Cover Chicago’s lakeshore, Millennium and Grant Parks, the Chicago River and Michigan Avenue on a guided, casual-paced run. Expect 75 minutes of history-rich stops, skyline views and manageable urban running on paved paths.
More ways to explore the area's outdoor wonders
You meet at the plaza across from the Wrigley Building, the pavement still warm from the city's pulse as waves on Lake Michigan dare you to look away. The tour moves at a conversational jog: the skyline rising like a stone gallery to your left, the lake's edge unfurling to your right, bridges lifting and lowering as you cross the Chicago River.
Difficulty
moderate
Duration
1–1.5 hours
Fitness Level
Comfortable with continuous running interspersed with short walking/photo stops; suitable for regular recreational runners
Wildlife
History
The tour runs through parts of the Loop shaped by post-1871 rebuilding and late 19th–early 20th century architects; the reversed Chicago River is an engineering milestone that rerouted the city’s flow.
Conservation
Stick to paved paths and public walkways to protect shoreline vegetation; dispose of trash in city receptacles and use refillable bottles to reduce single-use plastic.
Reserve your spot on the Chicago Highlights Running Tour today and enjoy a trusted, highly rated experience designed to help you make the most of your adventure.
Hydrate before and during the run
Bring a refillable bottle—there are water fountains along the lakefront but stops are limited between checkpoints.
Wear supportive running shoes
City sidewalks and the lake path are mostly flat but can be hard on feet; choose shoes with good cushioning.
Time it for fewer crowds
Early morning or weekday runs avoid heavy pedestrian and bike traffic, making bridge crossings and photos easier.
Watch for bike lanes and traffic
Keep to the right on multi-use paths and follow your guide’s instructions when crossing streets and bridges.
Supportive running shoes
Provide cushioning and traction on sidewalks and paved lakefront paths.
Refillable water bottle
Keeps you hydrated between guide stops—Chicago summers can be hot and humid.
summer
Light windbreaker or layers
Breezes off Lake Michigan can be cool in spring or evening runs.
spring
Hat and sunscreen
Protects against sun exposure along long stretches of open shoreline.
summer