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201 Awesome Chicago Instagram Captions + Chicago Quotes

Are you in search of some awesome Chicago Instagram captions and Chicago quotes for your social media, a presentation, blog post or any other type of document? Then you have come to the right place! Chicago is fun, it’s exciting and if you have recently visited, you are planning a Chicago itinerary or you live in Chicago you will definitely want to share some of your favourite photos Instagram! In this post I share 201 awesome Chicago Instagram captions and Chicago quotes that you can quite literally copy and paste into your app- are you ready for some Chicago Instagram captions inspiration? Read on…

The best Chicago Instagram captions

Lets start off this post by looking at some of the very best Chicago Instagram captions-

Bright lights, city nights in Chicago.

Big cities can have big hearts too.

Chicago dreamin’.

Somewhere over the rainbow, you will find Chicago.

I adore Chicago. It is the pulse of America.

Chicago floats my boat.

I fell in love, his name is Chicago.

Life’s better by the lake.

Chicago, I’m coming for you.

East or West, Chicago is the best.

Chicago shines even brighter at night.

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

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

Chicago is always a good idea.

Happiness is…. holding tickets that say Chicago.

I don’t keep calm I’m from Chicago.

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

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

Chicago Instagram Captions + Chicago Quotes

There are plenty of popular Chicago Instagram captions that are perfect for your social media, here are some examples-

Friends, drinks and Chi-Town.

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

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

All you need is love and skylines.

Never seen something like Chicago before.

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.

Chicago is calling and I must go.

Wherever you go, go with all you are heart especially if you are in Chicago.

Either you love Chicago or you are wrong.

My heart burns for the city lights.

Theatre in Chicago will always be my first love.

Keep calm and go to Chicago.

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

Chicago’s neighbourhoods have always been the city’s greatest strength.

Famous Chicago Instagram captions

There are plenty of famous Chicago Instagram captions too, here are my top picks-

This is my kind of town, Chicago is. – Frank Sinatra

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. – Richard Jeni

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

There is none other quite like my City of Big Shoulders. – Irv Kupcinet

Chicago Instagram Captions + Chicago Quotes

Chicago – a pompous Milwaukee.– Leonard Louis Levinson

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

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

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

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

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

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

Chicago Cubs fans are ninety percent scar tissue. – George F. Will

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

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

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

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

Chicago Instagram Captions + Chicago Quotes

Chicago is not the most corrupt American city. It’s the most theatrically corrupt. – Studs Terkel

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

Chicago is unique. It is the only completely corrupt city in America.– Charles Merriam

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

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

A roaring city, gunfire and applause and thunder. Gleaming but made of bone and stone. – Brian Doyle

Chicago is partly a fairy tale because it’s inside one person’s head, so that part of it’s made up and the rest of it is reality. – Colleen Atwood

Chicago, mistress of the lakes, controller of our inland trade, the freest city of our states, what wondrous strides thy fame has made!– Charles Frederick White

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?” – Mike Royko

In the twilight, it was a vision of power. – Upton Sinclair 

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

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

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 coluorful in its shadiness.– Studs Terkel

I have struck a city – a real city – and they call it Chicago. – Rudyard Kipling

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

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

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

A city without illusions but with vaulting imaginations and expectations. A city of burning energies on the shore of a huge northern sea.– Brian Doyle

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

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

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 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

Short Chicago Instagram captions

Sometimes only Chicago Instagram captions will do! Here are my favourite short Chicago Instagram captions-

Chicago, you look great.

Chicago Instagram Captions + Chicago Quotes

Welcome to Chicago.

Once upon a time in Chicago.

Sweet home Chicago.

Meet me in Chicago.

Meet me in Windy City.

Daydreaming in Chicago.

Chicago let’s do it.

Let the city set you free.

Views from the windy city.

A concrete version of paradise.

Cheers from Chicago!

Wanderlust and city dust.

Take me to Chicago.

My kind of town.

Chicago Instagram Captions + Chicago Quotes

Windy Wednesday in Chicago. 

Live, love, Chicago.

Stuck in this Chicago loop.

You cannot stop Chicago.

P.S. I love Chicago.

Funny Chicago Instagram captions

There are some really funny Chicago Instagram captions that are perfect for your grid if you want to make your followers smile, here are my top picks for funny Chicago Instagram captions-

The weather in Chicago really… blows me away.

Chicago stole a pizza of my heart.

Lake hair, don’t care.

Chicago Instagram Captions + Chicago Quotes

Just a cheesy selfie in Chicago.

In Chicago, I’m in the Loop.

What you talkin’ bout Willis Tower?

Chi likes you a lot!

Slice, Slice baby!

Let me be Frank, this is a tasty dog.

Chicago food is a Weiner!

Chicago Instagram Captions + Chicago Quotes

Chicago, I lake you a lot!

Chicago, it’s bean real!

I never sausage a beautiful hot dog.

The windy city is in my back pocket.

Chicago: Bean there, done that.

​​Make sure to relish the good times in Chicago.

A trip to Chicago takes quite a bit of dough.

Having a Fields day in Chicago.

A trip to Chicago is an L-evated experience.

Chicago Instagram Captions + Chicago Quotes

Let’s be Frank, Chicago is always a good idea.

Chi chi cheese. We’re in Chicago!

I’m blown away by the Chicago skyline.

