Where does Windy City come from?
In 1854, the city of Buffalo, New York was called a "city of winds" in a Boston publication, and the nickname Windy City was used to refer to Green Bay, Wisconsin in 1856.
Ever since the 1860s, though, the nickname Windy City has applied almost exclusively to Chicago, Illinois, a metropolis subject to intense, often frigid winds from Lake Michigan. But just as soon as Chicago became the Windy City, people began punning on the weather-based nickname to decry Chicago's politicians, businesspersons, and relators as "full of hot air," or wind, the city historically associated with corruption.
Contrary to popular myths, the mocking moniker Windy City predated 1893, when New York Sun editor Charles Dana is often cited as inventing Windy City. Dana is said to have dismissed the "nonsensical claims of that windy city" of superiority over New York in hosting the World's Fair: "Its people could not hold a world's fair even if they won it."
While making for a good story, there is no firm evidence that Dana's editorial ever existed, and even if it did, the pejorative Windy City already reaches back to the 1870s. The nickname Windy City, as far as we can tell, emerges, in fact, because Chicago can be very windy.
As Chicago's prominence expanded in the 1900s, Windy City became a firmly established nicknamed for Chicago, and usually without any derision.
Who uses Windy City?
Today, the nickname Windy City is regularly used by locals and outsiders alike, much like how New York City is called the Big Apple. It is often used in movies, books, television shows, marketing materials, and popular media to refer to Chicago in general and to its cold, windy weather.
As noted, Chicago's nickname is seldom used to insult the city, for all its history and stereotypes of corruption, unless in context of the folk etymology of Windy City.
Many Chicagoans look upon the Windy City with pride, using it as an inspiration for sports teams (onetime soccer club the Chicago Winds and minor hockey team the Chicago Wind). It is also incorporated into the names of many local business and souvenirs.
Chicagoans, tourists alike love summer in the Windy City
Nancy Trejos, USA Today (headline), July 2017
The city that's nicknamed "The Windy City", is, windy? 🤔 noooo never would have guessed
@marchmadness14, July 2017
#TBT when Louie and me were blown away by the Windy City at #pugstakechicago 😬💨
@tuesdaythepug, March 2018