206 Best Chicago Quotes & Captions That Express Emotions Toward The Great American City

Thanks for coming to my website in this article I will share with you 206 best Chicago quotes & captions.

Sitting on the banks of the great Lake Michigan in Illinois, established in the year 1837 now is most prolifically known as mini America. This city is great for the American culture food, nature, adventure, skyscrapers, and of course History.

It doesn’t matter where your interest lies, you’ll always find something excited from seriously fun to awesomely educational.

Without wasting your time I am going to share 206 quotes about Chicago you can also use them in your Instagram post.

I have divided this post into 5 Heading From Cool Chicago Quotes to Funny Chicago Quotes to Interesting Chicago Quotes To Chicago Quotes from Movies and songs and Short Chicago Instagram Captions. You can use the Jump link To jump into that particular section.

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206 Best Chicago Quotes & Captions That Express Emotions Toward The Great American City
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Cool Chicago Quotes & Captions

Chicago Quotes - Chicago Captions For Instagram - Quotes About Chicago - Chicago Quotes Instagram - Funny Chicago Quotes
Chicago Quotes – Chicago Captions For Instagram – Quotes About Chicago – Chicago Quotes Instagram – Funny Chicago Quotes
  1. “Either you love Chicago, or you are wrong.”

  2. “Eventually, I think Chicago will be the most beautiful great city left in the world.” ― Frank Lloyd Wright

  3. “Chicago is my hometown and will always have a special place in my heart.” – Kenneth Choi
  1. “Chicago is one city. We shall work as one people for our common good and our common goals.” – Harold Washington

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

  3. “Let me tell you something. I’m from Chicago. I don’t break.” ― Barack Obama
Chicago Quotes - Chicago Captions For Instagram - Quotes About Chicago - Chicago Quotes Instagram - Funny Chicago Quotes
Chicago Quotes – Chicago Captions For Instagram – Quotes About Chicago – Chicago Quotes Instagram – Funny Chicago Quotes
  1. “I have struck a city – a real city and they call it Chicago.”
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206 Best Chicago Quotes & Captions That Express Emotions Toward The Great American City
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  1. “I like the feeling of being anonymous in a big city, no one knows me, so it is easier to remember who I am”
Chicago Quotes - Chicago Captions For Instagram - Quotes About Chicago - Chicago Quotes Instagram - Funny Chicago Quotes
Chicago Quotes – Chicago Captions For Instagram – Quotes About Chicago – Chicago Quotes Instagram – Funny Chicago Quotes
  1. “I’m impressed with the people from Chicago. Hollywood is hype, New York is talk, Chicago is work.” — Michael Douglas
Chicago Quotes - Chicago Captions For Instagram - Quotes About Chicago - Chicago Quotes Instagram - Funny Chicago Quotes
Chicago Quotes – Chicago Captions For Instagram – Quotes About Chicago – Chicago Quotes Instagram – Funny Chicago Quotes
  1. “I have stuck in a city – a real city – and they call it Chicago… Having seen it, I urgently desire never to see it again… It is inhabited by savages.” – Ruyard Kipling

  2. “Ain’t Chicago got a lonely wind… Makes you want to stop and call some lonesome friend…” – Merle Haggard
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206 Best Chicago Quotes & Captions That Express Emotions Toward The Great American City
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  1. “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

  2. “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
Chicago Quotes - Chicago Captions For Instagram - Quotes About Chicago - Chicago Quotes Instagram - Funny Chicago Quotes
Chicago Quotes – Chicago Captions For Instagram – Quotes About Chicago – Chicago Quotes Instagram – Funny Chicago Quotes
  1. “Chicago has been characterized as the most segregated city in the United States, a city they said could never change.” – Harold Washington

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

  3. “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

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

  5. “Going to Chicago was like going out of the world…” – Muddy Waters
Chicago Quotes - Chicago Captions For Instagram - Quotes About Chicago - Chicago Quotes Instagram - Funny Chicago Quotes
Chicago Quotes – Chicago Captions For Instagram – Quotes About Chicago – Chicago Quotes Instagram – Funny Chicago Quotes
  1. “We’re Chicago – we can do anything, damn it.” – Elva Rupia

