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Chicago

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

307 mi 494 km of trail 12 Recommended Routes

Easy Trails 141 Trails Intermediate Trails 12 Trails Hard Trails 0 Trails
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Recommended Routes in Chicago - 12

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

The Chicago Outerbelt Route

208.3 mi 335.3 km 1,652' Up 503.43 m Up 1,651' Down 503.37 m Down

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 364' Up 110.8 m Up 364' Down 111.01 m Down

Palos Park, IL
Favorite An algae covered pond along the Waterfall Glen Main Trail.
Easy/Intermediate

Waterfall Glen Main Trail

9.7 mi 15.6 km 259' Up 78.82 m Up 259' Down 78.83 m Down

Darien, 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 Blue Trail in the fall.
Intermediate/Difficult

Bullfrog Loop

7.4 mi 11.8 km 625' Up 190.36 m Up 624' Down 190.16 m Down

Willow…, IL
Favorite Morton Arboretum road in the fall.
Easy/Intermediate

Morton Arboretum Loop

4.5 mi 7.3 km 176' Up 53.73 m Up 175' Down 53.47 m Down

Lisle, 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 Montrose Hill
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
Favorite Blue Trail in the fall.
Intermediate

Palos West Side Tour

12.2 mi 19.6 km 697' Up 212.5 m Up 697' Down 212.51 m Down

Burr Ridge, IL
Favorite boardwalk
Easy

Carlson Oxbow Park

1.2 mi 1.9 km 7' Up 2.23 m Up 7' Down 2.27 m Down

Highland, IN

Trails in Chicago - 141

Hiking Project is built by hikers like you. Add Your Trails

6.2 mi 9.9 km #1Orange Loop
Intermediate
Willow Springs, IL
Intermediate
Willow Springs, IL
1.9 mi 3.0 km #2Purple Trail
Intermediate
Willow Springs, IL
Intermediate
Willow Springs, IL
3.9 mi 6.2 km #3Stonehouse Trail (Black Trail)
Intermediate/Difficult
Palos Hills, IL
Intermediate/Difficult
Palos Hills, IL
1.0 mi 1.6 km #4Lake Loop
Easy
Palos Heights, IL
Easy
Palos Heights, IL
1.5 mi 2.4 km #5Main Trail Loop 2
Easy
Lisle, IL
Easy
Lisle, IL
9.7 mi 15.6 km #6Yellow Trail
Intermediate
Willow Springs, IL
Intermediate
Willow Springs, IL
0.8 mi 1.3 km #7Blue Trail North
Intermediate
Burr Ridge, IL
Intermediate
Burr Ridge, IL
0.6 mi 1.0 km #8Oxbow Park Trail
Easy
Highland, IN
Easy
Highland, IN
4.9 mi 7.9 km #9Spring Creek Greenway Trail
Easy
Homer Glen, IL
Easy
Homer Glen, IL
5.2 mi 8.4 km #10Red Loop
Easy
Orland Hills, IL
Easy
Orland Hills, IL
3.0 mi 4.9 km #11Brown Trail Loop
Easy/Intermediate
Goodings Grove, IL
Easy/Intermediate
Goodings Grove, IL
8.4 mi 13.6 km #12Major Taylor Trail
Easy
Riverdale, IL
Easy
Riverdale, IL
15.7 mi 25.2 km #13Illinois Prairie Path - Main Stem
Easy/Intermediate
Maywood, IL
Easy/Intermediate
Maywood, IL
1.5 mi 2.4 km #14Brown Trail
Easy/Intermediate
Burr Ridge, IL
Easy/Intermediate
Burr Ridge, IL
7.6 mi 12.2 km #15Red Loop
Easy
Elk Grove Village, IL
Easy
Elk Grove Village, IL
7.3 mi 11.8 km #16Red Trail
Easy
Riverside, IL
Easy
Riverside, IL
1.0 mi 1.7 km #17Main Trail Loop 4
Easy
Lisle, IL
Easy
Lisle, IL
1.6 mi 2.5 km #18Yellow (Arie Crown) Trail
Easy
Oak Brook, IL
Easy
Oak Brook, IL
1.1 mi 1.8 km #19Main Trail Loop 3
Easy
Lisle, IL
Easy
Lisle, IL
0.9 mi 1.4 km #20Campground Trail (Blue)
Intermediate
Burr Ridge, IL
Intermediate
Burr Ridge, IL

Photos of Chicago - 51

Hiking Project is built by hikers 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
Hidden waterfall in Waterfall Glen DuPage County Forest Preserve
Jan 26, 2016 near Lemont, IL
Montrose Hill
Aug 4, 2015 near Lincoln…, 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
Pedestrian and bike bridge over the Des Plaines River at Willow Springs Road
Mar 1, 2020 near Willow…, IL