80+ Chicago Quotes & Captions Perfect For a Windy City Getaway

Looking for some fun and famous quotes about Chicago? Well, look no further, as I’ve compiled this awesome list of Chicago Quotes and Chi-town captions perfect for that next Instagram post!

Located on Lake Michigan in Illinois, Chicago is a complex and large metropolitan city. It’s famed for its Midwestern character, rich history, and incredible architecture. Over the years, the city has inspired writers, innovators, politicians, and creative minds alike.

Known for its deep-dish pizza and the Bean, Chicago is a charismatic and friendly city that has attracted visitors both locally and internationally. Anyone that passes through the city will most probably have something captivating to say about it.

Needing a little more inspiration before taking the plunge and booking that ticket? Keep reading and enjoy some of the best quotes about Chicago. Intrigued by the city so far and want to discover the Windy City yourself? Check out these amazing Airbnbs in Chicago!

Famous Chicago Quotes

As a city that is loved by so many various people, there is an unbelievable amount of Chicago-adoring quotes available. These quotes show off the best of Chicago and why it’s cherished by so many of its visitors.

1) “Chicago’s neighborhoods have always been the city’s greatest strength.” – Jane Byrne

2) “I’d rather be a lamppost in Chicago than a millionaire in any other city.” – William A. Hulbert

3) “Let me tell you something. I’m from Chicago. I don’t break.” – Barack Obama

4) “The most beautiful modern city in the world is Chicago. 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

5) “But when I go to Chicago, I know I’m home.” – Hank Sauer

6) “Going to Chicago was like going out of the world…” – Muddy Waters

7) “We’re Chicago – we can do anything, damn it.” – Elva Rupio, Gensler Chicago

8) “I love Chicago; it is unique in the world. So much intellect, so many artistic voices – it has fantastic potential (as an Olympic candidate).” – Jerome Sans

9) “It’s one of the greatest cities on the planet. My heart beats differently when I’m in Chicago. It slows down and I feel more at ease.” – Jeremy Piven

10) “And then when I went to Chicago, that’s when I had these outer space experiences and went to the other planets.” – Sun Ra

11) “I’m impressed with the people from Chicago. Hollywood is hype, New York is talk, Chicago is work.” – Michael Douglas

12) “Theater in Chicago will always be my first love.” – William Petersen

13) “I adore Chicago. It is the pulse of America.” – Sarah Bernhardt

14) “Germany was the cause of Hitler as much as Chicago is responsible for the Chicago Tribune.” – Alexander Woollcott

15) “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 play-offs, the sculpture wore a baseball cap just like everything else.” – Pat Colander

16) “Chicago ain’t no sissy town.” – Michael Hinky Dink Kenna

17) “Maybe we can show government how to operate better as a result of better architecture. Eventually, I think Chicago will be the most beautiful great city left in the world.” – Frank Lloyd Wright

18) “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

19) “Out in Chicago, the only genuinely civilized city in the New World, they take the fine arts seriously and get into such frets and excitements about them as are raised nowhere else save by baseball, murder, political treachery, foreign wars, and romantic loves . . . almost one fancies the world bumped by a flying asteroid, and the Chicago River suddenly turned into the Seine.” – Henry Mencken in The Smart Set

20) “I am going to St. Petersburg, Florida, tomorrow. Let the worthy citizens of Chicago get their liquor the best they can. I’m sick of the job–it’s a thankless one and full of grief. I’ve been spending the best years of my life as a public benefactor.” – Al Capone

21) “There’s only one thing for Chicago to do, and that’s to move to a better neighborhood.” – Herman Fetzer

22) “You walk out of the Amphitheatre after watching the Rolling Stones perform and suddenly the Chicago Stockyards smell clean and good by comparison.” – Tom Fitzpatrick

23) “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

24) “Chicago is the product of modern capitalism, and, like other great commercial centers, is unfit for human habitation.” – Eugene Debs

25) “That’s great advertising when you can turn Chicago into a city you’d want to spend more than three hours in.” – Jerry Della Femina

26) “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

27) “New York is one of the capitals of the world and Los Angeles is a constellation of plastic, San Francisco is a lady, Boston has become Urban Renewal, Philadelphia and Baltimore and Washington wink like dull diamonds in the smog of Eastern Megalopolis, and New Orleans is unremarkable past the French Quarter. Detroit is a one-trade town, Pittsburgh has lost its golden triangle, St. Louis has become the golden arch of the corporation, and nights in Kansas City close early. The oil depletion allowance makes Houston and Dallas naught but checkerboards for this sort of game. But Chicago is a great American city. Perhaps it is the last of the great American cities.” – Norman Mailer

Famous Chicago Sayings

As a creative source of inspiration for writers and artists, it’s no surprise that there are some beautiful quotes about the city out there. Here are some of my favorites taken from poems, literature, pop culture, and writers.

