Chicago waffle

Taking a dump on someone’s latptop key board then shutting the lid
I Chicago waffled Greg the other day, needless to say he was not amused
by The meme god August 22, 2018
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Chicago Honeymoon

Having sex with your best friends sister while taking a shit back and forth and eating sausage while your racist grandma reads dutch love poetry to you
While in Chicago, Illinois Johnny decided to have a Chicago Honeymoon since he was there with Stephanie.
by ThunderKawK January 09, 2017
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Chicago Bears

The Chicago Bears
by Goonerbear93 May 02, 2010
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Chicago Cubs

Major League Baseball team in the amazing city of Chicago, Illinois. Though they've had a lack of winning the World Series for a long, long time, they're not always that bad a team and have a history winning a lot of games (Though they do really suck some times). I'm a true Cubs fan and I'm not some Sox hater either, they're just another Chicago team to me, and they're fine.
I went to a Chicago Cubs game last night.
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Chicago Bullethole

The act of insterting a man's penis into a woman's vagina during her menstrual period. When his penis is covered in blood, the man insterts his penis into the woman's anus. When he removes his penis, it looks as if the woman was shot and is bleeding.
Mandy was cranky but Luca cheered her up when he gave her a Chicago Bullethole.
by JonnyChicago April 20, 2009
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Chicago Sunroof

The act of defecting through the sunroof of a vehicle.
One little Chicago Sunroof and suddenly I'm Charles Manson? --Jimmy McGill
by Simpkill February 16, 2016
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chicago rosette

When a carpenter is hammering a nail into some wood and the head of his hammer misses the nail and hits the surrounding wood, it makes a small depression there in the shape of the hammer head. That is a Chicago Rosette.
1) Careful on that last piece of oak there boys, we don't want the customer seeing any Chicago Rosettes.

2) Who's the dumbshit who left a Chicago Rosette on that moulding?!
by Don Garb July 13, 2005
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