120+ Best Chicago Quotes About 'The Windy City'

Chicago is among the largest cities in the United States, with a dense population.

Chicago is an international hub of trade, transport, and many other activities, owing to which it is also among the most populous cities in the United States. It is no wonder it is highly favored among travelers.

Owing to the gusty wind sweeping across Lake Michigan, Chicago is called 'The Windy City'.  The city has been sadly affected by some of the deadliest tornadoes in the world. Some people also metaphorically attribute the nickname of the city to the heat of its political affairs.

Here we have compiled a list of interesting Chicago quotes that will inspire you for your next visit, or even work as great captions for Chicago pictures on Instagram. A good caption for a Chicago picture should reference something famous about the city (for example, the windy weather), and it's a bonus if there is a pun involved too!

If you like these Chicago quotes, please have a look at our America quotes and American dream quotes too.

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These Chicago quotes give an insight into 'The Windy City'. Discover Chicago quotes from Audrey Niffenegger, Neil Gaiman, Daniel Amory, Nelson Algren and more here.

1."Being Irish was a big thing for me, particularly growing up in Chicago."

- Lara Flynn Boyle.

2."Blessed are the people of Chicago, and blessed the strangers in their midst, in the article of malt liquor; for it is excellent, it is honest, and it is abundant."

- James Parton, 'Atlantic Monthly', 19 March 1867.

3."But when I go to Chicago, I know I'm home."

- Hank Sauer.

4."Chicago – a pompous Milwaukee."

- Leonard Louis Levinson.

5."We’re Chicago – we can do anything, damn it."

- Elva Rupio, 'Gensler Chicago'.

6."Chicago Cubs fans are ninety percent scar tissue."

- George F. Will.

7."Chicago happened slowly, like a migraine."

- Neil Gaiman, 'American Gods'.

8."Chicago has a strange metaphysical elegance of death about it."

- Claes Oldenburg.

9."Chicago has so much excellent architecture that they feel obliged to tear some of it down now and then and erect terrible buildings just to help us all appreciate the good stuff."

- Audrey Niffenegger.

10."Chicago is the product of modern capitalism, and, like other great commercial centers, is unfit for human habitation."  

- Eugene Debs.

11."Chicago is where the whole idea of community policing began."

- Mayor Rahm Emanuel, Speech, 9 December 2015.

12."Chicago sounds rough to the maker of verse. One comfort we have — Cincinnati sounds worse."

- Oliver Wendell Holmes.

13."Chicago was a town where nobody could forget how the money was made. It was picked up from floors still slippery with blood."

- Norman Mailer.

14."Chicago will give you a chance. The sporting spirit is the spirit of Chicago."

- Lincoln Steffens.

15."Chicago, Chicago, that toddlin’ town."

- Fred Fisher, 'Chicago', 1922.

16."That weekend the city blushed with a great heat wave but on Monday it rained, cooling the ache in the street’s burn."

- Daniel Amory, 'Minor Snobs'.

17."Every player should be accorded the privilege of at least one season with the Chicago Cubs. That's baseball as it should be played - in God's own sunshine. And that's really living."

- Alvin Dark.

18."Most tourists, having done some research on Chicago delicacies, order their Italian beef sandwiches 'wet', meaning that a slosh of extra meat gravy is dumped over the beef once it is in the bread."

- Stacey Ballis, 'Recipe For Disaster'.

19."Happiness is seeing Bear Bluff in your rearview mirror, but you better look damn quick."

- James Patterson.

20."Here is the difference between Dante, Milton, and me. They wrote about and never saw the place. I wrote about Chicago after looking the town over for years and years."

- Carl Sandburg.

21."Until 1974, it was actually illegal to appear in public in Chicago if you were ugly."

- Scott Matthews.

22."I was a Chicago Bulls, Michael Jordan fan growing up."

- LeBron James.

23."So that Chicago, with shipping and steel and livestock, came to think of itself as a burly city, tough and muscular, with rough-and-tumble football and politics and literature."

