A drink order that includes two traditional Chicago drinks (each oh which is sold almost exclusively in Chicago), a shot of malört and an Old Style beer.
My friends are visiting from out of town and I want them to get the real Chicago experience so I'm buying them a round of Chicago Handshakes!
by Mizami October 8, 2018
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1) A handshake in which money is exchanged for the purpose of bribing. 2) To pass bribe money via hand greeting.
Everyone knows the only way you get into Club 69 is be a celebrity, know the management or give the bouncer an old fashioned Chicago Handshake.
by Stan the Chi-town Man September 26, 2009
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A form of greeting first made popular on Chicago's South Side during the 1920's.

As you reach out to shake someone's hand, you smile, step on their foot
then fire your snub nose .38 revolver through the pocket of a cheap overcoat.

"Wat da fuck happened to Big Joe?"

"I dunno. Some guy was smiling and shaking his hand

like they wuz long lost friends then next t'ing ya know
I heard a coupla shots an' Joe's layin' dere wit' his dick

in da dirt an' the guy was gone!"

"Hey! Why is the toe of one of his $300.00 shoes all scuffed?"

"I dunno... This is some more South Side b.s.
Let's go before tha' cops get here."

"Yeah... It looks like Big Joe got himself

a Chicago Handshake."
by Ghost Car Operator April 15, 2020
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The act of killing someone by shaking their hand, pulling a gun out from a pocket, and then shooting said victim while pulling him towards you. Invented by Al Capone.
John: Hey Freddie,I just saw some guy in the street that was all bloody!

Freddie: Why was he bloody?

John: He said he got a Chicago Handshake from some random dude.
by logmiesta22 December 9, 2009
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