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Chicago

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J F M A M J J A S O N D

291 mi 468 km of trail 12 Featured Runs

Easy Trails 146 Trails Intermediate Trails 6 Trails Hard Trails 0 Trails
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Featured Runs in Chicago - 12

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Favorite The trail is full of life and diversity.

The Chicago Outerbelt Route

208.3 mi 335.3 km • Loop • 1,671 ft Ascent 509.26 m Ascent

Singletrack Chicago, IL

( 1 )
Favorite An algae covered pond along the Waterfall Glen Main Trail.

Waterfall Glen Main Trail

9.7 mi 15.6 km • Loop • 259 ft Ascent 78.82 m Ascent

Doubletrack Darien, IL

( 27 )
Favorite Watching the Chicago Air and Water show from the Lakefront. Near Diversey Ave looking south.

Chicago Lakefront Trail

18.4 mi 29.6 km • Point to Point • 154 ft Ascent 47.07 m Ascent

Paved Path Lincolnwood, IL

( 8 )
Favorite Oak trees begin to leaf out in a well-managed oak woodland. With plenty of sunlight, the spring wildflowers are abundant.

Sag Valley Main Trail

8.5 mi 13.6 km • Loop • 364 ft Ascent 110.8 m Ascent

Singletrack Palos Park, IL

( 17 )
Favorite Morton Arboretum road in the fall.

Morton Arboretum Loop

4.5 mi 7.3 km • Loop • 176 ft Ascent 53.73 m Ascent

Doubletrack Lisle, IL

( 6 )
Favorite Blue Trail in the fall.

Bullfrog Loop

7.4 mi 11.8 km • Point to Point • 625 ft Ascent 190.36 m Ascent

Singletrack Willow Springs, IL

( 10 )
Favorite 606 Trail at Whipple St.

The 606 (Bloomingdale Trail)

5.7 mi 9.2 km • Loop • 8 ft Ascent 2.42 m Ascent

Paved Path Chicago, IL

( 12 )
Favorite American Kestrel

Montrose Bird Sanctuary (The Magic Hedge)

0.4 mi 0.7 km • Loop • 10 ft Ascent 3.07 m Ascent

Singletrack Lincolnwood, IL

( 2 )
Favorite Watching the Chicago Air and Water show from the Lakefront. Near Diversey Ave looking south.

Chicago Lakefront Trail - North

8.9 mi 14.3 km • Point to Point • 112 ft Ascent 33.99 m Ascent

Paved Path Chicago, IL

( 4 )
Favorite The Chicago skyline from Montrose Park.

Montrose Park Beach Tour

4.2 mi 6.8 km • Loop • 54 ft Ascent 16.56 m Ascent

Singletrack Lincolnwood, IL

( 1 )
Favorite Blue Trail in the fall.

Palos West Side Tour

12.2 mi 19.6 km • Loop • 697 ft Ascent 212.5 m Ascent

Singletrack Burr Ridge, IL

( 3 )
Favorite boardwalk

Carlson Oxbow Park

1.2 mi 1.9 km • Loop • 7 ft Ascent 2.23 m Ascent

Singletrack Highland, IN

( 1 )

Trails in Chicago - 140

Trail Run Project is built by runners like you. Add Your Trails

3.9 mi 6.2 km #1 Stonehouse Trail (Black Trail)
Palos Hills, IL
3.9 mi 6.2 km Palos Hills, IL
Minor Issues
Update
Muddy
83 days ago
6.2 mi 9.9 km #2 Orange Loop
Willow Springs, IL
6.2 mi 9.9 km Willow Springs, IL
Minor Issues
Update
Muddy
83 days ago
1.9 mi 3.0 km #3 Purple Trail
Willow Springs, IL
1.9 mi 3.0 km Willow Springs, IL
Unknown
Update
9.7 mi 15.6 km #4 Yellow Trail
Willow Springs, IL
9.7 mi 15.6 km Willow Springs, IL
Minor Issues
Update
Muddy, Fallen Trees
83 days ago
1.0 mi 1.6 km #5 Lake Loop
Palos Heights, IL
1.0 mi 1.6 km Palos Heights, IL
Unknown
Update
0.8 mi 1.3 km #6 Blue Trail North
Burr Ridge, IL
0.8 mi 1.3 km Burr Ridge, IL
Unknown
Update
0.6 mi 1.0 km #7 Oxbow Park Trail
Highland, IN
0.6 mi 1.0 km Highland, IN
Unknown
Update
4.9 mi 7.9 km #8 Spring Creek Greenway Trail
Homer Glen, IL
4.9 mi 7.9 km Homer Glen, IL
Unknown
Update
5.2 mi 8.4 km #9 Red Loop
Orland Hills, IL
5.2 mi 8.4 km Orland Hills, IL
Unknown
Update
8.4 mi 13.6 km #10 Major Taylor Trail
Riverdale, IL
8.4 mi 13.6 km Riverdale, IL
Unknown
Update
3.0 mi 4.9 km #11 Brown Trail Loop
Goodings Grove, IL
3.0 mi 4.9 km Goodings Grove, IL
Unknown
Update
15.7 mi 25.2 km #12 Illinois Prairie Path - Main Stem
Maywood, IL
15.7 mi 25.2 km Maywood, IL
All Clear
Update
49 days ago
1.5 mi 2.4 km #13 Brown Trail
Burr Ridge, IL
1.5 mi 2.4 km Burr Ridge, IL
Unknown
Update
1.0 mi 1.7 km #14 Main Trail Loop 4
Lisle, IL
1.0 mi 1.7 km Lisle, IL
Unknown
Update
7.3 mi 11.8 km #15 Red Trail
Riverside, IL
7.3 mi 11.8 km Riverside, IL
Unknown
Update
1.1 mi 1.8 km #16 Main Trail Loop 3
Lisle, IL
1.1 mi 1.8 km Lisle, IL
Unknown
Update
2.4 mi 3.8 km #17 Yellow Trail Loop
Hodgkins, IL
2.4 mi 3.8 km Hodgkins, IL
Unknown
Update
0.9 mi 1.4 km #18 Campground Trail (Blue)
Burr Ridge, IL
0.9 mi 1.4 km Burr Ridge, IL
Unknown
Update
1.1 mi 1.8 km #19 Brown Spur
Schiller Park, IL
1.1 mi 1.8 km Schiller Park, IL
Unknown
Update
17.9 mi 28.9 km #20 Des Plaines River Trail: Yellow
Prospect Heights, IL
17.9 mi 28.9 km Prospect Heights, IL
Unknown
Update

Photos of Chicago - 50

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