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150 Ultimate Chicago Captions For Instagram!

Been to Chicago, took a load of photos and now you need inspiration for captions of your Chicago pictures on Instagram?

There are many Instagrammable places in Chicago – also known as The Windy City, from The Bean at Cloud Gate to the Chicago Skydeck and North Avenue Beach.

However crafting the perfect Instagram caption to go along with your Chicago pictures isn’t always easy so here you’ll find all the best quotes, funny puns and captions to help make it easier for you and save you the bother of thinking of a caption yourself!

Regardless of whether you’ve been to Chicago or not, these 150 Instagram captions, famous quotes and funny puns will surely give you some inspiration!

This article features all the best captions about Chicago for Instagram, as well as funny captions and meaningful quotes about this fabulous city, so all you need to do is choose your favourite caption and then copy it straight into Instagram!

the bean chicago

Looking for Instagram captions for other cities in America? Check out these articles:
170 Ultimate New York Captions & Quotes
155 Las Vegas Instagram Captions & Quotes


Best Chicago Captions for Instagram

1. “Chicago let’s do it.”

2. “Chicago is calling and I must go.”

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

4. “Meet me in Chicago.”

5. “Stuck in this Chicago loop.”

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

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

8. “Friends, drinks and Chi-Town.”

9. “Sweet home Chicago.”

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

11. “Chicago you have my heart.”

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

13. “PS. Chicago I love you.”

14. “You cannot stop Chicago.”

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

16. “Chi chi cheese. We’re in Chicago!”

17. “Either you love Chicago or you are wrong.”

18. “I’m blown away by the Chicago skyline.”

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

20. “My kind of town.”

21. “A concrete version of paradise.”

Looking for the best activities to do in Chicago? Check out these tours you can do!



Short Instagram Captions for Chicago

22. “Daydreaming in Chicago.”

23. “Chicago shines even brighter at night.”

24. “Chicago, you look great.”

25. “Windy Wednesday in Chicago.”

26. “Cheers from Chicago!”

27. “Things ain’t so bad in the windy city.”

28. “Big cities can have big hearts too.”

29. “Once upon a time in Chicago.”

30. “Bright lights, city nights.”

31. “I fell in love, his name is Chicago.”

32. “All you need is love and skylines.”

33. “Bright lights, city nights in Chicago.”

34. “Chi likes you a lot!”

35. “Meet me in The Windy City.”

36. “East or West, Chicago is the best.”

37. “Keep calm and go to Chicago.”

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

39. “Life’s better by the lake.”

40. “I’m just a small-town girl with big-city dreams.”

41. “Let the city set you free.”

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Short Chicago City Quotes for Instagram Captions

42. “Theatre in Chicago will always be my first love.” – William Petersen

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

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

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

46. “Chicago ain’t no sissy town.” – Hinky Dink Kenna

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

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

49. “A facade of buildings facing a lake and behind the facade, every type of dubiousness.” – E.M. Forster

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

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

52. “Chicago – a pompous Milwaukee.” – Leonard Louis Levinson

Check out some of the best river cruises you can do in Chicago!



Best Chicago Quotes for Instagram Captions

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

54. “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

55. “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

56. “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

Sayings About Chicago City

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

58. “Chicago does not go to the world, the world comes to Chicago!” – Peter Orner

59. “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

60. “Chicago is a city of contradictions, of private visions haphazardly overlaid and linked together. If the city was unhappy with itself yesterday-and invariably it was-it will reinvent itself today.” – Pat Colander

61. “The best food is in Chicago. There are great restaurants everywhere, from fancy places to burger joints.” – Steve Carell

62. “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

flamingo wall mural Chicago

Quotes from people who are from or live in Chicago

63. “I don’t keep calm I’m from Chicago.” – Unknown

64. “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

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

66. “But when I go to Chicago, I know I’m home.” – Hank Sauer

67. “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

Famous Quotes About Chicago City

68. “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

69. “This is my kind of town, Chicago is.” – Frank Sinatra

70. “Chicago is a city where the practical and the inspirational exist in harmony; where visionaries who made no small plans rebuilt after a great fire and taught the world to reach new heights. 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—a dream that no matter who we are, where we come from; no matter what we look like or what hand life has dealt us; with hard work, and discipline, and dedication, we can make it if we try.” – Barack Obama

71. “Out in Chicago, the only genuinely civilized city in the New World, they take the fine arts seriously and get into such frets and excitements about them as are raised nowhere else save by baseball, political treachery, foreign wars, and romantic loves . . . almost one fancies the world bumped by a flying asteroid, and the Chicago River suddenly turned into the Seine.” – Henry Mencken

72. “Chicago is a town, a city that doesn’t even 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 

73. “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

John Hancock centre chicago rooftop view

Funny Chicago Quotes For Instagram

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

75. “You’d never think of taking a cab if you had to walk a mile down Chicago’s Michigan Avenue.” – Helmut Jahn