  2. “Chicago is a town, a city that doesn’t ever have to measure itself against any other city. Other places have to measure themselves against it. It’s big, it’s outgoing, it’s tough, it’s opinionated, and everybody’s got a story.” — Anthony Bourdain

  3. “Chicago prides itself on being a mean city.” – Laura Jane Grace
Chicago Quotes - Chicago Captions For Instagram - Quotes About Chicago - Chicago Quotes Instagram - Funny Chicago Quotes
Chicago Quotes – Chicago Captions For Instagram – Quotes About Chicago – Chicago Quotes Instagram – Funny Chicago Quotes
  1. “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

  2. “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

  3. “But Chicago is a great American city. Perhaps it is the last of the great American cities.” – Norman Mailer
Chicago Quotes - Chicago Captions For Instagram - Quotes About Chicago - Chicago Quotes Instagram - Funny Chicago Quotes
Chicago Quotes – Chicago Captions For Instagram – Quotes About Chicago – Chicago Quotes Instagram – Funny Chicago Quotes
  1. “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
Chicago Quotes - Chicago Captions For Instagram - Quotes About Chicago - Chicago Quotes Instagram - Funny Chicago Quotes
Best Chicago Quotes – Chicago Captions For Instagram – Chicago Instagram Captions – Funny Quotes About Chicago – Funny Chicago Quotes
  1. “Being Irish was a big thing for me, particularly growing up in Chicago.” Lara Flynn Boyle

  2. “Chicago’s neighbourhoods have always been the city’s greatest strength.” – jane Byrne
Best Chicago Quotes - Chicago Captions For Instagram - Chicago Instagram Captions - Funny Quotes About Chicago - Funny Chicago Quotes
Best Chicago Quotes – Chicago Captions For Instagram – Chicago Instagram Captions – Funny Quotes About Chicago – Funny Chicago Quotes
  1. “I cannot watch the city of Chicago be destroyed by petty politics and bad government.” – Harold Washington

  2. “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

  3. “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.” — Elwood Blues

  4. “I must confess a shameful secret: I love Chicago best in the cold.” – Erik Larson
Best Chicago Quotes - Chicago Captions For Instagram - Chicago Instagram Captions - Funny Quotes About Chicago - Funny Chicago Quotes
Best Chicago Quotes – Chicago Captions For Instagram – Chicago Instagram Captions – Funny Quotes About Chicago – Funny Chicago Quotes
  1. “In most places in the country, voting is looked upon as a right and a duty, but in Chicago it’s a sport.” – Dick Gregory

  2. “Chicago seems a big city instead of merely a large place.” — A.J. Liebling

  3. “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

  4. “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

  5. “I am an organic Chicagoan. Living there has given me a multiplicity of characters to aspire for. I hope to live there the rest of my days.” — Gwendolyn Brooks

  6. “When I close my eyes to draw I always think Chicago in 1975.” – Daniel Clowes
Best Chicago Quotes - Chicago Captions For Instagram - Chicago Instagram Captions - Funny Quotes About Chicago - Funny Chicago Quotes
Best Chicago Quotes – Chicago Captions For Instagram – Chicago Instagram Captions – Funny Quotes About Chicago – Funny Chicago Quotes
  1. “Chicago is as full of crooks as a saw with teeth, but the era when they ruled the city is gone forever.” – John Gunther

  2. “‘But must we really see Chicago in order to be educated?’ asked Mr. Erskine, plaintively.” – Oscar Wilde

  3. “Perhaps the most typically American place in America.” – James Bryce

  4. “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

  5. “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

  6. “There have been times I have thought some dreams should never be dreamt, but I would hate a world where that was true.” ― Daniel Amory, Minor Snobs
  1. “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

  2. “She knew there was a big Chicago far off, where all the trains ran.” – Carl Sandburg
Best Chicago Quotes - Chicago Captions For Instagram - Chicago Instagram Captions - Funny Quotes About Chicago - Funny Chicago Quotes
Best Chicago Quotes – Chicago Captions For Instagram – Chicago Instagram Captions – Funny Quotes About Chicago – Funny Chicago Quotes
  1. “You’d never think of taking a cab if you had to walk a mile down Chicago’s Michigan Avenue.” — Helmut Jahn

  2. “The Chicago Tribune has come out against syphilis. Bet you 8 to 5 syphilis will win.”

