If you’ve recently visited Chicago or you plan to, you’ll need the best Chicago captions to post on social media with your stunning pics! Well, here they are!
Best Chicago Instagram Captions
1. Hello Chicago, you’re looking gorgeous today.
2. Big cities can have big hearts too.
3. Born and bred in Chicago.
4. Somewhere between living and dreaming, there’s Chicago.
5. Chicago – a pompous Milwaukee.
6. Somewhere over the rainbow, you will find Chicago.
7. Anything is possible. This is Chicago.
8. Chicago is not a place. It’s a feeling.
9. Chicago is always a good idea.
10. I’m having an affair with Chicago.
11. Once upon a time, in the enchanted land of Chicago.
12. Chicago, I’m coming for you.
13. The weather in Chicago really… blows me away.
14. I love Chicago; it is unique in the world.
15. Hello Chicago, your lights are fireflies in my heart.
16. Bright lights, city nights in Chicago.
17. Either you love Chicago, or you are wrong.
18. Chicago is calling, and I must go.
19. Dear Chicago, I will never get over you.
20. Friends, drinks, and Chi-Town.
21. Keep calm and go to Chicago.
22. Started from the bottom, now we are here. (Skydeck)
23. Chicago is always on my mind.
24. I fell in love, his name is Chicago.
25. My heart burns for the city lights.
26. All you need is love and skylines.
27. I’m off on another adventure. Can you guess where I’m going? All I have to say is… deep-dish pizza.
28. Meanwhile, in Chicago…
29. Chicago… It puts a spell on you.
30. Chicago sun on my face and wind in my hair. Loving it here!
Short Chicago Instagram Captions
1. Daydreaming in Chicago.
2. P.S. I love Chicago.
3. A concrete version of paradise.
4. Stuck in this Chicago loop.
5. Live, love, Chicago.
6. Chicago, let’s do it.
7. Meet me in Chicago.
8. I’m a Chicago girl.
9. Chicago floats my boat.
10. Once upon a time in Chicago.
11. Views from the windy city.
12. Windy Wednesday in Chicago.
13. Let the city set you free.
14. Meet me in the Windy City.
15. My kind of town.
16. You cannot stop Chicago.
17. Sweet home Chicago.
18. Cheers from Chicago!
19. Lake Michigan is pretty Great.
20. Lake hair, don’t care.
21. Chi chi cheese. We’re in Chicago!
22. Wanderlust and city dust.
23. Chicago dreamin’.
24. Chicago, you look great.
25. Welcome to Chicago.
26. Life’s better by the lake.
27. Chicago is tough, so are you.
28. In Chicago, I’m in the Loop.
29. Just a cheesy selfie in Chicago.
30. Take me to Chicago.
Love Chicago Captions For Instagram
1. The most American place in America, Chicago.
2. Feels like home.
3. I’m just a small-town girl with big-city dreams.
4. Who would have thought this would be a place I call home?
5. Never seen something like Chicago before.
6. Chicago shines even brighter at night.
7. Wherever you go, go with all your heart, especially if you are in Chicago.
8. Happiness is…. holding tickets that say Chicago.
9. The best views in Chicago are at Navy Pier.
10. Make sure to relish the good times in Chicago.
11. Follow your heart, even if it takes you all the way to Chicago.
12. Enjoying every Chicago minute.
13. Things ain’t so bad in the windy city.
14. Chicago, the city where you can experience four seasons in one day.
15. I don’t keep calm, I’m from Chicago.
16. A bad day in Chicago is still better than a good day anywhere else.
17. You can leave Chicago, but it will never leave you.
18. You never forget your first day in Chicago.
19. Feelings come and go like clouds in the Windy City.
20. I’m blown away by the Chicago skyline.
21. In a world filled with crazy, I hope you choose to live in Chicago.
22. Damn, this city just slays me. Every time.
23. What you talkin’ bout Willis Tower?
24. From the stone age… Here comes Chicago.
25. You’d have to be a weir-mixture not to like Chicago Deep Dish.
26. Get blown away by the sights of the windy city.
27. East or West, Chicago is the best.
28. There is something in the Chicago air that makes sleep useless.
29. The windy city is in my back pocket.
30. I am here, but my heart is in Chicago.
Chicago Bean & Chicago Puns Captions
1. Chi likes you a lot!
2. Having a Fields day in Chicago.
3. Chicago: Bean there, done that.
4. I never sausage a beautiful hot dog.
5. Chicago, where have you bean all my life.
6. A trip to Chicago is an L-evated experience.
7. I’ve never bean to Chicago before.
8. A day at Lake Michigan buoys my spirits!
9. You haven’t bean to Chicago unless you’ve bean here.
10. Let me be Frank, this is a tasty dog.
11. A trip to Chicago takes quite a bit of dough.
12. Chicago’s frozen bean.
13. Slice, Slice, baby!
14. Let’s be Frank, Chicago is always a good idea.
15. Cool beans.
16. Pier pressure brought me here. (Navy Pier)
17. Chicago, I lake you a lot!
18. I bean thinkin’ about you, Chicago.
19. Make sure to relish the good times in Chicago.
20. Finally made it to Chicago. It’s a boat time!
21. Chicago food is a Weiner!
22. Chicago, it’s bean real!
23. Chicago stole a pizza of my heart.
24. Just a couple of beanie babies.
25. Let minnow if you want to spend the day on Lake Michigan!
