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Running Trails in Chicago: A Local Guide
Chicago, Illinois has 46 trails in this directory — 11 paved. Of those, 3 are loops you can run without backtracking, 2 run under tree canopy and 3 publish a measured distance (the longest is 40 mi). 7 are open 24 hours, which is what you want if you run before work.
The running here leans toward smooth corridors — greenways, rail-trails and multi-use paths rather than woodland singletrack — which makes Chicago an easy place to hold a steady pace and rack up long-run miles.
What the running is like in Chicago
- Paved (11). Asphalt and concrete greenways and multi-use paths — fast, predictable, runnable year-round, and the surface that stays usable through winter and after rain. Expect to share them with cyclists.
- Loops (3). Start and finish at your car with no backtracking and no shuttle — the shape most runners want.
- Long-run trails (1). Enough continuous distance for a real long run without repeating the same mile six times.
- Shaded (2). Tree canopy, which in July is the difference between a pleasant run and a heat trap.
- Lit for night runs (1). Floodlit paths for dark mornings and after-work runs.
- Flat and fast (2). Even grade, no surprises — the profile for steady miles and pace work.
- Hilly (2). Real climbing if you want vert. Power-hiking the steep sections is normal, not failure.
- Scenic (30). Waterfront, river and park routes where the miles go by faster.
6 trails to start with
Ranked by what local runners say — rating weighted by review count. Open any of them for surface, loop distance, hours and what the reviews mention.
Dan Ryan Woods
4.5 ★★★★★ 3,208 reviews
A 257-acre forest preserve with play fields, a popular sledding hill & a paved multi-use trail.
The 606
4.8 ★★★★★ 2,198 reviews
Created on a former rail line, this elevated, 2.7 mile landscaped trail draws runners & bikers.
LaBagh Woods
4.7 ★★★★★ 1,915 reviews
This wooded area is a popular spot for nature observation & offers trails & picnic areas.
Horner (Henry) Park
4.6 ★★★★★ 1,744 reviews
Sizable park with playgrounds, multiple athletic fields, community events & cultural programming.
Schiller Woods
4.7 ★★★★★ 1,677 reviews
Fishing for bass & catfish, plus walking trails, picnic areas & roaming deer in protected woodland.
Bloomingdale Trail Park
4.7 ★★★★★ 1,211 reviews
This 2.7-mile elevated former rail track is open to both cyclists & walkers.
How to pick one
Start with the run you're actually doing, not the prettiest photo. For a long run, look for a continuous corridor with a known distance — a rail-trail or greenway with mile markers beats a park with a tangle of short spurs, and remember that "miles of trails" is a system total, not a route you can run. For an easy day, natural surface is kinder to the legs. For a tempo, you want predictable footing, so paved or crushed stone.
Then check the practical stuff: trailhead parking (19 here) , restrooms (14) , water fountains (7) . Running with a dog? 17trails are flagged dog-friendly. 9arestroller and wheelchair accessible.
And check the hours before you drive out. Plenty of parks close at dusk and gate the lot, so a trail that works at 6pm in June is locked at 6pm in November. Trail conditions move too — natural-surface paths stay muddy for days after rain, low-lying greenways flood, and sections close for construction — so the most recent reviews on a listing are worth thirty seconds of your time.
More running in Chicago
Browse every trail on the Chicago trails page, or widen the search to running trails across Illinois. You can also browse by surface, by feature, or check the best-rated trails.
New to trails? Read how to start trail running and what to bring on a trail run. Sharing a busy greenway with cyclists? Trail running etiquette. Running before sunrise or after work? Running trails at night.