Best Bike Rides Chicago

Written for the cyclists of all stripes, Best Bikes Rides Near Chicago marks the debut of a new series that offers a diverse array of scenic tours in some of America’s largest urban destinations—from easy excursions for the Sunday cyclist to challenging treks for the veteran. Here, veteran author and cyclist Ted Villaire presents 35 diverse rides in and around the Windy City.

As amply demonstrated by this guide, Chicago’s heritage as a transportation hub has reaped huge rewards for local cyclists. Twenty miles of lakeshore parkland and an elaborate system of leafy boulevards connect a series of mega-parks throughout the city. Coupled with this is an ever-expanding cycling infrastructure featuring more than 100 miles of bikes lanes. The Illinois Prairie Path, which runs between the Des Plaines River and Wheaton, was one of the first linear trails in the nation converted from a railroad line—and today it is part of the most extensive collection of rail trails in the Midwest, perhaps the nation.