More Chicago Instagram Captions
1. Admiring the magnificent view of our Chicagoland.
2. Enjoy the perks of living in this beautiful city.
3. These streets will make you feel brand new.
4. My first trip to Chicago! I can’t wait to explore this awesome city.
5. Chicago, the city of wind. But I will call it the city of dreams.
6. Chicago, you have my heart.
7. I’m so grateful for the time I’ve spent in Chicago.
8. I’m going to the windy city for a week of fun in the sun.
9. Can’t wait to see what Chicago has in store for me!
10. Just landed in Chicago, and I’m already loving it!
11. Sometimes, all you need to clear your head is a nice long walk in Chicago.
12. Just landed in Chicago! Time to hit the town and have some fun with my Chicago friends.
13. Chicago is a city of architecture, and I want to see it all.
14. Chicago is the best place to be if you want to chill with your friends on a beautiful summer day.
15. Chicago is the city that works. It’s where I got my hustle on.
16. This is going to be a sightseeing day in Chicago.
17. Chicago is the perfect place to be when it’s raining outside.
18. The Chicago skyline is so beautiful at night. I love the city lights!
19. The only thing better than Chicago in the summer is Chicago in the winter.
20. You’re a city of dreamers and doers, where the spirit of progress is alive and well.
Famous Chicago Quotes That Can Be Used As Captions
1. “This is my kind of town, Chicago is.” — Frank Sinatra
2. “A city without illusions but with vaulting imaginations and expectations. A city of burning energies on the shore of a huge northern sea.” — Brian Doyle
3. “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
4. “There is none other quite like my City of Big Shoulders.” — Irv Kupcinet
5. “Eventually, I think Chicago will be the most beautiful great city left in the world.” — Frank Lloyd Wright
6. “In the twilight, it was a vision of power.” — Upton Sinclair
7. “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
8. “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
9. “I have struck a city – a real city – and they call it Chicago.” — Rudyard Kipling
10. “Let me tell you something. I’m from Chicago. I don’t break.” — Barack Obama
11. “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
12. “Chicago is constantly auditioning for the world, determined that one day, on the streets of Barcelona, in Berlin’s cabarets, in the coffee shops of Istanbul, people will know and love us in our multidimensional glory, dream of us the way they dream of San Francisco and New York.” — Mary Schmich
13. “Perhaps the most typically American place in America.” — James Bryce
14. “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
15. “I’d rather be a lamppost in Chicago than a millionaire in any other city.” — William A. Hulbert
16. “I warn you, Jedediah, you’re not gonna like it in Chicago. The wind comes howling in off the lake and gosh only knows if they ever heard of lobster Newburg.” — Orson Welles
17. “Chicago is not the most corrupt of cities. The state of New Jersey has a couple. Need we mention Nevada? Chicago, though, is the Big Daddy. Not more corrupt, just more theatrical, more colorful in its shadiness.” — Studs Terkel
18. “Loving Chicago is like loving a woman with a broken nose.” — Nelson Algren
19. “Chicago ain’t no sissy town.” — Hinky Dink Kenna
20. “Chicago is unique. It is the only completely corrupt city in America.” — Charles Merriam
21. “Come and show me another city with lifted head singing so proud to be alive and coarse and strong and cunning…proud to be Hog Butcher, Tool Maker, Stacker of Wheat, Player with Railroads and Freight Handler to the Nation.” — Carl Sandburg
22. “Chicago is an October sort of city even in spring.” — Nelson Algren
23. “In Chicago, not only your vote counts, but all kinds of other votes – kids, dead folks, and so on.” — Dick Gregory
24. “They do things big, big I tell ya: Mike Ditka big. Michael Jordan big. Bill Murray big. Oprah! It’s one cultural Mount Everest after another.” — Anthony Bourdain
25. “Chicago seems a big city instead of merely a large place.” — A.J. Liebling
26. “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 backward? What other city makes traffic flow backward?” — Mike Royko
27. “Chicago Cubs fans are ninety percent scar tissue.” — George F. Will
28. “I must confess a shameful secret: I love Chicago best in the cold.” — Erik Larson
29. “Chicago is my hometown and will always have a special place in my heart.” — Kenneth Choi
30. “A facade of skyscrapers facing a lake and behind the facade, every type of dubiousness.” — E.M. Forster
Funny Chicago Quotes That Can Be Used As Captions
1. “Hell has been described as a pocket edition of Chicago.” — Ashley Montagu
2. “If you’re bored in Chicago, it’s your own fault.” — Unknown
3. “You can take the girl out of Chicago, but you can’t take Chicago out of the girl.” — Unknown
4. “You’d never think of taking a cab if you had to walk a mile down Chicago’s Michigan Avenue.” — Helmut Jahn