  3. “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

  4. “I’d rather be a lamppost in Chicago than a millionaire in any other city.” – William a. Hulbert
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206 Best Chicago Quotes & Captions That Express Emotions Toward The Great American City
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  1. “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

  2. “No Realistic, Sane Person Goes Around Chicago Without Protection.” – Saul Bellow

  3. “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

  4. “Chicago’s neighbourhoods have always been the city’s greatest strength.” — Jane Byrne

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

  6. “Chicago is a fantastic city, and I can easily see the Olympics setting themselves right here in Chicago.” – Edwin Moses
Best Chicago Quotes - Chicago Captions For Instagram - Chicago Instagram Captions - Funny Quotes About Chicago - Funny Chicago Quotes
Best Chicago Quotes – Chicago Captions For Instagram – Chicago Instagram Captions – Funny Quotes About Chicago – Funny Chicago Quotes
  1. “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

  2. “Because Chicago was to radio what Hollywood was to films and Broadway was to the theatre: it was the hub of radio.” – Mel Torme

  3. “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, The Time Traveler’s Wife

  4. “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

  5. “It is hopeless for the occasional visitor to try to keep up with Chicago-she outgrows his prophecies faster than he 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

  6. “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 colourful in its shadiness.” — Studs Terkel

  7. “…a city that was to live by night after the wilderness had passed. A city that was to forge out of steel and blood-red neon its own peculiar wilderness.” ― Nelson Algren

  8. “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.”

  9. “It is hopeless for the occasional visitor to try to keep up with Chicago—she outgrows his prophecies faster than he 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

  10. “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

  11. “Satan (impatiently) to Newcomer: 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
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206 Best Chicago Quotes & Captions That Express Emotions Toward The Great American City
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Best Chicago Quotes - Chicago Captions For Instagram - Chicago Instagram Captions - Funny Quotes About Chicago - Funny Chicago Quotes
Best Chicago Quotes – Chicago Captions For Instagram – Chicago Instagram Captions – Funny Quotes About Chicago – Funny Chicago Quotes
  1. “They do things big, big I tell ya: Mike Ditka big. Michael Jordan big. Bill Murray big. Oprah! It’s one cultural Mount Everest after another.” – Anthony Bourdain

  2. “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

  3. “You Walk Out Of The Amphitheatre After Watching The Rolling Stones Perform And Suddenly The Chicago Stockyards Smell Clean And Good By Comparison.”

  4. “In Chicago not only your vote counts, but all kinds of other votes-kids, dead folks, and so on.” – Dick Gregory

  5. “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

  6. “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 no where 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

  7. “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

  8. “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

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

  10. “There was no need to inform us of the protocol involved. We were from Chicago and knew all about cement.” – Groucho Marx
Best Chicago Quotes - Chicago Captions For Instagram - Chicago Instagram Captions - Funny Quotes About Chicago - Funny Chicago Quotes
Best Chicago Quotes – Chicago Captions For Instagram – Chicago Instagram Captions – Funny Quotes About Chicago – Funny Chicago Quotes
  1. “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

  2. “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

  3. “First in violence, deepest in dirt, lawless, unlovely, ill-smelling, irreverent, new; an overgrown gawk of a village, the “tough” among cities, a spectacle for the nation.” – Lincoln Steffens

  4. “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, Miami and the Siege of Chicago, 1968

