Help keep our trails and parks open during COVID-19 by committing to social distancing. Some trails or park services may be closed this weekend so check with local authorities before heading out.
Learn more

Best trails in Chicago

996 Reviews
Looking for a great trail near Chicago, Illinois? AllTrails has 31 great hiking trails, trail running trails, kid friendly trails and more, with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers, and nature lovers like you. If you're looking for the best trails in Indiana Dunes National Park, we've got you covered. You'll also find some great local park options, like Waterfall Glen Forest Preserve or Fullersburg County Forest Preserve. Just looking to take a quick stroll? We've got 28 easy trails in Chicago ranging from 0.7 to 220 miles and from 574 to 734 feet above sea level. Start checking them out and you'll be out on the trail in no time!
Show more
Map of trails in Chicago
Top trails (31)
#1 - Chicago Riverwalk
Chicago, Illinois
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(69)
Length: 3.4 mi • Est. 1 h 24 m
Chicago Riverwalk is a 3.4 mile heavily trafficked out and back trail located near Chicago, Illinois that features a river and is good for all skill levels. The trail is primarily used for walking andShow more
#2 - Lakeshore Path: North Ave Beach To Navy Pier
Chicago, Illinois
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(98)
Length: 1.8 mi • Est. 44 m
Lakeshore Path: North Ave Beach To Navy Pier is a 1.8 mile moderately trafficked point-to-point trail located near Chicago, Illinois that offers scenic views and is rated as moderate. The trail is priShow more
#3 - McCormick Place Bird Sanctuary
Chicago, Illinois
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(7)
Length: 0.2 mi • Est. 5 m
McCormick Place Bird Sanctuary is a 0.2 mile moderately trafficked loop trail located near Chicago, Illinois that offers scenic views and is rated as moderate. The trail is primarily used for walking,Show more
#4 - Magnificent Mile and Navy Pier - Chicago
Chicago, Illinois
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(61)
Length: 2.1 mi • Est. 51 m
Magnificent Mile and Navy Pier - Chicago is a 2.1 mile heavily trafficked point-to-point trail located near Chicago, Illinois that features a lake and is good for all skill levels. The trail is primarShow more
#5 - Chicago Riverwalk to Grant Park
Grant Park
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(16)
Length: 4.8 mi • Est. 1 h 58 m
Chicago Riverwalk to Grant Park is a 4.8 mile heavily trafficked out and back trail located near Chicago, Illinois that features a lake and is good for all skill levels. The trail is primarily used foShow more
#6 - Montrose Harbor Trail
Lincoln Park
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(47)
Length: 5.4 mi • Est. 2 h 12 m
The Lakefront path runs all along Lake Shore Drive. From where LSD ends at Sheridan Rd. to south of McCormick Place. It's paved and heavily used but is a great pedestrian pathway for running, rollerblShow more
#7 - Caldwell Woods Loop
Clayton F Smith Woods Preserve
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(105)
Length: 1.3 mi • Est. 32 m
Caldwell Woods Loop is a 1.3 mile moderately trafficked loop trail located near Chicago, Illinois that features a river and is good for all skill levels. The trail is primarily used for walking.Show more
#8 - South Shore Nature Sanctuary Loop
Chicago, Illinois
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(5)
Length: 0.5 mi • Est. 12 m
South Shore Nature Sanctuary Loop is a 0.5 mile loop trail located near Chicago, Illinois that offers scenic views and is good for all skill levels. The trail offers a number of activity options.Show more
#9 - Des Plaines River Trail Loop
Robinson Woods South
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(61)
Length: 3.7 mi • Est. 1 h 32 m
As of May 2020, users have reported some entrances to the park have a temporary closure due to COVID-19. Please see the park's website for up to date information. Show more
#10 - Bloomingdale Trail
Chicago, Illinois
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(52)
Length: 5.5 mi • Est. 2 h 13 m
As of June 2020, the trail reopened from 6am to 7pm. Show more
Showing results 1 - 10 of 31