85 Top Captions & Chicago Quotes for Instagram

Taking a trip to Chicago? Don’t forget to add some cute captions to your photos when you post them on Instagram! With the help of these Chicago quotes for Instagram, you’ll have all the inspiration you need to caption each one of your trip photos.

Chicago Quotes for Instagram

Show off your next trip to the windy city on social media with the help of these fun Chicago quotes for Instagram and social media caption ideas!

From famous quotes about Chicago to cute captions to accent your travel photos, you’ll have everything you need to show off all the fun you had on your city adventure.

Happiness is…. holding tickets that say Chicago.
“We’re Chicago – we can do anything, damn it.” – Elva Rubio
“I have struck a city – a real city – and they call it Chicago.” – Rudyard Kipling
Chicago: Bean there, done that.
“Let me tell you something. I’m from Chicago. I don’t break.” – Barack Obama
“In the twilight, it was a vision of power.” – Upton Sinclair
Blown away by the Windy City!
“Six bucks and my right nut says we’re not landing in Chicago.” – Planes, Trains and Automobiles
“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
“I’m impressed with the people from Chicago. Hollywood is hype. New York is talk. Chicago is work.” —Michael Douglas
“Chicago ain’t no sissy town.” – Hinky Dink Kenna
Chicago stole a pizza my heart.
Modern Chicago vibes.
“The best food is in Chicago. There are great restaurants everywhere, from fancy places to burger joints.” – Steve Carell
Slice, Slice baby!
Sweet home Chicago.
“I adore Chicago. It is the pulse of America.” – Sarah Bernhardt
Chicago, where have you bean all my life.
“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
Either you love Chicago or you are wrong.
Meet me in Windy City.
“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
Chicago, I’m coming for you.
Let me be Frank, this is a tasty Chicago dog.
“If you can’t be famous, be infamous!” — Chicago
I fell in love, his name is Chicago.
“He rules Chicago with absolute power. No one could touch him. No one could stop him.” – AL Capone
Lake hair, don’t care.
Let minnow if you want to spend the day on Lake Michigan!
“I must confess a shameful secret: I love Chicago best in the cold.” ―Erik Larson
Chicago dreamin’.
“This is my kind of town, Chicago is.” – Frank Sinatra
Chicago is a city of architecture, and I want to see it all.
“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.” – Gwendolyn Brooks
“Back in Chicago, all we cared about was Rock ‘n’ Roll and staying out of the army.” – John Belushi
A concrete version of paradise.
“Give them the old razzle dazzle.” — Chicago
Bright lights, city nights in Chicago.
“Chicago is an October sort of city even in spring.” – Nelson Algren
Let the city set you free.
“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
Chicago, the city where you can experience four seasons in one day.
“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
The weather in Chicago really… blows me away.
Stuck in this Chicago loop.
“Chicago seems a big city instead of merely a large place.” — A.J. Liebling
Dear Chicago, I will never get over you.
“You know what they say about Chicago. If you don’t like the weather, wait fifteen minutes.” — Ralph Kiner
Meet me in Chicago
It’s one of the greatest cities on the planet. My heart beats differently when I’m in Chicago.
“I adore Chicago. It is the pulse of America.” – Sarah Bernhardt
Windy Wednesday in Chicago.
“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
Chicago shines even brighter at night.
Chi likes you a lot!
A bad day in Chicago, is still better than a good day anywhere else.
Wanderlust and city dust.
“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
You can leave Chicago, but it will never leave you.
Follow your heart, even if it takes you all the way to Chicago.
“I’d rather be a lamppost in Chicago than a millionaire in any other city.” –William A. Hulbert
Make sure to relish the good times in Chicago.
“You’d never think of taking a cab if you had to walk a mile down Chicago’s Michigan Avenue.” — Helmut Jahn
Cool beans.
“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.” – Barack Obama
“Sometimes words are just music themselves. Like ‘Chicago’ is a very musical sounding name.” – Tom Waits
Chi chi cheese. We’re in Chicago!
I’m just a small-town girl with big-city dreams.
“You can like the life you’re living, you can live the life you like.” — Chicago
Chicago is calling and I must go.
“Going to Chicago was like going out of the world.” – Muddy Waters
Things ain’t so bad in the windy city.
Friends, drinks and Chi-Town.
“I must confess a shameful secret: I love Chicago best in the cold.” – Erik Larson
I’m blown away by the Chicago skyline.
A concrete version of paradise.
“I don’t keep calm I’m from Chicago.” – Unknown
Let the city set you free.
“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
Cheers from Chicago!
All you need is love and skylines.
Life’s better by the lake.
“Eventually, I think Chicago will be the most beautiful great city left in the world.” – Frank Lloyd Wright
What you talkin’ bout Willis Tower?
East or West, Chicago is the best.
Live, love, 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.” – Oprah Winfrey
Lake Michigan is pretty Great.
“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
Feelings come and go like clouds in the Windy City.

The city is a very special place in the United States, and we hope these best Chicago Instagram quotes inspire you to share your adventures in the windy city!

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