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AI illustration: A red sled resting in fresh snow at the top of a gentle hill. Not this location.

Chicago, IL · 5 hills

Hidden gem sledding hills in Chicago

5 of the 20 hills on our Chicago list are named by locals in public threads. 0 of these 5 are listed by the park or city itself. Each one links to its source, checked 2026-10-28. Details change, so check the source page or posted signs before you go.

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The 5 hills

James Park (Mount Trashmore)

Evanston, IL

  • Lights: Lights ?
  • Cost: Cost ?
  • Parking: Parking ?
  • Steepness: Slope ?

Named by locals in a Reddit thread. A local called it a "massive steep landfill hill with smaller hills" and mentioned free parking. The City of Evanston says sledding is not allowed on the large center hill, and tobogganing, skiing and snowboarding are not allowed in the park. Park sledding rules not stated by source.

Source: Reddit r/chicago thread, Nov. 30, 2025 · checked 2026-10-29

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All 20 Chicago hills

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