Chicago area skiing and snowboarding guide

Get your winter sports fix within a day trip from Chicago



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No one would accuse resorts in our region of impersonating those on a mountain range. Though this might not be Aspen, you still can fulfill your need for ski and snowboard action right here in the Midwest. Whether you ski or snowboard, the destinations below have slopes for everyone from beginners to semi-pros. Best of all, they’re reachable by car for a long weekend of activity. Feel free to cozy up by the fire after a full day of riding the white stuff. Always call or check websites ahead of time for snow and weather conditions.


Villa Olivia (1401 W Lake St, Bartlett, 630-289-1000)
Miles from Chicago 49 (about an hour drive)
The gist This local option features 7 downhill runs, the perfect options to cut your teeth on the snow.
Ticket to ride  adult lift tickets start at $29 on weekdays.

Raging Buffalo (Rt 31 at Wilbrandt Rd, Algonquin, 847-836-RAGE)
Miles from Chicago 45 (about an hour drive)
The gist You don’t even have to leave the ’burbs to find a hill dedicated to the oh-so-trendy sport of snowboarding. Raging, near the Fox River in the Northwest Suburbs, offers half pipes, kickers, table tops and other rad features, plus a “magic carpet” (basically a slanted moving sidewalk) on the beginner hill. During the summer it even offers wakeboarding or “skurfing,” water skiing on a snowboard.
Ticket to Ride weekday tickets are $32; weekends/holidays $45; equipment rentals start at $45.

Chestnut Mountain (8700 W Chestnut Rd, Galena, 800-798-0098)
Miles from Chicago 161 (about a three-hour drive)
The gist This resort’s 120-room lodge is situated high on the bluff of Chestnut Mountain, offering breathtaking views of the Mississippi River. And even though indoor activities include a pool, sauna and game room, the real reason for visiting is to take advantage of the largest snowmaking system in the Midwest. The seven-acre winter terrain is constantly covered with the white stuff, enticing skiers and boarders of all levels. Its 475-foot vertical drop runs 3,500 feet through 19 slopes ranging from beginning to black diamond. Two SunKid conveyor belts, two quad chairs and four triple chairs zip you to the top of the mountain as fast as you go down.
Ticket to ride The slopes stay open until midnight every Friday in January and February, lift tickets $40, ski/board rental $32.

Four Lakes Alpine Snowsports (5790 Forest View Rd, Lisle, 630-964-2551)
Miles from Chicago 28 (about a 40-minute drive)
The gist With an "Anyone Can Do" 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, and two intermediate inclines, each accessible by towropes. Lessons are scheduled throughout the day for all ages and a Race Program runs every Monday night from 6:30-8pm.
Ticket to ride daily slope tickets are $28; $20–$38 for rental equipment


Crystal Mountain (12500 Crystal Mountain Dr, Thompsonville, 231-378-2000)
Miles from Chicago 280 (about a five-hour drive)
The gist Voted the Best Terrain resort in the Midwest by OnTheSnow, this destination has it all: 48 ski or snowboard slopes, eight lifts, four terrain parks, snow-sports school and daily NASTAR racing. Accommodations include 250 luxury suites, hotel rooms, condos and resort homes, with amenities such as an outdoor 20-person hot tub, a fitness center and a spa.
Ticket to ride The resort’s website offers many deals, including a Simply Ski & Ride (one night of lodging and a one open-to-close lift ticket) starting at $109 per person.

Swiss Valley Ski & Snowboard Area (13421 Mann St, Jones, 269-244-5635)
Miles from Chicago 103 (about a two hour drive)
The gist This southwestern Michigan mainstay (it’s been in business for more than 40 years) features 11 slopes, a 225-foot vertical drop and a fireside lounge. Swiss Valley also offers race programs, lessons and group rates.
Ticket to ride College students with a school ID get discounts on lift tickets ($16, regularly $36–$38) and rentals ($16, regularly $20–$25) every Friday and weekdays after 3pm all season long.


Sundown Mountain Resort (16991Asbury Rd, Dubuque 52002, 563-556-6676)
Miles from Chicago 207 (less than a four hour drive) 
The gist The only Midwest ski slope to receive the National Ski Areas Association Award of Excellence six years in a row, this beautiful mountain takes you down a century-old cedar forest reminiscent of Colorado or Wyoming. With 21 trails, two terrain parks, and six lifts, this resort will have you up and down the hills in no time. 
Ticket to ride Adults (ages 12 and over) $42 all-day weekend lift rental; ski and snowboard rentals $29 all-day.


Alpine Valley Ski Resort (W2501 County Rd D, Elkhorn, 800-227-9395)
Miles from Chicago 87 (about a two-hour drive)
The gist Touting itself as the only resort in the Midwest with three high-speed quads and four Wonder Carpets (a type of conveyer lift), this Wisconsin resort’s longest run is 3,000 feet while its vertical drop is 388 feet. Adult and children’s classes are offered, but sledding and cross-country skiing are not.
Ticket to ride Adults can learn to ski Monday through Thursday at 10am for $60, which includes a one-day lift ticket, skis, boots, poles and a two-hour beginner group lesson.

Cascade Mountain (W10441 Cascade Mountain Rd, Portage, 608-742-5588)
Miles from Chicago 177 (about a three-hour drive)
The gist Cascade maintains a top rep with snowboarders, catering to radicals with four terrain parks outfitted with obstacles, a superpipe and halfpipe, and also to families with a snow-tubing park, beginner slopes and a modest hill (460 feet). The combination of manmade and natural snow keeps the north-facing side of the Baraboo Bluffs at a happy medium—neither too slushy nor fluffy. For its size, the mountain sports 36 diverse runs—most painfully short. The bunny slopes on the west side of the hill keep beginners out of experts’ way. Ten black-diamond runs won’t wow West Coasters, but should keep skiers entertained between the mogul fields and sharp descents. Rentals ($34–$44), lessons ($20 for 90-minute group instruction) and lift tickets aren’t dirt cheap; bargain hunters should opt for the two-day lift pass ($92).
Ticket to ride Cascade has partnered with a variety of area hotels to offer special rates for skiers, all available through its website.

Devil’s Head (S6330 Bluff Rd, Merrimac 53561, 608-493-2251)
Miles from Chicago 185 (about a three-hour drive)
The gist This South Central Wisconsin ski resort is only three hours away from Chicago, and has one of the highest mountains in Wisconsin. This resort takes care of its slopes just as well as its guests; the ski slopes are groomed twice a day to make for an exhilarating ride down the mountain.
Ticket to ride pricing is a bit more expensive for this powdered slope. Adult lift passes $45 weekdays; $52 weekends/holidays. Gear rental runs $28 for the whole day.

Justin Trails (7452 Kathryn Ave, Sparta, 800-488-4521)
Miles from Chicago 262 miles (about a four-hour drive)
The gist You could easily spend an entire weekend vegging out fireside in one of Justin Trails Resort’s cozy cabins. But if you’re determined to be active, try tackling an 1,000 foot long hill on an inner tube, getting pulled on skis by dogs and cross-country skiing through Wisconsin’s gorgeous wide-open spaces.
Ticket to ride Justin's rents snowshoes ($5) and skis ($10) to guests, but it’s thrilled when guests try the lesser-known sport of skijoring, an experience that’s much like water skiing, only on snow…and with dogs. If all the exercise leaves you starving, head into “downtown” Sparta to Angelini’s (142 N Water St, 608-269-6393), a family-owned Italian joint serving fresh pizza and huge hunks of lasagna.

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