A day at Lake Michigan buoys my spirits!

Pier pressure brought me here.

Chicago, where have you bean all my life.

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

Get blown away by the sights of the windy city.

Lake Michigan is pretty Great.

Chicago’s frozen bean.

Dogs love Chicago because they get to visit Wiggly Field.

I’ve never bean to Chicago before.

Chicago Instagram Captions + Chicago Quotes

You haven’t bean to Chicago unless you’ve bean here.

Just a couple of beanie babies.

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

“In a world filled with crazy, I hope you choose to live in Chicago.”

​​I bean thinkin’ about you Chicago.

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

Cool beans.

Interesting Chicago Instagram captions

Chicago is such an interesting place, so it is no surprise that there are so many interesting Chicago Instagram captions. Here are my favourite interesting Chicago Instagram captions-

A lot of real Chicago lives in the neighbourhood 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.

Things ain’t so bad in the windy city.

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’.

Chicago Instagram Captions + Chicago Quotes

Chicago is tough so are you.

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.

The best views in Chicago are at Navy Peer.

That weekend the city blushed with a great heat wave but on Monday it rained, cooling the ache in the street’s burn.

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.

Chicago Instagram Captions + Chicago Quotes

Being Irish was a big thing for me, particularly growing up in Chicago.

Out in Chicago, the only genuinely civilised 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.

…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.

A facade of skyscrapers facing a lake and behind the facade, every type of dubiousness.

After three years in Chicago, I decided to call it a career.

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.

Blessed are the people of Chicago, and blessed the strangers in their midst, in the article of malt liquor; for it is excellent, it is honest, and it is abundant.

Guys, you’re Chicago. You’re the home of Laurie Metcalf and Jessie Mueller and Steppenwolf. And a million, a million, a million brilliant theatre practitioners.

Chicago has a strange metaphysical elegance of death about it.

Chicago Instagram Captions + Chicago Quotes

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.

If man is, or is searching to be, omnipotent, I am willing to accept Chicago’s gigantism; but I should like the opposite to be accepted as well: a city which would fit in the hollow of one’s hand.

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.

Chicago Instagram Captions + Chicago Quotes

You never forget your first day in Chicago.

We struck the home trail now, and in a few hours were in that astonishing Chicago – a city where they are always rubbing a lamp, and fetching up the genii, and contriving and achieving new impossibilities.

A city that was to forge out of steel and blood-red neon its own peculiar wilderness.

Until 1974, it was actually illegal to appear in public in Chicago if you were ugly.

Chicago is a sort of journalistic Yellowstone Park, offering haven to a last herd of fantastic bravos.

Chicago is the product of modern capitalism, and, like other great commercial centres, is unfit for human habitation.

Chicago sounds rough to the maker of verse. One comfort we have – Cincinnati sounds worse.

Chicago has so much excellent architecture that they feel obliged to tear some of it down now and then and erect terrible buildings just to help us all appreciate the good stuff.

I miss everything about Chicago, except January and February.

You can have a pretty wonderful artistic life and never leave Chicago.

Chicago, the city where you can experience four seasons in one day.

Chicago Instagram Captions + Chicago Quotes

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.

Chicago is where the whole idea of community policing began.

No realistic, sane person goes around Chicago without protection.

The most American place in America, Chicago.

Make sure to relish the good times in Chicago.

Feelings come and go like clouds in the Windy City.

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

Chicago Instagram captions from the movies

Chicago often appears in the movies, therefore there are naturally many cool Chicago Instagram captions from the movies-

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 sunglasses.– The Blue Brothers

​​Chicago happened slowly, like a migraine. – Neil Gaiman, ‘American Gods’

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

One of the problems with people in Chicago, she remembered, was that they were never lonely at the same time. – Lorrie Moore, ‘Birds Of America’

Chicago Instagram Captions + Chicago Quotes

Let the worthy citizens of Chicago get their liquor the best way they can. I’m sick of the job-it’s a thankless one and full of grief. I’ve spent the best years of my life being a public benefactor. – Al Capone

Welcome to Chicago. This town stinks like a whorehouse at low tide.” – The Untouchables

Back in Chicago, all we cared about was Rock ‘n’ Roll and staying out of the army. – John Belushi 

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! – The Untouchables

He rules Chicago with absolute power. No one could touch him. No one could stop him.– AL Capone

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 have 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. – Running Scared

More Chicago Instagram captions

And here are a few final Chicago Instagram captions to finish off with-

Chicago is always on my mind.

I’m having an affair with Chicago.

Dear Chicago, I will never get over you.

Chicago has disappointed her enemies and astonished the world.

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

Hello Chicago, you’re looking gorgeous today.

Chicago Instagram Captions + Chicago Quotes

The people of Chicago are a proud people – and for good reason.

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

We’re Chicago – we can do anything, damn it.

I am here, but my heart is in Chicago.

Going to Chicago was like going out of the world.

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

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

Hello Chicago, your lights are fireflies in my heart.

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

Chicago Instagram Captions + Chicago Quotes

Started from the bottom, now we here.

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

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.

I love Chicago; it is unique in the world.

I’m a Chicago girl.

Born and bred in Chicago.

Chicago Instagram captions- further reading

If you enjoyed this post on Chicago Instagram captions then I am sure you will love these too-

By the way- are there are Chicago Instagram captions that I missed out? Let me know in the comments!