7 best ski resorts near Chicago

There’s a lot to love about a Midwestern ski vacation, from the friendliness of the locals to the charming accommodations tucked away in the quiet woods. And as you might have guessed, you don’t need to fly across the country to hit the slopes. You can find plenty of confidence-building bunny slopes and challenging, high-quality runs just a scenic drive away from the city, both within Illinois and across state lines. To help you plan your trip, we’ve rounded up seven of the best ski resorts near Chicago.

1. Wilmot Mountain Ski Resort

Wilmot, WI
Driving distance from Chicago: 66 miles (1 hours and 20 minutes)

About Wilmot Mountain Ski Resort

Wilmot Mountain, owned by Vail Resorts, quickly became one of the best skiing destinations near Chicago after a $13 million renovation project carried out in 2016. Luckily for weekend warriors, this well-maintained ski resort is also one of the closest to Chicago. With a vertical drop of 220 feet and 120 acres of skiable terrain, the mountain boasts 3 terrain parks and 25 trails, with 36% categorized as beginner, 32% as intermediate and 32% as advanced. There are also 22 lanes dedicated to snow tubing.

Lift ticket prices

There are a variety of options available, including the ability for avid skiers to buy a multi-resort pass that covers other properties owned by Vail Resorts. By purchasing a lift pass online, you’ll save money and guarantee a spot since there is limited availability each day.

Accommodations

Those planning to stay overnight will find options for every budget within a short drive of Wilmot Mountain. In Antioch, Illinois, there are quaint B&Bs, large vacation rentals and brand-name hotels. Over in Lake Geneva, Wisconsin, you can treat yourself to a stylish suite at a high-end property.

2. Swiss Valley Ski & Snowboard Area

Jones, MI
Driving distance from Chicago: 126 miles (2 hours and 20 minutes)

About Swiss Valley Ski & Snowboard Area

One of the most charming things about the Swiss Valley Ski & Snowboard Area is that it’s been family-owned since it was founded by Jim and Sandy Wiseman more than 50 years ago. But that doesn’t mean there are only bunny slopes in operation here. Within the area’s 225 vertical feet of slopes, there are 12 runs — all well-equipped with lighting for night skiing — with multiple options for beginner, intermediate and advanced skiers and snowboarders. There are also two terrain parks with dozens of features in rotation for freestyling.

Lift ticket prices

Lift tickets for the 2023-2024 season are now available. Prices vary by day of the week, time of day and one’s age, ranging from $30-$55.

Accommodations

Michigan’s southernmost ski area is an easy drive from Chicago, but you may want to stay the night after an exhausting day on the slopes. There are plenty of lodging options nearby, including quaint B&Bs, cabins and cottages. One thing to note about Swiss Valley’s location is that it’s in the eastern time zone, which makes the drive back to Chicago nice since you gain an hour! 

3. Devil’s Head Resort

Merrimac, WI
Driving distance from Chicago: 184 miles (3 hours)

About Devil’s Head Resort

Under the snow at Devil’s Head Resort is a landscape that was formed around 1.5 billion years ago — yes, billion with a B! Although the resort itself doesn’t have such ancient history, it has plenty to brag about when it comes to its terrain. Visitors get 500 feet of vertical rise and 30 runs with 30% rated as beginner, 40% as intermediate and 30% as advanced. The longest run at Devil’s Head is a mile and a half!

Lift ticket prices

Lift ticket rates vary wildly at Devil’s Head Resort, but in a good way. All ages can pay just $18 on Thursdays after 4pm or $40 on any other night of the week. General lift tickets range in price, depending on your age and the day of the week. Kids 5 years old and younger can ski for free.

Accommodations

After a day of some of the best skiing near Chicago, stay the night! There are plenty of top-rated accommodations in the area, many of which surround you in nature and provide incredible views to wake up to before another day on the slopes.

4. Cascade Mountain

Portage, WI
Driving distance from Chicago: 177 miles (3 hours)

About Cascade Mountain

Among these five options, Cascade Mountain stands out as the best ski resort near Chicago for families with young children. Not only do kids ages 12 and under get a free lift ticket when accompanied by a paying adult, but the mountain offers the opportunity to go snow tubing in addition to its plentiful runs for skiers and snowboarders and three terrain parks. The vertical drop at Cascade Mountain is 460 feet, and there are a whopping 48 runs across skill levels — the longest of which is 1.1 miles. 

Lift ticket prices

It’s recommended to pre-purchase lift tickets to ensure availability. Additionally, if you buy tickets (or anything else) on-site, know that cash is not accepted. Prices for open-to-close lift tickets range from $65-$95, while night tickets (for the last five hours of the evening) range from $43-$54. Snow tubing tickets are priced separately and are valid for two hours.

