Chicago Cubs

A baseball team best known for losing and playing in the world's largest gay bar. A franchise with the third biggest market and an inflated payroll, the teams has failed since 1908. Their fans prefer to blame a goat, a cat, and a Bartman for the team's failure rather than simply admitting one hundred years of disgrace. Every team has a bad century right?
Bro 1: Bro, you wanna watch the Chicago Cubs try to play baseball today?

Bro 2: Naw bro, my butt never healed from the last time I went to Wrigley!

Bro 1: Good point! Besides, winning in October is overrated anyways.
by happyg123456 May 11, 2009
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Chicago Towelbomb

When a woman is beat with a sheet full of poop.
During the act of sex, a man takes a dump. He proceeds to take the sheet the dump is in and wraps the dump up, takes the sheet and beats the girls with the sheet of poop. Hence it's like a Chicago TowelBomb of crap, works especially well in Chicago.
by Walleye King October 07, 2007
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Chicago Fire

Quite frankly the worst soccer team in the world. Known for both their poor style of play and poor sportsmanship.
"My son's peewee team played well today. They would crush the Chicago Fire."
by fireman2012 September 16, 2012
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Chicago-style

I tried to do my girl chicago-style last night and she loved every minute of it!
by nigdude July 20, 2010
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University of Chicago

Most Over Rated School in the Country.
My daughter went to University of Chicago, now she is working as stripper because she can't get into med school. she has $125,000 in student loans.
by Pissedoffdad March 15, 2011
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Chicago Bull

Have sex 3 days in a row, off for 2 days and then sex for another 3. Just like the Chicago Bulls championship run.
I was going for the Chicago Bull but my wife shot me down on day 8. So close.
by Maximus96 July 01, 2020
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Chicago Handshake

1) A handshake in which money is exchanged for the purpose of bribing. 2) To pass bribe money via hand greeting.
Everyone knows the only way you get into Club 69 is be a celebrity, know the management or give the bouncer an old fashioned Chicago Handshake.
by Stan the Chi-town Man September 26, 2009
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