34 Trails in Chicago, Illinois

Rank Trail Name Difficulty Length (mi) Rating City
1. Palos Forest Preserve Intermediate difficulty 0 **** Palos Hills
2. Bullfrog Lake Forest Preserve (Palos Forest Preserve) Advanced difficulty 50 ***** Willow Springs
3. Big Marsh Bike Park Easiest difficulty 40.0 ***** Chicago
4. Knoch Knolls Beginner difficulty 10 *** Naperville
5. Skokie Lagoons Intermediate difficulty 7.0 **** Glencoe
6. Waterfall Glen Easiest difficulty 10.0 *** Darien
7. Des Plaines River trail Beginner difficulty 56 **** Des Plaines
8. Deer Grove Beginner difficulty 10.0 *** Palatine
9. Salt Creek Singletrack Beginner difficulty 12.0 **** Brookfield
10. Polecat Creek Trail Intermediate difficulty 1 *** Springfield
11. Forest Glen Woods Intermediate difficulty 2 **** Chicago
12. Spears Woods (Palos Forest Preserve) Intermediate difficulty 2.7 *** Willow Springs
13. Indian Road Woods Intermediate difficulty 4.0 *** Chicago
14. Yellow loop trail (Palos Forest Preserve) Beginner difficulty 8 **** Palos Hills
15. Old Plank Road Trail Easiest difficulty 22.0 **** New Lenox
16. Thatcher Woods Beginner difficulty 5.0 ** River Forest
17. Harms Woods - Central Park Intermediate difficulty 0.0 *** Skokie, IL
18. Chicago River North Branch Trail Beginner difficulty 8.0 ** Chicago
19. Beargrease skillet Easiest difficulty 8.0 **** Homewood
20. Spring Creek Greenway trail Easiest difficulty 9.0 **** New Lenox
21. Yankee Woods Easiest difficulty 0.0 *** Oak Forest
22. Joe Orr Woods Easiest difficulty 0.0 *** Chicago Heights
23. Wauponsee Glacial Trail Easiest difficulty 22.0 **** Manhattan
24. Chipilly Woods Trail Intermediate difficulty 7.0 ** Northbrook
25. Cap Sauers Holding Easiest difficulty 11.0 *** Palos Hills
26. The Forge: Lemont Quarries difficulty 5 Lemont
27. DuPage River Sports Complex Beginner difficulty 2.5 *** Naperville
28. Hidden heaven Easiest difficulty 1.0 * Lake Zurich
29. Sweet Woods difficulty 8.0 Glenwood
30. Herrick Lake Forest Preserve Easiest difficulty 5.0 Wheaton
31. Caldwell Woods difficulty 0.0 Chicago
32. Mokena Regan Road Trails difficulty 2.0 Mokena
33. Portage woods difficulty 4.0 Forest View
34. Paul Douglas Preserve difficulty 13 Hoffman Estates

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