This is the Chicago Style Blowjob, Surprise variant.
This time, instead of ya girl giving you a blowjob with you dick in a hot-dog bun with mustard, relish, onion, pickle, tomato, and celery salt, in that order. (But never ketchup, ketchup never belongs on a Chicago Style Hotdog), you put your ween in said bun and surprise her (or him, we don't judge) by sticking the Chicago Style Ween in her puss or Bunghole.
I was feeling a little spicy last night, and you know my girl likes surprises, so I gave her the Chicago Style Surprise.

Michael was being a real d*ck, so I gave him a Chicago Style Surprise he would never forget.
by NateTheOriginal June 2, 2017
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A thoroughly disgusting, usually undercooked "Italian" style pie, hailing from the armpit of America... the city of Chicago Illinois. The entire pie weighs close to 46 lbs on average, and is overladen with acidic canned tomatoes and tomato paste in order to overpower the bitter taste of various grease and oils within the pie itself. Often filled with more gluttoning ingredients such as ground up pig innerds, or spicy red pig shavings. Usually eaten at every meal by the "gourmets" of Chicago, from the fattest women to even the meagerest metrosexual playboy.
I ate an entire Chicago-style pizza and later threw up all over my wife's hairy back.
by Stevie Bartman March 14, 2007
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When a bunch of hood rats from South side meet up with an afluent white woman to engage in a very vigerous and intense GANGBANG.
-Damn nigga, wanna Chicago Style Gangbang her tonight?
-Sure Jermarcus, leggo!!!
by massiveblackD January 11, 2012
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The ultimate in foodstuffs, aka Chicago Dog

consists of:
mustard
onion
sweet pickle relish (usually neon green)
a dill pickle spear
tomato slices or wedges
sport peppers
a dash of celery salt
steamed sesame seed bun
Vienna Beef Hot Dog

NEVER EVER put ketchup on a Chicago Dog, or there will be consequences
Tourist from Kansas: I'll take a Chicago style hot dog, with ketchup
Big Willy: Whatchu say?
Tourist from Kansas: I wanted ketchup on my wiener
Big Willy: *shoots him*
by FatJoker February 24, 2008
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The act of male masturbation where your hand is reversed. (Thumb and index finger towards the shaft towards the balls) and stroking slowly in a fluid motion.
kyle did you jerk off today?

Yea but I had to switch it up so I went reverse-grip Chicago style
by Buster Miller July 13, 2015
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The act of butt fucking a woman without penetration, in which the man's penis slides through the woman's butt cheeks, much like a hot dog enters it's buns. Ejaculation must occur on the woman's back, much like the hot dog toppings lie atop the bread. Debuted in Chicago in 2011.
She was so drunk and we didn't have condoms, so I gave her a Chicago style hot dog and got the f outta there.
by Hambone69 December 31, 2014
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When a guy has direahha and dumps it on a woman chest, and then titty fucks her.
Aaron Levy gave Mrs.Pafias a Chicage Style Chili Dog.
by Amy February 6, 2005
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