Best Places in Chicago to Go Sledding

Sledding in the Windy City isn’t like sledding on the hill behind your neighbor’s house in your small town. You’re more than likely going to have to share, but don’t let that get you down, because no one can frown while blasting down a snow-covered hill like a young Charles Foster Kane.

Caldwell Woods

Like something that would be a side feature at a ski lodge, Caldwell Woods’ sledding hill in Oak Park isn’t anything but a sledding hill. Walk up the gated side, which will have a bit of a line if you don’t come during the off-hours, and slide down the steep but smooth bank in gleeful wintery cheer.

Find more info here.

Dan Ryan Woods

The sledding hill at Dan Ryan Woods is tailored for the family outing. We’re talking ample parking, no crowds, and a 200 foot hill that’s not very steep, perfect for children while still being tolerably tame for the big’uns.

Find more info here.

Soldier Field

When they renovated the field, they added a sledding hill, and boy is it impressive. 220 feet of chilly thrills, and if there’s one downside to sledding, it’s lugging the sled back up the hill. Soldier Field’s sledding hill is rocking a T-Bar lift. Can’t beat that.

Find more info here.

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