Chicago Ski Resorts

Best Skiing Near Chicago: Plenty Of Choices For Windy City Skiers, Riders

Chicago will never be known as an outright "ski town," but Windy City residents do have some viable snowsports choices nearby for both day and weekend trips.

It's home to one of the largest ski councils in the country. The Chicago Metropolitan Ski Council (skicmsc.com) is an umbrella organization for 78 ski clubs scattered across seven Midwest states. You aren't far from some of the best choices in the Heartland.

One of the best choices is Chestnut Mountain, just a bit over a two-hour drive. The resort is perched on a tall ridge overlooking the Mississippi River above the historic town of Galena, Ill. Chestnut offers the biggest vertical drop and most variety within a few hour radius of Chicago.

There's a 475-foot vertical drop, 19 runs cut through rock outcroppings, some of the best steeps in the Tri-State Region, great beginner terrain, a seven-acre terrain park with its own triple chair, and one of the best rail gardens in the Heartland.

You can stay right at Chestnut's hotel, located on top of the bluff, or nearby Galena offers motel options and several historic B&Bs.

You'll have a three hour, mostly interstate drive, heading north into Wisconsin, to two of the Badger State's top ski and snowboard resorts. Devil's Head and Cascade are located just south of Wisconsin Dells in the rugged Baraboo Bluffs region of central Wisconsin.

The sandstone cliffs and quartzite hills give this area a unique natural beauty not found anywhere else around the Great Lakes. The two ski areas, located 12 miles apart, form a formidable one-two Midwest ski punch.

Devil's Head, a full service resort with slopeside lodging, has a great collection of cruiser-friendly trails snaking down a 500-foot bluff to the Frank Lloyd Wright-like lodge. The resort is tucked into the wooded ridgeline and slopeside lodgings blend well with its surroundings.

No bumps or glades at Devil's Head, but the 26 runs are long, impeccably groomed, and boast a nice pitch and roll just made for long GS turns. Ten chairlifts and six surface tows keep skiers and riders moving up the hill with minimal wait time.

Cascade Mountain doesn't have its own lodging, but packages with several of the Dell's motels; many with indoor waterparks. The ski hill overlooks I-90/94 and, from the top of the 460-foot ski hill, it almost looks like an overzealous jump could launch skiers into oncoming traffic. The antithesis of Devil's Head, Cascade's Mogul Monster and Northwall – straightforward fall-line plunges where moguls grow as big as buried Volkswagen Beetles – give it a well-earned reputation for being more of an advanced area.

Beginners should not despair, however. Cascade became a complete family area a few years ago with a concentrated effort to improve the beginner terrain. It was also one of the last ski areas in the Midwest to allow snowboards on its slopes. Today, it completely embraces riders with multiple terrain parks, a large halfpipe, and a rail garden complete with stadium lights.

Another nearby Wisconsin snowsports facility, Alpine Valley, is a full-service resort located near East Troy. It's about a two-hour drive north of downtown Chicago. The ski area, with nearly a 400-foot vertical drop, secluded wooded runs, a terrain park, and two high-speed lifts, offers a nice variety of terrain for the whole family. Three Wonder Carpet lifts gently transport new skiers and riders up a variety of beginner terrain. The slopeside lodge, in a nod to Wisconsin's German heritage, oozes an Old World motif.

Wilmot Mountain is close to home. Many Chicagoland skiers learned the sport at this tiny area (the vertical drop is only 230 feet) located just north of the city along the Wisconsin border.

Helmut "Pepe" Teichner, considered the Dean of Midwest ski school directors, established the ski school in 1939 and, over the next half-century, taught more than a half-million Windy City residents to ski. Teichner died in 2001, but the Wilmot ski school is still going strong and teaching a whole new generation the sport of skiing and now snowboarding.

Wilmot, with 25 runs, a terrain park, and eight lifts to keep skiers and snowboarders moving, offers a variety of runs to keep you tuned for trips to larger resorts in the Midwest or to perhaps a Rocky Mountain destination. Most Chicagolanders can reach Wilmot within an hour or less.