The best running trails around Chicago
4.6
(116)
23,696
runners
389
runs
Last updated: November 8, 2025
4.7
(17)
1,212
runners
1. Riverwalk East to Northerly Island via Lakefront Trail — Chicago
9.38km
00:58
20m
20m
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4,386
runners
2. Benches – Chicago Riverwalk loop from Van Buren Street
40.0km
04:07
70m
70m
Expert run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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4.7
(7)
518
runners
3. Maggie Daley Park via Lakefront Trail — Chicago
17.7km
01:49
30m
30m
Expert run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
249
runners
4. The Bloomingdale Trail (The 606) — Chicago
9.38km
00:58
0m
0m
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
223
runners
5. Wilson to North Avenue Beach via Lakefront Trail loop — Chicago
15.7km
01:37
20m
20m
Expert run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
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