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This is a slang term referring to a handjob.
Paying to get yourself jerked off by another man
"Johnny boy went and got himself a Chicago Handshake down at Robert's. I'm surprised they have em for only 10 dollars"
A good luck pre-game ritual for Chicago White Sox fans where your girlfriend slips on a black sock (normally used for feet) on your cock and jacks you off until you cum into the sock while you sit back, relax, and strap it down with a beer, preferably a Miller lite (or modelo if your girl is Latina)
This is similar to the Clark Street Cock Sock, which is performed exclusively among men within the gay community and into a blue sock before Cubs games instead.
My girl surprised me with the ole Chicago White Sock before the game that was so good I nutted through the sock and Giolito threw a no-hitter!
Mexican Taco Cart found near Chicago.
Hey Brian me and Austin are going to Chicago Diablo do you want a mexican fish taco?
The Chicago Bear is when after receiving a Green Bay Packer from the bear variety of men; the recipient then finds a football field and just shits all over it. The shitting on the field may be figuratively or literally.
"Illinois football fans gather in a stadium to watch their local heroes perform The Chicago Bear. "
The Chicago Bear is when you have received a Green Bay Packer rectally, from the Bear variety of men; you then find a football field and just shit all over it.
"In Illinois, people of large numbers gather in a stadium to watch local heroes perform The Chicago Bear, in person."
The Chicago Change Dispenser is where you put Change into a Persons Asshole and they fart it out
I want you to give the Chicago Change Dispenser
When a female relative who owns a Chicago style pizza place uses the leftover grease from a pizza to give you a hand job after closing time.
“Hey Aunt Beatrice, do you have the time to give me a Chicago back handy, I saw some leftover grease in the kitchen”