28) “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

29) “Come and show me another city with lifted head singing so proud to be alive and coarse and strong and cunning…proud to be Hog Butcher, Tool Maker, Stacker of Wheat, Player with Railroads and Freight Handler to the Nation.” – Carl Sandburg

30) “Chicago does not go to the world, the world comes to Chicago!” – Peter Orner

31) “But never, among all the cities I have wandered over the years, cities all over the earth, did I feel and smell and sense anything quite like the verb that is Chicago; and always, no matter how many years passed, I could hear and see and touch something inside me that only Chicago has…” – Brian Doyle

32) “There seems to be a different Chicago around every street corner, behind every bar, and within every apartment, two-flat, cottage, or bungalow. City of immigrants or city of heartless plutocrats, say what you will, Chicago almost defies interpretation. In many ways, 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

33) “There are almost no beautiful cities in America, though there are many beautiful parts of cities, and some sections that are glorious without being beautiful, like downtown Chicago. Cities are too big and too rich for beauty; they have outgrown themselves too many times.” – Noel Perrin, Third Person Rural

34) “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

35) “Chicago, Chicago, that toddlin’ town.” – Fred Fisher, Chicago

36) “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.” – Harold Ramis

37) “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? What other city makes traffic flow backwards?” – Mike Royko

38) “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, A Metropolis of No Little Plans

39) “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

40) “Chicago will give you a chance. The sporting spirit is the spirit of Chicago.” – Lincoln Steffens

41) “It’s 106 miles to Chicago, we’ve got a full tank of gas, half a pack of cigarettes; it’s dark and we’re wearing sunglasses. Hit it!” – The Blues Brothers

42) “Chicago is one city. We shall work as one people for our common good and our common goals.” – Harold Washington

43) “Chicago is known for good steaks, expensive stores and beautiful architecture.” – Bob Barr

44) “Chicago has disappointed her enemies and astonished the world.” – Erik Larson

45) “Chicago happened slowly, like a migraine. First, they were driving through the countryside, then, imperceptibly, the occasional town became a low suburban sprawl, and the sprawl became the city.” – Neil Gaiman

Windy City Quotes

The origins as to why Chicago is referred to as the Windy City remain unclear. Some say it has to do with the chilly breeze that comes off Lake Michigan, while others suggest it has to do with its political history.

Interestingly, despite its nickname, it’s actually not the breeziest town in the United States. Meteorological surveys have indicated that towns like Boston and San Francisco experience much higher wind speeds.

Even so, as it’s known as the Windy City to many, here are some quotes about the famous wind and weather in Chicago.

46) “You know what they say about Chicago. If you don’t like the weather, wait fifteen minutes.” – Ralph Kiner

47) “Chicago is an October sort of city even in spring.” – Nelson Algren

48) “I miss everything about Chicago, except January and February.” – Gary Cole

49) “I must confess a shameful secret: I love Chicago best in the cold.”- Erik Larson

50) “You’re not going to 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

51) “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

Funny Quotes About Chicago

It is common for people to have a love/hate relationship with the city. There are aspects of Chicago that they love, like its architecture. But also parts that are less liked such as its links to the mafia. This tumultuous relationship has resulted in hilarious quotes about Chicago, check them out below.

52) “Loving Chicago is like loving a woman with a broken nose.” – Nelson Algren

53) “In some Chicago neighborhoods, looking for a parking space is not unlike panning for gold.” – Gary Washburn

54) “Chicago Cubs fans are ninety percent scar tissue.” – George F. Will

55) “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

56) “I’m a little hoarse tonight. I’ve been living in Chicago for the past two months, and you know how it is, yelling for help on the way home every night. Things are so tough in Chicago that at Easter time, for bunnies the little kids use porcupines.” – Fred Allen, Much Ado About Me

57) “Chicago is not a very fashion-driven place. Nobody says, ‘Oh, you’ve got to come see these fabulous people!’ Nobody cares.” – Mike Nichols