5. “I love Chicago, but I’m ready to get the L out of here.” — Unknown
6. “You know what they say about Chicago. If you don’t like the weather, wait fifteen minutes.” — Ralph Kiner
7. “There is only one thing for Chicago to do, and that’s to move to a better neighborhood.” — Herman Fetzer
8. “Welcome to Chicago, enter at your risk.” — Unknown
9. “I think that’s how Chicago got started. A bunch of people in New York said, ‘Gee, I’m enjoying the crime and poverty, but it just isn’t cold enough. Let’s go west.” — Richard Jeni
10. “I miss everything about Chicago, except January and February.” — Gary Cole
More Chicago Quotes That Can Be Used As Captions
1. “Chicago does not go to the world, the world comes to Chicago!” — Peter Orner
2. “But when I go to Chicago, I know I’m home.” — Hank Sauer
3. “Chicago’s neighborhoods have always been the city’s greatest strength.” — Jane Byrne
4. “Sometimes words are just music themselves. Like ‘Chicago’ is a very musical sounding name.” — Tom Waits
5. “It is wonderful to be here in the great state of Chicago.” — Dan Quayle
6. “We’re Chicago – we can do anything, damn it.” — Elva Rubio
7. “That weekend, the city blushed with a great heat wave, but on Monday, it rained, cooling the ache in the street’s burn.” — Daniel Amory
8. “Being Irish was a big thing for me, particularly growing up in Chicago.” — Lara Flynn Boyle
9. “Chicago is a sort of journalistic Yellowstone Park, offering a haven to a last herd of fantastic bravos.” — Ben Hecht
10. “Chicago is partly a fairy tale because it’s inside one person’s head, so that part of it’s made up and the rest of it is reality.” — Colleen Atwood
11. “I adore Chicago. It is the pulse of America.” — Sarah Bernhardt
12. “Anywhere in the world you hear a Chicago bluesman play, it’s a Chicago sound born and bred.” — Ralph Metcalfe
13. “Chicago sounds rough to the maker of verse. One comfort we have — Cincinnati sounds worse.” – Oliver Wendell Holmes
14. “A lot of real Chicago lives in the neighborhood taverns. It is the mixed German and Irish and Polish gift to the city, a bit of the old country grafted into a strong new plant in the new.” — Bill Granger
15. “Going to Chicago was like going out of the world.” — Muddy Waters
16. “Chicago is where the whole idea of community policing began.” — Mayor Rahm Emanuel
17. “I am an organic Chicagoan. Living there has given me a multiplicity of characters to aspire for. I hope to live there for the rest of my days.” — Gwendolyn Brooks
18. “I just wanted to see every single musical I could. The very first one I saw was ‘Beauty and the Beast’, the only one I could get a ticket for, and then ‘Les Miserables’ and then ‘Chicago’.” — America Ferrera
19. “It’s a bustling metropolis with the warmth of a small town; where the world already comes together every day to live and work and reach for a dream.” – Barack Obama
20. “The people of Chicago are a proud people – and for a good reason.” — Jane Byrne
21. “Until 1974, it was actually illegal to appear in public in Chicago if you were ugly.” — Scott Matthews
22. “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
23. “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
24. “Chicago is the product of modern capitalism, and, like other great commercial centers, is unfit for human habitation.” — Eugene Debs
25. “Theater in Chicago will always be my first love.” — William Petersen
26. “Chicago has disappointed her enemies and astonished the world.” — Erik Larson
27. “…a city that was to live by night after the wilderness had passed. A city that was to forge out of steel and blood-red neon its own peculiar wilderness.” — Nelson Algren
28. “I’m impressed with the people from Chicago. Hollywood is hype. New York is talk. Chicago is work.” — Michael Douglas
29. “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
30. “A city that was to forge out of steel and blood-red neon its own peculiar wilderness.” — Nelson Algren
31. “The best food is in Chicago. There are great restaurants everywhere, from fancy places to burger joints.” — Steve Carell
32. “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
33. “We struck the home trail now, and in a few hours were in that astonishing Chicago – a city where they are always rubbing a lamp, and fetching up the genii, and contriving and achieving new impossibilities.” — Mark Twain, ‘Life On The Mississippi’
34. “Chicago will give you a chance. The sporting spirit is the spirit of Chicago.” — Lincoln Steffens
35. “He rules Chicago with absolute power. No one could touch him. No one could stop him.” — Al Capone
To Sum Up
Have you found your favorite caption in my collection of Chicago Instagram captions?
Do share it with us in t“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 Pivenhe comments below!
I hope you enjoyed reading this article about the great Windy City and got lots of ideas and inspiration from my list of Chicago Instagram captions.
Stay tuned for some more interesting content on our page.
Until next time!
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