Winter: Go Skiing. No, Really.

When: December to April

Where: Half a dozen ski areas


Chestnut Mountain. Photo courtesy of

Chicago is known for its winters. This is a city of extremes; wind blasts off the lake, chilling the city to well below zero. Just a few years ago, the wind chill hit –33 degrees Fahrenheit—and the public transportation system still continued to grind. Chicagoans have learned to make the most of their situation by turning winter into a season to happily anticipate. Sure, there’s the ComEd Zoo Lights exhibition at the Lincoln Park Zoo, and there’s ice skating at Millennium Park. What you might not know, however, is that there are more than a just a couple opportunities for skiing in and around Illinois. We’re not talking Colorado-sized mountains, but there’s enough elevation to squeeze a couple of runs onto a nearby hill.

Chicago’s nearby ski resorts, which exist in Illinois, Michigan, Wisconsin, and Iowa, are all within a few hours’ driving distance. Though Michigan’s are the most popular in the Midwest, we’re going to focus on those located in Illinois. There’s Chestnut Mountain, for example, in Hanover, which features a 475-foot vertical drop and nineteen runs. The largest ski resort in the state, this resort is near the Mississippi River—though still relatively flat, the glacial path that razored the Midwest flat missed this small portion of the state. Plus, it’s just two and a half hours away from downtown Chicago.

Similarly, Four Lakes Village is widely recognized as the most convenient place to ski in the state. Offering both night and day skiing, they can accommodate most residents’ busy schedules. Villa Olivia is closest to Chicago and an excellent place for beginners, accommodating large groups and even offering to host weddings. If you want to spend your weekend practicing more winter sports, try Ski Snowstar in Andalusia, a bonified winter sports park with both skiing and tubing.

While ski fanatics won’t get the vertical thrill of Colorado or New Hampshire resorts, they’ll get something just as special: excellent terrain parks. Chicago and the greater Midwest are notoriously flat, but ski resorts have figured out how to make their mountains interesting. If you’re a transplant, Illinois ski resorts are an excellent opportunity to hone your freestyle technique; try larger jumps, longer rails, and interesting boxes to test your limits. If you’re interested in trying freestyle equipment for the weekend, check out one of the area’s several ski rental companies.

Sure, Chicago isn’t known for its abundance of vertical drop—or even hills, for that matter. But for the truly devoted, there are several excellent skiing opportunities within a few hours of the city. Who knows—maybe you’ll find a new love of the terrain park.


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