Green’s Dictionary of Slang

Chicago adj.

used in combs., esp. with ref. to Chicago as a centre of 1920s–30s gangsterism.

In compounds

Chicago bankroll (n.)

(US black/gambling) a show bankroll, with a large denomination note rolled around lesser ones.

S. Stevens Go Down Dead 44: Big George just has a lot of green paper with a real bill on the outside and one on the inside. The rest worth nothing. Chicago bankroll. Kansas City bankroll. All the same. What it means is no money [HDAS].
[US]E. Folb Runnin’ Down Some Lines.
[US]J. Ciardi Good Words 67: Chicago bankroll. A large roll of paper money consisting of one or two large bills wrapped around a core of ones, used as flash money.
[US]C. Major Juba to Jive.
M. Guberman at CasinoGaming.com 22 July 🌐 How about this one: ‘I see you’ve got a Chicago bankroll there. You seem to be a decent enough player. If you want to move, I’ll go cow with you.’ There’s half a chance he’ll know that a Chicago ’roll is a bunch of dollar bills with a bigger bill folded over them to give the impression one has a lot of money but will he know what you’re talking about when you want to cow with him? (To go cow with someone means to go half and half with him and splitting profits.).
Chicago black (n.) (also Chicago green)

(drugs) varieties of marijuana, characterized by the colour, popular (and presumably grown) in and around Chicago.

[US]Wash. Post 21 Aug. E1: The best pot is supposed to be Acapulco Gold. Panama Red is good and so is Chicago Green.
[US]E.E. Landy Underground Dict. (1972).
[US]E. Folb Urban Black Argot 135: Chicago Green, a particular type of marijuana.
[US]E. Folb Runnin’ Down Some Lines 170: Stronger mixtures like [...] Chicago green, Jamaica or Panama red, Acapulco gold. [Ibid.] 232: Chicago green Type of marijuana said to be grown in Chicago (medium to dark green in color).
[US]ONDCP Street Terms 5: Chicago black — Marijuana, term from Chicago; Chicago green — Marijuana.
Chicago boxcar (n.)

a form of hairstyle first popular in the 1950s.

[US]T. Wolfe Kandy-Kolored Tangerine-Flake Streamline Baby (1966) 222: The ‘Chicago Boxcar,’ a combination of the flat top and the ducktail .
[US]J. Stahl Pain Killers 147: Butch-waxed crew cuts and Chicago boxcars - brushed high on the sides, flat down the middle to a perfect spit curl.
Chicago chicken (n.) [the meat-packing industry of the city]

(US, Western) salt pork or bacon.

(con. 1880s) Tough Trip 110: This was the proper way for an Indian maid to eat Chicago chicken and it was no time till the greasy chunk had disappeared and they stood around licking their greasy fingers [HDAS].
Chicago overcoat (n.) [the practice of sealing corpses in cement prior to disposing of them at sea]

(US) a coffin; thus fig., death, murder.

[US]R. Chandler Big Sleep 170: ‘Go ahead and blast and see what it gets you.’ ‘A Chicago overcoat is what it would get you, little man.’.
[US]T. Dorsey Cadillac Beach 258: ‘What jumps into your head?’ [...] ‘Chicago overcoats, Harlem sunsets, a jorum of skee, a chippie with boss getaway sticks.’.
Chicago piano (n.) (also devil’s piano) [note WWII RN jargon Chicago piano, a multiple pom-pom]

a Thompson sub-machinegun, which achieved notoriety as the preferred weapon of Chicago gangsters in the 1920s and later.

[US]‘Soldiers’ Talk’ in Tampa Trib. (FL) 21 July 5/4: devil’s piano, machine gun.
[US]‘Bill O. Lading’ You Chirped a Chinful!! n.p.: Chicago Piano: Tommy gun.
[US]Charleston (WV) Daily Mail 2 Sept. 6/5: Me schmaltzy gabber couldn’t red a Chicago piano rap, so the D.A. conks me with a whole mag.
[US]H. Rawson Dict. of Invective (1991) 289: Sometimes they play Chicago pianos, which are submachine guns (also called Chicago coffee grinders, Chicago mowing machines, Chicago sewing machines etc).
Chicago typewriter (n.) (also Chicago atomizer)

a Thompson sub-machinegun, but note 1941 (2).

[US]S.F. Chronicle 1 June H5/7: The draftees assigned to Camp Claiborne, in Louisiana, got out a glossary of slang terms to describe everyday things in army life [...] The Louisiana lads call [...] machine guns, ‘Chicago atomizers.’.
[US]‘Soldiers’ Talk’ in Tampa Trib. (FL) 21 July 5/4: Chicago atomizer: automatiic rifle.
[UK] Partridge DU (2nd edn) 805/2: since the early 1920s.
[US]Playboy Feb. 28: The book offers a gun-sight view of the mugs and molls who once wrote headlines with their ‘Chicago Typewriters.’ [HDAS].
in W. Safire Coming to Terms 156: Your reference to a submachine gun being called a ‘Chicago piano’ was wrong. It was called a ‘Chicago typewriter.’.
T. Samuel Twenties Reconstruction Society 🌐 Thompson Machine Gun. Also known as ‘Tommy Gun’ or ‘Chicago Typewriter.’ Developed by John Thompson and Warren Center as a ‘Trench Broom’ for World War I.
Unofficial Tommy Gun Page 🌐 Even heavy doors and automobile bodies could not shield a victim from a TSMG firing armor piercing ammunition. It was these fearsome qualities that inspired the nicknames bestowed on it. Chopper, Gat, Chicago Typewriter and Tommy Gun all became popular terms used by criminals and the public at large.