Green’s Dictionary of Slang

Windy City n.

also Windy Town
[the climate; note B. Popik (American Dialect Society List 22/8/01): ‘Troy was first known as the “windy city.” Later, Siena, Italy, was called the “city of winds” (Citta dei Venti). In the early 1880s, the Chicago Trib. wanted to promote Chicago as a summer resort. An attraction was the cool breeze off the lake. By 1885, Chicago was the “city of winds” and “windy city.”’]

1. (US, also Big Wind(y), City of Winds, Madame Windy, Town of the Wind, the Windy, Windtown, Windville) Chicago, Illinois.

[[US]Chicago Daily Trib. 7 Apr. n.p.: (ProQuest Historical Newspapers) An hundred militia officers, from corporal to commander, condemned to air their vanity and feathers only for the delectation of the boys and servant girls in this windy city [i.e. Chicago]].
[Milwaukee Dly Sentinel (WI) 4 July 1: (19th Century U.S. Newspapers) We are proud of Milwaukee because she is not overrun with a lazy police force as is Chicago -- because her morals are better, he [sic] criminals fewer, her credit better; and her taxes lighter in proportion to her valuation than Chicago, the windy city of the West].
Daily Cleveland Herald 4 June n.p.: (19th Century U.S. Newspapers) CLEVELAND vs. CHICAGO. The Great Game Between the Forest City and Chicago Clubs -- The Windy City Wins by a Score of 15 to 9.
Fort Wayne (IN) Daily Gazette 22 July n.p.: Going between the town aforesaid and the windy city yclept Chicago.
[UK]Sporting Life 19 Aug. 1/2: There will be a mad baseball reporter in the ‘city of winds’ before sundown.
[US]Chicago Trib. 11 Sept. [editorial] 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.
Mrs Mackin Two Continents 30: Denver was then but a village, but now it almost rivals the Windy City.
[US]C.L. Cullen Tales of the Ex-Tanks 47: With $420 I could be an ace and get a start out in the Town of the Wind. [Ibid.] 329: Something may happen to give you a lift up to Windville.
[US]Cincinnati Enquirer 2 Jan. 3/1: The majority of Windtown’s baseball writers doubted the possibility of peace when the project was broached [DA].
[US]Salt Lake Trib. 15 Feb. 35/3: I told the folks it was me for the Windy City [...] so I trekked for Chicago.
[US]E. Hemingway letter 18/19 May in Baker Sel. Letters (1981) 7: Does he still classify the Chicagoan, Noblest Scion of the Windy City as a well meaning fellow.
[US]Broadway Brevities Aug. 38: [headline] Some News from Windy Town.
[US]M.C. Sharpe Chicago May (1929) 295: My man got a thousand dollars out of our bank and gave it to me to go to Chicago to have an operation. As I have explained elsewhere, I simply loafed round the Windy City.
[UK]P. Cheyney Don’t Get Me Wrong (1956) 81: I’m not stoppin’ for anythin’ until I get around to Chicago because [...] the next act in this big drama is goin’ to be played out in the Windy City.
[US]Pittsburgh Courier (PA) 25 Nov. 7/1: As you know [...] I had to cut out this slave and stache here in the Windy City.
[US]Ruth Ladson [song title] ‘Windy City Blues.’.
[US]D. Burley Orig. Hbk of Harlem Jive 16: Well, here’s her beef; she says, Pops, I just fell in from the Big Wind.
[US] ‘Jiver’s Bible’ in D. Burley Orig. Hbk of Harlem Jive 134/1: Big Wind (or Windy) – Chicago, the Windy City.
[US]N.Y. Herald Trib. 8 Sept. 17/1: The home town of the Cubs and the White Sox is known only as the Windy City.
[US]P. Crump Burn, Killer, Burn! 329: The waters of the Most High will consign dear old Madame Windy back to the swamp.
[US]‘Iceberg Slim’ Pimp 21: His plan was to cop Mama and make it to the ‘Windy.’.
[US]‘Red’ Rudensky Gonif 44: Back in the Windy City I hooked up with a smooth con named Art Stacey.
[US]S. King Stand (1990) 719: He didn’t care a fig for the Windy City.
[US]‘Iceberg Slim’ Airtight Willie and Me 38: Candy Slim, from the Big Windy is gonna cut his cake. [Ibid.] 47: She split with him back to the Windy.
Odessa American (TX) 17 Nov. 24/2: The Windy City, Chicago, is all that.
[Aus]N. Cummins Tales of the Honey Badger [ebook] Nic White joined me as assistant ambassador to the Windy City.

2. attrib. use of sense 1.

Nat. Police Gazette 11: It was here that the late lamented Hulbert, president of the Chicagos, saw him and signed him for the Windy City club, where he has been playing ever since. – Cincinnati Enquirer.
[US]N.-Y. American 9 Aug. in Fleming Unforgettable Season (1981) 161: Everything was lovely while the Windy City lads were showing a stern chase.
[US]S.F. Bulletin 25 Mar. 16: Receptions have been accorded the Windy City braves on numerous occasions.
[US]Mezzrow & Wolfe Really the Blues 111: [We would] blow our tops under the twinklers, shooting riffs at the moon through the courtesy of the Windy City Police Force.

3. (S.Afr.) Port Elizabeth.

[SA]Fair Lady 20 Dec. 16: One of Port Elizabeth’s best loved restaurants [...] offers carefully prepared meals and a cosy atmosphere steeped in the Windy City’s past [DSAE].
[SA]Weekend Post 17 Nov. 10: Can one really still call PE the Friendly City? I disagree. Call it Windy City by all means, but PE has lost its claim to be the Friendly City [DSAE].