50 Best Chicago Quotes and Chicago Captions for Instagram 

Chicago’s moving and shaking, whether it’s the powerful politicians, influential celebrities, daring artists, or restless consumers. Making the city a source of many well-said Chicago quotes by known figures as Chicago captions for Instagram. 

The city of Chicago, aka the Windy City, is rated as one of the most beautiful cities globally. It’s no surprise why many of the greatest pictures can be found throughout this city, and it’d be even greater with a handful of catchy Chicago quotes or funny Chicago captions for Instagram to engage your followers. 

If you’re reading this article, you’re looking for nothing but the most perfect Chicago quotes and Chicago captions for Instagram. Our article has it all, whether it be wise sayings about Chicago, witty and short Chicago quotes, or puns for funny Chicago captions to entice your audience! 

With that being said, we did all the work for you as we scoured the web for various top Chicago quotes and creative Chicago captions for Instagram just for you. Here is the compilation of our favorite quotes about Chicago, famous sayings about Chicago, and Chicago captions for Instagram. 

Best Chicago Quotes 

Chi-town (a nickname for Chicago) is on the rise, and has been for many years now. This city is so worldly and culturally diverse that it’s no wonder Chicago quotes for Instagram are so interesting. 

Whether it be a landscape, a building or the daily life of a random Chicagoer, these Chicago quotes, coupled with your photographs, will show just how beautiful Chicago really is. 

Chicago quotes

On Instagram, you can use pictures of Chicago to add meaning to your captions and Chicago quotes on your Instagram account. If you’re a local or just visiting Chicago, you should definitely use some of these handpicked Chicago quotes to add some flavor and meaning to your Instagram feed. 

Whether you’re looking for short and sweet Chicago quotes or quotes about Chicago from your favorite stars, the list has it all. On that note, here are some of our favorite inspirational Chicago quotes and witful quotes about Chicago. 

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

2. “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

3. “It’s 106 miles to Chicago, we’ve got a full tank of gas, half a pack of cigarettes; it’s dark, and we’re wearing sunglasses.” – Elwood Blues

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

5. “Going to Chicago was like going out of the world.” – Muddy Waters

6. “I am an organic Chicagoan. Living there has given me a multiplicity of characters to aspire for. I hope to live there the rest of my days.” – Gwendolyn Brooks

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

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

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

10.  “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

11. “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

12.  “Yet once you’ve come to be part of this particular patch, you’ll never love another. Like loving a woman with a broken nose, you may well find lovelier lovelies. But never a lovely so real.” – Nelson Algren, “Chicago: City on the Make” (1951)

13. “It is the most perfect presentation of nineteenth-century individualistic industrialism I have ever seen. Chicago is one hoarse cry for discipline.” – H. G. Wells

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

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

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

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

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

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

20. “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

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

22. “Perhaps the most typically American place in America.” – James Bryce

23. “Theater in Chicago will always be my first love.” – William Petersen

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

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

No matter what kind of quotes about Chicago you had in mind, we’re pretty sure we covered most if not all of them. If you found these Chicago quotes useful in boosting your Instagram reach, then wait until you see our list of captions that’ll add the cherry on top to achieve heaps of likes and comments.

Best Chicago Captions for Instagram 

Chicago. The name itself makes people respond with a mix of excitement, drama, and emotion. The city is known for its colorful history, famous citizens, rich culture, and strong architecture. 

Understanding a few key themes in Chicago helps you capture the essence of the Windy City in your photos. Chicago is a place to root for, a place that people dream of and want to be. 

Whether they want the city’s skyline, its sports culture or cultural life, all these words describe why you should visit or live in Chicago, found in these one-of-a-kind Chicago captions for Instagram Here are some of the standouts of captions about Chicago we found in the world wide web. 

1. “Chicago: Bean there, done that.”

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

3. “Chicago, I lake you a lot!”

4. “Blown away by the Windy City!”

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

6.  “You never forget your first day in Chicago.”

7. “Lake hair, don’t care.”

8. “Either you love Chicago, or you are wrong.”

9. “In Chicago, I’m in the Loop.”

10. “Hello Chicago, your lights are fireflies in my heart.”

11. “Somewhere over the rainbow, you will find Chicago.”

12. “Follow your heart, even if it takes you all the way to Chicago.”

13. “Chicago stole a pizza my heart.”

14. “You can leave Chicago, but it will never leave you.”

15. “Chicago, let’s do it.”

16. “Happiness is…. holding tickets that say Chicago.”

17. “A day at Lake Michigan buoys my spirits!”

18. “Stuck in this Chicago loop.”

19. “Meet me in Windy City.”

20. “Make sure to relish the good times in Chicago.”

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

22. “Chicago, you look great.”

23. “Daydreaming in Chicago.”

24. “A trip to Chicago is an L-evated experience.”

25. “I fell in love; his name is Chicago.”

Type in these Chicago Quotes and Chicago Instagram Captions today

If you love Chicago, this awesome collection of the best Chicago quotes and captions for Instagram will be right up your alley.

Chicago is one of the most beautiful cities in the United States, and it has its own unique charm. When you are looking for some cool quotes about Chicago or funny Chicago quotes and captions to use on your next trip to Chicago, you can look back here and use any of your favorite Chicago quotes and captions on this list of the best 50 Chicago quotes and captions for Instagram.

We hope you enjoyed our list of the best Chicago quotes for Instagram captions. If you have any other suggestions or great Chicago quotes we missed, please let us know! If you loved this set of Chicago quotes and captions, then you should check out our Philadelphia ones!

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