Winter Activities and Day Trips – Chicago and Surrounding Area

Chicago winters are known to be brutal. But for those of us that enjoy the cold, more snow means more fun. Although the Midwest isn’t known for its big mountains, there are plenty of places you can visit to get your winter sports fix without having to go all the way to the Rockies. Whether you want to ice skate, cross-country ski or hit the slopes to snowboard, there are plenty of options that are driving distance from the city.

We’ve put together a list of some of the best winter sports destinations in and around the city. Everything is either within city limits or perfect for a day trip. 

Don’t forget! Check in with your local park district to see what winter activities they offer. Many parks have indoor ice skating rinks, too; we chose to list only the outdoor seasonal rinks in this article. Also, note that many of the ski resorts listed offer other activities like snow-tubing, sledding, and toboggan slides. Be sure to check on weather conditions and updates on company websites before heading out, so you don’t run into any issues.

Ice Skating

Maggie Daley Park
McCormick Tribune Ice Rink at Millennium Park
Winterland Ice Rink at Gallagher Way
Watts Ice Center (45 minutes)
Winter Wonderland Ice Rink in Orland Park
(1 hour)

Cross-Country Skiing

Morton Arboretum (1 hour)
Arrowhead Golf Course (1 hour)
Sagawau Trails (1-2 hours)
Lake County Forest Preserves (1 hour)
Forest Preserve District of DuPage County
(1 hour)


Four Lakes Alpine Snowsports (1 hour)
Grand Geneva – The Mountain Top (1-2 hour)
Alpine Valley (1-2 hour)
Wilmot Mountain Ski Resort (1-2 hour)
The Rock Snowpark (2 hour)
Chestnut Mountain Resort (3 hour)


If you’re in the mood for some fun in the snow, be sure to check one of these places out. Most ski locations offer classes and slopes for beginners, so if you are new to winter sports, don’t fret. There’s something for every skill level and a warm place to take a breather and have some hot cocoa. If you’ve never taken part in any winter sports activities, it’s not too late to start! Winter may be seen as hibernation season, but staying active during these cold months will surely make you feel better while getting you ready for beach season!