Best trails near Chicago

97 trails · 97 ranked · updated 2026-06-28 · off-season

Explore the best trails near Chicago, Illinois — every spot ranked by our conditions-aware Snoflo score: live conditions first, then visitor reviews and logged trips. Click a pin on the map for the score and what's driving it.

Showing the top 15 of 97 trails · best 15 shown on the map
C⛰
Chicago Riverwalk
#1 Chicago Riverwalk
2.7 mi away
Why 56: intrinsic quality
56Solid
1⛰
18th Street Access to Lakefront Trail
#2 18th Street Access to Lakefront Trail
2.8 mi away
Why 56: intrinsic quality
56Solid
S⛰
South Peoria Street
#3 South Peoria Street
1.2 mi away
Why 55: intrinsic quality
55Solid
M⛰
Museum Campus Access Path
#4 Museum Campus Access Path
2.6 mi away
Why 55: intrinsic quality
55Solid
R⛰
Roosevelt Avenue Access to Lakefront Trail
#5 Roosevelt Avenue Access to Lakefront Trail
2.6 mi away
Why 55: intrinsic quality
55Solid
C⛰
Chicago Riverwalk
#6 Chicago Riverwalk
2.7 mi away
Why 55: intrinsic quality
55Solid
E⛰
East 18th Street Footbridge
#7 East 18th Street Footbridge
2.7 mi away
Why 55: intrinsic quality
55Solid
1⛰
18th Street Access Path
#8 18th Street Access Path
2.8 mi away
Why 55: intrinsic quality
55Solid
P⛰
Pedway
#9 Pedway
2.4 mi away
Why 54: intrinsic quality
54Solid
M⛰
Main Line (Columbus-Chicago)
#10 Main Line (Columbus-Chicago)
1.3 mi away
Why 51: intrinsic quality
51Solid
N⛰
North River Walk
#11 North River Walk
2.5 mi away
Why 51: intrinsic quality
51Solid
S⛰
South Hermitage Avenue
#12 South Hermitage Avenue
0.4 mi away
Why 50: intrinsic quality
50Solid
W⛰
West Cottage Place
#13 West Cottage Place
1.0 mi away
Why 50: intrinsic quality
50Solid
S⛰
South Campus Parkway
#14 South Campus Parkway
1.1 mi away
Why 50: intrinsic quality
50Solid
W⛰
West College Parkway
#15 West College Parkway
1.1 mi away
Why 50: intrinsic quality
50Solid

Trails near Chicago

The Chicago area has 97 trails on Snoflo, ranked by live conditions, visitor reviews, and logged trips — so the best, closest options rise to the top.

How we rank the best trails near Chicago

How are these trails ranked?

Each gets a daily Snoflo score blending live conditions, visitor review ratings, and logged trips. The order reflects what's best right now and re-ranks every day.

How often does it update?

Daily, as new conditions, reviews, and trips arrive — so "best right now" means right now.

What do the numbers on the map mean?

Each pin shows that spot's current Snoflo score; tap it for the breakdown and a link to the full report.

More trails in Illinois

All Illinois trails →