Best trails near Near South Side

86 trails · 86 ranked · updated 2026-06-28 · off-season

Explore the best trails near Near South Side, 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 86 trails · best 15 shown on the map
L⛰
Lakefront Trail
#1 Lakefront Trail
2.7 mi away
Why 71: intrinsic quality
71Top-rated
1⛰
18th Street Access to Lakefront Trail
#2 18th Street Access to Lakefront Trail
0.5 mi away
Why 56: intrinsic quality
56Solid
C⛰
Chicago Riverwalk
#3 Chicago Riverwalk
2.1 mi away
Why 56: intrinsic quality
56Solid
E⛰
East 18th Street Footbridge
#4 East 18th Street Footbridge
0.4 mi away
Why 55: intrinsic quality
55Solid
1⛰
18th Street Access Path
#5 18th Street Access Path
0.5 mi away
Why 55: intrinsic quality
55Solid
M⛰
Museum Campus Access Path
#6 Museum Campus Access Path
0.9 mi away
Why 55: intrinsic quality
55Solid
R⛰
Roosevelt Avenue Access to Lakefront Trail
#7 Roosevelt Avenue Access to Lakefront Trail
0.9 mi away
Why 55: intrinsic quality
55Solid
S⛰
South Dearborn Street
#8 South Dearborn Street
1.5 mi away
Why 55: intrinsic quality
55Solid
S⛰
South Peoria Street
#9 South Peoria Street
1.8 mi away
Why 55: intrinsic quality
55Solid
3⛰
35th St Pedestrian Bridge
#10 35th St Pedestrian Bridge
2.0 mi away
Why 55: intrinsic quality
55Solid
3⛰
35th Street Access Path
#11 35th Street Access Path
2.0 mi away
Why 55: intrinsic quality
55Solid
3⛰
35th Street Access to Lakefront Trail
#12 35th Street Access to Lakefront Trail
2.0 mi away
Why 55: intrinsic quality
55Solid
C⛰
Chicago Riverwalk
#13 Chicago Riverwalk
2.1 mi away
Why 55: intrinsic quality
55Solid
L⛰
Lake Shore East
#14 Lake Shore East
2.1 mi away
Why 55: intrinsic quality
55Solid
N⛰
Navy Pier Flyover
#15 Navy Pier Flyover
2.4 mi away
Why 55: intrinsic quality
55Solid

Trails near Near South Side

The Near South Side area has 86 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 Near South Side

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.

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