200+ Chicago Instagram Captions For Your Windy City Photos

Find the perfect captions to go with your Chicago photos with this huge collection of Chicago Instagram Captions!

Best Chicago Instagram Captions

Captions and Quotes About Chicago

Chicago is a city full of culture, history, and excitement. There's always something to do in Chicago, and you never know what you'll find around the next corner.

Some of the best things to do in Chicago include exploring the city's vast array of museums, checking out the architecture, and enjoying the city's incredible food scene.

This means you'll be taking plenty of photos, so you'll need some great Chicago Instagram captions to go along with them!

Here are over 200 Chicago Instagram captions that will perfectly capture your city experience:

Best Chicago Instagram Captions

There's no place like Chicago.

Welcome to The Windy City.

Chicago is my kind of town.

If you're not in Chicago, you're not in the game.

I'm a Chicagoan through and through.

Just another day in the Windy City.

I adore Chicago.

I'll never tire of this city.

The best thing about Chicago is the people.

My favorite thing about Chicago is the food.

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Funny Chicago Captions

You can't be grumpy in Chicago because the city won't let you.

If you don't like the weather in Chicago, just wait a minute.

In Chicago, we know how to keep our heads up during a downpour.

There's always a reason to smile in Chicago.

No matter the season, Chicago is always beautiful.

Things ain’t so bad in the windy city

Let the city set you free

I must confess a shameful secret: I love Chicago best in the cold.- by Erik Larson

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Instagram Captions For Chicago

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.- by Orson Welles

Once upon a time, in the enchanted land of Chicago

I adore Chicago. It is the pulse of America.- by Sarah Bernhardt

Stuck in this Chicago loop

Daydreaming in Chicago

Chicago is an October sort of city even in spring.- by Nelson Algren

You cannot stop Chicago

PS. Chicago I love you

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Chicago Puns

Chicago stole a pizza my heart

A day at Lake Michigan buoys my spirits!

Relishing the good times in Chicago

It's bean real, Chicago!

I'm in a relationship with Chicago and pizza

Chicago has my heart on lock

You're always a Red Line away from a good time

No matter what, deep dish always love you

Proud to be Chi

There's no place like home, except for Chicago

My favorite color is Chicago skyline blue

I'll never stop falling in love with Chicago

Just another brick in the Windy City

My happy place is the Bean

I could never live anywhere but Chicago

Life is just a hot dog stand away from being perfect

Instagram Captions About Chicago

Bright lights, city nights in Chicago

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

Loving Chicago is like loving a woman with a broken nose.- by Nelson Algren

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.- by Dominic A. Pacyga

But when I go to Chicago, I know I’m home.- by Hank Sauer

Happiness is…. holding tickets that say Chicago

Chicago- by a pompous Milwaukee.- by Leonard Louis Levinson

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 backward? What other city makes traffic flow backward?- by Mike Royko

You’re a phony celebrity and in two weeks no one’s going to give a sh.t about you… that’s Chicago

Sweet home Chicago

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Chicago Captions For Instagram

Chicago does not go to the world, the world comes to Chicago!- by Peter Orner

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.- by Studs Terkel

Dear Chicago, I will never get over you

Follow your heart, even if it takes you all the way to Chicago

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

East or West, Chicago is the best

Keep calm and go to Chicago

I think that’s how Chicago got started. A bunch of people in New York said, ‘Gee, I’m enjoying the crime and poverty, but it just isn’t cold enough. Let’s go west.- by Richard Jeni

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

Let me tell you something. I’m from Chicago. I don’t break.- by Barack Obama

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More Captions For Chicago Photos

My client feels that it was a combination of liquor and jazz that led to the downfall

All you need is love and skylines

Chi chi cheese. We’re in Chicago!

I’m gonna be a celebrity, that means somebody everyone knows. They’re gonna recognize my eyes, my hair, my teeth, my boobs, my nose

Chicago ain’t no sissy town.- by Hinky Dink Kenna

Either you love Chicago or you are wrong

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.- by Harold Ramis

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.- by H. L. Mencken

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. by Mark Twain

Chicago, you look great

Great Chicago Phrases To Use With Your Photos

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

Meet me in Chicago

Hell has been described as a pocket edition of Chicago.- by Ashley Montagu

I fell in love, his name is Chicago

Life’s better by the lake

I don’t keep calm I’m from Chicago.

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

Chicago is a town, a city that doesn’t even 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.- by Anthony Bourdain

Chi likes you a lot!

Eventually, I think Chicago will be the most beautiful great city left in the world.- by Frank Lloyd Wright

Chicago Puns And Sayings

Big cities can have big hearts too

Chicago you have my heart

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.- by Barack Obama

Going to Chicago was like going out of the world.- by Muddy Waters

Chicago is calling and I must go

Theatre in Chicago will always be my first love.- by William Petersen

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.- by Mary Schmich

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.- by Pat Colander

Chicago’s neighbourhoods have always been the city’s greatest strength.- by Jane Byrne

It’s a very bad sign when a cop thinks that Chicago will fall apart without him.- by Running Scared

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Instagram Chicago Updates You Can Use

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.- by William A. Hulbert

Windy Wednesday in Chicago

A concrete version of paradise

Friends, drinks and Chi-Town

I miss everything about Chicago, except January and February.- by Gary Cole

You wanted advice? Well here it is, straight from me to you, keep your paws off my underwear

I’m blown away by the Chicago skyline

Somewhere over the rainbow, you will find Chicago

You can leave Chicago, but it will never leave you

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Captions To Use With Chicago Updates

Cheers from Chicago!

Meet me in The Windy City

There is only one thing for Chicago to do, and that’s to move to a better neighbourhood.- by Herman Fetzer


Roxie Hart: You’re, the Velma Kelly. I was there the night you got arrested.- by Velma Kelly: Yeah? You and half of Chicago

Once upon a time in Chicago

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.- by Oprah Winfrey

You can like the life you’re living, you can live the life you like

I’m impressed with the people from Chicago. Hollywood is hype. New York is talk. Chicago is work.- by Michael Douglas

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.- by Anthony Bourdain

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Fantastic Chicago Instagram Text

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 a ticket for, and then ‘Les Miserables’ and then ‘Chicago’.- by America Ferrera

You never forget your first day in Chicago

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.- by Jeremy Piven

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, 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.- by Henry Mencken

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

Chicago seems a big city instead of merely a large place.- by A.J. Liebling

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.- by Nelson Algren

Perhaps the most typically American place in America.- by James Bryce

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

Hello Chicago, your lights are fireflies in my heart

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Chicago Caption Collection

Kitty Baxter: I’ll give you three: go to hell

This is my kind of town, Chicago is.- by Frank Sinatra

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.- by Bill Granger

Sometimes words are just music themselves. Like ‘Chicago’ is a very musical sounding name.- by Tom Waits

My kind of town

Chicago let’s do it

We’re Chicago- by we can do anything, damn it.- by Elva Rubio

My audience loves me. And I love them. And they love me for lovin’ them and I love them for lovin’ me. And we love each other. And that’s ’cause none of us got enough love in our childhoods. And that’s showbiz, kid

Chicago shines even brighter at night

It is the most perfect presentation of nineteenth-century individualistic industrialism I have ever seen. Chicago is one hoarse cry for discipline.- by H. G. Wells


Dave Briggs visiting an island in GreeceDave Briggs
Dave is a travel writer who spends his time traveling around and writing about Greece. As well as putting together this list of Chicago Instagram Captions, he has written hundreds of travel blog posts about destinations and adventure activities. Follow Dave on social media for travel inspiration from around the world:

Instagram Captions About Chicago