

Route template
Oak Park to Chicago
Start your cycling journey in the charming suburb of Oak Park, just a stone's throw from Chicago. Known for its stunning architecture and the birthplace of writer Ernest Hemingway, Oak Park is a tranquil beginning point for your ride.
As you pedal towards the bustling city of Chicago, you’ll cruise along mostly quiet roads, making for a peaceful trek to the big city. The route spans nearly 18 kilometers, so it’s perfect for a leisurely ride.
The path gently meanders, with only a mild ascent and descent, allowing you to soak in the surroundings without too much challenge. With the unique blend of surfaces like asphalt and paved pathways, the journey is bound to be smooth as you roll into the vibrant cityscape of Chicago.
You'll arrive in Chicago, the Windy City, famous for its bold architecture, deep-dish pizza, and lively arts scene. Whether you're parking your bike to explore the Magnificent Mile or heading for a slice of that famous pizza, this ride is both scenic and rewarding. So, grab your bike, hit the road, and let the path lead you from quaint to quintessentially urban!
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The best bike routes from Oak Park to Chicago
Logan Square
Cycling route in Oak Park, Illinois, United States of America
- 15.3 km
- Distance
- 41 m
- Ascent
- 3 m
- Descent
Jun 11, 2014, 9:58 AM
Cycling route in Oak Park, Illinois, United States of America
- 13.9 km
- Distance
- 32 m
- Ascent
- 38 m
- Descent
1651 N Kimball Ave, Chicago to 519 N Oakley Blvd, Chicago
Cycling route in Oak Park, Illinois, United States of America
- 5 km
- Distance
- 376 m
- Ascent
- 376 m
- Descent
Handlebar By The Middle Passgae
Cycling route in Oak Park, Illinois, United States of America
- 14.7 km
- Distance
- 19 m
- Ascent
- 29 m
- Descent
1652 N Kimball Ave, Chicago to 1601 W North Ave, Chicago
Cycling route in Oak Park, Illinois, United States of America
- 4.6 km
- Distance
- 190 m
- Ascent
- 6 m
- Descent
HB Direct!
Cycling route in Oak Park, Illinois, United States of America
- 13.2 km
- Distance
- 26 m
- Ascent
- 33 m
- Descent
Bike Ride Home Day 1
Cycling route in Oak Park, Illinois, United States of America
- 7.8 km
- Distance
- 8 m
- Ascent
- 14 m
- Descent
Thursday Training 7/6/17
Cycling route in Oak Park, Illinois, United States of America
- 48.7 km
- Distance
- 124 m
- Ascent
- 128 m
- Descent
1653 N Kimball Ave, Chicago to 1819–1825 N Marshfield Ave, Chicago
Cycling route in Oak Park, Illinois, United States of America
- 4.1 km
- Distance
- 7 m
- Ascent
- 13 m
- Descent
Bloomingdale and Back
Cycling route in Oak Park, Illinois, United States of America
- 17.1 km
- Distance
- 30 m
- Ascent
- 42 m
- Descent
Lyman Avenue 1100, Oak Park to North Racine Avenue 2011, Chicago
Cycling route in Oak Park, Illinois, United States of America
- 15.9 km
- Distance
- 7 m
- Ascent
- 17 m
- Descent
1649 N Kimball Ave, Chicago to 516 N Oakley Blvd, Chicago
Cycling route in Oak Park, Illinois, United States of America
- 4.6 km
- Distance
- 0 m
- Ascent
- 0 m
- Descent
Discover more routes
- 1652 N Kimball Ave, Chicago to 1601 W North Ave, Chicago
- Distance
- 4.6 km
- Ascent
- 190 m
- Descent
- 6 m
- Location
- Oak Park, Illinois, United States of America
- HB Direct!
- Distance
- 13.2 km
- Ascent
- 26 m
- Descent
- 33 m
- Location
- Oak Park, Illinois, United States of America
- Bike Ride Home Day 1
- Distance
- 7.8 km
- Ascent
- 8 m
- Descent
- 14 m
- Location
- Oak Park, Illinois, United States of America
- Thursday Training 7/6/17
- Distance
- 48.7 km
- Ascent
- 124 m
- Descent
- 128 m
- Location
- Oak Park, Illinois, United States of America
- 1653 N Kimball Ave, Chicago to 1819–1825 N Marshfield Ave, Chicago
- Distance
- 4.1 km
- Ascent
- 7 m
- Descent
- 13 m
- Location
- Oak Park, Illinois, United States of America
- Bloomingdale and Back
- Distance
- 17.1 km
- Ascent
- 30 m
- Descent
- 42 m
- Location
- Oak Park, Illinois, United States of America
- Lyman Avenue 1100, Oak Park to North Racine Avenue 2011, Chicago
- Distance
- 15.9 km
- Ascent
- 7 m
- Descent
- 17 m
- Location
- Oak Park, Illinois, United States of America
- 1649 N Kimball Ave, Chicago to 516 N Oakley Blvd, Chicago
- Distance
- 4.6 km
- Ascent
- 0 m
- Descent
- 0 m
- Location
- Oak Park, Illinois, United States of America
Routes to Chicago
Cycling day trip from
Lincolnwood to Chicago