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The 12 best sledding hills in Chicago

Make the most of winter at these sledding hills in Chicago, which offer skyline views and hours of outdoor fun.

By Emma Krupp
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Sure, you could hop in a car to try skiing near Chicago or slide around on local ice skating rinks for some entertainment on a winter afternoon. But if you're looking for free things to do in Chicago during the snowy season, it's tough to beat sledding—and you likely don't have go far to find a good hill in your neighborhood. We've compiled a list of Chicago parks and forest preserves that are home to formidable slopes and beginner hills, perfect for cruising down on a toboggan or inner tube. Don't forget your snow pants and mittens when you check out the best sledding hills in Chicago.

Due to COVID-19 precautions, some hills may be operating in a more limited capacity than usual this year. When in doubt, call ahead!

RECOMMENDED: Find more things to do in Chicago this winter

Sledding hills in Chicago

sledding
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1. Dan Ryan Woods

Things to do Ashburn

Take a trip to Beverly to gaze at the distant Chicago skyline before plunging down a 200-foot hill—among the largest, if not the largest, slope in the entire city. The Cook County Forest Preserve lights up the slope and keeps it staffed seven days a week (assuming that there's actually snow on the ground—a minimum of three inches is needed). Want to check whether the hill is open? Call 773-233-3766 ahead of your visit to make sure.

Crocheron Park
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2. Cricket Hill

Things to do Lincoln Park

You'll be able to take in views of Lake Michigan from atop this relatively steep four-sided hill on the northern end of Lincoln Park (near Montrose Beach), making for some beautiful slipping and sliding.

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3. Caldwell Woods

Attractions Forests Norwood Park

Pick up some snacks at Superdawg before hitting the slopes at this Northwest Side forest preserve. Enter Caldwell Woods at West Devon and North Nagle Avenues and you'll find the sledding spot nearby. Like Dan Ryan Woods, this hill is lit up and staffed when conditions are right; call 847-647-2240 to double check before making the trek.

sledding
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4. Palmisano Park

Attractions Parks and gardens Bridgeport

Known by locals as "Mount Bridgeport," the site of Palmisano Park is a former garbage dump that has been reclaimed as a recreation area. It's surrounded by roads and parts of the hill are quite steep, so Palmisano might not be the best spot for novice sledders.

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sleddingHillParkSoliderField.venue.jpg
Photograph: Courtesy Soldier Field

5. Soldier Field

Sports and fitness Museum Campus

Located just to the north of Soldier Field's south parking lot, this 35-foot-tall, 220-foot-long hill was created during the stadium's landscaping redesign, giving local kids a bit of elevation for winter fun. Best of all, the Park District uses snow machines to keep it coated in powder as long as temps are low enough, even if there's no naturally-occurring snow on the ground.

sledding
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6. James Park

Things to do Evanston

The largest hill in James Park—a 65-foot peak dubbed Mt. Trashmore, since its the site of a former landfill—is so intense that the Park District has banned sledding on it, but thrill-seekers can still speed down a couple of smaller mounds in this Evanston park. 

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7. Warren Park

Things to do Literary events West Ridge

Kids in Rogers Park flock to this hill lined by stairs, making it easier to trudge back up to the top after whizzing down on a sled.

sledding
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8. Riis Park

Things to do Literary events Belmont Cragin

You can plan a full day of wintertime fun at this Belmont-Cragin park, which is also home to an ice skating rink in addition to its modest sledding hill. 

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9. Humboldt Park

Things to do Humboldt Park

Hills in Humboldt Park? Yep, there's one to the west of the fieldhouse (right by the lagoon) where those who simply must go sledding in the winter can get an oh-so-brief fix. Watch out for snowmen!

Snowy tree
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10. Horner Park

Things to do Albany Park

Located at the nexus of Irving Park and Albany Park, most of this urban oasis is pretty flat, but there are few gradual slopes that small kiddos might have some fun scooching down.

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11. Oz Park

Things to do Lincoln Park

Even a Cowardly Lion can handle the miniature sledding hill in Oz Park, which is just slightly more magical than other gradual slopes in the city due to the presence of Dorothy, Toto and Scarecrow statues.

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