Chicago, IL · 9 hills
9 of the 20 hills on our Chicago list are described as free by the source. 9 of these 9 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.
1410 S. Museum Campus Dr., Chicago, IL
About 220 ft long and 33 ft high. Call 312-235-7000 for status.
Source: Chicago Park District · checked 2026-10-28
Get directions to Soldier Field Sledding Hill (opens in a new tab)Apple Maps (opens in a new tab)6350 W. Devon Ave., Chicago, IL
Lit and staffed. 847-647-2240. Opens with frozen ground and 3 in. of snow.
Source: Forest Preserves of Cook County · checked 2026-10-28
Get directions to Caldwell Woods (opens in a new tab)Apple Maps (opens in a new tab)S. Western Ave. & W. 87th St., Chicago, IL
Lit and staffed. 773-233-3766.
Source: Forest Preserves of Cook County · checked 2026-10-28
Get directions to Dan Ryan Woods (opens in a new tab)Apple Maps (opens in a new tab)Palos Park, IL
Lit and staffed. Needs 6 in. of snow. 708-839-5617.
Source: Forest Preserves of Cook County · checked 2026-10-28
Get directions to Swallow Cliff Woods North (opens in a new tab)Apple Maps (opens in a new tab)Westchester, IL
Lit and staffed. 708-447-0090.
Source: Forest Preserves of Cook County · checked 2026-10-28
Get directions to Westchester Woods (opens in a new tab)Apple Maps (opens in a new tab)Palatine, IL
Unlit. 847-437-8330.
Source: Forest Preserves of Cook County · checked 2026-10-28
Get directions to Deer Grove (opens in a new tab)Apple Maps (opens in a new tab)Arlington Heights, IL
Unlit.
Source: Forest Preserves of Cook County · checked 2026-10-28
Search on Google Maps to Pioneer Woods (opens in a new tab)Apple Maps (opens in a new tab)Chicago, IL
Unlit.
Source: Forest Preserves of Cook County · checked 2026-10-28
Get directions to Thaddeus Lechowicz Woods (opens in a new tab)Apple Maps (opens in a new tab)Chicago, IL
Unlit.
Source: Forest Preserves of Cook County · checked 2026-10-28
Get directions to Schiller Woods East (opens in a new tab)Apple Maps (opens in a new tab)Questions about how we list hills? See the FAQ.
