Cheap Chicago Ski Vacations

Where are the cheap Chicago ski vacations? Residents of the Windy City that want to get away for a fun ski vacation have lots of options. From quick Chicago getaways to some thrilling regional ski resorts to more elaborate vacations at some of the nation’s best world-class destinations, there’s something for people of all tastes – and budgets.

When you’re ready to plan your next ski vacation on a budget, consider these strong options below that have sweet deals on our website. These popular ski destinations for Chicagoans provide lots of exciting skiing, relaxing accommodations and plenty to do off the slopes, all on an affordable budget. Let’s look at the ski resorts closest to Chicago first, then explore some inexpensive options a little further away.

There are some great ski resorts within a short drive of the Windy City that are exciting and affordable.
There are some great ski resorts within a short drive of the Windy City that are exciting and affordable. For example, Wilmot Mountain Resort is only 65 miles from downtown Chicago.

Granite Peak

Granite Peak is Wisconsin’s highest peak and is only about four and a half hours from downtown Chicago via Interstate 90 and I-39. The ski area has 68 runs to entertain skier and snowboarders for days on end. There’s no waiting at Granite Peak because the resort’s high-speed six-passenger chair, pair of quads and other lifts keep visitors moving. With the deals found on our site, Granite Peak tops the list of cheap Chicago ski vacations!

There’s a total of 209 acres of skiable terrain with plenty of challenges for skiers of all ages and abilities. The resort also offers night skiing, which is a unique experience if you’ve never tried it.

The town of Wausau has lots to keep families, singles and romantic couples entertained after a day on the slopes. The city has an abundance of tasty restaurants, neat shopping and educational experiences like museums and theater performances.

Devil’s Head Resort

The thrilling Devil’s Head Resort in south-central Wisconsin has about 30 runs that include some extra-challenging blacks and double blacks, and more than 500 feet of vertical drop. There’s some nice room for beginners, who can ski comfortable around 30% of the resort. The other 70% is for intermediate and advanced skiers.

There’s lots to do around Devil’s Head, ranging from gambling trips for adults at nearby casinos to more family-oriented outings like ice skating, sledding and cultural experiences around the town of Merrimac.

Devil’s Head Resort is about 184 miles (a little more than three hours’ drive) from Chi-Town. From Chicago, hit Interstate 90/94 and take it to the Merrimac Exit (108A), then follow Highway 78 south for 8 miles. Turn right onto Highway DL and then right at Bluff Road. When you see the sign for Devil’s Head Resort, turn right and you’re there.

Wilmot Mountain Resort

Wilmot Mountain is the closes ski resort to Chicago, about 65 miles from downtown. The ski area is in beautiful Wilmot, Wisconsin and serves up more than 20 unique ski trails across 120 acres. Nicknamed the “Matterhorn of the Midwest,” the mountain has gentle, wide-open runs, limited trees and is easy to navigate. It’s a great location for a family getaway or a quick trip for those who want to try skiing or snowboarding for the first time. The full-service resort offers gear rentals, ski lessons and five terrain parks.

The entire slope is also lit for night skiing, so visitors can make turns all day and enjoy peaceful runs in the evening under the stars. At Wilmot Mountain, you can start the day learning to ski and – by the end of the day – you’ll be cruising down the slopes with confidence during night skiing. Its a great place to find cheap ski vacations for Chicago skiers.

Wilmot is accessible from Chicago via Interstate 94W/Eden’s Expressway toward Milwaukee for about 30 miles, then exit at IL-173/Rosencrans Road and follow UL-173 West to Wilmot until you see the signs for the resort.

Alpine Valley Ski Resort

Alpine Valley is another great place for beginners, about 90 miles from downtown Chi-Town. (It’s about a two-hour drive depending on traffic.) It’s also a convenient ski getaway for residents of Madison and Milwaukee, too. The ski area has eight trail runs covering 90 skiable acres. The resort has three high-speed lifts, so there’s never any waiting in line at the resort.

