In the Streets

Cycling Series

Prior to the invention of air conditioning and the popularization of the automobile, early Chicagoans lived the bulk of the lives in the streets of the city. Whether it was buying or selling goods, catching up on the latest news, escaping the heat of stuffy tenement houses, or chasing down a runaway goat, the streets were more than a transportation network; it was where people lived, worked, and played.

For much of its history, Chicago held the title, "Bicycle-Building Capital of America" and is the birthplace of the famous Schwinn brand. This history of cycling has left its literal mark on the city by way of our streets. Our In the Streets City Series re-introduces locals to the ease and joy of navigating the city on roads specifically designed for cyclists. Learn to safely travel the city by bike while exploring the many diverse neighborhoods of Chicago. A stop at a neighborhood favorite for a bite to eat makes this the best way to see, hear, smell, and taste Chicago in a brand new way!

Your health is our top priority. We've put special measures in place to keep all guests safe during and after your tour. Learn more by reviewing our Health & Safety Policy.

Milwaukee Ave.

In a car-centric era, Milwaukee Ave. has developed as a major business corridor with restaurants, shopping centers and entertainment venues leading from the city's northwest side into downtown. However, prior to the 1950's, this "Hipster Highway" was considered an “unspeakable ten miles of drainage ditch they call a road" by visitors and residents alike. On this ride, we'll explore how--in a city run by bikes--residents got to work, The Loop, and favorite local sights using the network of quiet side streets that branch off of "questionable" Milwaukee Ave.

The West Parks

In 1869, the State of Illinois passed legislation to create a new system of parks and boulevards in Chicago. Three park commissions, Lincoln, South and West, were created to oversee the parks’ development. This was done in response to a lack of open air/green space in the city that forced residents to picnic in local cemeteries. Using parts of our lush boulevard system, we ride through the man-made parks of Humboldt, Douglas, and Garfield and explore the impact these parks (listed in the National Register of Historic Places) have had on life in Chicago and the nation as a whole.

Coming Soon!

The Boulevards

The boulevards are wide, tree-lined streets, which connect Chicago's largest parks. This system of parks and boulevards was the first of its kind in the country - imagined nearly 150 years ago. On this ride we take a new look at the old neighborhoods that emerged along these boulevards in the 19th Century and into today. Discover "hidden" parks and green spaces throughout the city that are often overlooked, but are just as beautiful as our famous lakefront parks.