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85 Best Chicago Quotes for Your Trip to the Windy City 2024

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Known for its deep dish pizza and the Bean, the vibrant city of Chicago is one of the best cities in the USA for culture and cuisine. 

So if you’re looking to learn more then you’re in the right place. Below I’ve curated a bumper list of the best Chicago quotes that are guaranteed to have you booking your next trip to the Windy City! 

Not only can you use these quotes about Chicago to inspire your vacation, but they are also perfect for those looking for Chicago Captions for Instagram!

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Funny Chicago Puns for Instagram

Chicago: Bean there, done that.

A trip to Chicago is an L-evated experience. 

Blown away by the Windy City!

The best views in Chicago are at Navy Peer.

Finally made it to Chicago. It’s a boat time!

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Best Chicago Pun

Pier pressure brought me here (Navy Pier)

In Chicago, I’m in the Loop.

Having a Fields day.

Dogs love Chicago because they get to visit Wiggly Field.

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Puns about Chicago Food

Slice, Slice baby!

Taking cheesy selfies in Chicago.

A trip to Chicago takes quite a bit of dough.

Chicago stole a pizza my heart.

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Chicago Instagram Captions

You’d have to be a weir-mixture not to like Chicago Deep Dish.

Make sure to relish the good times in Chicago.

I never sausage a beautiful hot dog!

Let me be Frank, this is a tasty dog.

Chicago food is a weiner!

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Funny Chicago Quotes for Instagram

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

Chicago floats my boat.

What you talkin ’bout Willis Tower?

Chicago, I lake you a lot!

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Funny Chicago Phrases

Lake hair, don’t care.

Let minnow if you want to spend the day at Lake Michigan!

A day at Lake Michigan buoys my spirits!

Lake Michigan is pretty Great.

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Quotes from Chicago

“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

“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

“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

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Quotes on Chicago

“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

“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

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

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

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

“Going to Chicago was like going out of the world.” — Muddy Waters

“Sometimes words are just music themselves. Like ‘Chicago’ is a very musical sounding name.” — Tom Waits

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Famous Chicago Quotes

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

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

“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, 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

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

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Quotes about Chicago

“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

“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

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

“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

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Funny Chicago Captions for Instagram

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

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

“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

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

“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

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Chi Town Quotes

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

“In the twilight, it was a vision of power.” — Upton Sinclair 

“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

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

“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

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

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Chicago Sayings and Chicago Instagram Caption

“Chicago is an October sort of city even in spring.” — Nelson Algren

“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

“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

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

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

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Sayings about Chicago

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

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

“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 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 

“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

“…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

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Best Chicago Quotes Instagram

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

“You’d never think of taking a cab if you had to walk a mile down Chicago’s Michigan Avenue.” — Helmut Jahn

“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

“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

“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

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Chicago Captions Instagram

“Stuck in this Chicago loop.”

“Somewhere over the rainbow, you will find Chicago.”

Chicago is my kind of town.

Bright lights, city nights in Chicago

“Happiness is…. holding tickets that say Chicago.”

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Instagram Captions about Chicago

Big cities can have big hearts too, Chicago you have my heart

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

I’m just a small-town girl with big-city dreams

I’d rather be a lamppost in Chicago than a millionaire in any other city.- William A. Hulbert

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That’s over 85 Best Chicago IG Captions to Inspire You

I hope you’ve managed to find the perfect Chicago quote

I’d love to know which one is your favourite, and if I’ve missed any phrases about Chicago then please let me know in the comments below!

Love inspirational quotes and captions

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