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.
by Carl Willis August 25, 2004
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
by Dude that fucks Jessica Alba August 20, 2008