150+ Copy & Paste Chicago Captions For Instagram

chicago captions for instagram, instagram captions for chicago

Are you looking for ready-to-post Chicago captions for Instagram? Here are the best puns, captions, sayings, and Quotes about Chicago that you can copy & paste for your Instagram post!

Chicago is one of the best places I’ve seen in the United States and truly one of the best places to see in Illinois. It is definitely a go to and must be included in your bucket list especially when you visit the US.

As a flight attendant, I’m always looking forward to visit Chicago because it is the home of the famous Willi’s Tower, The Bean, Chicago River Walk, Lake Michigan, deep dish pizza, and a lot more. 

These instagrammable places & photographic sceneries from the Windy City need to have the best Chicago captions for justice!

So here are the best Chicago captions you can use for your Chicago trip!

Table of Contents

Short & Cute Chicago Instagram Captions

cute chicago captions for instagram

“Meet me in the Windy City!”


“Chicago shines even brighter at night.”


“Chicago Dreamin”.”


“Chicago, I haven’t forgotten you!”


“Chicago – the windy city.”


“Chicago visit.”


“Hello Chicago, it’s been a while!”


“Got Chi Town on my mind”


“My heart is in Chicago.”


“Falling for the windy city”


“Chicago is my favorite color.”


“Chicago, you are beautiful!”


“Dear Chicago, I will never get over you!”


“Hello, big city dreams!”


“Stuck in this Chicago loop.”


“Chicago floats my boat.”


“Lake hair, don’t care.”


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


“Chicago let’s do it.”


“Chicago is calling and I must go.”


“Chicago, you look great.”


“East or West, Chicago is the best.”


“Sweet Home Chicago”


“I love Chicago!”


“Chicago stole my heart.”


My heart beats differently in Chicago.

Chicago Bean Captions for Instagram

The Bean is one the most instagrammable work of public art in the heart of Chicago. The sculpture, which is officially titled Cloud Gate, is one of the world’s largest permanent outdoor art installations.



If you are one of the travelers that didn’t skip this beautiful art work in Chicago, here are the best captions for you!

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“Chicago’s frozen Bean.”


“I’ve BEAN lovin’ my week in Chicago.”


“Chicago: BEAN there, done that!”


“Cold Beans.”


“Where have you BEAN all my life?”


“No trip to Chicago is complete until you visit The Bean.”


“Me & The Bean.”


“The Bean. The public art in the heart of Chicago.”


“Won’t you meet me by the bean”


“Let’s BEAN together!”


“Skyline view delivered by The Bean.”


“Bean traveling a lot lately.”


“The obligatory BEAN selfie!”


“Loved this bean, because it didn’t have me in the bathroom the rest of the day.”


“Mirror, mirror, on the wall..”

First day in Chicago? Check Out More of Chicago!

Instagram Captions for Chicago Deep Dish Pizza

deep dish pizza of chicago - chicago captions

“Thin crust could NEVER. “


“Serving it up, Chicago style!”


“Pizza is the only love triangle anyone should ever want.”


“When your head says salad, but your heart says pizza!”


“But first, PIZZA!”


“Pizza is always a good idea!”


“Mamma Mia, that’s a pie!”


“Y’all see this slice? This is a slice of HEAVEN.”


“I wanna be where the pizza is!”


“Chicago stole a pizza in my heart.”


“Big city, big pizza!”

Other Chicago Food Instagram Captions

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“Life is uncertain. Eat dessert first.”  -Ernestine Ulmer


“My weaknesses have always been food and men – in that order.”  -Dolly Parton


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

Chicago Puns, Funny Chicago Captions for Instagram

“I never sausage a beautiful hot dog.”


“I love Chicago, but I’m ready to get the L out of here!”


“Dogs love Chicago because they get to visit Wiggly Field.”


“Chi chi cheese. We’re in Chicago!”


“The weather in Chicago really… blows me away.”


“Let me be Frank, this is a tasty dog.”


“Chicago food is a Weiner!”

