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  • Writer's pictureCaitlyn C

26 Chicago Instagram Caption Ideas

Updated: Aug 31, 2022

When out and about traveling, one of my favorite things to do is take photos to show my family and everyone back home what I did on my adventures. But when it comes to posting on social media, I never know what to use as a quick caption when I don't want to write full-blown paragraphs.

So to assist in that, I have compiled 26 ideas of quotes to use for Instagram captions on your next trip to Chicago!


Famous Quotes

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

-Nelson Algren

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

-Erik Larson

"Chicago, Chicago, its a city that's inviting its a city that's exciting its a city for a woman just like me,"

-Trina Vega (Victorious)

"I'm impressed with the people from Chicago. Hollywood is hype. New York is talk. Chicago is work."

-Michael Douglas

"I miss everything about Chicago, except January and February."

-Gary Cole

"You know what they say about Chicago. If you don't like the weather, wait fifteen minutes." -Ralph Kiner

"Chicago is everything to me."

-Patrick Beverley

"Chicago ain't no sissy town,"

-Hinky Dink Kenna

"Perhaps the most American place in America,"

-James Bryce

"This is my kind of town, Chicago is,"

-Frank Sinatra

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

-Nelson Algren


Aesthetic Chicago Quotes

"Chicago is calling and I must go,"

"Chicago, You have my heart,"

"I fell in love, (his/her/their) name is Chicago"

"Meet me in The Windy City,"

"This must be the place,"

"Dear Chicago, I will never get over you,"

"Stuck in this Chicago Loop."


Funny Chicago Quotes

"Chicago stole a pizza my heart,"

"I a-dough Chicago,"

"Nevermind, it's too cheesy,"

"Slice to meet you Chicago,"

"Me, Chicago, Pizza. The only love triangle I want,"

"Chicago: Bean there, done that,"

"I've bean thinking bout you,"

"Blown away by the windy city,"

"In Chicago, I'm in the loop,"

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