How many moderate hikes are listed near Chicago?

24 routes currently meet both this guide’s filter and the directory quality gate. Each submitted route has a traceable source, mapped geometry and sampled elevation data.

What is the average distance and ascent?

The average mapped distance is 9.7 km with 44 m (144 ft) of recorded ascent. The longest route in this set is 18.3 km.

How are the routes ordered?

DLT h - N. Lake to Midwest Rd currently ranks first. Ordering uses the directory score and route-data completeness; it is not a claim that editors have field-tested every route.

Does an easy rating mean beginner-safe?

No route in this set is currently rated easy. In every category, verify surface, exposure, access and current conditions independently.

Moderate Hiking Trails near Chicago

The directory currently contains 24 quality-checked routes matching this guide near Chicago. Their average mapped distance is 9.7 km and average recorded ascent is 44 m (144 ft); the longest route in the set is 18.3 km.

This subset represents 22% of the 110 quality-checked routes near Chicago. Its average distance is 9.7 km, compared with 7.7 km across the full local set.

Every route in this set is rated moderate by the directory’s distance-and-elevation model. Technical terrain and live conditions are not part of that rating. Within this set, 0 routes (0%) are rated easy, 0 (0%) are rated hard or expert, and 5 (21%) 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

5.5 km

Fort Sheridan Forest Preserve

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

Lowest recorded ascent in this sample

0 m

Pedway

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

Return logistics

0 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.

Moderate

DLT h - N. Lake to Midwest Rd

Indiana · United States

Distance: 8.8 km
Elevation gain: 34 m
Typical duration: 1 hr 54 min

Lake

Moderate

Fort Sheridan Forest Preserve

Illinois · United States

Distance: 5.5 km
Elevation gain: 62 m
Typical duration: 1 hr 15 min

Forest
Castle and ruins

Moderate

West Beach Trail - Three Loops

Indiana · United States

Distance: 6.0 km
Elevation gain: 77 m
Typical duration: 1 hr 22 min

Coastal

Moderate

Pedway

Illinois · United States

Distance: 13.7 km
Typical duration: 2 hr 51 min

Waymarked route

Moderate

DLT j - Midwest to Howe

Indiana · United States

Distance: 11.8 km
Elevation gain: 41 m
Typical duration: 2 hr 31 min

Moderate

DLT n - Howe Rd to Broadway

Indiana · United States

Distance: 16.6 km
Elevation gain: 62 m
Typical duration: 3 hr 36 min

Moderate

OBT-1

Illinois · United States

Distance: 10.0 km
Typical duration: 2 hr 5 min

Moderate

OBT-2

Illinois · United States

Distance: 18.3 km
Typical duration: 3 hr 54 min

Moderate

OBT-9

Illinois · United States

Distance: 9.0 km
Elevation gain: 13 m
Typical duration: 1 hr 53 min

Moderate

Glenwood Dunes Trails

Indiana · United States

Distance: 16.6 km
Elevation gain: 51 m
Typical duration: 3 hr 35 min

Desert

Moderate

Main Trail

Illinois · United States

Distance: 15.3 km
Elevation gain: 65 m
Typical duration: 3 hr 17 min

Forest

Moderate

Orange Unpaved Loop

Illinois · United States

Distance: 9.3 km
Elevation gain: 122 m
Typical duration: 2 hr 7 min

Forest

Moderate

Purple Single Track Loop

Illinois · United States

Distance: 3.1 km
Elevation gain: 53 m
Typical duration: 44 min

Forest

Moderate

Red Paved Loop

Illinois · United States

Distance: 11.8 km
Elevation gain: 7 m
Typical duration: 2 hr 28 min

Forest

Moderate

Red Paved Trail

Illinois · United States

Distance: 8.9 km
Typical duration: 1 hr 51 min

Forest

Moderate

Yellow East Trail

Illinois · United States

Distance: 15.4 km
Elevation gain: 100 m
Typical duration: 3 hr 22 min

Forest

Moderate

Yellow Paved Trail

Illinois · United States

Distance: 14.9 km
Elevation gain: 12 m
Typical duration: 3 hr 7 min

Forest

Moderate

Trail 8

Indiana · United States

Distance: 1.7 km
Elevation gain: 90 m
Typical duration: 30 min

Moderate

Openlands Open Space

Illinois · United States

Distance: 1.1 km
Elevation gain: 46 m
Typical duration: 18 min

Moderate

Trail 10

Indiana · United States

Distance: 9.2 km
Elevation gain: 46 m
Typical duration: 2 hr

Moderate

Trail 7

Indiana · United States

Distance: 0.9 km
Elevation gain: 35 m
Typical duration: 15 min

Moderate

Herrick Lake Regional Trail

Illinois · United States

Distance: 9.3 km
Elevation gain: 21 m
Typical duration: 1 hr 59 min

Lake

Moderate

Green Belt Trail

Indiana · United States

Distance: 3.5 km
Elevation gain: 42 m
Typical duration: 47 min

Moderate

Yellow Loop

Illinois · United States

Distance: 13.0 km
Elevation gain: 81 m
Typical duration: 2 hr 49 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
Route	Distance	Ascent	Time	Difficulty	Best season
DLT h - N. Lake to Midwest RdIndiana	8.8 km	34 m	1 hr 54 min	Moderate	April to October
Fort Sheridan Forest PreserveIllinois	5.5 km	62 m	1 hr 15 min	Moderate	April to October
West Beach Trail - Three LoopsIndiana	6.0 km	77 m	1 hr 22 min	Moderate	April to October
PedwayIllinois	13.7 km	0 m	2 hr 51 min	Moderate	April to October
DLT j - Midwest to HoweIndiana	11.8 km	41 m	2 hr 31 min	Moderate	April to October
DLT n - Howe Rd to BroadwayIndiana	16.6 km	62 m	3 hr 36 min	Moderate	April to October
OBT-1Illinois	10.0 km	0 m	2 hr 5 min	Moderate	April to October
OBT-2Illinois	18.3 km	0 m	3 hr 54 min	Moderate	April to October
OBT-9Illinois	9.0 km	13 m	1 hr 53 min	Moderate	April to October
Glenwood Dunes TrailsIndiana	16.6 km	51 m	3 hr 35 min	Moderate	April to October

DLT h - N. Lake to Midwest Rd, DLT j - Midwest to Howe, West Beach Trail - Three Loops 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

Plan with more confidence

All planning articles →

Choosing a route

How to choose a hike beyond the difficulty label

Compare distance, climbing, route shape and missing information to build a shortlist that fits your day.

Read article →

Understanding the map

Read an elevation profile without misreading the climb

Understand total ascent, net height change, profile scale and the section breakdown on each mapped route.

Read article →

Planning your day

Build a hiking time plan with room for your own pace

Separate moving time, climbing allowance and stops, then explore how changing your assumptions changes the plan.

Read article →

Related guides

Other shortlists covering the same area or the same kind of terrain.

How do these routes differ?

Shortest mapped distance in this sample

Lowest recorded ascent in this sample

Return logistics

Trails

The shortlist, side by side

Frequently asked questions

How many moderate hikes are listed near Chicago?

What is the average distance and ascent?

How are the routes ordered?

Does an easy rating mean beginner-safe?

Plan with more confidence

How to choose a hike beyond the difficulty label

Read an elevation profile without misreading the climb

Build a hiking time plan with room for your own pace

Related guides

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