Back in the 1800s cities and towns vied for preeminence a little less diplomatically than they do today. Journalists used their talents at their local papers to pile insults on rival cities, and Chicago had a few competitors. Milwaukee and Cincinnati used "windy city" to refer to our politicians and civic leaders as basically a bunch of blowhards, with the earliest reference way back in 1860. So it would seem the nickname really did originate as a derogatory appellation, just not from New York.
But wait - two years earlier the Daily Tribune called Chicago "this windy city", and they actually were talking about the breeze. Shortly after that the paper launched a marketing campaign touting Chicago as a summer resort. The main selling point? The breeze off the lake was heralded as tempering the climate and keeping the air fresh (one word - stockyards).
Later on, the nickname began to refer to the stronger and more robust winds that funnel from the lake through the man-made canyons of skyscrapers. That same grid system that makes getting around Chicago easier also serves to increase the speed of those refreshing breezes until they're strong enough to whip hats off of heads and break umbrellas.And that oft-referred to editorial by Charles Dana? It was mentioned in the Daily Tribune on June 11, 1933, but the actual editorial has never been found.
Next time the origin of the Windy City nickname comes up in conversation (and if you're in Chicago any length of time, it will) and someone says it was those darn New Yorkers, you can say "well, actually...".
Check out Barry Popik's research. He has spent countless hours at the Library of Congress researching the origins of the nickname and includes citations of all articles mentioned.