Funny Chicago Quotes

Best Chicago Quotes - Chicago Captions For Instagram - Chicago Instagram Captions - Funny Quotes About Chicago - Funny Chicago Quotes
Best Chicago Quotes – Chicago Captions For Instagram – Chicago Instagram Captions – Funny Quotes About Chicago – Funny Chicago Quotes
  1. “My uncle was the town drunk – and we lived in Chicago.” – George Gobel

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

  3. “In Chicago, we love our crooks!” – David Mamet
Best Chicago Quotes - Chicago Captions For Instagram - Chicago Instagram Captions - Funny Quotes About Chicago - Funny Chicago Quotes
Best Chicago Quotes – Chicago Captions For Instagram – Chicago Instagram Captions – Funny Quotes About Chicago – Funny Chicago Quotes
  1. “Hell has been described as a pocket edition of Chicago.” – Ashley Montagu
  1. “You know what they say about Chicago. If you don’t like the weather, wait fifteen minutes.” – Ralph Kiner
Best Chicago Quotes - Chicago Captions For Instagram - Chicago Instagram Captions - Funny Quotes About Chicago - Funny Chicago Quotes
Best Chicago Quotes – Chicago Captions For Instagram – Chicago Instagram Captions – Funny Quotes About Chicago – Funny Chicago Quotes
  1. “I must confess a shameful secret: I love Chicago best in the cold.” – Erik Larson
Best Chicago Quotes - Chicago Captions For Instagram - Chicago Instagram Captions - Funny Quotes About Chicago - Funny Chicago Quotes
Best Chicago Quotes – Chicago Captions For Instagram – Chicago Instagram Captions – Funny Quotes About Chicago – Funny Chicago Quotes
  1. “Sometimes words are just music themselves. Like ‘Chicago’ is a very musical sounding name.” – Tom Waits

  2. “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
  1. “I think that what comes through in Chicago humour is the affection. Even though you’re poking fun at someone or something, there’s still an affection for it.” – Bob Newhart

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

  3. “I love Chicago, but I’m ready to get the L out of here.”

  4. “I HAD THOUGHT CHICAGO WAS INEVITABLE, LIKE DIARRHEA.” – JOHN VARLEY
Best Chicago Quotes - Chicago Captions For Instagram - Chicago Instagram Captions - Funny Quotes About Chicago - Funny Chicago Quotes
Best Chicago Quotes – Chicago Captions For Instagram – Chicago Instagram Captions – Funny Quotes About Chicago – Funny Chicago Quotes
  1. “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

  2. “After three years in Chicago, I decided to call it a career.” – Ted Lindsay
  1. “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
Best Chicago Quotes - Chicago Captions For Instagram - Chicago Instagram Captions - Funny Quotes About Chicago - Funny Chicago Quotes
Best Chicago Quotes – Chicago Captions For Instagram – Chicago Instagram Captions – Funny Quotes About Chicago – Funny Chicago Quotes
  1. “When I left Chicago, people said, ‘Careful with that Texas heat’. I’m like, ‘I’m from Puerto Rico. I know heat.” – Amaury Nolasco

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

  3. “Sharks are as tough as those football fans who take their shirts off during games in Chicago in January, only more intelligent.” – Dave Barry

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

  5. “You know what they say about Chicago. If you don’t like the weather, wait fifteen minutes.” – Ralph Kiner
Best Chicago Quotes - Chicago Captions For Instagram - Chicago Instagram Captions - Funny Quotes About Chicago - Funny Chicago Quotes
Best Chicago Quotes – Chicago Captions For Instagram – Chicago Instagram Captions – Funny Quotes About Chicago – Funny Chicago Quotes
  1. “Dogs love Chicago because they get to visit Wiggly Field.”
Chicago Quotes - Quotes About Chicago
Best Chicago Quotes – Chicago Captions For Instagram – Chicago Instagram Captions – Funny Quotes About Chicago – Funny Chicago Quotes
  1. “I’m impressed with the people from Chicago. Hollywood is hype. New York is talk. Chicago is work.” – Michael Douglas
Best Chicago Quotes - Chicago Captions For Instagram - Chicago Instagram Captions - Funny Quotes About Chicago - Funny Chicago Quotes
Best Chicago Quotes – Chicago Captions For Instagram – Chicago Instagram Captions – Funny Quotes About Chicago – Funny Chicago Quotes
  1. “You’d have to be a weir-mixture not to like Chicago Deep Dish.”

