101 Chicago Captions to Make Your Instagram Feed Pop

Are you struggling to come up with captivating captions for your Instagram photos of the Windy City? It’s frustrating when you have the *perfect* photo but can’t think of the right words to accompany it. With so much to see and do in Chicago, it’s hard to know where to start! With that being said, here is a list of 101 funny and inspirational Chicago captions to spice up your feed!

From stunning skyline views to deep-dish pizza, I’ve got you covered. These captions will help your social media posts stand out and capture the essence of this vibrant city.

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Short Chicago captions

Sometimes all you need is something short and sweet. These cheeky, to-the-point Chicago captions will sum up your trip to the Windy City perfectly.

1. Greetings from the Windy City
2. Meet me in Chicago
3. Chicago is calling and I must go
4. Life’s better by the lake
5. Live, love, Chicago
6. Bright lights and Chicago nights
7. Either you love Chicago or you’re wrong
8. Blown away by the Windy City
9. Cheers from Chicago!
10. The Second City is second to none
11. Views from the Windy City
12. Chicagoland adventures
13. Keep calm and go to Chicago
14. Daydreaming in Chicago
15. Wanderlust and city dust
16. Sweet home Chicago
17. Chicago dreamin’
18. Somewhere over the rainbow, you’ll find Chicago
19. Chicago is always a good idea
20. P.S. I love Chicago

Funny Chicago captions and quotes

From humorous plays on words to amusing observations, these funny Chicago captions and quotes will add a bit of pizzazz to your Instagram posts.

21. “Chi love you a lot!”
22. “Chicago: The city where you can experience four seasons in one day.”
23. “Follow your heart, even if it takes you all the way to Chicago.”
24. “I miss everything about Chicago, except January and February.” — Gary Cole
25. “I don’t keep calm, I’m from Chicago.”
26. “A bad day in Chicago is still better than a good day anywhere else.”
27. “Chicago shines even brighter at night.”
28. “Chicago ain’t no sissy town.” — Hinky Dink Kenna
29. “Loving Chicago is like loving a woman with a broken nose.” — Nelson Algren
30. “You’d never think of taking a cab if you had to walk a mile down Chicago’s Michigan Avenue.” — Helmut Jahn
31. “Hell has been described as a pocket edition of Chicago.” — Ashley Montagu
32. “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
33. “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
34. “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
35. “There is only one thing for Chicago to do, and that’s to move to a better neighborhood.” — Herman Fetzer
36. “Chicago — a pompous Milwaukee.” — Leonard Louis Levinson
37. “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
38. “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

Hilarious Chicago puns

Who doesn’t love a good (or bad) pun?! From Chicago’s food scene to its unpredictable weather, here’s a list of some hilarious Chicago puns to make your followers laugh — if you know you know.

39. A trip to Chicago is an L-evated experience.
40. Finally made it out on Lake Michigan. It’s aboat time!
41. I’m deep dish-appointed I didn’t eat more pizza in Chicago.
42. Slice, slice baby.
43. Chicago stole a pizza my heart!
44. Relish-ing my last few days in Chicago.
45. Let me be Frank, this is a tasty dog.
46. Brrr from Chiberia.
47. “What you talkin’ ’bout Willis?”
48. Lake Michigan is pretty Great.
49. Having a Fields day in Chicago.
50. Feeling a bit of Pier pressure today.
51. Dogs love Chicago because they get to visit Wiggly Field.
52. Stuck in this Chicago Loop.
53. I love Chicago, but I’m ready to get the L out of here.

Punny Chicago Bean captions

Chicago’s famous Bean, also known as the Cloud Gate, is a must-see when in the city. Here are some bean-themed puns that you can use for your Chicago captions.

54. Bean there or bean square.
55. Chicago? Bean there, done that.
56. Cool beans.
57. We are meant to bean.
58. With my favorite human beans.
59. Chicago, it’s bean a while.
60. I’ve bean real busy here in Chicago.
61. Bean traveling around the world lately.
62. I’ve bean telling jokes about Chicago all day.
63. I got sunburnt in Chicago — I guess you could say I’m a baked bean.
64. Visiting Chicago in the winter — I guess you could say I’m a chili bean.
65. Happier than I’ve ever bean.
66. Queen bean.
67. Just a couple of beanie babies.
68. Two beans in a pod.
69. Don’t worry, we’ve all bean there.
70. Just bean a tourist here in Chicago.
71. Chicago, where have you bean all my life?
72. Life’s bean good.
73. Chicago, you’ve bean real.

Famous Chicago quotes

When you don’t know what to say, look to others for inspiration. Here’s a list of famous quotes about Chicago that you can use in your Chicago Instagram captions!

74. “Let me tell you something. I’m from Chicago. I don’t break.” — Barack Obama
75. “This is my kind of town, Chicago is.” — Frank Sinatra
76. “Eventually, I think Chicago will be the most beautiful great city left in the world.” — Frank Lloyd Wright
77. “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
78. “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
79. “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
80. “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
81. “I adore Chicago. It is the pulse of America.” — Sarah Bernhardt
82. “Perhaps the most typically American place in America.” — James Bryce
83. “Chicago’s neighborhoods have always been the city’s greatest strength.” — Jane Byrne
84. “Chicago does not go to the world, the world comes to Chicago!” — Peter Orner
85. “There is none other quite like my City of Big Shoulders.” — Irv Kupcinet
86. “Chicago is an October sort of city even in spring.” — Nelson Algren
87. “I must confess a shameful secret: I love Chicago best in the cold.” — Erik Larson
88. “I’d rather be a lamppost in Chicago than a millionaire in any other city.” — William A. Hulbert
89. “The best food is in Chicago. There are great restaurants everywhere, from fancy places to burger joints.” — Steve Carell
90. “You know what they say about Chicago. If you don’t like the weather, wait fifteen minutes.” — Ralph Kiner
91. “It’s wonderful to be here in the great state of Chicago.” — Dan Quayle
92. “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.
93. “I’m impressed with the people from Chicago. Hollywood is hype. New York is talk. Chicago is work.” — Michael Douglas

Chicago songs and lyrics

There have been so many incredible songs written about Chicago. Here’s a selection of inspirational lyrics about the Windy City.

94. “Each time I roam, Chicago is calling me home, Chicago is why I just grin like a clown, it’s my kind of town.” — My Kind Of Town by Frank Sinatra
95. “I fell in love again, all things go, all things go, drove to Chicago, all things know, all things know.” — Chicago by Sufjan Stevens
96. “Take me back to Chicago, lay my soul to rest, where my life was free and easy, remember me at my best.” — Take Me Back To Chicago by Chicago
97. “Every interview I’m representin’ you, makin’ you proud, reach for the stars, so if you fall, you land on a cloud, jump in the crowd, spark your lighters, wave ’em around, if you don’t know by now, I’m talkin’ ’bout Chi-Town.” — Homecoming by Kanye West
98. “Got to get back to the windy city, with them funky ole sweet home blues, meet me in Chicago, baby I’ll show you around, meet me in Chicago, let me take you downtown.” — Meet Me In Chicago by Buddy Guy
99. “Two-thirty, baby, won’t you meet me by the bean?” — Chicago Freestyle by Drake
100. “It feel like LA, it feel like Miami, it feel like NY, summertime Chi, ahh! This is the good life!” — Good Life by Kanye West
101. “Two words, Chi-Town raised me, crazy, so I live by two words: ‘fuck you, pay me.'” — Two Words by Kanye West

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Thanks for reading this post on the best Chicago captions for Instagram! Which one was your favorite? Let me know in the comments below!

xoxo Niki