Hiking routes around Chicago

No national or international trail comes within 30 km; the longest-distance routes here are regional. OuterBelt Trail has more of its length here than any other route: 197 km within 30 km, of 362 km in all. Regional routes account for the largest share: 228 of the 416 km of waymarked route within 30 km. Most of the 70 local routes are short walks: 64 of them are under 10 km. Operators named on the routes listed here include Chicago Park District and Outerbelt Alliance NFP.

• OuterBelt TrailRegional · OBT197 km within 30 km · 362 km in allOuterbelt Alliance NFP
• Lakefront TrailRegional · LT31 km within 30 kmChicago Park District
• RiverwalkLocal · CRW21 km within 30 km
• Yellow East TrailLocal15 km within 30 km
• Yellow LoopLocal13 km within 30 km
• PedwayLocal13 km within 30 km
• Orange Unpaved LoopLocal8.9 km within 30 km
• Red Paved TrailLocal8.9 km within 30 km
• Yellow Paved TrailLocal7.3 km within 30 km
• Brown East TrailLocal6 km within 30 km
• Trailside Museum of Natural History TrailsLocal · TMNH5.6 km within 30 km
• Black Unpaved TrailLocal5.2 km within 30 km

Each name opens the route on Waymarked Trails.

• Routes from Waymarked Trails, which draws the hiking routes mapped on OpenStreetMap (data © OpenStreetMap contributors, ODbL); counted on Oct 19, 2026.
• Only routes someone has mapped as a route on OpenStreetMap are counted. Signposted paths no one has mapped, and walks without waymarks, are not.
• Lengths within 30 km are measured on Waymarked Trails’ simplified lines and take in a route’s branches and variants; a path two routes share counts for each. A route’s length in all follows its main line along the mapped ways, and those marked “about” come from the simplified lines.

How the layers work, where their data comes from and what they can’t tell you: Hiking routes