Chicago Captions

Best Chicago Captions and Quotes for Instagram

Chicago is one of the world’s most popular cities. Chicago is well-known for its history, cuisine, culture, professional sports teams, and climate. Because Chicago is one of the world’s most Instagrammable cities, I’ve compiled a list of the best Chicago captions and quotes that will inspire you to visit the third-most populous city in the United States.

Funny Quotes About Chicago

Let’s enhance your Instagram photo with some amusing captions. You’re going to find what you’re looking for in this collection of funny Chicago captions.

  • In Chicago not only your vote counts, but all kinds of other votes-kids, dead folks, and so on. -Dick Gregory
  • You know what they say about Chicago. If you don’t like the weather, wait fifteen minutes.— Ralph Kiner
  • Let me tell you something. I’m from Chicago. I don’t break. —Barack Obama
  • 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
  • Chicago is not the most corrupt American city. It’s the most theatrically corrupt. -Studs Terkel
  • Chicago has a strange metaphysical elegance of death about it. -Claes Oldenburg
  • It is wonderful to be here in the great state of Chicago. –Dan Quayle
  • What a place to put a city, right on the front line of absolute zero. No wonder a cow burned it down. –Mark Helprin
  • I had thought Chicago was inevitable, like diarrhea. –John Varley

Chicago Travel Puns

A few puns to help you improve your Instagram game. Here is a list of Chicago travel puns, have a look.

  • Chicago floats my boat.
  • Chicago: Bean there, done that.
  • The best views in Chicago are at Navy Pier.
  • What you talkin ’bout Willis Tower?
  • Dogs love Chicago because they get to visit Wiggly Field.

  • Having a Fields day.
  • I love Chicago, but I’m ready to get the L out of here.
  • In Chicago, I’m in the Loop.
  • A trip to Chicago is an L-evated experience.
  • Finally made it to Chicago. It’s boat time!
  • Blown away by the Windy City!

Chicago Quotes

There are some days when you just can’t seem to come up with the right words to post on your Instagram pictures. Please find below some amazing Chicago quotes that can be used as captions if you wish to use them in your photos or videos.

  • You know what they say about Chicago. If you don’t like the weather, wait fifteen minutes.— Ralph Kiner
  • 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
  • I’d rather be a lamppost in Chicago than a millionaire in any other city. — William A. Hulbert
  • This Chicago caption is pulled from The Jungle–and if you’ve never read it, you should definitely add it to your reading list!
  • Chicago seems like a big city instead of merely a large place. — A.J. Liebling
  • Eventually, I think Chicago will be the most beautiful great city left in the world.” — Frank Lloyd Wright
  • In the twilight, it was a vision of power. — Upton Sinclair
  • Going to Chicago was like going out of the world… — Muddy WatersAnywhere in the world you hear a Chicago bluesman play, it’s a Chicago sound born and bred.— Ralph Metcalfe
  • You’d never think of taking a cab if you had to walk a mile down Chicago’s Michigan Avenue. — Helmut Jahn
  • 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
  • Theater in Chicago will always be my first love — William Petersen
  • I’m impressed with the people from Chicago. Hollywood is hype. New York is talk. Chicago is work.— Michael Douglas

Puns About Chicago Food

Chicago and Food, just WOW. Here is a list of captions for all of your amusing moments that you can use to accompany your delicious Chicago food photographs.

  • Taking cheesy selfies in Chicago.
  • Let me be Frank, this is a tasty dog.
  • A trip to Chicago takes quite a bit of dough.
  • I never sausage a beautiful hot dog!
  • Chicago stole a pizza in my heart.
  • Chicago food is a weiner
  • Slice, Slice baby!
  • You’d have to be a weir-mixture not to like Chicago Deep Dish.
  • Make sure to relish the good times in Chicago.


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