- Brian Doyle.

24."I’m impressed with the people from Chicago. Hollywood is hype. New York is talk. Chicago is work."

- Michael Douglas.

25."I'd love to do a film like 'Chicago'. Something musical because I've obviously come from that background."

- Leona Lewis.

26."If man is, or is searching to be, omnipotent, I am willing to accept Chicago’s gigantism; but I should like the opposite to be accepted as well: a city which would fit in the hollow of one’s hand."

- Jean Genet.

27."I give you Chicago. It is not London and Harvard. It is not Paris and buttermilk. It is American in every chitling and sparerib. It is alive from snout to tail."

- H. L. Mencken.

28."I always visit the Art Institute, walk on Lake Shore Drive and take the architecture boat ride. The Chicago Tribune building is one of my favorites."

- Nicola Bulgari.

29."A city that was to forge out of steel and blood-red neon its own peculiar wilderness."

- Nelson Algren.

30."In Chicago, we may not think the Picasso presiding over the Richard J. Daley Center Plaza is art, but we know it’s a big Picasso and it’s the city’s Picasso, and when the cubs made the playoffs, the sculpture wore a baseball cap just like everything else."

- Pat Colander.

31."It is the most perfect presentation of nineteenth-century individualistic industrialism I have ever seen. Chicago is one hoarse cry for discipline."

- H. G. Wells.

32."It is wonderful to be here in the great state of Chicago."

- Dan Quayle.

33."My heart beats differently when I’m in Chicago. It slows down and I feel more at ease."

- Jeremy Piven.

34."Its music is the blues, of course. Sad and uplifting at once, elevating and haunting at the same time."

- Brian Doyle.

35."Jane Addams too knew that Chicago's blood was hustler's blood."

- Nelson Algren, 'Chicago: City On The Make'.

36."'But must we really see Chicago in order to be educated?' asked Mr. Erskine, plaintively."

- Oscar Wilde, 'The Picture Of Dorian Gray'.

37."Let the worthy citizens of Chicago get their liquor the best way they can. I'm sick of the job-it's a thankless one and full of grief. I've spent the best years of my life being a public benefactor."

- Al Capone.

38."My uncle was the town drunk - and we lived in Chicago."

- George Gobel.

39."No realistic, sane person goes around Chicago without protection."

- Saul Bellow.

40."You will walk out of the Amphitheatre after watching the Stones perform and suddenly the Chicago stockyards smell clean and good by comparison."

- Tom Fitzpatrick.

41."One of the problems with people in Chicago, she remembered, was that they were never lonely at the same time."

- Lorrie Moore, 'Birds Of America'.

42."She knew there was a big Chicago far off, where all the trains ran."

- Carl Sandburg.

43."So if you visit Chicago, enjoy the many great courses, the Midwestern friendliness, and the city's other amenities."

- Mike Royko.

44."Some people around here say that we're a Ferris wheel away from being somewhere."

- Ryan Collins.

45."Sometimes words are just music themselves. Like Chicago is a very musical sounding name."

- Tom Waits.

46. "It’s a bustling metropolis with the warmth of a small town; where the world already comes together every day to live and work and reach for a dream."

– Barack Obama.

47."The joy of working with the Chicago Symphony was immeasurable."

- Georg Solti.

48."Chicago is a great American city. Perhaps it is the last of the great American cities."

– Norman Mailer.

49."The people of Chicago are a proud people – and for good reason."

- Jane Byrne.

50."Theater in Chicago will always be my first love."

- William Petersen.

51."They do things big, big I tells ya: Mike Ditka big. Michael Jordan big. Bill Murray big. Oprah! It’s one cultural Mount Everest after another."

- Anthony Bourdain.

52."Tim, playing ball with them [the Chicago Mob] doesn’t mean you lost the game—it means you’re finally in the game."

- Jennifer Samson, 'Piece Of Work'.

53."We struck the home trail now, and in a few hours were in that astonishing Chicago - a city where they are always rubbing a lamp, and fetching up the genii, and contriving and achieving new impossibilities."