Best Chicago quotes by famous people

“Let me tell you something. I’m from Chicago. I don’t break.” –Barack Obama


“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.” –Anthony Bourdain


“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


“I adore Chicago. It is the pulse of America.” –Sarah Bernhardt


“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


“I’m impressed with the people from Chicago. Hollywood is hype. New York is talk. Chicago is work.” –Michael Douglas


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


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


“Like ‘Chicago’ is a very musical sounding name.” -Tom Waits


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


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

chicago quotes for instagram - barack obama

Best Sayings About Chicago City

My heart beats differently when I’m in Chicago. It slows down and I feel more at ease.” – Jeremy Piven


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


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


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


“Chicago – a pompous Milwaukee.” – Leonard Louis Levinson


“Chicago’s neighborhoods have always been the city’s greatest strength.” – Jane Byrne


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


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


“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.” – Pat Colander


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


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


“We’re Chicago – we can do anything, damn it.” – Elva Rupio


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

chicago captions - lake michigan buoys

Best Chicago Quotes For Instagram About Chicago Weather

“I miss everything about Chicago, except January and February.” – Gary Cole


“I wan’t about to let no -8 degree weather ruin this Chicago trip! Galvanting all over the city in layers today!”


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


“Winter in Chicago… with a slice of the moon.”


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


“Windy Wednesday in Chicago.” 


The weather in Chicago really… blows me away.

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Best Chicago Instagram Captions From Movies

Pizza? Thin Or Thick? Chicago. -Ghostbusters II


When I get back to Chicago, I’m gonna start my life all over again. I’m Sorry! –Airplane (1980)


Well, New York, Chicago. To a girl on her own, it’s all the same. -Johnny Dangerously


I’d like one ticket to Chicago! No baggage! -Airplane (1980)


That’s the best in the city of Chicago! -Johnny Dangerously


Hi, baby! How’s everything in Chicago Land? -Pet Sematary (1989)

More Chicago Instagram Captions, Chicago Puns

If you’ve just taken a trip to the windy city then you know how special it is.


Sunset and the Chicago skyline just go hand in hand


“Chicago ain’t no sissy town.” – Hinky Dink


“Dear Chicago, I will never get over you.”

More Quotes About Chicago City

“Chicago’s neighborhoods have always been the city’s greatest strength.” – Jane Byrne


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


“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


“I adore Chicago. It is the pulse of America.” – Sarah Bernhardt

More Captions For Chicago Photos

A day at Lake Michigan buoys my spirits!


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


Bye, San Francisco! Hello, Chicago!

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More Chicago Phrases To Use With Your Photos

“daydreaming in Chicago”


“bright lights, city nights”


“find Chicago”


“adore Chicago”


“love Chicago”


“Chicago river suddenly turned”


“dogs love Chicago”


“Chicago shines”


“big city, big dreams”


“in the enchanted land of Chicago”

More Chicago Puns And Sayings

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


Somewhere over the rainbow, you will find Chicago.

Best Skyline Chicago Captions

I’m blown away by the Chicago skyline.


A little magic in front of that Chicago skyline!


Chicago Skyline from Lake Michigan


City lights and lake views – a perfect combination!

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Want to Visit Other City In Illinois Aside From Chicago?

Check out Viator’s popular bus & tours from Chicago.

Funny Quotes About Chicago

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


I never sausage a beautiful hot dog.

Song Lyrics Captions for Chicago City

“Chi nigga, but these hoes love my accent” – Monster


“You already know I’m straight from the Chi, all day, nigga/South, south, south side! All day, nigga.” – All Day


“I’m back from the future seen it with my own eyes/And yep, I’m still the future of the Chi” – Southside


“What if somebody from the Chi’ that was ill got a deal/On the hottest rap label around?/But he wasn’t talking about coke and birds/It was more like spoken word/Except he’s really putting it down?” – Through The Wire


“I wanna tell the whole world about a friend of mine/This little light of mine and I’m finna let it shine/I’m finna take y’all back to them better times/I’m finna talk about my mama if y’all don’t mind/I was three years old when you and I moved to the Chi” – Hey Mama


“I can’t let these people play me/Name one genius that ain’t crazy/Follow our father/You borrow our motto/I’m a Chicago Southsider/I’m a Chicago Southsider” -Feedback

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I warmly welcome you on board!

Hi, I'm Jezee!

How To Become a Flight Attendant - WingsPro Jezee

I’ve always had a spirit of adventure, a desire to traverse the globe, meet diverse people, and immerse myself in different cultures. Being a flight attendant has allowed me to fulfill these aspirations, turning my dreams into reality. It’s been an incredible journey, one that allowed me to overcome self-doubt and transcend my personal challenges. My career has been more than just a job, it’s been a life-changing experience that has shaped me into the person I am today. If you want to know more about my journey, you can find it here.