->''"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.]] The whitest areas of Chicago are basically Portland, with douchey experimental restaurants where people eat food foraged from public parks, but you get to pretend you're HARD because 82 people get shot every weekend seven miles and 19 police jurisdictions away."''
-->--'''[[http://deadspin.com/why-your-team-sucks-2014-chicago-bears-1627368933 Drew Magary]]''', "Why Your Team Sucks 2014: Chicago Bears"