6676 | sundownmtn.com
That’s a roundup of the best ski resorts near Chicago, Illinois. It’s time to pack up the car and hit the slopes. Safe travels from the Windy City!
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