- Mark Twain, 'Life On The Mississippi'.

54."Welcome to Chicago."

- David Mamet.

55."You can have a pretty wonderful artistic life and never leave Chicago."

- Harold Ramis.

56."You know what they say about Chicago. If you don’t like the weather, wait fifteen minutes."

- Ralph Kiner.

57."You’d never think of taking a cab if you had to walk a mile down Chicago’s Michigan Avenue."

- Helmut Jahn.

58."Chicago is a sort of journalistic Yellowstone Park, offering haven to a last herd of fantastic bravos."

- Ben Hecht.

59."Chicago is not a very fashion-driven place. Nobody says, ‘Oh, you’ve got to come see these fabulous people!’ nobody cares."

- Mike Nichols.

60."Chicago is partly a fairy tale because it’s inside one person’s head, so that part of it’s made up and the rest of it is reality."

- Colleen Atwood.

Chicago gives us many reasons to admire this lovely city.  Here are some beautiful captions which you can use to describe pictures showing its scenic beauty from Ralph Metcalfe and more.

61."Perhaps the most typically American place in America."

- James Bryce.

62."Anywhere in the world you hear a Chicago bluesman play, it’s a Chicago sound born and bred."

- Ralph Metcalfe.

63."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."

- Harold Ramis.

64."I adore Chicago. It is the pulse of America."

- Sarah Bernhardt.

If you are far from Chicago and wish to know more about the city, these quotes are all about the city of Chicago.

65."A facade of skyscrapers facing a lake and behind the facade, every type of dubiousness."

- E.M. Forster.

66."A roaring city, gunfire and applause and thunder. Gleaming but made of bone and stone."

- Brian Doyle.

67."Big cities can have big hearts."

- Mary Elise Monsell, 'The Mysterious Cases Of Mr. Pin'.

68."A city without illusions but with vaulting imaginations and expectations. A city of burning energies on the shore of a huge northern sea."

- Brian Doyle.

69."Chicago is as full of crooks as a saw with teeth, but the era when they ruled the city is gone forever."

- John Gunther, 'Inside USA', 1947.

70."Chicago is one city. We shall work as one people for our common good and our common goals."

- Harold Washington.

71."I’d rather be a lamppost in Chicago than a millionaire in any other city."

- William A. Hulbert.

72."Chicago has been characterized as the most segregated city in the United States, a city they said could never change."

- Harold Washington.

73."Chicago is a city of contradictions, of private visions haphazardly overlaid and linked together. If the city was unhappy with itself yesterday-and invariably it was-it will reinvent itself today."

-  Pat Colander.

74."Chicago is a city where the practical and the inspirational exist in harmony; where visionaries who made no small plans rebuilt after a great fire and taught the world to reach new heights."

- Barack Obama.

75."Chicago is a town, a city that doesn’t ever have to measure itself against any other city."

- Anthony Bourdain.

76."Chicago is an October sort of city even in spring."

- Nelson Algren.

77."Chicago is not the most corrupt American city. It’s the most theatrically corrupt."

- Studs Terkel, 1978.

78."Chicago is unique. It is the only completely corrupt city in America."

- Charles Merriam.

79."Chicago seems a big city instead of merely a large place."

- A.J. Liebling.

80."Chicago, mistress of the lakes, controller of our inland trade, the freest city of our states, what wondrous strides thy fame has made!"

– Charles Frederick White.

81."I cannot watch the city of Chicago be destroyed by petty politics and bad government."

- Harold Washington.

82."I have struck a city – a real city – and they call it Chicago."

- Rudyard Kipling.

83."There is none other quite like my City of Big Shoulders."

- Irv Kupcinet.

84."Chicago is not the most corrupt of cities. The state of New Jersey has a couple. Need we mention Nevada? Chicago, though, is the Big Daddy. Not more corrupt, just more theatrical, more colorful in its shadiness."

- Studs Terkel.

