Chicago, IL Trails and Parks

Chicago has 112 trails in the vicinity, including 46 for walking and 45 for road biking. These trails range from 0.5 to 65.6 miles in length. The most popular trails are Chicago Lakeshore Path: South Hike, Jackson Park Loop and Chicago Boulevard Lakefront Ramble. Trails.com member Olivier S. recently completed Chicago Lakefront and Boulevard Ramble.
  • Chicago Lakefront

    2 Reviews

    Chicago, IL

    The Chicago lakefront walk is saved for last because it is something a little different. Unlike most of the other walks, which can easily be completed in a day or less, this excursion is a challenge ...
    •  3 days
    •  18 miles
    •  Guide

    The Chicago lakefront walk is saved for last because it is something a little different. Unlike most of the other walks, ...

  • Lincoln Park Ride

    2 Reviews

    Chicago, IL

    This ride brings you through some of the best parks just west of Lake Shore Drive. It also brings you through one of the most affluent areas in Chicago, the Gold Coast. There's light shade, with ...
    •  7.9 miles
    •  Guide

    This ride brings you through some of the best parks just west of Lake Shore Drive. It also brings you through one of the ...

  • Chicago Lakeshore Path: South Hike

    2 Reviews

    Chicago, IL

    Enjoy stunning views of the downtown skyline as you hike along this strip of parkland that links the city and the lake. Pass Chicago landmarks such as Soldier Field, the Field Museum, and Buckingham ...
    •  2 .5 hours
    •  4.4 miles
    •  Guide

    Enjoy stunning views of the downtown skyline as you hike along this strip of parkland that links the city and the lake. Pass ...

  • Chicago Boulevard Lakefront Ramble

    1 Reviews

    Chicago, IL

    A bike tour in downtown Chicago? You must be crazy! A reasonable reaction if you've ever been in the Windy City on a weekday. But on a Sunday morning, Chicago is a different place. This is ...
    •  34.8 miles
    •  Guide

    A bike tour in downtown Chicago? You must be crazy! A reasonable reaction if you've ever been in the Windy City on a weekday. ...

  • Lakefront South

    1 Reviews

    Chicago, IL

    East of Lake Shore Drive is the land of milk and honey. There's no better place for city dwellers who need to get away in a flash. Composed almost exclusively of lake and park, the southern lakefront ...
    •  25 miles
    •  Guide

    East of Lake Shore Drive is the land of milk and honey. There's no better place for city dwellers who need to get away in ...

  • Bohemian Bucktown

    1 Reviews

    Chicago, IL

    Bucktown might more appropriately be called X-town, due to all the Gen-X types that have made it popular. Make no mistake, however: What has really made Bucktown is its restaurants. For those ...
    •  4.5 miles
    •  Guide

    Bucktown might more appropriately be called X-town, due to all the Gen-X types that have made it popular. Make no mistake, ...

  • Chicago River

    1 Reviews

    Chicago, IL

    This may be the best downtown urban paddle in the country! By heading up the Chicago River in a kayak, you pass some of the largest and most interesting buildings that Chicago has to offer. As ...
    •  Part day
    •  8 miles
    •  Guide

    This may be the best downtown urban paddle in the country! By heading up the Chicago River in a kayak, you pass some of the ...

  • Chicago Lakefront

    1 Reviews

    Chicago, IL

    Kayaking along the Lake Michigan waterfront provides a unique view of the city skyline. You get all of the beauty of the tall buildings, while sitting far enough from shore to avoid the noise ...
    •  Part day
    •  10 miles
    •  Guide

    Kayaking along the Lake Michigan waterfront provides a unique view of the city skyline. You get all of the beauty of the ...

  • Hyde Park

    0 Reviews

    Chicago, IL

    The main attractions in Hyde Park are the University of Chicago and the charming neighborhood that has built itself up around it, but the Museum of Science and Industry is nothing to scoff at. ...
    •  6.8 miles
    •  Guide

    The main attractions in Hyde Park are the University of Chicago and the charming neighborhood that has built itself up around ...

  • Grant Park to Northerly Island

    0 Reviews

    Chicago, IL

    Grant Park has often been called Chicago’s front yard, and in its present guise it is a showpiece. But that wasn’t always the case. In the late 1800s it was a swampy wasteland littered with debris ...
    •  3.5 miles
    •  Guide

    Grant Park has often been called Chicago’s front yard, and in its present guise it is a showpiece. But that wasn’t always ...

  • Burnham Park

    0 Reviews

    Chicago, IL

    Seemingly serene, this long and linear lakefront walk through Burnham Park covers a lot of ground that’s been contentious, embarrassing or simply notorious in the city’s past. The park is named ...
    •  5.5 miles
    •  Guide

    Seemingly serene, this long and linear lakefront walk through Burnham Park covers a lot of ground that’s been contentious, ...

  • Kenwood

    0 Reviews

    Chicago, IL

    Kenwood became fashionable in the late 1800s when rich Chicagoans fled the industrialization and prostitution of Prairie Ave. to the north (see Walk 13). Vast mansions were built over a period ...
    •  4 miles
    •  Guide

    Kenwood became fashionable in the late 1800s when rich Chicagoans fled the industrialization and prostitution of Prairie ...

