33 Trails in Chicago, Illinois

Trail Name Difficulty Length (mi) Rating City
Yellow loop trail Beginner 8.0 **** Palos Hills
Yankee Woods Easiest 0.0 *** Oak Forest
Wauponsee Glacial Trail Easiest 22.0 **** Manhattan
Waterfall Glen Easiest 10.0 *** Darien
The Forge: Lemont Quarries 5 Lemont
Thatcher Woods Beginner 5.0 ** River Forest
Sweet Woods 8.0 Glenwood
Spring Creek Greenway trail Easiest 9.0 **** New Lenox
Spears Woods (Palos Forest Preserve) Intermediate 2.7 *** Willow Springs
Skokie Lagoons Intermediate 7.0 **** Glencoe
Salt Creek Singletrack Beginner 12.0 **** Brookfield
Portage woods 4.0 Forest View
Polecat Creek Trail Beginner 1.0 *** Springfield
Palos Forest Preserve Intermediate 0 ****
Old Plank Road Trail Easiest 22.0 **** New Lenox
Mokena Regan Road Trails 2.0 Mokena
Knoch Knolls Beginner 10.0 *** Naperville
Joe Orr Woods Easiest 0.0 *** Chicago Heights
Indian Road Woods Intermediate 4.0 *** Chicago
Hidden heaven Easiest 1.0 * Lake Zurich
Herrick Lake Forest Preserve Easiest 5.0 Wheaton
Harms Woods - Central Park Intermediate 0.0 *** Skokie, IL
Forest Glen Woods Intermediate 2 **** Chicago
DuPage River Sports Complex Beginner 2.5 *** Naperville
Des Plaines River trail Beginner 56 **** Des Plaines
Deer Grove Beginner 10.0 *** Palatine
Chipilly Woods Trail Intermediate 7.0 ** Northbrook
Chicago River North Branch Trail Beginner 8.0 ** Chicago
Cap Sauers Holding Easiest 11.0 *** Palos Hills
Caldwell Woods 0.0 Chicago
Bullfrog Lake Forest Preserve (Palos Forest Preserve) Advanced 50.0 ***** Willow Springs
Big Marsh Bike Park Easiest 40.0 ***** Chicago
Beargrease skillet Easiest 8.0 **** Homewood