Walking Trails Near Chicago, IL
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Walking Trails Near Chicago, IL

43
Walking
0 - 65 mi
Range
Chicago has 43 walking trails. These trails range from 0.9 to 65.6 miles in length. The most popular trails are South Lakefront Trail, Jackson Park Loop and Illinois Prairie Path: Main Stem. Trails.com member RE M. recently completed Waterfall Glen Trail. See all Chicago trails.
Best Trails in Chicago 43 Results
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 PREMIUM MEMBER
While following this winding trail through the diverse and sometimes rugged landscape ...
Grant Park has often been called Chicago’s front yard, and in its present guise it is ...
The Illinois Prairie Path, one of the first rail trails in the nation, runs along the ...
Seemingly serene, this long and linear lakefront walk through Burnham Park covers a lot ...
Kenwood became fashionable in the late 1800s when rich Chicagoans fled the industrialization ...
Hyde Park’s raison d’etre, the University of Chicago, has kept the neighborhood vibrant ...
An area of great renown in the late 1800s, the swath of the South Side that includes Washington ...
Never as toney as other lakeside neighborhoods, South Shore has long been a middle-class ...
The phrase Urban Oasis comes to mind when many Chicagoans think of Humboldt Park. For ...
Enjoy stunning views of the downtown skyline as you hike along this strip of parkland ...
Dan Ryan Black Trail Loop is a hiking trail in Chicago, Illinois. It is within Dan Ryan ...
Major Taylor Bicycle Trail is a hiking and biking trail in Chicago, Illinois. It is within ...
Lincoln Park is sort of like the old Certs ad or the Saturday Night Live fake ad for Shimmer: ...
The Gold Coast has always been just that: the place where the folks with the gold live ...
For many it’s their favorite urban walk in America, and with its flowers and architectural ...
First it was a lethargic little stream flowing into swamplands at Lake Michigan. Later ...
Once the marshy home to Chicago’s earliest non-indigenous citizens, who needed a place ...
Tour groups crisscross the Loop in any weather and with good reason: it’s home to an astonishing ...
Just imagine if Daniel Burnham, instead of saying “Make no little plans. They have no ...
For years a world unto itself, Chinatown has broken the shackles of expressways and railroads ...
Beginning in the 1870s, scores of Bohemian immigrants filled the neighborhood that came ...
Once hemmed in by railroads, the South Loop and Near South Side have a history as varied ...
Little Italy was never populated exclusively by Italians. In fact the Irish were the majority ...
In the sunrise shadow of the Loop, the West Loop has always been its Rodney Dangerfield ...
For decades residents of Bronzeville and Bridgeport avoided each other’s neighborhoods. ...
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