At Alpine Valley, newer skiers can build confidence under the leadership of top ski instructors and then hone their skills on some fun terrain and three challenging terrain parks. The resort has an excellent lodge at the base of the resort that has 120 rooms that’s perfect for stay and ski getaways.

To get to Alpine Valley from Chicago, take Interstate 94 West toward Milwaukee and exit to Wisconsin Highway 20, then go west to Highway D. Many people find cheap ski vacations for Chicago skiers here.

Cascade Mountain Resort

Cascade Mountain is about a three-hour drive from Chicago and has lots of trails to feed your powder hunger. The full-service ski resort located in Portage, Wisconsin present close to 50 named trails covering about 160 acres of terrain, along with ski rentals, lessons, a ski shop and authentic atmosphere. A popular spot for beginners, the ski area does have a few nice advanced trails that will keep more experienced skiers entertained. The resort has 10 lifts, 34 runs that are geared for snowboarders, and four terrain parks with jumps and rails, a superpipe and a halfpipe. 

If that’s not enough, Cascade Mountain Resort has awesome sledding and tubing on the hill and a bunch of fun adventures in the town of Portage. Take the Snow Shuttle to town and explore the cool shops and restaurants, then head back for more skiing!

Conveniently located, Cascade Mountain Resort is only about three hours from the heart of downtown Chicago. To drive from the Windy City, take Interstate 90/94 to exit 106, then go west on Highway 33 for a quarter mile before turning left on Cascade Mountain Road.

Cascade Mountain Resort is family friendly and has some easy runs for beginners. More determined skiers and snowboarders should try Devil's Head Resort because it's geared more toward advanced skiers.
Cascade Mountain Resort is family friendly and has some easy runs for beginners. More determined skiers and snowboarders should try Devil’s Head Resort because it’s geared more toward advanced skiers.

Fly to Denver from Chicago to Ski

One of the biggest benefits to skiers living in Chicago is the number of convenient flights available at O’Hare Airport. The airport is one of the largest in the world and has a vast number of national and international flights daily.

You should be able to find some cheap airfare from Chicago to Denver for a ski vacation if you spend a little time browsing online. It’s not uncommon to find direct flights from Chicago for under $150 through airlines like American and United. Southwest has additional flights through Chicago’s Midway Airport. We’ve even seen tickets drop to even less than $100 through occasional incredible discounts and promotions during the season. Search often and book early are our best recommendations for snagging cheap air travel.

Having flexibility in your travel dates can help keep travel costs down. Once you get to Denver, you’re close to several world-class resorts in Colorado like Arapahoe Basin, Breckenridge, Keystone and Winter Park. Don’t forget: You’ll need to arrange transportation from Denver to your resort through either a shuttle service or a private car rental. Both options are available at Denver International Airport.

We have specials for savings at all the top Colorado ski resorts. Check out our exclusive Ski Deals and package to save the most!

Chicago has excellent rates for direct flights to major ski hubs like Denver or Salt Lake City.
Chicago has excellent rates for direct flights to major ski hubs like Denver or Salt Lake City.

Fly to Salt Lake City from Chicago to Ski

Colorado gets most of the ski love, but don’t sleep on Utah – especially Salt Lake City – when it comes to an epic vacation. Believe it or not, Salt Lake City is less than an hour away from more than 10 top ski resorts. From massive favorites like Park City, Deer Valley and Alta to a fine selection of unique smaller resorts with intimate runs, chills and thrills and less crowds.

You can even stay in Salt Lake City and ski a different resort each day of your vacation. Hotels are inexpensive in the competitive big-city marketplace, and there’s plenty to do – from fine dining to exploring the area’s rich history and beautiful Mormon landmarks as well as other unique features and adventures. We have saving at some great lodges in Salt Lake City and have deals on ski rentals!

If you do head to a specific resort in Utah, check out all our specials and bargains for savings on every aspect of your ski vacation! Use a coupon for everything and save a little here and a little there. It really adds up, especially if you’re a family on a budget or a romantic couple trying to keep prices low. From singles to groups, we certainly have a little something special to save you big!