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100 Awesome Chicago Captions for Instagram

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We hope you enjoy this ultimate list of the best Chicago captions for Instagram. If you’ve just taken a trip to the windy city then you know how special it is. The skyline is absolutely breathtaking, especially at night!

If you’ve taken some awesome photos you’ll love our section on the best Chicago quotes for Instagram photos. Simply choose your favorite and post the picture!

For those that like humor there’s also a hilarious list of the funniest Chicago puns for your entertainment!

Chicago Captions for Instagram

Chicago captions for Instagram
  • You can leave Chicago, but it will never leave you.
  • Meet me in Chicago.
  • Live, love, Chicago.
  • Meet me in Windy City
  • East or West, Chicago is the best.
  • Life’s better by the lake.
  • Chicago dreamin’.
  • Bright lights and Chicago nights.
  • Stuck in this Chicago loop
  • Let minnow if you want to spend the day at Lake Michigan!
  • Slice, Slice baby!
  • Chicago is calling and I must go.
  • In Chicago, I’m in the Loop
  • Lake Michigan is pretty Great.

Next: Travel Captions for Instagram

Chicago captions
  • Say cheers! To Chicago.
  • Daydreaming in Chicago
  • Welcome to Chicago, boys
  • I never sausage a beautiful hot dog.
  • I fell in love, his name is Chicago.
  • Windy Wednesday in Chicago
  • Dogs love Chicago because they get to visit Wiggly Field.
  • Blown away by the Windy City!
  • Moving to Chicago was a breeze.
  • The Windy City has my heart.

Next: Rooftop Bar Captions for Instagram

Chicago Instagram Captions
  • Lake hair, don’t care.
  • Chicago is always a good idea.
  • Hunting in Chicago!
  • Having a Fields day in Chicago
  • Big cities can have big hearts too.
  • Today’s forecast: 98% chance of wind.
  • Windy days and sunny rays.
  • I should probably move here, right?
Chicago caption
  • When Chicago smiles at you, please, smile back
  • Oh, Chicago! When I will be here again.
  • Let the city set you free.
  • Living in the moment, happy days are here
  • P.S. I love Chicago.
  • I’m excited to explore Chicago this week!
  • Chicago is my favorite place to be.
Chicago bean Instagram captions
  • A concrete version of paradise.
  • Friends, drinks and Chi-Town.
  • Modern Chicago vibes.
  • First adventures in Chicago are impossible to forget.
  • Slice, Slice baby!
  • My kind of town
  • All you need is love and skylines.
  • Make sure to relish the good times in Chicago.
  • Made in Chicago.
  • Greetings from Chicago.
  • There’s no place like Chicago.
Captions for Chicago
  • Chicago let’s do it.
  • If the question involves Chicago, the answer is yes.
  • Hello Chicago, your lights are fireflies in my heart.
  • Damn this city just slays me. Every time
  • Bright lights, city nights in Chicago.
  • Life’s better by the lake.
  • It’s a Chicago thing, you wouldn’t understand.
Instagram captions for Chicago
  • I’m blown away by the Chicago skyline.
  • It’s never too late for a Chicago adventure!
  • I wonder if Chicago misses me too.
  • My heart burns for the city lights.
  • Thank you, Chicago, for making me feel so alive.
  • My heart’s GPS location is fixed here.
  • Chicago always manages to blow me away.
  • Any day is a good day in Chicago.
  • Meanwhile, in Chicago…
  • Today’s good mood is sponsored by Chicago.
Captions about Chicago
  • The best views in Chicago are at Navy Peer.
  • Chicago is calling my name. I’m ready to hit the town!
  • Chicago shines even brighter at night.
  • You never forget your first day in Chicago.
  • I’m in a good place right now. Not emotionally, I’m just in Chicago.
  • You can’t buy happiness, but you can buy a plane ticket to Chicago and that’s pretty much the same thing.

You Might Also Like: Washington DC Captions for Instagram

Chicago Insta Captions
  • Let’s be Frank, Chicago is always a good idea.
  • Chicago is certainly one-of-a-kind.
  • I’m blown away by the Chicago skyline.
  • Who would have thought this would be a place I call home.
  • I’m just a small-town girl with big-city dreams
  • Chicago dreams coming alive
  • Chicago, I’m coming for you.

You Might Also Like: New York Captions for Instagram

Chicago Quotes for Instagram

Chicago Quotes for Instagram
  • “I adore Chicago. It is the pulse of America.” – Sarah Bernhardt
  • “This is my kind of town, Chicago is.” – Frank Sinatra
  • “Perhaps the most typically American place in America.” – James Bryce
  • “I’d rather be a lamppost in Chicago than a millionaire in any other city.” – William A. Hulbert
  • “Chicago’s neighbourhoods have always been the city’s greatest strength.” – Jane Byrne
  • “Going to Chicago was like going out of the world.” – Muddy Waters
  • “Chicago does not go to the world, the world comes to Chicago!” – Peter Orner
  • “I have struck a city – a real city – and they call it Chicago.” – Rudyard Kipling
  • “Anywhere in the world you hear a Chicago bluesman play, it’s a Chicago sound born and bred.” ― Ralph Metcalfe
Quotes about Chicago for Instagram
  • “Let me tell you something. I’m from Chicago. I don’t break.” – Barack Obama
  • “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
  • “Chicago seems a big city instead of merely a large place.” – A.J. Liebling
  • “There is none other quite like my City of Big Shoulders.” – Irv Kupcinet
  • “Chicago is an October sort of city even in spring.” – Nelson Algren
  • “You know what they say about Chicago. If you don’t like the weather, wait fifteen minutes.” — Ralph Kiner
  • “Chicago ain’t no sissy town.” – Hinky Dink Kenna
  • “Sometimes words are just music themselves. Like ‘Chicago’ is a very musical sounding name.” — Tom Waits
Chicago quotes Instagram

Chicago Puns for Instagram

Chicago puns for Instagram
  • Chicago food is a weiner!
  • Chicago’s frozen Bean.
  • Chicago, it’s bean real!
  • Chicago, I lake you a lot!
  • Pier pressure brought me here (Navy Pier)
  • Finally made it to Chicago. It’s a boat time!
  • A day at Lake Michigan buoys my spirits!
  • Chicago stole a pizza my heart.
  • Just a couple of beanie babies.
  • Chicago, where have you bean all my life!

Check Out: 50 Illinois Captions for Instagram

Chicago puns
Image of Iain The Founder Of The Road Trip Expert

Iain Salter

Founder & Editor of The Road Trip Expert

Iain founded The Road Trip Expert in 2019 and continues to manage the website to this day. The inspiration to start the blog came during an extensive road trip around Europe with two friends that spanned several months and involved over 25,000km of driving. He first developed a passion for backpacking in 2014 and has had the pleasure of exploring over 60 countries.