The Great Gatsby Questions and Answers
by F. Scott Fitzgerald

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What does Chicago symbolize in The Great Gatsby

In The Great Gatsby, Chicago symbolizes all that was licentious and criminal in the 1920s. It is referenced so often, especially in relation to Gatsby, to suggest the criminal connections that lurk beneath the surface of Gatsby's carefully crafted persona.

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In the 1920s, Chicago was home to some of America's most infamous gangsters, including Al Capone, Bugs Moran, and Tony Accardo. In 1929, the infighting between Chicago's gangsters led to the Saint Valentine's Day Massacre. Chicago was also home to John Dillinger, the notorious bank robber.

In chapter 3 of The Great Gatsby, we hear that Gatsby receives a call from Chicago. His butler "hurrie[s] toward him with the information that Chicago [is] calling him." In chapter 7 , we learn that Gatsby and Wolfsheim own "a lot of side-street...

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