Each city in the world has a unique charm. Read these famous Chicago quotes from Frank Lloyd Wright and more, that the residents of the city would feel proud to hear.

85."Eventually, I think Chicago will be the most beautiful great city left in the world."

- Frank Lloyd Wright.

86."Let me tell you something. I’m from Chicago. I don’t break."

- Barack Obama.

87."Yet once you've come to be part of this particular patch, you'll never love another. Like loving a woman with a broken nose, you may well find lovelier lovelies. But never a lovely so real."

- Nelson Algren, 'Chicago: City On The Make'.

88."One of the hallmarks of Chicago is that we do so many things in an original manner. What other city has made a river flow backwards?"

- Mike Royko.

89."Going to Chicago was like going out of the world."

- Muddy Waters.

90."Chicago does not go to the world, the world comes to Chicago!"

- Peter Orner.

The city is known for its gusts of wind and cold weather.  These Chicago quotes give us an idea of how it is.

91."I miss everything about Chicago, except January and February."

- Gary Cole.

92."Ain't Chicago got a lonely wind... Makes you want to stop and call some lonesome friend..."

-Merle Haggard, 'Chicago Wind'.

93."I warn you, Jedediah, you’re not gonna like it in Chicago. The wind comes howling in off the lake and gosh only knows if they ever heard of lobster Newburg."

- Orson Welles.

94."I just know that I could never spend a winter in Chicago or someplace like that. I’m just not a cold weather person."

- Emily Robinson.

95."I must confess a shameful secret: I love Chicago best in the cold."

- Erik Larson, 'The Devil In The White City'.

96."I think that's how Chicago got started. A bunch of people in New York said, 'Gee, I'm enjoying the crime and the poverty, but it just isn't cold enough. Let's go west'."

- Richard Jeni.

Here are some Chicago quotes from travelers across the world who have had the opportunity to visit the city.  These Chicago quotes narrate their personal experiences.

97."Everyone here seems to appreciate the sunshine way more than we do in California. We tend to take it for granted, but in Chicago, it's like Woodstock love every time it gets above 70 degrees."

- Miranda Rae Mayo.

98."My first day in Chicago, September 4, 1983. I set foot in this city, and just walking down the street, it was like roots, like the motherland. I knew I belonged here."

- Oprah Winfrey.

99."Guys, you're Chicago. You're the home of Laurie Metcalf and Jessie Mueller and Steppenwolf. And a million, a million, a million brilliant theater practitioners."

- Lin-Manuel Miranda.

100."After three years in Chicago, I decided to call it a career."

- Ted Lindsay.

101."And then when I went to Chicago, that’s when I had these outer space experiences and went to the other planets."

- Sun Ra.

102."It is hopeless for the occasional visitor to try to keep up with Chicago - she outgrows her prophecies faster than she can make them. She is always a novelty; for she is never the Chicago you saw when you passed through the last time."

- Mark Twain, 'Life On The Mississippi'.

103."My first job, actually, was a Chicago Bulls commercial. I was a ninja. I walked with a limp for a week afterward and got paid 500 dollars six months later."

- Samuel Witwer.

Chicago is among the busiest American cities. The quotes below, from Erik Larson and more, reflect its relationship with its neighbors and the rest of the world.

104."There's only one thing for Chicago to do, and that's to move to a better neighbourhood."

- Herman Fetzer.

105."Chicago's neighborhoods have always been the city's greatest strength."

- Jane Byrne.

106."A lot of real Chicago lives in the neighborhood taverns. It is the mixed German and Irish and Polish gift to the city, a bit of the old country grafted into a strong new plant in the new."

- Bill Granger.

107."I love Chicago; it is unique in the world."

- Jerome Sans.

108."Chicago is constantly auditioning for the world, determined that one day, on the streets of Barcelona, in Berlin’s cabarets, in the coffee shops of Istanbul, people will know and love us in our multidimensional glory, dream of us the way they dream of San Francisco and New York."

- Mary Schmich.

100."I like to go to Marshall Field’s in Chicago just to see how many things there are in the world that I do not want."

