->''"I have struck a city—a real city—and they call it Chicago … I urgently desire never to see it again. It is inhabited by savages."''
-->-- '''Creator/RudyardKipling''', 1891

->''"It rained and fogged in Chicago and muddy-flowing people oozed thick in the canyon-beds of the streets. [[TakeThat Yet it seemed to more alive and more real than]] [[BigApplesauce New York]]."''
-->-- '''D. H. Lawrence'''

->''"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"''
-->-- '''WebVideo/TheNostalgiaCritic''', [[WebVideo/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''', ''Literature/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'''

->''"I lived in Chicago for three years, and even if they grew up in the super-white, John Hughes parts of Chicago like I did, dipshits from Chicago will always ''act'' as if they grew up near Cabrini Green and spent their formative years bootlegging for Al Capone. [[Film/TheUntouchables HE PULLS A KNIFE, YOU PULL A ZIMA.]]"''
-->--'''[[http://deadspin.com/why-your-team-sucks-2014-chicago-bears-1627368933 Drew Magary]]''', "Why Your Team Sucks 2014: Chicago Bears"