There is actually no definition at all, because this is not a real thing.
Dan: "Hey guys, I'm new in town and I cannot wait to get some Chicago Style Chips and Salsa"
Everyone else: "Dafuq? That's not a real thing bro. Go home, you're drunk."
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When someone partially swallows semen then regurgitates and sprays the entirety of the load out of their mouth towards the person who issued it.
Lindsey took a nice creaming in her mouth then Chicago snowballed it all over John.
A Chicago line is where a group (5people +) sit in a circle and pass 2-4 blunts. It's something commonly done at parties, and can get you really high.
Person1: Yo, did ou get high in that Chicago line last night ?
Person2: Yeah, all 6 of us did. It was pretty dank.
A shot of Malört with a bacon salt rim
Clark asked, “Shots anyone, all we have is Malört and bacon salt.” Todd replied, “Chicago Rimjobs it is!” “I’ll take two,” Ryan replied with glee.
The act of leaving ass pennies around town for unsuspecting pedestrians to find.
I was walking by the Willis tower when I bent down to pick up something shiny. "Wow," I thought, "a lucky penny. My luck is surely changing!" I couldn't have been more wrong. As I drew the penny near my face for a closer look, I could tell that I was being punked. The smell of copper laced with rotting feces left no doubt. I'd just found a Chicago Surprise.
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"
When you jerk off 2 people while also taking it in every hole including eye and ear hole
Jack wanted to do a Chicago sausage shuffle but I said no