West Randolph Street

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Gambling dens and gunfights. That’s what first comes to mind when I think about West Randolph Street’s past. West Randolph Street isn’t just a street in Chicago. It’s a story etched in time, a ribbon of asphalt that has witnessed the city’s transformation. It runs east-west through the heart of Chicago, right through the bustling Loop. West of Michigan Avenue, it crosses the Chicago River on the iconic Randolph Street Bridge. Did you know West Randolph Street even has a connection to Virginia? It’s named after Randolph County, Illinois, which in turn honors Edmund Randolph, Virginia’s governor and the first US Attorney General. Now, imagine West Randolph Street back in the 1850s and 60s. Forget fine dining, picture saloons and the glint of steel. Gambling was the rage, and gunfights were so common that this part of Randolph earned a chilling nickname: “Hairtrigger Block.” It’s a far cry from the elegant restaurants and theaters that grace West Randolph today. The street’s seen a lot of changes over the years. For instance, the construction of Lake Shore Drive in 1937 involved building a double-decker viaduct over the Illinois Central Railroad yard, connecting Michigan Avenue to Lake Shore Drive. This structure actually still stands west of Columbus Drive, a reminder of a bygone era. Today, West Randolph Street pulsates with a different kind of energy. From the sleek lines of the Boeing International Headquarters to the theatrical grandeur of the Cadillac Palace Theatre, it’s a showcase of Chicago’s dynamism.

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