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100 + Chicago Quotes for Inspiring Instagram Captions

Chicago should be on the very top of your USA bucket list.

Here are 100+ Chicago Quotes to (hopefully) inspire you to visit Chicago or if you have already been use as awesome Instagram captions!   

And, If you love Instagram we developed some kick ass Instagram presets (filters) so you can edit your photos in 1 click!

100+ Chicago Quotes for inspiring instagram captions

Chicago Instagram Captions

Chicago is one of the best places in the world for Instagrammers. Here are our favourite Chicago Instagram captions:

“My kind of town.”

“There’s no place like Chicago.”

“Sweet home Chicago.”

“This is the city that I love.”

“P.S. I love Chicago.

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

 “Chicago – windy city.”

 “Keep calm and go to Chicago.”

“The windy city.”

“Either you love Chicago or you are wrong.”


Funny Chicago Quotes

Here are our favourite Chicago Funny Quotes:

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

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

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

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

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

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

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

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

“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

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

“Hell has been described as a pocket edition of Chicago.” Ashley Montagu


Quotes from Chicago the Musical

One of the most famous musicals! Here are our favourite quotes from Chicago the Musical:

Billy Flynn: I don’t like to blow my own horn, but believe me if Jesus Christ had lived in Chicago today and if he had five thousand dollars and he’d come to me, lets just say things would have turned out differently.

“If you can’t be famous, be infamous.”

“I’d love to do a film like ‘Chicago’. Something musical because I’ve obviously come from that background.” – Leona Lewis

“It would be criminal to miss it.”

“Give them the old razzle dazzle.”

“I just wanted to see every single musical I could. The very first one I saw was ‘Beauty and the Beast’, the only one I could get tickets for, and then ‘Les Miserables’ and then ‘Chicago’.” – America Ferrera

“I can’t do it alone.”

“When you’re good to Mama, Mama’s good to you.”

“Stay away from jazz and liquor; and the men who play for fun.”

“I should shoot 2 warning shots into my husband’s head if he pops that gum one more time.”


Famous Chicago Quotes

Our absolute favourite famous chicago quotes are as follows:

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

“Chicago is my hometown and will always have a special place in my heart.” – Kenneth Choi

“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

“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

“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

“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

“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

“But Chicago is a great American city. Perhaps it is the last of the great American cities.” Norman Mailer

“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” NY Times 5 May 85

“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” NY Times 5 May 85

“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,” 1902

Chicago Puns

Pop – It’s better to order a pop when you’re in Chicago instead of soda.

Da – Saturday Night Live fans surely know “DA BEARS” phrase, so the word ‘da’ in Chicago is used instead of ‘the’

LSD – you probably have already heard this word but as a drug, in Chicago people refer to Lake Shore Drive

Gaspers’ Block – traffic jam

Grachki – garage key

Washroom – when Chicagoans need to go to WC they say ‘I’m going to the washroom’.

Sammich – hungry? Try Chicagoan sammiches – sandwich

A couple, two, three or A cuppa two three – means ‘a few’

Dip – they use this word when they want to leave, like ‘Let’s dip from here’

Gym shoes – Sneakers

Frunchroom – Front room

Chicago Movie Quotes

“-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!” – movie ‘The Blues Brothers’

“I’m going to do all my movies here in Chicago. The Tribune referred to me as a ‘former Chicagoan’. As if, to do anything, I had to leave Chicago. I never left. I worked until I was 29 at the Leo Burnett advertising agency, and then I quit to do this. This is a working city, where people go to their jobs and raise their kids and live their lives.” – John Hughes

“It’s a very bad sign when a cop thinks that Chicago will fall apart without him.” – movie ‘Running Scared’

“Welcome to Chicago.This town stinks like a whorehouse at low tide.” – movie ‘The Untouchables’, 1987

“- 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.” – movie ‘The Untouchables’, 1987

“I’m from Chicago, my family started a chain of movie theatres in Chicago that was around for 70 years and then one of them became the head of Paramount and the other was the head of production at MGM and we all came out of Chicago.” – Bob Balaban

“Six bucks and my right nut says we’re not landing in Chicago.” – movie ‘Planes, Trains and Automobiles’, 1987

“He ruled Chicago with absolute power. No one could touch him. No one could stop him.” – AL Capone


“My dad was born in Chicago in 1908… his parents came from Russia. They settled in Chicago, where they lived in a little tiny grocery store with eight or nine children – in the backroom all together – and my grandmother got the idea to go into the movie business.” – Bob Balaban

“I warn you, Jedediah, 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 as Citizen Kane


“Chicago, Chicago, that toddlin’ town, that toddlin’ town Chicago, Chicago, I’ll show you around, I love it Betcha bottom dollar you’ll lose your blues In Chicago, Chicago The town that Billy Sunday could not shut down.” – Frank Sinatra, Chicago

“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

“Cryin baby – honey don’t you want to go? Back to the land of California, to my sweet home Chicago.” – Ben Harpen, Sweet Home Chicago

“So come on, baby don’t you wanna go Back to that same old place Sweet home Chicago.” – The Jimmy Rogers All-Stars, Sweet Home Chicago

