12 Best Sledding Hills In Chicago - Time Out

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Photograph: ShutterstockThe 18 best sledding hills in Chicago

Sledding hills offer a small silver lining to Chicago's snowy season—here's where you can find some of the best ones.

Tuesday November 12 2024ShareCopy LinkFacebookTwitterPinterestEmailWhatsAppWritten by Emma Krupp & Erin YarnallAdvertising

Winter in Chicago can be pretty brutal—with freezing cold temperatures and icy sidewalks—but there’s still outdoor adventure to be had, especially if you own a sled. While the Midwest isn’t known for its elevation, there are snowboarding and skiing resorts within driving distance as well as some reasonably sized sledding hills throughout the city that are worth a visit, from toddler-friendly bunny hills to a steep “mount” that looms over Palmisano Park. Sledding is not just a daytime activity either—plenty of Chicago parks and forest preserves in the suburbs are lighted, allowing the fun to continue all night (or until the lights turn off). So the next time there's snow on the ground, layer up and head to the best hills in and near Chicago to go sledding.

RECOMMENDED: Find more things to do in Chicago this winter

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Sledding hills in Chicago

1. Sledding Hill at Soldier Field

• Sports and fitness
• Museum Campus

While most people visit Soldier Field for sports or concerts, winter sees visitors toting plastic sleds who are there for the sledding hill. Along the south side of the stadium, near Burnham Harbor, there’s a 220-foot hill that’s steep enough for thrills, but not too steep that kids are unwelcome. Don’t worry about the weather, either. The Park District makes snow if there’s not a big enough snowfall for sledding.

Erin Yarnall Read more

2. 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 hill and keeps it staffed seven days a week (Sunday–Thursday 10am–7:30pm, Friday–Saturday 10am–8:30pm) when there's at least three inches of snow on the ground. Want to check whether the hill is open? Call 773-233-3766 ahead of your visit to make sure.

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3. 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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4. 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.

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5. 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. FYI: Parts of the hill are quite steep, so Palmisano might not be the best spot for novice sledders.

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6. James Park

• Things to do
• Evanston

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

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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!

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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
• Recommended

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.

Read more

12. A. Montgomery Ward Park

• Things to do
• River North
• Recommended

Located on the banks of the Chicago River in River North, this small hill is located near the A. Montgomery Ward Park playground, making it perfect for little ones. The slope sends your toward the water, but the fence on the shore is sturdy enough to stop runaway sleds.

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13. Schiller Woods–East

• Things to do
• O'Hare

There's no lighting at this Cook County Forest Preserve nature area on the Northwest Side—so the sledding fun will have to end come sundown—but you'll find a medium-sized hill on its east end that's good for daytime runs. Call 773-625-0606 to check sledding status before you visit.

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14. Techny Prairie Park and Fields

Though the golf course, picnic areas and batting cages at Northbrook’s Techny Prairie Park and Fields aren’t really used during the winter, the park’s sledding hill certainly is. Operated by the Northbrook Park District, the hill is lit at night. The slope is pretty mild at just 28 feet tall, so it’s perfect to bring even the youngest kids to.

Erin Yarnall Advertising

15. Swallow Cliff Woods

• Attractions
• Suburbs

The toboggan run at Palos Park’s Swallow Cliff Woods may have been removed more than a decade ago, but that doesn’t mean the suburban forest preserve isn’t still a great place to go sledding. The 100-foot bluff that the run used to go down is still used for sledding during winter, although six inches of snow, or more, is required for sledding to be permitted.

Erin Yarnall Read more

16. Westchester Woods

Head to nearby Brookfield Zoo to check out its holiday light display after a day of sledding at Westchester Woods, in suburban Westchester. The forest preserve has a lighted hill from 10am-7:30pm Sundays through Thursdays, and 10am-8:30pm on Fridays and Saturdays. Call 708-447-0090 before your visit to check on the sledding hill’s status.

Erin Yarnall Advertising

17. Caboose Park

About an hour’s drive from the city, Caboose Park, in Lake Villa, is pretty far to travel for just sledding. Fortunately, the suburban park is also home to one of the few toboggan runs in Chicagoland, which was rebuilt in 2023 by Eagle Scout Michael Cronkite from Troop 85. The park is open for daytime and nighttime rides down its hill, as its lights are on every day from 5:30-10pm.

Erin Yarnall

18. Deer Grove Forest Preserve

Deer Grove Forest Preserve, the first forest preserve in Cook County, is equipped with several picnic groves, hiking trails and two sledding hills. The slopes are located at picnic groves four and five, and they don’t have lighting so they’re open from 10am until sunset every day. Call 847-437-8330 ahead of your visit to check the sledding status at the Palatine forest preserve.

Erin Yarnall

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