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Loop Trails near Chicago

The directory currently contains 28 quality-checked routes matching this guide near Chicago. Their average mapped distance is 3.8 km and average recorded ascent is 17 m (56 ft); the longest route in the set is 15.4 km.

This subset represents 25% of the 110 quality-checked routes near Chicago. Its average distance is 3.8 km, compared with 7.7 km across the full local set.

Every route in this set is classified as a loop and returns to its starting area. A loop can still reuse part of the same path. Within this set, 23 routes (82%) are rated easy, 0 (0%) are rated hard or expert, and 28 (100%) are recorded as loops. Ratings are computed from available distance and elevation data and do not establish current terrain or access.

Data refreshed September 2026

Choose by the details

How do these routes differ?

A closer look at the first 6 routes in this page’s default ordering. These comparisons describe this sample, not the entire destination or a field-tested recommendation.

Shortest mapped distance in this sample

0.5 km

North Island Loop Trail

Compare the climbing too; shortest does not necessarily mean easiest.

Lowest recorded ascent in this sample

0 m

Black Oak Trail

6 of 6 have ascent data. Missing measurements are excluded.

Return logistics

6 recorded loops

Check start and finish for every option. An unknown shape does not mean a loop, and a loop does not establish access to its start.

Plan the return journey →

Distances follow stored route lines; ascent and time are estimates. Current access, surface and technical difficulty need separate checks. How to turn a comparison into a shortlist.

Trails

Moderate

Illinois · United States

Distance
15.3 km
/ 9.5 mi
Elevation gain
65 m
Typical duration
3 hr 17 min
  • Forest
Easy

Illinois · United States

Distance
1.9 km
/ 1.2 mi
Typical duration
24 min
  • Forest
Easy

Illinois · United States

Distance
0.9 km
/ 0.6 mi
Typical duration
11 min
  • Forest
Easy

Illinois · United States

Distance
3.7 km
/ 2.3 mi
Elevation gain
7 m
Typical duration
47 min
  • Forest
Moderate

Illinois · United States

Distance
9.3 km
/ 5.8 mi
Elevation gain
122 m
Typical duration
2 hr 7 min
  • Forest
Moderate

Illinois · United States

Distance
11.8 km
/ 7.3 mi
Elevation gain
7 m
Typical duration
2 hr 28 min
  • Forest
Easy

Illinois · United States

Distance
2.1 km
/ 1.3 mi
Elevation gain
7 m
Typical duration
26 min
  • Forest
Easy

Illinois · United States

Distance
1.2 km
/ 0.8 mi
Elevation gain
8 m
Typical duration
16 min
  • Forest
Moderate

Illinois · United States

Distance
15.4 km
/ 9.6 mi
Elevation gain
100 m
Typical duration
3 hr 22 min
  • Forest
Easy

Illinois · United States

Distance
1.1 km
/ 0.7 mi
Elevation gain
6 m
Typical duration
15 min
Lincoln Park South Pond and Lincoln Park Zoo Nature Boardwalk in Chicago
Easy

Illinois · United States

Distance
1.0 km
/ 0.6 mi
Typical duration
12 min
Easy

Illinois · United States

Distance
1.3 km
/ 0.8 mi
Elevation gain
6 m
Typical duration
17 min
  • Lake
Easy

Illinois · United States

Distance
5.1 km
/ 3.2 mi
Typical duration
1 hr 4 min
  • Forest
Easy

Illinois · United States

Distance
3.6 km
/ 2.3 mi
Elevation gain
14 m
Typical duration
47 min
Moderate

Illinois · United States

Distance
13.0 km
/ 8.1 mi
Elevation gain
81 m
Typical duration
2 hr 49 min
Easy

Illinois · United States

Distance
1.8 km
/ 1.1 mi
Elevation gain
12 m
Typical duration
23 min
  • Forest
Easy

Illinois · United States

Distance
0.9 km
/ 0.6 mi
Elevation gain
7 m
Typical duration
12 min
  • Forest
Easy

Illinois · United States

Distance
0.8 km
/ 0.5 mi
Elevation gain
16 m
Typical duration
11 min
Easy

Illinois · United States

Distance
2.6 km
/ 1.6 mi
Elevation gain
6 m
Typical duration
33 min
  • Forest
Easy

Illinois · United States

Distance
2.8 km
/ 1.7 mi
Elevation gain
6 m
Typical duration
36 min
Easy

Illinois · United States

Distance
4.7 km
/ 2.9 mi
Elevation gain
19 m
Typical duration
1 hr 1 min
  • Forest
Easy

Illinois · United States

Distance
0.9 km
/ 0.6 mi
Typical duration
11 min

The shortlist, side by side

The ten highest scoring routes on this page, so you can compare effort before opening any of them.

Distance, ascent, walking time and difficulty for the top routes
RouteDistanceAscentTimeDifficultyBest season
Main TrailIllinois15.3 km65 m3 hr 17 minModerateApril to October
Black Oak TrailIllinois1.9 km0 m24 minEasyApril to October
Farm Pond TrailIllinois0.9 km0 m11 minEasyApril to October
Night Heron TrailIllinois3.7 km7 m47 minEasyApril to October
North Island Loop TrailIllinois0.5 km0 m6 minEasyApril to October
Orange Unpaved LoopIllinois9.3 km122 m2 hr 7 minModerateApril to October
Red Paved LoopIllinois11.8 km7 m2 hr 28 minModerateApril to October
Riverbend TrailIllinois2.1 km7 m26 minEasyApril to October
White Oak TrailIllinois1.2 km8 m16 minEasyApril to October
Yellow East TrailIllinois15.4 km100 m3 hr 22 minModerateApril to October

Black Oak Trail, North Island Loop Trail, Riverbend Trail currently rank highest in this filtered set according to the directory score. Open an individual route to inspect its mapped line, elevation profile, data source and planning caveats. Check live access, conditions and local rules with an official source before travelling.

Frequently asked questions

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