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Time to hit the slopes!

Hit the slopes at the best snowboarding and skiing resorts near Chicago!

Bunny hills, steep slopes and breathtaking vistas—there’s a lot to love about the best ski resorts near Chicago.

Written by Samantha NelsonTuesday December 28 2021 from

Plunging temperatures might make you want to stay cozy inside, but the athletic and adventurous can take advantage of the winter weather and hit the slopes for some skiing and snowboarding near Chicago. Illinois may not have the mountains of Vail or Salt Lake City, but you can still find hills around Chicago and some more impressive peaks if you’re up for a day trip or weekend getaway to Wisconsin or Michigan. Ranging from park district facilities to posh resorts, the best hills for snowboarding and skiing near Chicago will teach you the basics or provide fresh challenges.

Skiing and snowboarding at these slopes is contingent upon weather conditions. Always call ahead or check resort websites.

RECOMMENDED: The best things to do outdoors this winter in Chicago

The best ski and snowboard slopes near Chicago

Alpine Valley Resort

Photograph: ShutterstockAlpine Valley Resort

W2501 County Road, Elkhorn, WI, 800-227-9395

Driving time from Chicago: about two hours

The gist: Winter sports enthusiasts will find plenty of variety at this southern Wisconsin ski resort, which features 21 ski runs, a vertical drop of 388 feet and three terrain parks.

Season dates: Weather permitting.

Ticket to ride: Daily slope tickets starting at $60 ($40 for beginner hills only); equipment rentals are $40 for a half-day and $50 for a full-day plus $10 for a helmet.

Bittersweet Resort

Photograph: ShutterstockBittersweet Resort

600 River Rd, Otsego, MI, 269-694-2820

Driving time from Chicago: about 2.5 hours

The gist: Boasting 20 runs, seven chairlifts, two wonder carpets and two rope tows, Bittersweet caters to skiers and snowboarders of all ages. The resort offers private and group lessons to teach the basics to first timers or help more experienced skiers sharpen their skills and try racing.

Season dates: Weather permitting.

Ticket to ride: Weekday tickets $50 (beginner hill $40); Saturday and holiday tickets $65 (beginner hill $55), Sunday tickets $63 (beginner hill $53); reduced rates available in the evenings; equipment rentals $10–$40.

Cascade Mountain

Photograph: Courtesy Cascade Mountain Cascade Mountain

W10441 Cascade Mountain Rd, Portage, WI, 608-742-5588

Driving time from Chicago: about three-hours

The gist: Kids under the age of 12 ski for free at this Wisconsin resort as long as they’re accompanied by an adult—and if you’re looking for more family fun, the 900-foot-long snow tubing chute doesn’t disappoint.

Season dates: December 18–March 19

Ticket to ride: Eight-hour ticket $82; day and night ticket $86; kids under 12 ski free with adult; equipment rentals $10–$119.

Chesnut Mountain Resort

Photograph: Courtesy Chesnut Mountain ResortChesnut Mountain Resort

8700 W Chestnut Rd, Galena, 800-397-1320

Driving time from Chicago: about three-hours

The gist: This resort’s 100-room lodge is situated high on the bluff of Chestnut Mountain, offering breathtaking views of the Mississippi River. Its 475-foot vertical drop runs 3,500 feet through 19 slopes ranging from beginner to black diamond. Two conveyor lifts, two quad chairs, a surface lift and four triple chairs zip you to the top of the mountain nearly as fast as you go down.

Season dates: Weather permitting.

Ticket to ride: Weekday tickets $45; weekend and holiday tickets $65; ski/board rental $35 and up.

Crystal Mountain

Photograph: Courtesy Crystal MountainCrystal Mountain

12500 Crystal Mountain Dr, Thompsonville, MI, 855-995-5146

Driving time from Chicago: about five hours

The gist: This northern Michigan destination has it all: 58 ski or snowboard slopes, eight lifts, five terrain parks, six wooded glade areas and NASTAR racing Wednesday through Sunday. Accommodations include luxury suites, hotel rooms, condos and resort homes.

Season dates: Weather permitting through the first week of April.

Ticket to ride: Day passes start at $35; equipment rentals $25–$50.

Devil's Head Resort

Photograph: Courtesy Devil’s Head ResortDevil’s Head Resort

S6330 Bluff Rd, Merrimac, WI, 608-493-2204

Driving time from Chicago: about three hours

The gist: This South Central Wisconsin ski resort located in the Baraboo Bluffs contains one of the highest mountains in Wisconsin, with a 500-foot vertical rise. At 300 acres, it’s also the third-largest resort of its kind in the Midwest.

Season dates: Weather permitting.

Ticket to ride: Weekday tickets $62; night tickets $40; weekends $72; equipment rental $39.

