The City of Chicago has been known by many nicknames, but its most widely recognized is The Windy City. Potential explanations for this particular nickname include Chicago's:

• Weather
• Politics
• World's Fair
• Cincinnati rivalry

The earliest known "Windy City" citations are from 1876, and involve Chicago's rivalry with Cincinnati. A popular myth states that "Windy City" was first used by New York Sun editor Charles Dana in the bidding of the Columbian Exposition of 1893. All four of the explanations below help to explain the enduring popularity of the "Windy City" term, even after the Cincinnati rivalry and the Columbian Exposition had both ended.

Meaning

Weather

Geographic conditions in the area (e.g., proximity to Lake Michigan, local prevailing winds, etc.) make Chicago a naturally windy area. Another contributing factor is how the city was rebuilt after the Great Chicago Fire. With a clean slate planners modeled new streets on the grid system. In high density areas, such as the Loop, man-made wind tunnels are created on high windy days as there are even "columns and rows" for wind to travel down and pick up speed.

This "windy" explanation is from the Freeborn County Standard of Albert Lea, Minnesota, November 20, 1892 (digitized citation available on Newspaperarchive.com}:

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 acquainted with 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 to-day 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.

Chicago had long billed itself as an ideal summer resort because of its cool lake breeze. The Boston Globe of July 8, 1873 pointed this out: "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 The Philadelphia Inquirer called Chicago "the great city of winds and fires."

Politics

Others say that the name comes from Chicago's political history. Specifically referencing the "spectator sport" style of politics practiced in the last century. It is meant to be a jab towards the Chicago Democratic Machine which for the most part has been led by the Daley family for the past 50 years. Machine politics may have fallen out of style every where else in the country but it is for the most part alive and well in Chicago. To sum it up, when Chicago politicians speak they are "blowing a lot of wind".

World's Fair

It had been a popular myth that the first person to use the term "Windy City" was the New York Sun editor Charles Dana. In 1893, Chicago won the bid to host the World's Fair, also known as the World's Columbian Exposition. This was a big deal because the French had just put the Americans to shame at the previous World's Fair with the building of the Eiffel Tower. The next world's fair was seen as a chance by many Americans to show the world that it too was a great country.

Another factor that made this bid competitive was the list cities competing for the right to host the fair. At the top New York, St. Louis and Washington D.C. all fought hard for the right and many New Yorkers thought they had it in the bag. In the end it came down to New York and Chicago. Chicago finally won in a run off vote and many prominent New Yorkers were extremely irritated that a "frontier town" could best them.

Charles Dana was New York's leading fair booster, but there is little evidence that he even used the "Windy City" term. The first known attribution of Dana to the origin of "Windy City" was 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."

Cincinnati rivalry

Cincinnati and Chicago were rival cities in the 1860s and 1870s. Cincinnati was well known in the meatpacking trade, and the Queen City 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.

The first known citations of "Windy City" are three from 1876, and all involve Cincinnati:

1. Cincinnati Enquirer, May 9, 1876 headline: "THAT WINDY CITY. Some Freaks of the Last Chicago Tornado."
2. Cincinnati Enquirer, May 13, 1876: "Only the plucky nerve of the eating-house keeper rescued the useful seats from a journey to the Windy City."
3. Chicago Tribune, July 2, 1876: "The Cincinnati Enquirer, in common with many other papers, has been waiting with great anxiety for the fulfillment of its prophecy: that the Chicago papers would call the Whites hard names when they lost. Witness these scraps the day after the Whites lost to the Athletics: There comes a wail to us from the Windy City."

For the Cincinnati papers, "Windy City" had meant a Chicago that was full of bluster.

The Hawk, or Hawkins

Chicago's wind is often called "The Hawk." This term has long been popular in African-American English. A Baltimore Sun series of columns in 1934 attempted to examine the origin of the phrase "Hawkins is coming" for a cold winter wind. The first recorded Chicago citation is in the Chicago Defender, October 20, 1936: "And these cold mornings are on us—in other words “Hawkins” has got us."