  • Hyde Park

    0 Reviews

    Chicago, IL

    Hyde Park’s raison d’etre, the University of Chicago, has kept the neighborhood vibrant even as surrounding areas of the South Side have struggled. Perhaps, however, “vibrant” is the wrong word ...
    •  2.5 miles
    •  Guide

    Hyde Park’s raison d’etre, the University of Chicago, has kept the neighborhood vibrant even as surrounding areas of the ...

  • Washington Park and Jackson Park

    0 Reviews

    Chicago, IL

    An area of great renown in the late 1800s, the swath of the South Side that includes Washington and Jackson parks was the destination of millions during the 1893 Columbian Exposition, an early-day ...
    •  4.2 miles
    •  Guide

    An area of great renown in the late 1800s, the swath of the South Side that includes Washington and Jackson parks was the ...

  • South Shore

    0 Reviews

    Chicago, IL

    Never as toney as other lakeside neighborhoods, South Shore has long been a middle-class refuge featuring excellent lakeshore views (the land bulging east means that you can easily look north ...
    •  4.7 miles
    •  Guide

    Never as toney as other lakeside neighborhoods, South Shore has long been a middle-class refuge featuring excellent lakeshore ...

  • Jackson Park Loop

    0 Reviews

    Chicago, IL

    At the heart of Jackson Park is a wooded island containing a serene Japanese garden and placid lagoons lined with cattails. Much of this quiet refuge is a remnant of one of the most important ...
    •  30–45 minutes
    •  1.35 miles
    •  Guide

    At the heart of Jackson Park is a wooded island containing a serene Japanese garden and placid lagoons lined with cattails. ...

  • North Shore Cruise

    0 Reviews

    Chicago, IL

    If you’re like many cyclists, sometimes the momentum behind a bike ride is generated wholly by the desire to find a scenic spot to relax and enjoy the lunch you packed along. This ride offers ...
    •  35.4 miles
    •  Guide

    If you’re like many cyclists, sometimes the momentum behind a bike ride is generated wholly by the desire to find a scenic ...

  • Chicago South Side Ramble

    0 Reviews

    Chicago, IL

    This ride reveals a south side of Chicago that is vast and persistently interesting. Visit four great Chicago south-side parks, follow the Lake Michigan coastline, and explore Pullman, a nineteenth-century ...
    •  27.7 miles
    •  Guide

    This ride reveals a south side of Chicago that is vast and persistently interesting. Visit four great Chicago south-side ...

  • Chicago Lakefront and Boulevard Ramble

    0 Reviews

    Chicago, IL

    Enjoy a classic Chicago bike ride along the Lakefront Path as it winds past harbors, beaches, the dazzling skyline, and the big blue lake. After passing the museum campus and Soldier Field, you’ll ...
    •  29.6 miles
    •  Guide

    Enjoy a classic Chicago bike ride along the Lakefront Path as it winds past harbors, beaches, the dazzling skyline, and the ...

  • Route 66 Starting Point

    0 Reviews

    Chicago, IL

    What's more appropriate to say than "Route 66 Rocks"? The mother road, the main street of America, the glory road, starts in the heart of Chicago at Grant Park. It travels busy city streets; ...
    •  7.2 miles
    •  Guide

    What's more appropriate to say than "Route 66 Rocks"? The mother road, the main street of America, the glory road, starts ...

  • Logan Square

    0 Reviews

    Chicago, IL

    The Logan Square ride is a study in Chicago boulevards. There are few other places in Chicago that feature so many boulevards this close to one another. As you drive to Humboldt Park, you'll ...
    •  5.7 miles
    •  Guide

    The Logan Square ride is a study in Chicago boulevards. There are few other places in Chicago that feature so many boulevards ...

  • Uptown

    0 Reviews

    Chicago, IL

    Uptown is what you'd call a vintage ride. It's one of the last great architectural neighborhoods not yet gentrified - which is probably why at Uptown's famous Green Mill, I once heard a bongo ...
    •  8 miles
    •  Guide

    Uptown is what you'd call a vintage ride. It's one of the last great architectural neighborhoods not yet gentrified - which ...

  • River North

    0 Reviews

    Chicago, IL

    This is a ride for Chicago newcomers who need a quick tour of what's just on the edge of the Loop. It's also for art lovers and shoppers, because everything about this area is chic - it's the ...
    •  5.2 miles
    •  Guide

    This is a ride for Chicago newcomers who need a quick tour of what's just on the edge of the Loop. It's also for art lovers ...

  • Prairie Avenue Historic South Loop

    0 Reviews

    Chicago, IL

    The Prairie District is one of the lesser-known Chicago sights. It's south of Grant Park and west of Soldier Field on the other side of the train tracks. It's that place you can see from Lake ...
    •  6.6 miles
    •  Guide

    The Prairie District is one of the lesser-known Chicago sights. It's south of Grant Park and west of Soldier Field on the ...

  • Lakefront North

    0 Reviews

    Chicago, IL

    An oasis for urban outdoor enthusiasts in need of a quick fix, the northern lakefront is a Chicago gem. Starting on the North Side of Chicago at Ardmore-Hollywood Beach and extending clear down ...
    •  17.4 miles
    •  Guide

    An oasis for urban outdoor enthusiasts in need of a quick fix, the northern lakefront is a Chicago gem. Starting on the North ...