This city challenge spans around Lake Michigan, Lincoln Park, the riverwalk, high line and more. Complete all five routes to win gold, silver or bronze.

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Complete all five routes. A total of 29.8 miles (48 km).


7.6 miles

Lakefront Trail is one of the most spectacular urban runs in the country. This route has it all: gorgeous views of Lake Michigan and the Chicago skyline, urban beaches, marinas, and beautiful parks, passing by some of the city’s famous cultural institutions.


4.1 miles

The Chicago Riverwalk is one of the city’s most beautiful outdoor spaces, where you can find public art, boat tours, kayak rentals, and open green spaces. Chicago Riverwalk is a fantastic way to do an off-road run combining views of the water, the Chicago skyline, and some of the city’s architectural highlights. 

Lincoln Park

4.7 miles

Lincoln Park is a nature lover’s dream — manicured gardens, a hidden lily pond, a historic indoor botanical garden, and tons of lakefront green space with sweeping city views.

The 606

5.6 miles

The Bloomingdale Trail, part of “The 606” park system, is a elevated rail-trail on Chicago’s northwest side. Built on a former rail line, the trail sits 17 feet above four of the city’s neighborhoods: Wicker Park, Bucktown, Humboldt Park, and Logan Square.

Humboldt & Garfield

7.7 miles

This beautiful parks offers nice pathways, lakes, lots of wild flowers, a beach, and much more. The Humboldt Park neighborhood is known for its dynamic social and ethnic demographic.


Finish the challenge in one day for gold, one week for silver, or one month for bronze.



Shop a tee in black or white (optional).

The Challenge


Entry to the challenge
Simple instructions
Maps & Images
GPX files for Tracking
Digital Medal
The Merch


Unisex COTTON T-shirt
Black / White color
7 sizes (View Guide)
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