- Mother Mary Madeleva, 'My First Seventy Years'.

101."It’s one of the most progressive cities in the world."

- Will Rogers, 22 June 1930.

102."Out in Chicago, the only genuinely civilized city in the New World, they take the fine arts seriously."

- Henry Mencken.

103."The most beautiful modern city in the world is Chicago."

- Nicola Bulgari.

104."Chicago has disappointed her enemies and astonished the world."

- Erik Larson.

105."It’s one of the greatest cities on the planet."

- Jeremy Piven.

You might like to have a dose of fun by going through these hilarious Chicago quotes.

106."I had thought Chicago was inevitable, like diarrhea."

- John Varley, 'The Persistence Of Vision'.

107."A Chicago alderman once confessed he needed physical exercise but didn’t like jogging, because in that sport you couldn’t hit anyone."

- Andrew H. Malcolm.

108."But no matter how good the beer, how many honors or awards, how innovative Goose Island would ever be again, someone deep in the crowd would always boo."

- Josh Noel.

109."Because Chicago was to radio what Hollywood was to films and Broadway was to the theatre: it was the hub of radio."

- Mel Torme.

110."Chicago is like a snake that sheds its skin every thirty years or so and puts on a new coat to conform to a new reality."

- Dominic A. Pacyga.

111."Hell has been described as a pocket edition of Chicago."

- Ashley Montagu, 'The American Way Of Life'.

112."I think that what comes through in Chicago humor is the affection. Even though you're poking fun at someone or something, there's still an affection for it."

- Bob Newhart.

Chicago has inspired many writers, including Nelson Algren, to pen their thoughts on the city.  Here is a collection of Chicago quotes picked from books and films.

113."Dipped Italian beef sandwiches in Chicago require a full commitment. Once you start, you are all in till the last bit of slushy bread and shred of spicy beef is gone."

- Stacey Ballis, 'Recipe For Disaster'.

114."When you feel like tellin a feller to go to the devil -- tell him to go to Chicago -- it'll anser every purpose, and is perhaps, a leetle more expensive."

- Mark Twain, 'Snodgrass' Ride On The Railroad'.

115."We'd speak French like a bunch of high school kids from Chicago, but we'd at least speak French."

- Michelle Obama, 'Becoming'.

116."The city divided by the river is further divided by racial and lingual differences."

- Nelson Algren, 'Chicago: City On The Make'.

117."The trouble with you Chicago people is, that you think you are the best people down here; whereas you are merely the most numerous."

- Mark Twain, 'Pudd'nhead Wilson's New Calendar.'

118."It was so easy to disappear, so easy to deny knowledge, so very easy in the smoke and din to mask that something dark had taken root. This was Chicago, on the eve of the greatest fair in history."

- Erik Larson, 'The Devil In The White City'.

119."Could anything be more indicative of a slight but general insanity than the aspect of the crowd on the streets of Chicago?"

- Charles Horton Cooley, 'Human Nature And The Social Order'.

120."Chicago divided your heart. Leaving you loving the joint for keeps. Yet knowing it never can love you."

- Nelson Algren, 'Chicago: City On The Make'.

121."Well, if you’re a native Chicagoan, you know how dumb he [Dr. Robert Hartley] is. He gets on the Ravenswood El, he goes past his stop on Sheridan Road, he gets off in Evanston, where the El is on the ground, and then he walks back 55 blocks to his apartment."

- Bob Newhart.

122."In most places in the country, voting is looked upon as a right and a duty, but in Chicago it’s a sport. In Chicago not only your vote counts, but all kinds of other votes..."

- Dick Gregory, 'Dick Gregory’s Political Primer'.

Here at Kidadl, we have carefully created lots of interesting family-friendly quotes for everyone to enjoy! If you liked our suggestions for the best Chicago quotes about 'The Windy City,' then why not take a look at these California quotes, or [Alaska quotes]?

‍second image credit: Photo Spirit / Shutterstock.com