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The city of Chicago has been known by many nicknames, but it is most widely recognized as the "Windy City".

The earliest known reference to the "Windy City" was actually to Green Bay in 1856.  The first known repeated effort to label Chicago with this nickname is from 1876 and involves Chicago's rivalry with Cincinnati. The term "Windy City" came into common usage when it was popularized by New York City editor, Charles Dana, in The Sun during the bidding for the 1893 Columbian Exposition. Chicago won the Exposition, which did not please Dana. The popularity of the nickname has endured, long after the Cincinnati rivalry and the Columbian Exposition ended.

There are four main possibilities to explain the city's nickname: the weather, as Chicago is near Lake Michigan; the World's Fair; politics; and the rivalry with Cincinnati.

Weather

While Chicago is widely known as the "Windy City", it is not the windiest city in the United States.

The following "windy city" explanation is from the Freeborn County Standard of Albert Lea, Minnesota, on November 20, 1892.

Chicago has been called the "windy" city, the term being used metaphorically to make out that Chicagoans were braggarts. The city is losing this reputation, for the reason that as people got used to it they found most of her claims to be backed up by facts. As usual, people go to extremes in this thing also, and one can tell a stranger almost anything about Chicago today and feel that he believes it implicitly.

But in another sense Chicago is actually earning the title of the "windy" city. It is one of the effects of the tall buildings which engineers and architects apparently did not foresee that the wind is sucked down into the streets. Walk past the Masonic Temple or the Auditorium any day even though it may be perfectly calm elsewhere, and you will meet with a lively breeze at the base of the building that will compel you to put your hand to your hat.

An explanation for Chicago being a naturally breezy area is that it is on the shores of Lake Michigan.Chicago had long billed itself as an ideal summer resort because of its cool lake breeze. The Boston Globe of July 8, 1873, wrote that "a few years ago, Chicago advertised itself as a summer resort, on the strength of the lake breezes which so nicely tempered the mid-summer heats." The Chicago Tribune of June 14, 1876, discussed "Chicago as a Summer Resort" at length, proudly declaring that "the people of this city are enjoying cool breezes, refreshing rains, green fields, a grateful sun, and balmy air—winds from the north and east tempered by the coolness of the lake, and from the south and west, bearing to us frequent hints of the grass, flowers, wheat and corn of the prairies."

The February 4, 1873, Philadelphia Inquirer called Chicago "the great city of winds and fires."^[6]

Cincinnati rivalry

Cincinnati and Chicago were rival cities in the 1860s and 1870s. Cincinnati was well known in the meatpacking trade and it was called "Porkopolis" from at least 1843. Starting from the early 1860s, Chicago surpassed Cincinnati in this trade and proudly claimed the very same "Porkopolis" nickname.

The baseball inter-city matches were especially intense. The 1869 Cincinnati Red Stockings were the pride of all of baseball, so Chicago came up with a rival team called the White Stockings to defeat them. "Windy City" often appeared in the Cincinnati sporting news of the 1870s and 1880s.

World's Fair

As the 400th anniversary of Columbus' arrival in the Americas approached, the United States planned to hold a world's fair to celebrate. This was considered an important time, due to the French successes at the previous World's Fair with the construction of the Eiffel Tower.

The prestige of holding the fair enticed several prominent cities to compete to host the fair. At the top, New York City, St. Louis and Washington, D.C. all fought hard for the right and many New Yorkers thought they had a win guaranteed. In the end, it came down to New York and Chicago. In 1890, Chicago won the bid to host the World's Fair, also known as the World's Columbian Exposition, after eight ballots. Many prominent New Yorkers were extremely irritated that a "frontier town" could beat them.

It is a popular myth that the first person to use the term "Windy City" was The New York Sun editor, Charles Dana. Charles Dana was New York's leading fair booster, but there is little evidence that he ever used the "Windy City" term. The first known attribution of Dana to the origin of "Windy City" was 40 years later in the Chicago Tribune, "Chicago Dubbed 'Windy' in Fight for Fair of '93," June 11, 1933:

"Don't pay any attention", wrote Charles A. Dana, day in and day out in his New York Sun, "to the nonsensical claims of that windy city. Its people could not build a World's Fair even if they won it".

Politics

Long-winded politicians and the frequent political conventions in Chicago have been suggested as the source of the nickname. Another related suggestion is the business boosterism that other cities resented.