Explore the most popular trail running trails near Chicago with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers and nature lovers like you.

hiking
11 days ago

trail running
23 days ago

Small trails but link with city street or sidewalk runs and Grant park trails or lakefront make perfect starting point. But run off times to avoid crowds. Great city views. Parking garage beneath the park is perfect... or park along lakefront up north at Montrose harbor for a longer run down to Grant Park area.

road biking
1 month ago

I've wanted to bike along Lake Michigan for years and we finally did it yesterday. It was everything I'd wanted. The path is well-used but not overcrowded. The views are amazing the entire way. We went from north of Irving Park all the way down to the museum campus. Terrific outing.

Yes! This is The 606 :)

Great view of the city just too many people

mountain biking
1 month ago

walking
2 months ago

hiking
2 months ago

road biking
2 months ago

2.7 miles, mostly flat, mostly straight. Great for biking, walking or running. I love that there is a place I can ride and run without having to worry about cars. There is a great park on the east end and several smaller parks along the trail. I would rate this as an easy trail.

https://www.bloomingdaletrail.org

walking
2 months ago

Easy, paved trails.
Some stairs, depending on where you enter the river walk.
Beautiful on a crisp Chicago morning.

hiking
2 months ago

hiking
3 months ago

on Millennium Park Trail

3 months ago

road biking
3 months ago