Things to Do This Winter in Chicago: Outdoor Activities

Entry-level venues for winter sports, three mountains for great skiing, and a park-and-walk guide to winter fun around the Loop

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RELATED: Our calendar of things to do this winter—from December to February »

Climb Every Mountain

The less experienced a skier you are, the closer to the city your downhill thrills.

For beginners, the bunny hill at VILLA OLIVIA is the best. It’s a 180-foot vertical drop and a quarter-mile run. Lessons are available. A day pass plus boot and ski rental is $65. 1401 W. Lake St., Bartlett; 630-289-1000,

CASCADE MOUNTAIN offers 36 ski trails; more than a third of them are suitable for beginners. The vertical drop here is 460 feet. A day pass is $45. Snowboarding lessons are available too. W10441 Cascade Mountain Rd., Portage, Wis.; 800-992-2754,

Refresh your skills with lessons at CRYSTAL MOUNTAIN RESORT & SPA and then hit some of the 45 slopes, three terrain parks, or the cross-country course. When you’re all worn out, retreat to the lodge or the spa. The lift ticket is $45 to $50 a day; rentals and lodging are extra. 12500 Crystal Mountain Dr., Thompsonville, Mich.; 800-968-7686,



3 years ago
Posted by BeautifulSnow

Living in Chicago & across the lake, I wait 10 months of the year for snow. I teach a lot of couples from Chicago how to ski along the lit trails of Lake Michigan. It's dirt cheap, even in my book! These are usually very cool ppl who take a weekend getaway. I recommend trying to ski at night on the lit groomed trails (or unlit trails if you dare) - it is so beautiful at night, esp if it is snowing, and less intimidating if you are new.

And thank you for the tips, a lot of ppl are clueless, so it is extra cool. Thank you my Chicago friends. You made ski instruction more fun last year.

2 years ago
Posted by Eliza

These are some great recommendations! They just don't seem to scratch the surface of our great city in the winter. I LOVE Intelligentsia and all the ice skating rinks. But if you've only got one day, I'd sneak in a little history too. I love the walking tours by Chicago Detours. I went on a few this summer, but they're mostly inside, so I'm sure they'd be great for the winter too.

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