Accommodations

There are a handful of brand-name chain hotel options in nearby Portage, just a 10-minute drive northeast. If you drive 20 minutes west, Baraboo offers inns, B&Bs, motels and other hotel options. Or go a little further afield to Wisconsin Dells, a 25-minute drive from Cascade Mountain, where options abound.

5. Chestnut Mountain Resort

Galena, IL
Driving distance from Chicago: 167 miles (3 hours)

About Chestnut Mountain Resort

Eager for ski season to start again? Chestnut Mountain Resort, which sits just before the Iowa border in northwestern Illinois, is gearing up for opening day on November 24. Take your pick of 19 runs that span 3,500 feet and range from bunny hills to black diamonds on a 475-foot vertical drop. Talk about one of the best ski resorts near Chicago! Snowboarders with skill can freestyle at Farside, the resort’s terrain park that has more than 25 rails and is touted as the largest of its kind in the region. 

Lift ticket prices

Lift ticket prices for the season range from $50 to $80 depending on day of the week and whether or not its a holiday, and Chestnut Mountain Resort also offers season pass options for regular skiers. Ages 7 and older are subject to adult pricing, while those ages 6 and younger can ride the lift for free with a paid adult. 

Accommodations

When it’s time to defrost and kick up your feet for the night, the resort’s 100-room slopeside lodge is convenient and comfortable, with a bone-warming sauna and an indoor pool and hot tub. Or stay in town at a cozy bed and breakfast, log cabin guesthouse or charming local inn.

6. Sundown Mountain Resort

Dubuque, IA
Driving distance from Chicago: 188 miles (3.5 hours)

About Sundown Mountain Resort

Drive a half hour into Iowa from Chestnut Mountain Resort and you’ll reach one of the Midwest’s top family-friendly skiing destinations. Sundown Mountain Resort boasts a 475-foot vertical drop, two terrain parks and 21 runs that stay lit well into the night with the help of 166 lights. The Kids Park offers lessons to those ages 3-11 on weekends, with a private hill and park cabin just for the little ones. 

Lift ticket prices

Lift ticket prices have yet to be announced for the 2023-2024 season as of the publication of this article. To give you an idea of costs, the 2022-2023 season pricing for adults (ages 12 and older) and youth (ages 6-11) both started at $36, while those 5 and younger can ride free with a paid adult. Sundown Mountain Resort is open Tuesdays through Sundays and only on select Mondays throughout the season. 

Accommodations

After a 3.5-hour drive and full day on the slopes, it’s unlikely you’ll have the energy to drive back to Chicago. Although there isn’t lodging on-site, there are plenty of places to bed down near Sundown Mountain Resort. If there isn’t a specific hotel brand you’re loyal to, check out the special package deals offered by the resort’s Ski & Stay lodging partners.

7. Granite Peak Ski Area

Wausau, WI
Driving distance from Chicago: 280 miles (4 hours and 15 minutes)

About Granite Peak Ski Area

Don’t let the drive time deter you from Granite Peak. This is one of the biggest and best ski resorts near Chicago, with 5 terrain parks, 68 trails and a whopping 700-foot vertical drop. There are a variety of instructional programs for kids and adults, including freestyle lessons at the terrain parks for ages 7 to 15. Granite Peak also hosts a slew of events throughout the winter season, including live music, and three annual family festivals taking place during the holidays, Mardi Gras and St. Patrick’s Day weekend.

Lift ticket prices

Ski during the early season from opening day to December 25 and enjoy reduced weekend and holidays rates starting at $70, and night tickets for $30. Prime season runs December 26 to April 7, with daily lift ticket rates starting at $89. Kids ages 5 and younger, as well as seniors ages 80 and older, ski for free.

Accommodations

The charming towns of Wausau and Rothschild are minutes from the mountain and offer visitors plenty of lodging options, from cozy inns to large chain hotels. But before you book, contact Granite Peak to see if they are running any Ski & Stay Packages with lodging partners so you can snag a deal if one is available.

Get there with Avail

Whether you’re visiting Chicago or need a car to drive out to the slopes, Avail car sharing can help you get there. We have dozens of convenient locations in neighborhoods across Chicago, and all of them provide self-service pick-up and drop-off so you can get on your way without waiting in a single line. Bookings include a second driver at no added cost. Every trip is protected by Allstate insurance and 24/7 roadside assistance, so you can drive off to one of the best ski resorts near Chicago worry-free.