A shitty industrial city next to Lake Michigan that is home to the Bears, the Cubs, and one dude who is PISSED THE FUCK OFF that he can't get any action named JOSH BOYLE.
by Tuccimustdie March 1, 2020

by Ecrotex March 14, 2021

The team people are thought to be insane if they root for after over a hundred years of no titles or championships, and people still root for them anyway, because winning is not the point of everything in life.
Not many other sports teams would keep people rooting for them after not winning for so many years, a lot of people would abandon a different team than the Chicago Cubs.
by The Original Agahnim July 1, 2021

the best fucking city around, am i right or am i right.
we’ve got some bomb ass pizza (best pizza ever don’t @me)
we’ve got some dope as rappers. love ya chance.
fucking shameless that’s a great show. and Carl Gallagher can have my children.
we know how to throw a parade too. i mean st. patty’s day that shits a hit.
home to the cubs like cmon we all know everyone’s rootin for the cubbies.
you can’t tell me you don’t think our city skyline isn’t just perfect.
so yeah chicago’s the best city.
we’ve got some bomb ass pizza (best pizza ever don’t @me)
we’ve got some dope as rappers. love ya chance.
fucking shameless that’s a great show. and Carl Gallagher can have my children.
we know how to throw a parade too. i mean st. patty’s day that shits a hit.
home to the cubs like cmon we all know everyone’s rootin for the cubbies.
you can’t tell me you don’t think our city skyline isn’t just perfect.
so yeah chicago’s the best city.
by yeah i’m dope April 9, 2018

When you have the irrational belief that you home team with be victorious despite all the bad decisions they make.
DaBears were down by 21 with under 2 minutes to go but my CFS (Chicago Fan Syndrome) knew they would somehow pull off the win.
by MoreDumbStuff November 15, 2020

Person 1: "Dude that chick last night was crazy!"
Person 2: "how come?"
Person 1: "she had her cats in the room while we were having sex!"
Person 2: "Oh like a Chicago Cat Mom."
Person 2: "how come?"
Person 1: "she had her cats in the room while we were having sex!"
Person 2: "Oh like a Chicago Cat Mom."
by SpankyHanky69 August 23, 2020

The act of sticking your glock up your loved ones ass ...letting her shit on it then sticking the glock down her throat
by Randomshit34 February 9, 2017
