Which is the Longest Street in Chicago?

June 14, 2023

When you think of Chicago, it’s likely you have a lot of interesting historical and cultural tidbits rolled up in your mind. From world-class museums to prohibition-era speakeasies, the Windy City has a lot to offer for history buffs and tourists alike.

However, one aspect of the city that is often overlooked are its streets. From the cosmopolitan business district of Halsted street to the raucous stockyards of the South Side, there are many interesting stories about the streets that make up this amazing city. But which is the longest street in chicago?

Western Avenue is arguably the city’s longest street. Stretching 24 miles from Howard street to 119th Street, it connects the north city limits of Chicago to the southern city limits near the Will/Kankakee county line. Along the way, you’ll see everything from famous car dealerships to neighborhoods, Rosehill Cemetery, and even a few old churches.

But despite it’s length, there are a few other streets in the city that are longer than Western Avenue. In order to rank the longest streets in the city, we used a combination of factors. These included the length of each street, its name, and what area it is located in. We also took into account how well the street is known for its historical or cultural significance.


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