Eagle Ridge Resort & Spa

Photograph: Courtesy Eagle Ridge Resort & SpaEagle Ridge Resort & Spa

444 Eagle Ridge Drive, Galena, 815-777-5000

Driving time from Chicago: about 2.5 hours

The gist: This resort offers complimentary transportation to the nearby Chestnut Mountain for skiing, though if you want to have some winter fun onsite you can take advantage of the Nordic Center, which offers sledding, ice skating, and snowshoeing. Warm-up around a bonfire or with a relaxing spa treatment.

Season dates: Weather permitting.

Ticket to ride: Equipment rentals $8 for sleds, $10 for skates, $25 for snowshoes.

Four Lakes Alpine Snowsports

Photograph: ShutterstockFour Lakes Alpine Snowsports

5750 Lakeside Dr, Lisle, 630-964-2550

Driving time from Chicago: about one hour

The gist: With an “anyone can do it” method, beginners can learn to navigate the slopes in no time. These hills in the western ’burbs consist of two bunny slopes, a terrain park, an intermediate trail and an advanced learn to race program.

Season dates: December–March

Ticket to ride: Daily slope tickets starting at $24; equipment rentals $20 (skis), $30 (boards).

The Mountain Top at Grand Geneva Resort & Spa

Photograph: Courtesy Grand Geneva Resort & SpaThe Mountain Top at Grand Geneva Resort & Spa

7036 Grand Geneva Way, Lake Geneva, WI, 262-248-8811

Driving time from Chicago: about 1.5 hours

The gist: The beginner- and family-friendly resort offers 21 runs, a 211-foot vertical, a six-acre terrain park, three chairlifts, two carpet lifts, and skiing and snowboarding lessons. You can also enjoy cross-country skiing, snowshoeing, ice skating, and sledding. Warm up by the fireplace at the mountaintop lodge while watching other skiers rush past.

Season dates: Opens Dec 13

Ticket to ride: $50 weekdays, $65 weekends and holidays ($45 evenings); rentals $10 for helmets, $40 for skis or snowboards

Sundown Mountain Resort

Photograph: ShutterstockSundown Mountain Resort

16991 Asbury Rd, Dubuque, IA, 563-556-6676

Driving time from Chicago: about 3.5 hours

The gist: This beautiful mountain, which overlooks 100 square miles of countryside, takes you down through a century-old cedar forest reminiscent of Colorado or Wyoming. With 21 trails, two terrain parks, a kids park, and ski and snowboarding lessons, you’ll find something fun for any age or skill level.

Season dates: Weather permitting.

Ticket to ride: Weekday tickets $32; weekends and holidays $34–$50; equipment rentals $5–$34.

Swiss Valley Ski & Snowboard Area

Photograph: Mason HaineySwiss Valley Ski & Snowboard Area

13421 Mann St, Jones, MI, 269-244-5635

Driving time from Chicago: about two hours

The gist: This southwestern Michigan mainstay (it’s been in business for more than 50 years) features 11 slopes, two terrain parks, a 225-foot vertical drop and a fireside lounge. Swiss Valley also offers race programs, lessons and Skibanas, heated slopeside tents where small groups can store their gear, eat and warm up between runs.

Season dates: Weather permitting.

Ticket to ride: Weekday tickets $38 (evenings $30); weekends and holidays $49; equipment rental $10–$25.

Timber Ridge

Photograph: ShutterstockTimber Ridge

07500 23 1/2 St, Gobles, MI, 269-694-9449

Driving time from Chicago: about 2.5 hours

The gist: This Michigan ski hill has been around for 60 years. Visitors can relax with drinks and some grub at the Snowshoe Bar and take advantage of multiple beginner hills, wooded trails, a snow tubing park and two terrain parks.

Season dates: Weather permitting.

Ticket to ride: Weekday tickets $45; evening tickets $40; weekend and holiday tickets $55; equipment rentals $10–$30.

Villa Olivia

Photograph: Joe OrbanVilla Olivia

1401 W Lake St, Bartlett, 630-289-1000

Driving time from Chicago: about an hour

The gist: This local slope run by the Bartlett Park District, which makes its own snow, features seven downhill runs, a quad chair lift and six rope tows, plus snow tubing.

Season dates: December 17–March 6

Ticket to ride: Weekend/winter break/holiday (9am–10pm) $44; night slope (Thursday, Friday and Sunday after 5pm, Saturday 5–10pm) $33; equipment rental $8–$42.

Wilmot Mountain

Photograph: Michael Moenning / Wilmot MountainWilmot Mountain

11931 W Fox River Rd, Wilmot, WI 630-289-1000

Driving time from Chicago: 
about 1.5 hours

The gist: Wilmot Mountain offers 120 acres outfitted with 25 trails, four terrain parks, seven lifts and two conveyor lifts, ensuring that beginner and experts alike will feel at home. Not so keen on skiing and snowboarding? Try out the resort’s 22-lane snow tubing set up.

Season dates: December through March

Ticket to ride: Epic Day Passes, which grant visitors half off of lift tickets, starts at $119. Read more

Questions? Contact The Hajdu Group

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