->''"There's a bright, sunny day in Chicago\\
There's a bright, sunny day in Chicago\\
Corruption's as high as an elephant's eye\\
And the meters cost $74.25"''
-->--'''TheNostalgiaCritic''', [[TGWTGYearOneBrawl "Oh, What an Adequate Morning"]]

->''{{Bartlet and Leo are on their way to a meeting with Babish.}}''
->'''Leo:''' You're scared of Babish.\\
'''Bartlet:''' Oh, like you're not.\\
'''Leo:''' No, because we are both men of Chicago.\\
'''Bartlet:''' What is it with people from Chicago that they're so happy to have been born there? I meet so many people who can't wait to tell me they're from Chicago and when I meet them, [[HypocriticalHumor they're living anywhere but Chicago.]]\\
'''Leo:''' You wouldn't understand.
-->'''--Series/TheWestWing''' 2x19, "Bad Moon Rising"

->''"Chicago was founded by two guys from UsefulNotes/{{New York|City}} who said, 'You know, I really like the crime and congestion, but the weather's just not crappy enough.'"''
-->-- '''Paul Reiser'''

->''"Hog Butcher for the World, Tool Maker, Stacker of Wheat, Player with Railroads and the Nation's Freight Handler; Stormy, husky, brawling, City of the Big Shoulders . . . "''
-->-- '''Carl Sandburg''', "Chicago"

->''Chicago happened slowly, like a migraine.''
-->--'''Creator/NeilGaiman''', AmericanGods

->The city of "I will." ''Born in a battle against slough and swale, a land that showed neither promise nor purpose, won with metal, with concrete, with our own hands, hammering, forging and building [...] They say that greatness is not a matter of chance, it's a matter of choice. I say that greatness is not something we can wait for. It's something we achieve. Because we are the city of'' "I will."
-->--'''Mayor Tom Kane''', ''Series/{{Boss}}''

->''"Chicago still remains a Mecca of the Midwest - people from both coasts are kind of amazed how good life is in Chicago, and what a good culture we've got. You can have a pretty wonderful artistic life and never leave Chicago."''
-->-- '''Creator/HaroldRamis'''