Chicago is the windy city. Most people think it's called the windy city because it's so cold during the winter. The nickname originally came about during the 1850 world's fair which was held in Chicago. News spread to New York City from Chicagoans about how grand the world's fair was. Thus, the New Yorkers called Chicago the "Windy City" because of how Chicagoans bragged about the fair and how fast the word got around.
I'm ghetto but I'm informed. I'm from the Windy city.
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