Find the perfect captions to go with your Chicago photos with this huge collection of 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.
Related: Captions about Winter
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
Related: Lake Captions
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
Related: Spring Instagram Captions
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
Related: Best Movies About Travel
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
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
Related: Best Road Trip Songs
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
Related: Rainbow Captions
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
Related: Weekend Captions
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
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
RECENT TRAVEL POSTS
- 100+ Perfect Florida Instagram Captions For Sunshine State Photos
- 100+ Best Skiing Instagram Captions, Quotes, And Puns
- Over 200 Boston Instagram Captions And Quotes For Your Pictures
- 200+ Amsterdam Instagram Captions, Quotes, And Puns
- 300+ Perfect New York Instagram Captions To Go With Your NYC Photos
- Summer Captions For Instagram
- Camping Captions
- Atlanta Instagram Captions
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: