Chicago winters offer more than just chilly temperatures – they offer opportunities for frosty fun! And what's more fun than sledding? If you're looking for the best places to take your kids sledding in Chicago, you've come to the right place. From gentle slopes perfect for little ones to thrilling hills that will excite even the most seasoned sledders, the city and surrounding suburbs boast some fantastic sledding spots. So, grab your warmest gear, dust off those sleds, and get ready for some downhill excitement! We've highlighted some of the top Chicago area sledding hills, ensuring your family has a memorable and exhilarating winter adventure.

Caldwell Woods
W. Devon Ave. & N. Nagle Ave., Chicago
Caldwell Woods offers a decent-sized hill for kids to sled down. It's a great spot for families, and typically the waits are short. When available, the location offers a warming center and heated restrooms. The sledding hill is lit and staffed, and open Sunday – Thursday: 10am – 7:30pm; Friday-Saturday: 10am – 8:30pm daily when conditions allow. It's best to call ahead to confirm. Call 847-647-2240 for sledding hill status.
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Dan Ryan Woods
S. Western Ave. and W. 87th St., Chicago
This is a great sledding hill for younger children, with a not-too-steep slope and a nice long ride. This is generally considered a child-safe hill with a well-marked "up" path and a wide area. The sledding hill is lit and staffed, and open Sunday – Thursday: 10am – 7:30pm; Friday-Saturday: 10am – 8:30pm daily when conditions allow. It's best to call ahead to confirm. There's also a separate snowboarding area. Call 773-233-3766 for sledding hill status.
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Oz Park
2021 N. Burling St., Chicago
You may have picnicked at Oz Park and not even noticed the grassy hills, but in winter you'll find this to be a great place for little ones to hop on their sleds. This area is not staffed or lit.
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Westchester Woods
W Cermak Rd, east of S Manheim Rd/S La Grange Rd, (708) 447-0090
The sledding hill is lit and staffed, and open Sunday – Thursday: 10am – 7:30pm; Friday-Saturday: 10am – 8:30pm daily when conditions allow. It's best to call ahead to confirm. Call 708-447-0090 for sledding hill status.
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Cricket Hill at Montrose Harbor
601 W. Montrose Drive, Chicago
This is the hill with a view, right on the lakefront and offering vistas looking onto Lake Michigan and Montrose Harbor. It's a 360 degree hill, so kids can slide down whatever side they choose, which means more sledding and less waiting. Note: there are no restrooms or warming spots nearby. This hill is not staffed or lit.
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Montgomery Ward Park
630 N. Kingsbury St., Chicago
This cozy park is in the River North neighborhood is right along the river at Erie Street and little ones can sled the easy hills. Kids can also play on the playground by the hills.
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Gompers Park
4222 W. Foster Ave., Chicago
This 39-acre park is in the North Park neighborhood, just about 10 miles north of Chicago. It's actually a rehabilitated wetland and lagoon. The hills at Gompers Park are just the right size for little ones trying out sledding for the first time.
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Villa Olivia
1401 W. Lake Street, Bartlett
At Villa Olivia, kids can go snowboarding, snow tubing and even downhill skiing. Reservations are currently required. Call the Snow Phone at (630) 540-4199 for more details.
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Techny Prairie Park and Field
1401 W. 1700 Techny Road, Northbrook
The popular sled hill remains from the former Meadowhill Park South, along with a warming house, stairs and lights for evening use. The hill measures 28 feet in height.
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