“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

“Take me back to Chicago Lay my soul to rest Where my life was free and easy Remember me at my best.” – Chicago, Take me back to Chicago

“I fell in love again All things go, all things go Drove to Chicago All things know, all things know.” – Sufjan Stevens, Chicago

“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

“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.” – Merle Haggard, Chicago Wind

“Now when she went to Chicago that night She faced a wall And she woke up outside with all those leaves in her her mouth And felt the pall An all night the rain came on down But then, she’d never been to Chicago at night Before the fall.” – Spoon, Chicago at night

Romantic Quotes about Chicago

“Dear Chicago, when I wake up in the morning and see your skyline – the terra cotta of the Wrigley Building, the height of the Willis Tower, the shiny sides of my beloved Trump Tower – I know I’m home. I feel a certain energy walking between your spires, but recognize that what makes you special to me is that my roots are here.” – Bill Rancic

“I must confess a shameful secret: I love Chicago best in the cold.” ―Erik Larson, The Devil in the White City: Murder, Magic, and Madness at the Fair That Changed America

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

“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

“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

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

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

“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

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

“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


Chicago Travel Quotes

“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

“The first time I went to Chicago was on a family road trip. We had our dog with us, and when we hit Chicago, I couldn’t believe how many people kept coming up to us, telling us how handsome our dog was! He’s a Rottweiler-Australian Shepherd mix, and he is a good-looking dog, but obviously Chicago is very dog-friendly.” – Hong Chau

“It’s wonderful to be here in the great state of Chicago.” – Dan Quayle

“I look forward to going to Chicago because it’s where I grew up, and the food there is so munch. Especially during the winter, I get deep dish pizza or Italian beef, and it warms me up. It’s something I don’t normally get, especially here in L.A. where you’re always trying to be healthy.” – Ron Funches

“I just know that I could never spend a winter in Chicago or some place like that. I’m just not a cold weather person.” – Emily Robinson

“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, Life On The Mississippi 1883

“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

“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,” 1902

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

“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


Chicago Architecture Quotes

“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

“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

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

“I have lived in other cities but been inside of only one. I once wore all the windows of Chicago and all its doorways on a key ring. Salons, mansions, alleys, courtrooms, depots, factories, hotels, police cells, the lake front, the rooftops and the sidewalks were my haberdashery.” – Ben Hecht

“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

“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

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

“Nor is it out of character that Chicago’s grandest achievement- a largely manmade arc of lakefront parks and beaches – began as a mistake, from waste thrown into Lake Michigan – a 75-year-old dump.” Pat Colander

Chicago Bears Quotes

“If I get back into coaching, it would have to be a situation where there was a realistic opportunity to win a Super Bowl.” – Mike Shanahan

“We have a strange and wonderful relationship – he’s strange and I’m wonderful.” – Mike Ditka

“I don’t always scream at my TV, but when I do, it’s Bears season.”

“If God had wanted man to play soccer, he wouldn’t have given us arms.” – Mike Ditka

“Times can change and players come and go. And though the memories may fade. MONSTERS never die. Thank you for doing us proud.” – Brian Urlacher

“Success isn’t permanent and failure isn’t fatal.” – Mike Ditka

“Before you can win, you have to believe you are worthy.” – Mike Ditka

“And on the 8th day God looked all over his creation and said “America needs a football team”. So God created the Chicago Bears.”

“I just want to watch Bears football and ignore all of my adult problems.”

“Win, lose or tie I’m a Bears fan til I die.”

Chicago Cubs Quotes

“The Chicago cubs A franchise barely alive. Gentlemen, we can rebuild it. We have the technology. We have the capability to build the first World Series roster since 1908. It will not be easy. But it will be better than it was before. Better. Stronger.Faster.” – Theo Epstein

“One of the best feelings in the world is watching things fall into place after having watched them fall apart for so long. Go CUBS! Go!!”

“There is one thing I will never believe: and that is The Sox are better than The Cubs.” – West Wrigley

“Real women love baseball, smart women love The Cubs.”

“Cubs win. We’ll skip the exclamation point until they win a couple more.”

“No matter what you have achieved or accomplished, keep pushing to get better. Don’t let good enough, be GOOD ENOUGH.” – Kris Bryant

“Make sure your worst enemy doesn’t live between your ears. Self-doubt kills dreams. You are more capable than you think.” – Kris Bryant

“I don’t know how good I can be. That’s what I am trying to figure out. That’s why I do what I do every day in between starts to prepare myself as best as possible to go out there and see what the results are.” – Jake Arrieta

“What you do speaks louder than what you say.” – Anthony Rizzo

“If someone says I can’t do something, I’ll try to prove them wrong. If it’s not good enough, so be it, but I’m going to give it my best shot.” – Kyle Schwarber

So let us know, which one is your favourite?

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  • MC Miller

    MC Miller is a travel blogger and writer who has travelled America extensively and abroad to over 80 countries. He founded Couple Travel The World in 2017. Since then, he has spent over 6 years on the road as a full time travel couple. When he not traveling he likes to spend quality time with his partner Bett, planning our their next date or romantic getaway!