Understand that "Windy City" has nothing to do with weather

One of the first known instances of Chicago’s “windy city” nickname came from a New York Sun reporter named Charles A. Dana in 1893, who editorialized that the city’s politicians were “full of hot air.” Chicago and New York were in a head-to-head competition at the time to host the next World’s Fair, and Chicago’s “windbag” advocates were not shy about campaigning for their hometown in order to win. Despite Dana’s best efforts to discredit Chicago as a “windy city”, the 1893 World’s Fair was held in Illinois, not New York.

Even before the World’s Fair debate, there were other published instances of the windy city nickname. The Cincinnati Enquirer used the term in 1876 in reference to a tornado that blew through the city, while also capitalizing on the term’s double meaning to highlight local speakers who were “full of wind.” The Chicago “windy city” nickname usually is what sticks in people’s minds, but there are several other names Chicago is known for:

• Chi-town: Pronounced shy-town, this is a shortened version of the city’s name
• The City of Big Shoulders: Taken from the first line of Carl Sandburg’s poem, “Chicago”
• The Second City: This one has two possible meanings. The first refers to when Chicago was the second largest metropolitan city in the United States during the early 20th century; the second calling on when the city had to rebuild itself for the second time after the Great Chicago Fire in 1871.