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Chicago Instagram Captions

These Chicago Instagram captions hope to capture some of the grandeur of the Windy City.

Noted for its bold architecture punctuated by perhaps the most impressive city skyline in the world, the city of Chicago stands tall for many reasons. Museums, hard-working citizens, Lake Michigan’s proximity, and deep-dish pizza are just a few things that come to mind.

And there is so much more. A visit to the city should be on everyone’s bucket list. These captions will help your photos come to life.

Best Chicago Instagram Captions

Chicago is always a good idea.

What you talkin’ about Willis Tower?

Either you love Chicago, or you’re wrong.

Friends, drinks, and Chi-town.

Having a Fields Day.

My kind of Chi-town.

The White City.

No ketchup on hot dogs — Ever!

Sweet home, Chicago.

Best Chicago captions.

All I have to say is “deep-dish pizza.”

Cheers from Chicago!

East or West, Chicago is the best.

You will never forget your first day in Chicago.

The City of Beautiful.

Stuck in the Chicago Loop.

I fell in love; his name is Chicago.

Chicago: A concrete version of paradise.

The Big Onion.

The Jewel of the Midwest.

The Bean Captions

Chicago: Bean there, done that.

Chicago, where have you bean all my life?

Bean thinking about you.

Chicago, where have you bean all my life.

I’ve never bean to Chicago before.

All the corny captions have bean used.

Chicago’s frozen bean.

Cool beans.

I’ve never bean to Chicago before.

Just a couple of Beanie Babies.

Good Slogans for Chicago

Chicago, you have my heart!

Lucky to be Chi-rish!

What you talkin’ bout Willis Tower?

Chicago stole a pizza my heart.

This is my kind of town – Chicago is.

I miss everything about Chicago, except January and February.

When I go to Chicago, I know I am home.

Finally made it to Chicago; it’s a boat time!

All you need is love and skylines.

Stuck in this Chicago loop.

Either you love Chicago, or you are wrong.

Sweet home Chicago.

You can take a girl out of Chicago, but you can’t take the “Chicago” out of the girl.

Chicago — “City of Wind.” But, I call it the “City of dreams.”

Keepin’ it Chicago.

Normal is boring, Christmas in Chicago.

We are on Chicago time.

Chicago floats my boat.

Windy City Phrases

The summer weather in Chicago really blows me away.

Meet me in the Windy City.

I’m going to the Windy City for a week of fun in the sun.

Things ain’t so bad in the Windy City.

Enjoying Chicago is a breeze.

Blown away by the Windy City!

The Windy City: Sweet home, Chicago.

Throw caution to the Windy City.

The answer, my friend, is blowing in the Windy City.

But when I go to Chicago, I know I’m home.

Next Stop Chitown Captions

The Chi.

Chi town, Chi town, we gonna show em how to get down.

Home of America’s original gangster.

The Friendly Confines.

Just around the river bend.

We’re going to Chicago — Hot Dog!

I got a ‘lil taste for Chicago.

Life moves pretty fast. If you don’t stop and look around once in a while, you could miss it.
Ferris Bueller

Summertime Chi!

Go, Cubs, go!

Let’s play two!

Meet me in Chicago.

Dogs love Chicago because they get to visit Wiggly field.

Slice, slice, baby!

City in a Garden.

Cloud Gate: Selfie Capital of the World!

Let me be frank; this is a tasty dog.

Inspirational Chicago Instagram Captions

Taking cheesy selfies in Chicago.

Let me be Frank, this is a tasty dog.

Wright around the lake.

Get the L outta here!

I saw Sue!

The Magnificient Mile!

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

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

Lake Michigan is pretty Great!

A trip to Chicago is an L-evated experience.

Make sure to Relish the good times in Chicago.

Once upon a time in Chicago.

Follow your heart all the way to Chicago.

You can leave Chicago, but it will never leave you.

LSD (Lake Shore Drive).

City of Big Shoulders Captions

Once upon a time, in the enchanted land of Chicago.

Somewhere over the rainbow, you will find Chicago.

I’d rather be a lamppost in Chicago than a millionaire in another city.

Stinky onions!

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

Hello city, your lights are fireflies in my heart.

I love places that make you realize how tiny you and your problems are.

There’s no time to be bored in a world as beautiful as this.

But first, Chicago.

The 312.

Bright lights, big city.

Notable Chicago Instagram Captions

I haven’t been everywhere, but it’s on my list.

Wherever you go becomes a part of you somehow.

Dear Chicago, I will never get over you.

You never forget your first day in Chicago.

Somewhere over the rainbow you will find Chicago.

Chicago is calling and I must go.

You cannot stop Chicago.

Theater in Chicago will always be my first love.

The Second City Captions

“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, outgoing, it’s tough, it’s opinionated, and everybody’s got a story.”
Anthony Bourdain

But when I go to Chicago, I know I’m home.

Chicago food is a weiner!

Live, love, Chicago.

Bright lights and Chicago nights.

Welcome to Chicago, boys.

Either you love Chicago or you are wrong.

Lake hair, don’t care.

Let the city set you free.

P.S. I love Chicago.

Life is better by the lake.

I wonder if Chicago misses me too.

Chicago dreams coming alive.

Chicago, I lake you a lot!

Keep Calm and go to Chicago.

City by the Lake.

To be a Cubs fan is both a birthright and a curse.

Big cities can have big hearts too.

“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

Classic Chicago.

When in doubt, visit Chicago.

Paris of the Prairie.

My kind of town.

Heart of America.

Funny Captions for the City of Chicago

The skyline view of Chicago needs no introduction.

Chicago is the kind of city that is above the clouds.

After visiting Chicago, anything normal feels boring.

People call it the city of wind; I call it the city of dreams.

Money can’t buy happiness, but it can surely buy tickets to Chicago.

What happens in Chicago, stays in Chicago.

Make sure you cheer the good times staying in Chicago.

Going to Chicago was one of the best mistakes I made in my life.

I am impressed by everything in Chicago, from the architecture to the people, everything.

There is something in the Chicago air that makes sleep useless.

Chicago is an October sort of city, even in the spring.

Worldly Chicago Captions

Chicago does not go to the world, the world comes to Chicago.

If you don’t know by now, I’m talkin’ bout Chi-town.

Chicago will give you a chance.

Chicago has disappointed her enemies and astonished the world.

Bad, bad, Leroy Brown. The baddest man in the whole damn town.

Chi-town, Chi-town, we gonna show em how we get down.

Chicago, that’s my hometown.

Don’t leave me now, Chicago.

Bear down.

You can’t make everyone happy. You are not Chicago.

This city just showed you it is full of people ready to believe in good.

Big dreams, good music, and even better food.

We are in Chicago, we can do anything.

I adore Chicago. It is the pulse of America.

Chicago-a pompous Milwaukee.

It’s wonderful to be here in the great state of Chicago.

The City That Works Phrases

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

Chicago will give you a chance. The Sporting spirit is the spirit of Chicago.

Chicago, ain’t no sissy town.

We operate on Chicago time.

Chicago Cubs fans are ninety percent scar tissue.

Chicago will give you a chance.

But there is a light on in Chicago and I should be home.

Chicago, here we come.

Born and bred in Chicago.

Chicago dreams coming alive.

Chicago is calling my name.

Take me out to the ball game, but more importantly, take me out to Wrigley Field.

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

Happiness is holding tickets that say Chicago.

Chicago shines even brighter at night.

A bad day in Chicago is still better than a good day anywhere else.

By Molly O’Halloran

Molly loves the Chicago skyline, Lou Malnati’s pizza, and the Chicago Magic Lounge.


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