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

  3. “A facade of skyscrapers facing a lake and behind the facade, every type of dubiousness.” — E.M. Forster

  4. “The best food is in Chicago. There are great restaurants everywhere, from fancy places to burger joints.” – Steve Carell

  5. “Gigantic, Willful, Young, Chicago Sitteth At The Northwest Gates.”

  6. “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

  7. “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

  8. “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. 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—a dream that no matter who we are, where we come from; no matter what we look like or what hand life has dealt us; with hard work, and discipline, and dedication, we can make it if we try.” — Barack Obama

Interesting Quotes on Chicago

Chicago Quotes & Captions
Chicago Quotes – Chicago Captions For Instagram – Quotes About Chicago – Chicago Quotes Instagram – Funny Chicago Quotes
  1. “I fell in love, his name is ” Chicago”.”

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

  3. “Chicago is where the whole idea of community policing began.” – Mayor Rahm Emanuel

  4. “somewhere between living and dreaming, there’s a Chicago city”

  5. “They say that a good city tells a story, I must say, Chicago is a great storyteller”
  1. “A stranger visiting Chicago seems to enter into a new world.”

  2. “Until 1974, it was actually illegal to appear in public in Chicago if you were ugly.” – Scott Matthews

  3. “Chicago Has Disappointed Her Enemies And Astonished The World.”

  4. “My heart beats differently when I’m in Chicago. It slows down and I feel more at ease.” – Jeremy Piven

  5. “In Chicago, everyone is different and that means anyone can fit in”
Chicago Quotes - Quotes About Chicago
Chicago Quotes – Chicago Captions For Instagram – Quotes About Chicago – Chicago Quotes Instagram – Funny Chicago Quotes
  1. “I love Chicago; it is unique in the world. So much intellect, so many artistic voices.”

  2. “I should add that I very much enjoy certain cities especially Paris, New York and Chicago.” – Jim Harrison

  3. “Chicago does not go to the world, the world comes to Chicago!”

  4. “London is satisfied, Paris is resigned, but Chicago is always hopeful. Always it believes that something good is about to come off and it must hurry to meet it.”
  1. “I’m not sure whether I’m liking the life I’m living or living the life I like, but I feel blessed”

  2. “WELCOME TO CHICAGO. THIS TOWN STINKS LIKE A WHOREHOUSE AT LOW TIDE.” – DAVID MAMET
Chicago Quotes - Quotes About Chicago
Chicago Quotes – Chicago Captions For Instagram – Quotes About Chicago – Chicago Quotes Instagram – Funny Chicago Quotes
  1. “So if you visit Chicago, enjoy the many great courses, the Midwestern friendliness, and the city’s other amenities.” – Mike Royko

  2. .“A lot of real Chicago lives in the neighbourhood 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

  3. “Chicago’s one of the rare places where architecture is more visible.” – Frank Gehry

  4. “I’d love to do a film like ‘Chicago’. Something musical because I’ve obviously come from that background.” – Leona Lewis
Chicago Quotes - Chicago Captions For Instagram - Quotes About Chicago - Chicago Quotes Instagram - Funny Chicago Quotes
Chicago Quotes – Chicago Captions For Instagram – Quotes About Chicago – Chicago Quotes Instagram – Funny Chicago Quotes
  1. “Chicago is a sort of journalistic Yellowstone Park, offering a haven to a last herd of fantastic bravos.” – Ben Hecht

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

  3. “We’d speak French like a bunch of high school kids from Chicago, but we’d at least speak French.” – Michelle Obama

  4. “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

  5. “Chicago Is Known For Good Steaks, Expensive Stores And Beautiful Architecture.”
  1. “In Some Chicago Neighborhoods, Looking For A Parking Space Is Not Unlike Panning For Gold.”

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

  3. “Chicago is a town, a city that doesn’t ever have to measure itself against any other city.” – Anthony Bourdain
Chicago Quotes - Chicago Captions For Instagram - Quotes About Chicago - Chicago Quotes Instagram - Funny Chicago Quotes
Chicago Quotes – Chicago Captions For Instagram – Quotes About Chicago – Chicago Quotes Instagram – Funny Chicago Quotes
  1. “ 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

  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

  3. “Chicago divided your heart. Leaving you loving the joint for keeps. Yet knowing it never can love you.” – Nelson Algren
  1. “Chicago is the product of modern capitalism, and, like other great commercial centres, is unfit for human habitation.” – Eugene Debs

  2. “The city divided by the river is further divided by racial and lingual differences.” – Nelson Algren, ‘Chicago: City On The Make’
Chicago Quotes - Chicago Captions For Instagram - Quotes About Chicago - Chicago Quotes Instagram - Funny Chicago Quotes
Chicago Quotes – Chicago Captions For Instagram – Quotes About Chicago – Chicago Quotes Instagram – Funny Chicago Quotes
  1. “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

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

  3. “Chicago is unique. It is the only completely corrupt city in America.” – Charles Merriam
  1. “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, 1976

  2. “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

  3. “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

  4. “Chicago sounds rough to the maker of verse. One comfort we have — Cincinnati sounds worse.” – Oliver Wendell Holmes, January, 1880

Quotes About Chicago From Movies and Songs

Chicago Quotes - Chicago Captions For Instagram - Quotes About Chicago - Chicago Quotes Instagram - Funny Chicago Quotes
Chicago Quotes & Captions
  1. “It’s a very bad sign when a cop thinks that Chicago will fall apart without him.” – Running Scared

  2. Come on Baby,
    don’t you wanna go home
    Come on
    Baby, don’t you wanna go home
    Back from the land of California
    To my sweet home Chicago
    — Buddy Guy, Meet me in Chicago

  3. She came down from Chicago
    Where the mighty winds blow
    She was a picture in a frame
    And she said I gotta hit the highway
    — Stu Larsen, Chicago

  4. If we all go
    Maybe things will be better in Chicago
    To leave all we’ve ever known
    For a place we’ve never seen
    – Tom Waits, Chicago
  1. “Welcome to Chicago. This town stinks like a whorehouse at low tide.” – The Untouchables
Chicago Quotes - Quotes About Chicago
Chicago Quotes – Quotes About Chicago
  1. My kind of town, Chicago is
    My kind of people, too
    People who smile at you
    And each time I roam, Chicago is
    Calling me home, Chicago is
    Why I just grin like a clown
    It’s my kind of town
    — Frank Sinatra – My Kind Of Town

  2. Chicago, Chicago that toddling town
    Chicago, Chicago I will show you around
    I love it bet your bottom dollar you’ll lose the blues in Chicago, Chicago
    The town that Billy Sunday couldn’t shut down
    –Frank Sinatra, Chicago

  3. Well, one and one is two
    Six and two is eight
    Come on baby don’t ya make me late
    Hidehey
    Baby don’t you wanna go
    Back to that same old place
    Sweet home Chicago
    — Blue Brothers
  1. Ain’t Chicago got a lonely wind
    Makes you want to stop and call some lonesome
    friend Fightin’ the storm outside
    Rolling my windows high
    Blowin’ like no place I’ve ever been
    Ain’t Chicago got a lonely wind
    Ain’t Chicago got a lonely wind
    — Merle Haggard, Chicago Wind