58) “Sharks are as tough as those football fans who take their shirts off during games in Chicago in January, only more intelligent.” – Dave Barry, Sex and the Single Amoeba: What Every Teen Should Know

59) “It is wonderful to be here in the great state of Chicago…” – Dan Quayle

60) “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

61) “I had thought Chicago was inevitable, like diarrhea.” – John Varley

62) “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

63) “What a place to put a city, right on the front line of absolute zero. No wonder a cow burned it down.” – Mark Helprin

Quotes About Living in the Chicago

Chicago has a dark history when it comes to gangsters and the mafia. One of the cities most notorious gangsters was Alphonse Gabriel Capone. Better known as Al Capone or by his nickname “Scarface.” He found fame during the Prohibition era and was the co-founder and boss of the Chicago Outfit.

As a result, life in the city during that time was tough. Murders happening around each corner, people feeling unsafe because of the violence occurring on the Chicago streets. In some cases, it left a deep and dark scar on some of its occupants.

Here are some quotes that best capture how harsh and tough life could be in Chicago.

64) “When you feel like tellin a feller to go to the devil – tell him to go to Chicago – it’ll answer every purpose, and is perhaps, a little more expensive.” – Mark Twain

65) “Welcome to Chicago. This town stinks like a whorehouse at low tide.” – David Mamet

66) “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

67) “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

68) “Chicago is unique. It is the only completely corrupt city in America.” – Charles Merriam

69) “Here is the difference between Dante, Milton, and me. They wrote about hell and never saw the place. I wrote about Chicago after looking the town over for years and years.” – Carl Sandburg

70) “Hell has been described as a pocket edition of Chicago.” – Ashley Montagu, The American Way Of Life

71) “Gigantic, willful, young, Chicago sitteth at the northwest gates.” – William Vaughn Moody, An Ode in Time of Hesitation

72) “Chicago has a strange metaphysical elegance of death about it.” – Claes Oldenburg

73) “No realistic, sane person goes around Chicago without protection.” – Saul Bellow

74) “I don’t have any great love for Chicago. What the hell, a childhood around Douglas Park isn’t very memorable. I remember the street fights and how you were afraid to cross the bridge ’cause the Irish kid on the other side would beat your head in. I left Chicago a long time ago.” – ‘King of Swing’ Benny Goodman

75) “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

76) “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–kids, dead folks, and so on.” – Dick Gregory

77) “The last copy of the Chicago Daily News I picked up had three crime stories on its front page. But by comparison to the gaudy days, this is small-time stuff. Chicago is as full of crooks as a saw with teeth, but the era when they ruled the city is gone forever.” – John Gunther

78) “Chicago sounds rough to the maker of verse. One comfort we have – Cincinnati sounds worse.” – Oliver Wendell Holmes

79) “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

80) “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.” – Rudyard Kipling

81) “I’ve reported murders, scandals, marriages, premieres and national political conventions. I’ve been amused, intrigued, outraged, enthralled and exasperated by Chicago. And I’ve come to love this American giant, viewing it as the most misunderstood, most underrated city in the world. There is none other quite like my City of Big Shoulders.” – Irv Kupcinet

82) “Chicago – a pompous Milwaukee.” – Leonard Louis Levinson

83) “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, To Chicago

Chicago Sayings and Quotes Inspired by the Arts

The city has an incredible art scene. No matter the weather, people flock out to events such as concerts and art gallery openings.

Home to the Muddy Waters, who is often referred to as the ‘father of modern Chicago Blues’ Chicago is perhaps most commonly known for its amazing Blues scene. However, the city offers various types of music festivals each year, which will keep you dancing all night long.

Here are some sayings that best capture the wonderful creative scene that Chicago embraces.

84) “Anywhere in the world you hear a Chicago bluesman play, it’s a Chicago sound born and bred.” – Ralph Metcalfe

85) “I got that first record out, it came out in ’47… Then my name began to ring around. I began to take over. From that point, I tell you, Chicago was in my hand, all the more time that those guys had to listen to me.” – Muddy Waters

86) “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. 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

87) “Chicago is a great place because you can experience theatre, film, television, anything and everything, so for an actor it’s exciting. The doors are kind of open.” – Charlie Barnette

Did I Miss Any Famous Quotes About Chicago?

There are so many Chicago quotes and saying out there that if I listed them all, we would have reading material for days. I did my best to put together a collection of the finest.

However, if you feel that there are any quotes on Chicago missing from the list and it deserves to be included- get in touch! I’ll do my best and see if I can add it to the list.

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