This 6.7-mile path starts near Lawrence and Francisco and runs parallel to the North Shore Channel to Evanston. It will be even better once the construction of a 180-foot-long, bridge over the North Shore Channel is officially completed, allowing cyclists to avoid a Lincoln Avenue detour.

The city’s first Greenway project, this mile-long corridor that prioritizes non-motorized traffic, stretches from Clark Avenue to Lincoln along Berteau Avenue. It also serves to connect four other bike-friendly routes—Damen, Lincoln, Clark, and Southport.

The 2.7-mile elevated Bloomingdale Trail, casually known as The 606, is a refreshingly car-free way to pass through some heavily trafficked Northwest Side neighborhoods—Bucktown, Logan Square, Humboldt Park.

Of all of the diagonal streets that defy Chicago’s famed grid system—Elston Avenue ranks the best for cyclists who want a low-stress route. The southern portion of the road especially (from its starting point on near Chicago Avenue to Webster Avenue) goes through emptier industrial corridors and features a 1.68-mile protected bike lane.

The paved path on the southern tip of Northerly Island is a relatively short ride (less than a mile) but it’s a tranquil one filled with wildflowers and prairie grass, and beautiful views of the lake and city skyline. Be warned, it’s partially closed currently as the city repairs some of the concrete damaged by erosion.

Avoid it during Riot Fest, but otherwise Douglas Park is a pleasant park to explore on your bike. 

That’s especially true when you travel north on Sacramento Avenue using a curb-protected bike lane that stretches for a quarter mile from Ogden Avenue to Douglas Drive.

This leafy 3-mile ride keeps you mostly in South Side parks near Hyde Park. You start in the western park of Washington Park through Ellsworth Drive and then head south on Morgan and Payne Drives. Then take a left on the chill Midway Plaisance and cruise through historic Jackson Park.

Named after legendary African American cyclist Marshall “Major” Taylor, this 6-mile trail is one the few car-free routes in the city. The trail goes from Dan Ryan Woods in the north to Whistler Woods in the south—connecting several neighborhoods on the city’s Southwest Side.