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71 Chicago Captions For Instagram – Puns, Quotes & Short Captions

If you’re visiting Chicago then you’re bound to have hundreds of stunning photos that you’ll want to post to Instagram.

Nothing goes better with a beautiful photo than a cute caption.

To save you the trouble of thinking up a caption yourself, I’ve put together this list of the best Chicago Instagram captions.

Just copy and paste the Chicago caption straight into Instagram.

Best Chicago Instagram Captions

Funny Chicago Captions & Chicago Puns

  1. I’ve never bean to Chicago before
  1. I bean thinkin’ about you
  1. Chicago: Bean there, done that
  1. Chicago, where have you bean all my life
  1. Blown away by the Windy City!
  1. Finally made it to Chicago. It’s a boat time!
  1. In Chicago, I’m in the Loop
  1. I love Chicago, but I’m ready to get the L out of here
  1. A trip to Chicago is an L-evated experience
  1. Chicago, I lake you a lot!
  1. Pier pressure brought me here (Navy Pier)

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Cute Chicago Captions For Instagram

  1. Chicago you have my heart
  1. All you need is love and skylines
  1. I fell in love, his name is Chicago
  1. Stuck in this Chicago loop
  1. Things ain’t so bad in the windy city
  1. Started from the bottom, now we here (Skydeck)
  1. Big cities can have big hearts too
  1. Once upon a time in Chicago
  1. Either you love Chicago or you are wrong
  1. Theater in Chicago will always be my first love
  1. You never forget your first day in Chicago
  1. Happiness is…. holding tickets that say Chicago

Short Chicago Captions

  1. Meet me in Windy City
  1. Chicago let’s do it
  1. Daydreaming in Chicago
  1. Bright lights, city nights
  1. Sweet home Chicago
  1. P.S. I love Chicago
  1. Life’s better by the lake
  1. Cool beans
  1. My kind of town
  1. Chicago, you look great
  1. Friends, drinks and Chi-Town
  1. Meet me in Chicago
  1. You cannot stop Chicago
  1. Chicago is calling and I must go

Inspirational & Beautiful Chicago Captions

  1. Follow your heart, even if it takes you all the way to Chicago
  1. A concrete version of paradise
  1. Dear Chicago, I will never get over you
  1. You can leave Chicago, but it will never leave you
  1. Hello Chicago, your lights are fireflies in my heart
  1. I’m just a small-town girl with big-city dreams
  1. Once upon a time, in the enchanted land of Chicago
  1. Somewhere over the rainbow you will find Chicago
  1. Let the city set you free

Chicago Quotes For Instagram Captions

  1. “I’d rather be a lamppost in Chicago than a millionaire in any other city.” – William A. Hulbert
  1. “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.” – Jeremy Piven
  1. “Eventually, I think Chicago will be the most beautiful great city left in the world.” – Frank Lloyd Wright
  1. “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
  1. “Chicago’s neighborhoods have always been the city’s greatest strength.” – Jane Byrne
  1. “Chicago does not go to the world, the world comes to Chicago!” – Peter Orner
  1. “Perhaps the most typically American place in America.” – James Bryce
  1. “Going to Chicago was like going out of the world.” – Muddy Waters
  1. “Chicago ain’t no sissy town.” – Hinky Dink Kenna
  1. “The best food is in Chicago. There are great restaurants everywhere, from fancy places to burger joints.” – Steve Carell
  1. “You know what they say about Chicago. If you don’t like the weather, wait fifteen minutes.” – Ralph Kiner
  1. “I adore Chicago. It is the pulse of America.” – Sarah Bernhardt
  1. “I must confess a shameful secret: I love Chicago best in the cold.” – Erik Larson
  1. “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
  1. “I’m impressed with the people from Chicago. Hollywood is hype. New York is talk. Chicago is work.” – Michael Douglas
  1. “Sometimes words are just music themselves. Like ‘Chicago’ is a very musical sounding name.” – Tom Waits
  1. “I miss everything about Chicago, except January and February.” – Gary Cole
  1. “Let me tell you something. I’m from Chicago. I don’t break.” – Barack Obama
  1. “But when I go to Chicago, I know I’m home.” – Hank Sauer
  1. “Theater in Chicago will always be my first love.” – William Petersen
  1. “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
  1. “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
  1. “Chicago seems a big city instead of merely a large place.” – A.J. Liebling
  1. “Chicago is an October sort of city even in spring.” – Nelson Algren
  1. “We’re Chicago – we can do anything, damn it.” – Elva Rupio

Hopefully this list gave you plenty of ideas for cute Chicago Instagram captions. 

There’s a caption here for any photo, from puns to beautiful quotes. 

Feel free to copy and paste these Instagram captions for your Chicago photos.

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