By bicycle from Oak Park to Chicago

Pedal your way from Oak Park, a leafy suburb known for its Frank Lloyd Wright homes and vibrant arts scene, straight into the heart of Chicago! This roughly 18 km ride is mostly flat, with minimal ascent and a gentle drop as you make your way east.

The route keeps things chill, sticking mostly to quiet roads with very little time spent on busier streets—perfect for a relaxed ride. About a fifth of the surfaces are paved or asphalt, so most of the journey is smooth sailing. As you roll into Chicago, soak in the transition from residential calm to city buzz—maybe make a pit stop for coffee or check out some parks along the way. Fun fact: Oak Park is just west of Chicago’s downtown and is considered the birthplace of Ernest Hemingway. You’ll end your ride in one of the world’s most iconic cities, famous for its skyline, deep-dish pizza, and stunning lakefront. Happy cycling!