How many over 20 km hikes are listed near Chicago?

9 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 43.5 km with 50 m (164 ft) of recorded ascent. The longest route in this set is 68.8 km.

How are the routes ordered?

OBT-7 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.

Hiking Trails Over 20 km near Chicago

The directory currently contains 9 quality-checked routes matching this guide near Chicago. Their average mapped distance is 43.5 km and average recorded ascent is 50 m (164 ft); the longest route in the set is 68.8 km.

This subset represents 8% of the 110 quality-checked routes near Chicago. Its average distance is 43.5 km, compared with 7.7 km across the full local set. Average recorded ascent is 50 m (164 ft), versus 24 m (79 ft) for all quality-checked routes in the same area.

Every route in this set is at least 20 km long. Whether it is normally completed in one day or in stages is not inferred from distance alone. Within this set, 0 routes (0%) are rated easy, 9 (100%) are rated hard or expert, and 0 (0%) 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

31.4 km

Lakefront Trail

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

Lowest recorded ascent in this sample

6 m

OBT-3

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.

Expert

OBT-7

Illinois · United States

Distance: 68.8 km
Elevation gain: 36 m
Typical duration: 16 hr

Mountain
Long-distance path

Expert

OBT-8

Illinois · United States

Distance: 60.2 km
Elevation gain: 68 m
Typical duration: 14 hr

Mountain
Long-distance path

Expert

OBT-5

Illinois · United States

Distance: 57.6 km
Elevation gain: 123 m
Typical duration: 13 hr

Mountain

Expert

ADT - Illinois - I - Seg 1

Illinois · United States

Distance: 63.6 km
Elevation gain: 81 m
Typical duration: 14 hr

Mountain
Long-distance path

Hard

Lakefront Trail

Illinois · United States

Distance: 31.4 km
Elevation gain: 30 m
Typical duration: 7 hr 4 min

Hard

OBT-3

Illinois · United States

Distance: 31.6 km
Elevation gain: 6 m
Typical duration: 7 hr 5 min

Hard

OBT-4

Illinois · United States

Distance: 32.4 km
Elevation gain: 26 m
Typical duration: 7 hr 18 min

Hard

OBT-6

Illinois · United States

Distance: 24.1 km
Elevation gain: 62 m
Typical duration: 5 hr 23 min

Hard

Riverwalk

Illinois · United States

Distance: 22.3 km
Elevation gain: 21 m
Typical duration: 4 hr 53 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
OBT-7Illinois	68.8 km	36 m	16 hr	Expert	April to October
OBT-8Illinois	60.2 km	68 m	14 hr	Expert	April to October
OBT-5Illinois	57.6 km	123 m	13 hr	Expert	April to October
ADT - Illinois - I - Seg 1Illinois	63.6 km	81 m	14 hr	Expert	April to October
Lakefront TrailIllinois	31.4 km	30 m	7 hr 4 min	Hard	April to October
OBT-3Illinois	31.6 km	6 m	7 hr 5 min	Hard	April to October
OBT-4Illinois	32.4 km	26 m	7 hr 18 min	Hard	April to October
OBT-6Illinois	24.1 km	62 m	5 hr 23 min	Hard	April to October
RiverwalkIllinois	22.3 km	21 m	4 hr 53 min	Hard	April to October

OBT-7, OBT-8, OBT-5 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 over 20 km 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

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