  2. Cryin baby – honey don’t you want to go?
    Back to the land of California, to my sweet home Chicago.
    — Ben Harper, Sweet Home Chicago
Chicago Quotes - Quotes About Chicago
Chicago Quotes – Quotes On Chicago
  1. Now when she went to Chicago that night, she faced a wall
    And she woke up outside with all those leaves in her mouth
    And felt the pall
    And all night, the rain came on down
    But then she’d never been to Chicago at night before the fall
    — Spoon, Chicago at night

  2. “-It’s 106 miles to Chicago, we got a full tank of gas, half a pack of cigarettes, it’s dark… and we’re wearing glasses. -Hit it!” – The Blues Brothers

  3. Take me back to Chicago
    Lay my soul to rest
    Where my life was free and easy
    Remember me at my best
    – Take me back to Chicago
  1. I fell in love again
    All things go, all things go
    Drove to Chicago
    All things know, all things know
    — Sufjan Stevens, Chicago
Chicago Quotes - Quotes About Chicago
Chicago Quotes – Quotes On Chicago
  1. “Six bucks and my right nut says we’re not landing in Chicago.” – Planes Trains and Automobiles 1987

  2. “Back in Chicago, all we cared about was rock ‘n’ roll and staying out of the army.” John Belushi

  3. “- Eliot Ness: I want to get Capone! I don’t know how to do it. – Jim Malone: You wanna know how to get Capone? They pull a knife, you pull a gun. He sends one of yours to the hospital, you send one of his to the morgue. That’s the Chicago way! And that’s how you get Capone.” – The Untouchables 1987

Short Instagram Chicago Quotes & Captions

Chicago Quotes & Captions
Chicago Quotes & Captions
  1. “I am here, but my heart is in Chicago.”
  2. “I love Chicago; it is unique in the world.”
  3. “Live, love, Chicago”
  4. “Chicago, Chicago, that toddlin’ town.” Fred Fisher
  5. “Chicago is an October sort of city even in spring.” — Nelson Algren
  6. “Blown away by the Windy City!”
  7. “Chicago Ain’t No Sissy Town.”
  1. “Chicago my love, can’t wait to see you again”
Chicago Quotes - Quotes About Chicago
Chicago Quotes – Quotes About Chicago
  1. “Chicago is always a good idea.”
  2. “Chicago, I lake you a lot!”
  3. “It is wonderful to be here in the great state of Chicago.” ― Dan Quayle
  4. “Chicago is an October sort of city even in spring.” — Nelson Algren
  5. “I’m a chicago girl”
  6. “Chi like you a lot”
  7. “Make sure to relish the good times in Chicago.”
  8. “Chicago happened slowly, like a migraine.” – Neil Gaiman
  9. “The most American place in America, Chicago!” .
  10. “The best views in Chicago are at Navy Peer.”
  11. “A trip to Chicago takes quite a bit of dough.”
  12. “Dogs love Chicago because they get to visit Wiggly Field.”
Chicago Quotes - Quotes About Chicago
Chicago Quotes – Quotes About Chicago
  1. “A trip to Chicago is an L-evated experience.”
  2. “Sweet Home Chicago.”
  3. Chicago floats my boat.
  4. Chicago – windy city.
  1. Chicago stole a pizza my heart.
  2. Chicago – a pompous Milwaukee.
  3. We’re Chicago We Can Do Anything, Damn It.
  4. Chicago, where have you bean all my life
  5. I’m in love with cities, I’ve never been to and people I’ve never met.
  6. I love the town, No clocks, No locks, no restriction.
  7. Chicago Cubs Fans Are Ninety Percent Scar Tissue.
  8. In the twilight, it was a vision of power.
  9. Finally made it to Chicago. It’s a boat time!
  10. To be a Cubs fan is both a birthright and a curse.
  11. My kind of town
  12. Cool beans
  13. Go cubbies, go
  14. Chicago, you look great
  15. Just some beanie babies

End Of This Post

That’s all for this post I have shared with you 206 Best Funny Interesting Quotes about Chicago. Tell Me which one you liked the most in the comment section.

If you want to give me any suggestion or if you have any question feel free to ask me.

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