Follow the Lakefront Trail south from Northerly Island to lose the crowds and discover water views, two prairies and a woodland dotted with public art along an 8.5-mile Chicago hike.
Chicago hiking map
Chicago hiking map

Erin Chan Ding stretches her arms almost as wide as her smile as she balances atop a fallen tree. She's met her goal: an 8.5-mile hike through native Illinois prairie and forest at the height of fall color. She's also chatted with salmon fishermen on a Lake Michigan harbor, lunched in a funky bicycle shop and paused to appreciate one of the world's most striking city skylines.

Now, she hops down and settles back in a shady grove in Chicago's South Shore Nature Sanctuary, closing her eyes to let the "city air that feels like forest air" tickle her lashes.

Like many outdoors enthusiasts, Erin has embraced urban hiking, which blends flora, fauna and endurance with city skylines and culture. She accepted the challenge of designing an urban trails for us, scaling hills and stairs, rambling along riverbanks, and exploring neighborhoods and nature preserves. Check out her route, lace up your boots, and head out into the urban unknown.

Erin Chan Ding along Chicago's lakefront
Erin Chan Ding, a native Chicagoan, has hiked the Presidential Range in New Hampshire's White Mountains and the Inca Trail to Machu Picchu, Peru.

Chicago Hike

Follow the Lakefront Trail south from Northerly Island to lose the crowds and discover water views, two prairies and a woodland dotted with public art. "It's an oasis of tranquility," Erin says. "Those who don't venture down here have no idea what beauty they're missing."

Chicago hiking map
Chicago hiking map

1) Start at 12th Street Beach.

2) Cross the sand to Del Campo Tacos.

Del Campo Tacos  

3) Follow the sidewalk west, north along the docks, then west between East Solidarity Drive and the harbor, catching views of Shedd Aquarium.

4) Go south on the Lakefront Trail until you're just south of Soldier Field. Hike up the sledding hill.

Sledding hill near Soldier Field
Sledding hill near Soldier Field

5) Watch for ruby-crowned kinglets at McCormick Bird Sanctuary.

6) Continue south to 31st Street Beach. Drag your toes in the sand, then enjoy the view from the harbor overlook.

7) Snap a selfie with Burnham Centennial Prairie South's golden backdrop.

8) Enjoy public art in the Burnham Wildlife Corridor woodlands.

9) Pause to admire Tom Friedman's Looking Up sculpture.

Tom Friedman's Looking Up sculpture 

10) About a half-mile south of 47th Street, take the pedestrian bridge to Harold Washington Playlot Park, following South Hyde Park Boulevard around the park to East 53rd Street.

11) Head west on East 53rd Street for about a half-mile. Pass under a viaduct, then stop at Ancien Cycles and Cafe for Erin's fave: lox and avocado toast. Retrace your steps to the pedestrian bridge.

Ancien Cycles and Cafe  
Ancien Cycles and Cafe

12) Cross the bridge and rejoin the trail, following as it winds toward Promontory Point. Traverse the boulders along its outermost curve, then take a seat to savor the skyline.

13) Return to the Lakefront Trail and continue south to the South Shore Cultural Center, where you can explore native grasses and wildflowers in the South Shore Nature Sanctuary before catching a cab or an Uber back to your starting point.

Read about our urban hikes through Indianapolis and Milwaukee.