WindyCity.com

“Windy City”
It is indeed often said that the word windy in the name refers to the long-winded and boastful speech of Chicago politicians.
The story you will commonly find is that it dates to shortly before the great World’s Columbian Exhibition of 1893. Chicago was putting forward its claim with great verve and bombast. This really got up the nose of people in New York, which was competing with Chicago to host the exhibition. Animosity became so bad that the editor of the New York Sun, wrote an editorial telling New Yorkers to pay no attention to the “nonsensical claims of that windy city. Its people could not hold a world’s fair even if they won it”. The history books tell us that Chicago did win it and did hold it . Books also tell us that the nickname of Windy City dates from that editorial.
This story is wrong. There are several recorded instances of Chicago being called the Windy City before.
For example, found in the Chicago Tribune for 11 September 1886: “The name of ‘Windy City,’ which is sometimes used by village papers in New York and Michigan to designate Chicago, is intended as a tribute to the refreshing lake breezes of the great summer resort of the West, but is an awkward and rather ill-chosen expression and is doubtless misunderstood”.
It has only recently been discovered that the term appears even earlier, in a headline on the front page of the Cleveland Gazette for 19 September 1885, reporting several items of news from Chicago, particularly a judicial decision: “From the Windy City: Judge Foote’s Civil Right decision”. For the nickname to be well enough known in Cleveland that it appeared in a headline without explanation indicates that it was by 1885 getting to be an established term.
It is suggested that the name actually originated in a scheme by the Chicago Tribune about that date to promote the city as a summer resort, using the cool breeze off the lake as the basis of its attraction. Before then, Chicago was usually nicknamed Garden City (its Latin motto was and is Urbs in Horto, “city in a garden”). There seems to have been a shift from the old name to the new in the middle 1880s.

"Windy City"

The City of Chicago has been known by many nicknames, but it is most widely recognized as The Windy City. Possible explanations for this particular nickname include Chicago's weather, politics, World's Fair, and rivalry with Cincinnati.
The earliest known reference to Chicago as the "Windy City" is from an 1858 Chicago Tribune article. 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" was first used by New York Sun editor Charles Dana in the bidding for the 1893 Columbian Exposition. The popularity of the nickname has endured, even after the Cincinnati rivalry and the Columbian Exposition both ended.
Chicago has been called the “windie” 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 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.