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Chicago

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307 mi 494 km of trail 12 Runs

Easy Trails 141 Trails Intermediate Trails 12 Trails Hard Trails 0 Trails
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Runs in Chicago - 12

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Favorite The trail is full of life and diversity.
Intermediate

The Chicago Outerbelt Route

208.3 mi 335.3 km • Loop • 1,652 ft Ascent 503.43 m Ascent

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

Sag Valley Main Trail

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

(20) Palos Park, IL
Favorite An algae covered pond along the Waterfall Glen Main Trail.
Intermediate

Waterfall Glen Main Trail

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

(29) Darien, IL
Favorite Watching the Chicago Air and Water show from the Lakefront. Near Diversey Ave looking south.
Easy

Chicago Lakefront Trail

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

(9) Lincoln…, IL
Favorite Blue Trail in the fall.
Difficult

Bullfrog Loop

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

(12) Willow…, IL
Favorite Morton Arboretum road in the fall.
Easy

Morton Arboretum Loop

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

(6) Lisle, IL
Favorite 606 Trail at Whipple St.
Easy

The 606 (Bloomingdale Trail)

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

(12) Chicago, IL
Favorite American Kestrel
Easy

Montrose Bird Sanctuary (The Magic Hedge)

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

(2) Lincoln…, IL
Favorite Watching the Chicago Air and Water show from the Lakefront. Near Diversey Ave looking south.
Easy

Chicago Lakefront Trail - North

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

(4) Chicago, IL
Favorite The Chicago skyline from Montrose Park.
Intermediate

Montrose Park Beach Tour

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

(1) Lincoln…, IL
Favorite Blue Trail in the fall.
Intermediate

Palos West Side Tour

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

(3) Burr Ridge, IL
Favorite boardwalk
Easy

Carlson Oxbow Park

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

(1) Highland, IN

Trails in Chicago - 141

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

6.2 mi 9.9 km #1Orange Loop
Intermediate
Willow Springs, IL
Intermediate
6.2 mi 9.9 km Willow Springs, IL
1.9 mi 3.0 km #2Purple Trail
Intermediate
Willow Springs, IL
Intermediate
1.9 mi 3.0 km Willow Springs, IL
3.9 mi 6.2 km #3Stonehouse Trail (Black Trail)
Difficult
Palos Hills, IL
Difficult
3.9 mi 6.2 km Palos Hills, IL
1.0 mi 1.6 km #4Lake Loop
Easy
Palos Heights, IL
Easy
1.0 mi 1.6 km Palos Heights, IL
1.5 mi 2.4 km #5Main Trail Loop 2
Easy
Lisle, IL
Easy
1.5 mi 2.4 km Lisle, IL
9.7 mi 15.6 km #6Yellow Trail
Intermediate
Willow Springs, IL
Intermediate
9.7 mi 15.6 km Willow Springs, IL
0.8 mi 1.3 km #7Blue Trail North
Intermediate
Burr Ridge, IL
Intermediate
0.8 mi 1.3 km Burr Ridge, IL
0.6 mi 1.0 km #8Oxbow Park Trail
Easy
Highland, IN
Easy
0.6 mi 1.0 km Highland, IN
4.9 mi 7.9 km #9Spring Creek Greenway Trail
Easy
Homer Glen, IL
Easy
4.9 mi 7.9 km Homer Glen, IL
5.2 mi 8.4 km #10Red Loop
Easy
Orland Hills, IL
Easy
5.2 mi 8.4 km Orland Hills, IL
3.0 mi 4.9 km #11Brown Trail Loop
Intermediate
Goodings Grove, IL
Intermediate
3.0 mi 4.9 km Goodings Grove, IL
8.4 mi 13.6 km #12Major Taylor Trail
Easy
Riverdale, IL
Easy
8.4 mi 13.6 km Riverdale, IL
15.7 mi 25.2 km #13Illinois Prairie Path - Main Stem
Easy
Maywood, IL
Easy
15.7 mi 25.2 km Maywood, IL
1.5 mi 2.4 km #14Brown Trail
Intermediate
Burr Ridge, IL
Intermediate
1.5 mi 2.4 km Burr Ridge, IL
7.6 mi 12.2 km #15Red Loop
Easy
Elk Grove Village, IL
Easy
7.6 mi 12.2 km Elk Grove Village, IL
7.3 mi 11.8 km #16Red Trail
Easy
Riverside, IL
Easy
7.3 mi 11.8 km Riverside, IL
1.0 mi 1.7 km #17Main Trail Loop 4
Easy
Lisle, IL
Easy
1.0 mi 1.7 km Lisle, IL
1.1 mi 1.8 km #18Main Trail Loop 3
Easy
Lisle, IL
Easy
1.1 mi 1.8 km Lisle, IL
2.4 mi 3.8 km #19Yellow Trail Loop
Intermediate
Hodgkins, IL
Intermediate
2.4 mi 3.8 km Hodgkins, IL
1.6 mi 2.5 km #20Yellow (Arie Crown) Trail
Easy
Oak Brook, IL
Easy
1.6 mi 2.5 km Oak Brook, IL

Photos of Chicago - 51

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

The trail is full of life and diversity.
Jul 7, 2016 near River F…, IL
Blue Trail in the fall.
Aug 12, 2016 near Burr Ridge, IL
Near W Bryn Mawr Ave
Sep 13, 2018 near Schille…, IL
Sunset and mosquitoes!
Sep 13, 2018 near Schille…, IL
A misty morning over Lake Marmo.
Nov 10, 2016 near Lisle, IL
Hidden waterfall in Waterfall Glen DuPage County Forest Preserve
Jan 26, 2016 near Lemont, IL
Pedestrian and bike bridge over the Des Plaines River at Willow Springs Road
Mar 1, 2020 near Willow…, IL
Wandering off the trail at North Avenue Beach yields these incredible views of the Chicago Skyline
Jul 30, 2017 near Chicago, IL

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