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 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.
1. Select a player (real or fantasy) during a sports draft to spite or anger one or more of your opponents because they had intended to select him/her.
2. Select a player (real or fantasy) during a sport draft to put one or more of your opponents at a strategic disadvantage.
1. Billy hate drafted Chad OchoCinco because he knew Sam had wanted him since he is from Cincinnati. Billy already had plenty of players to fill that position but wanted to make sure Sam didn't get him.
2. Billy hate drafted Peyton Manning because he was the only good quarterback left and he knew Sam had been planning on drafting him.