Top Definition
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

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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.
by The Return of Light Joker October 02, 2007

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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

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The Urban Dictionary Mug

Lotsa space for your liquids.

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The Urban Dictionary Mug

Your favorite word on a white mug.

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The Urban Dictionary Mug

One side has the word, one side has the definition. Microwave and dishwasher safe. Lotsa space for your liquids.

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The Urban Dictionary T-Shirt

Soft and offensive. Just like you.

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The Urban Dictionary T-Shirt

Smooth, soft, slim fit American Apparel shirt. Custom printed. 100% fine jersey cotton, except for heather grey (90% cotton).

Buy the t-shirt