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Chicago

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Recommended Routes in Chicago - 6

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Favorite The trail is full of life and diversity.
Easy/Intermediate

The Chicago Outerbelt Route

208.6 mi 335.7 km 1,684' Up 513.38 m Up 1,684' Down 513.32 m Down

Chicago, IL
Favorite Watching the Chicago Air and Water show from the Lakefront. Near Diversey Ave looking south.
Easy/Intermediate

Chicago Lakefront Trail

18.4 mi 29.6 km 154' Up 47.07 m Up 150' Down 45.69 m Down

Lincoln…, IL
Favorite 606 Trail at Whipple St.
Easy

The 606 (Bloomingdale Trail)

5.7 mi 9.2 km 8' Up 2.42 m Up 8' Down 2.41 m Down

Chicago, IL
Favorite American Kestrel
Easy

Montrose Bird Sanctuary (The Magic Hedge)

0.4 mi 0.7 km 10' Up 3.07 m Up 12' Down 3.62 m Down

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 112' Up 33.99 m Up 120' Down 36.43 m Down

Chicago, IL
Favorite The Chicago skyline from Montrose Park.
Intermediate

Montrose Park Beach Tour

4.2 mi 6.8 km 54' Up 16.56 m Up 54' Down 16.41 m Down

Lincoln…, IL

Chicago Running

  • 330 Miles 532 Kilometers of Trail
  • 6 Recommended Routes
  • 57 Easy Trails Easy Trails
  • 1 Intermediate Trail Intermediate Trails
  • 0 Difficult Trails Difficult Trails
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Areas Within Chicago

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Trails in Chicago - 52

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1.3 mi 2.1 km #1Northerly Island Loop Trail
Easy/Intermediate
Chicago, IL
Easy/Intermediate
Chicago, IL
8.4 mi 13.6 km #2Major Taylor Trail
Easy
Riverdale, IL
Easy
Riverdale, IL
15.7 mi 25.2 km #3Illinois Prairie Path - Main Stem
Easy/Intermediate
Maywood, IL
Easy/Intermediate
Maywood, IL
7.3 mi 11.8 km #4Red Trail
Easy
Riverside, IL
Easy
Riverside, IL
1.6 mi 2.5 km #5Yellow (Arie Crown) Trail
Easy
Oak Brook, IL
Easy
Oak Brook, IL
1.0 mi 1.5 km #6Black Loop
Easy/Intermediate
Lyons, IL
Easy/Intermediate
Lyons, IL
1.8 mi 2.8 km #7Blue Loop
Easy
North Riverside, IL
Easy
North Riverside, IL
3.7 mi 5.9 km #8Black Trail
Easy
Lyons, IL
Easy
Lyons, IL
1.8 mi 2.9 km #9Orange Loop
Easy
Western Springs, IL
Easy
Western Springs, IL
2.6 mi 4.2 km #10Burnham Greenway: Black
Easy
Burnham, IL
Easy
Burnham, IL

Photos of Chicago - 12

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
American Kestrel
Apr 21, 2018 near Lincoln…, IL
Wandering off the trail at North Avenue Beach yields these incredible views of the Chicago Skyline
Jul 30, 2017 near Chicago, IL
Watching the Chicago Air and Water show from the Lakefront. Near Diversey Ave looking south.
Jul 30, 2017 near Chicago, IL
The Chicago skyline from Montrose Park.
Aug 6, 2015 near Lincoln…, IL
Uptown Chicago Park
Aug 6, 2015 near Lincoln…, IL
Sunrise at Foster Beach.
Aug 6, 2015 near Lincoln…, IL
View from the Chicago Lakefront Trail.
Jun 7, 2015 near Chicago, IL
606 Trail at Whipple St.
May 9, 2018 near Elmwood…, IL
Former Lincoln Logs toy factory in Chicago
May 9, 2018 near Elmwood…, IL
Montrose Hill
Aug 4, 2015 near Lincoln…, IL
Walking your dog on the 606.
Jan 26, 2016 near Chicago, IL