Running trails in Chicago, IL
Chicago has 46 trails in the directory — 11 paved, 3 loops that return to the trailhead, 3 with a stated distance, 2 shaded, and 7 open 24 hours. 34 of them post opening hours, so you can check the gate before an early start. They're ranked here by rating weighted by review volume, across 20,845 Google reviews. Filter by surface, loop, distance, shade or lighting to get to the run you're actually planning — no made-up difficulty score, just the facts you'd check before driving out.
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.
Catherine Chevalier Woods
4.6 ★★★★★ 1,097 reviews
This expansive tract features a variety of nature habitats, plus areas for picnicking & hiking.
North Park Village Nature Center
4.8 ★★★★★ 941 reviews
46-acre nature preserve with hiking trails, a birding area & a center with educational programs.
West Ridge Nature Park
4.7 ★★★★★ 858 reviews
Walking, bird-watching & fishing are popular in this lush, outdoor area with a large pond.
Forest Glen Woods
4.6 ★★★★★ 707 reviews
Nature & recreation area featuring paths amid woods & wildlife, plus a picnic pavilion.
Eggers Grove
4.5 ★★★★★ 665 reviews
Vibrant nature park featuring hiking paths, marshes, waterfowl, picnic spots & open spaces.
Big Marsh Park
4.7 ★★★★★ 565 reviews
280.13-acre open space with an off-road bike park, nature areas for bird watching & hiking trails.
Schiller Woods-East
4.7 ★★★★★ 510 reviews
Nature preserve featuring forests, a public restroom, picnic tables, and kid-friendly hikes.
Oriole Park
4.5 ★★★★★ 363 reviews
This recreational park provides multiple athletic fields, playgrounds, a spray pool & paved trails.
Lakefront Trail - North Trailhead - Ardmore Ave - 5800 N
4.8 ★★★★★ 338 reviews
Cycling lanes, picnic areas, and a beach highlight this park featuring a lake for swimming and kid-friendly hikes.
Lakefront Trail - Fullerton - 2400 N
4.9 ★★★★★ 310 reviews
This 18-mile-long route features separate lanes for walkers & cyclists, plus views of Lake Michigan.
Thaddeus S. "Ted" Lechowicz Woods
4.7 ★★★★★ 266 reviews
Wooded riverside park featuring walking/jogging trails & a picnic shelter in a clearing.
Edgebrook Woods
4.4 ★★★★☆ 265 reviews
Forested preserve featuring hiking & biking trails, birding & nature observation in a spacious area.
Lakefront Trail - Grant Park
4.8 ★★★★★ 200 reviews
Popular waterfront recreational strip with 18 miles of side-by-side walking & biking trails.
Caldwell Woods (Forest Preserves of Cook County)
4.7 ★★★★★ 176 reviews
Cook County park offering a trail for walking and biking, plus a picnic area.
Sidney Yates Flatwoods
4.6 ★★★★★ 176 reviews
Peaceful, leafy nature preserve along a river, with unpaved walking trails & local wildlife.
Norwood Park
4.7 ★★★★★ 121 reviews
Neighborhood park with a pool, playground, dog park, rollerblading skate park, and athletic facilities.
Brooks (Oscar) Park
4.5 ★★★★★ 119 reviews
This site features a rec center with fitness programs, horseshoe pits, tennis courts & ball fields.
Robinson Woods-South
4.6 ★★★★★ 103 reviews
Nature preserve featuring deer, trails for running, picnicking, and biking, and a public restroom.
Lakefront Trail - Dusable Harbor - 150 N
4.8 ★★★★★ 63 reviews
Popular 28-mile waterside route spanning 2 sides of the city and used for biking, running and walking.
Bogan Park
3.8 ★★★★☆ 46 reviews
Local destination, with a playground for kids, basketball courts, and a running track.
North Park Walking Stick Woods Natural Area
4.7 ★★★★★ 34 reviews
The Bloomingdale Trail - East Trailhead - Ashland Ave - 1600 W
4.8 ★★★★★ 32 reviews
Lakefront Trail - South Trailhead - 71st Street
4.8 ★★★★★ 21 reviews
North Branch Trail South End at Gompers Park
4.9 ★★★★★ 15 reviews
Lakefront Trail - Division - 1200 N
4.8 ★★★★★ 13 reviews
Lakefront Trail - 55th Street
4.9 ★★★★★ 12 reviews
Che Che Pin Qua Woods
4.9 ★★★★★ 11 reviews
Lakefront Trail Northern Entrance
4.7 ★★★★★ 10 reviews
Dunning Read Natural Area
4.1 ★★★★☆ 10 reviews
Story Trail at Unity Park
4.1 ★★★★☆ 8 reviews
Lakefront Trail - 31st Street Harbor
4.8 ★★★★★ 6 reviews
Friends of The Bloomingdale Trail
5 ★★★★★ 1 reviews
No trails match those filters.
How to pick a trail in Chicago
- Match the surface to your legs. Chicago gives you a choice: 11 paved and 4 mixed. Asphalt and concrete are fast, predictable and runnable year-round but the least forgiving; crushed limestone and dirt take the sting out of high mileage; boardwalk is flat and scenic but slick in the wet. If your shins or knees are complaining, the fix that actually works is varying the surface you run on rather than chasing one "best" one. More paved trails →
- Loop or out-and-back? 3 trails here are loops, so you finish back at the car with no backtracking — the easiest way to run a set distance without thinking about it. On an out-and-back you turn round at half your target distance, which makes any trail fit any run. The longest stated distance in Chicago is Lakefront Trail - Grant Park at 40 mi. 1 trail is long enough for a 5-mile-plus run without repeating yourself.
- Check the hours before a 6am run. 7 trails in Chicago are open 24 hours — the rest can sit inside a park that gates at dusk and doesn't unlock until well after sunrise. 34 of the 46 listings carry posted opening hours — worth a look before you set an alarm. 1 is lit, which is what you want for winter evenings.
- Long run? Check water and restrooms first. 19 have trailhead parking, 14 have restrooms, and 7 have a water fountain in Chicago. Anything over an hour and those stop being nice-to-haves — and in summer, shade counts double.
- The small things that decide it. 2 shaded, 11 that runners describe as quiet, 17 dog-friendly, and 9 smooth and wide enough for a stroller or a wheelchair. Busy or quiet isn't a good-or-bad thing here: a busy path is the safer choice for a solo run at dawn, a quiet one is better for intervals.
More on all of this in the trail-running guides.
Browse Chicago trails by type
Running trails near Chicago
Worth the short drive — the closest towns with trails in the directory.