Chicago Typewriter 

n. A Thompson submachine gun, as used by Prohibition-era gangsters. So-named because the sound of a Tommy being fired in the distance resembled the sound of typing on a typewriter, and because the weapon was in popular use throughout south-side Chicago in Al Capone's day.

Vinnie always wrote his enemies on a Chicago typewriter.

Chicago Typewriter by Carl Willis August 25, 2004

Chicago typewriter 

a thompson submachine gun (from the similarity of the sound of it's firing to that of a typewriter)

The robber was armed with a Chicago typewriter and wore a green suit.

Chicago typewriter by The Return of Light Joker October 17, 2007

Chicago Typewriter 

When you fuck a chick from behind (anal or vaginal) and you pull your cock out right before you cum and tap it on her back as you cum making a sound like a typewriter

I left a red mark on shirley's back when I gave her a chicago typewriter

Chicago Typewriter by Dude that fucks Jessica Alba October 15, 2008