76. “There is only one thing for Chicago to do, and that’s to move to a better neighbourhood.” – Herman Fetzer

77. “In Chicago not only your vote counts, but all kinds of other votes-kids, dead folks, and so on.” – Dick Gregory

78. “Hell has been described as a pocket edition of Chicago.” – Ashley Montagu

79. “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

80. “Loving Chicago is like loving a woman with a broken nose.” – Nelson Algren

Chicago best photo spots instagrammable places

Beautiful & Cute Quotes About Chicago

81. “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

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

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

84. “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

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

86. “A facade of skyscrapers facing a lake and behind the facade, every type of dubiousness.” – E.M. Forster

87. “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

88. “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

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Meaningful & Inspirational Quotes About Chicago

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

90. “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

91. “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

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

93. “There seems to be a different Chicago around every street corner, behind every bar, and within every apartment, two-flat, cottage, or bungalow. City of immigrants or city of heartless plutocrats, say what you will, Chicago almost defies interpretation. In many ways, Chicago is like a snake that sheds its skin every thirty years or so and puts on a new coat to conform to a new reality.” – Dominic A. Pacyga

94. “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 colourful in its shadiness.” – Studs Terkel

Quotes From Chicago The Musical

95. “You’re a phony celebrity and in two weeks no one’s going to give a sh.t about you… that’s Chicago.”

96. “- Reporter: Would you like to give us a word or two?
– Kitty Baxter: I’ll give you three: go to hell.”

97. “My audience loves me. And I love them. And they love me for lovin’ them and I love them for lovin’ me. And we love each other. And that’s ’cause none of us got enough love in our childhoods. And that’s showbiz, kid.”

98. “You can like the life you’re living, you can live the life you like.”

99. “I’m gonna be a celebrity, that means somebody everyone knows. They’re gonna recognize my eyes, my hair, my teeth, my boobs, my nose.”

100. “- Roxie Hart: You’re, the Velma Kelly. I was there the night you got arrested.
– Velma Kelly: Yeah? You and half of Chicago.”

101. “You wanted advice? Well here it is, straight from me to you, keep your paws off my underwear.”

102. “My client feels that it was a combination of liquor and jazz that led to the downfall.”

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Movie Quotes About Chicago

103. “It’s a very bad sign when a cop thinks that Chicago will fall apart without him.” – Running Scared

104. “Welcome to Chicago. This town stinks like a whorehouse at low tide.” – The Untouchables

105. “It’s 106 miles to Chicago, we got a full tank of gas, half a pack of cigarettes, it’s dark… and we’re wearing sunglasses.” – The Blue Brothers

106. “He rules Chicago with absolute power. No one could touch him. No one could stop him.” – AL Capone

107. “Eliot Ness: I want to get Capone! I don’t know how to do it. – Jim Malone: You wanna know how to get Capone? They pull a knife, you pull a gun. He sends one of yours to the hospital, you send one of his to the morgue. That’s the Chicago way! And that’s how you get Capone!” – The Untouchables

108. “Six bucks and my right nut says we’re not landing in Chicago.” – Planes, Trains and Automobiles

109. “I’m going to do all my movies here in Chicago. The Tribune referred to me as a ‘former Chicagoan’. As if, to do anything, I have to leave Chicago. I never left. I worked until I was 29 at the Leo Burnett advertising agency, and then I quit to do this. This is a working city, where people go to their jobs and raise their kids and live their lives.” – John Hughes

Cindys Rooftop Bar Millenium Park instagrammable

Funny Chicago Puns & Captions For Instagram

110. “In Chicago, I’m in the Loop.”

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

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

113. “The weather in Chicago really… blows me away.”

114. “Feelings come and go like clouds in the Windy City.”

115. “Chicago, the city where you can experience four seasons in one day.”

116. “Blown away by the Windy City!”

117. “The best views in Chicago are at Navy Peer.”

118. “Pier pressure brought me here.”  (Navy Pier)

119. “Chicago floats my boat.”

120. “Finally made it to Chicago. It’s a boat time!”

121. “Lake hair, don’t care.”

122. “Let minnow if you want to spend the day at Lake Michigan!”

123. “Chicago, I lake you a lot!”

124. “Dogs love Chicago because they get to visit Wiggly Field.”

Chicago best photo spots instagrammable places

Funny Puns About Chicago Food

125. Taking cheesy selfies in Chicago.

126. Chicago stole a pizza my heart.

127. Chicago food is a weiner!

128. You’d have to be a weir-mixture not to like Chicago Deep Dish.

129. Make sure to relish the good times in Chicago.

130. I never sausage a beautiful hot dog!

131. Slice, Slice baby!

132. Let me be Frank, this is a tasty dog.

133. A trip to Chicago takes quite a bit of dough.

Chicago Bean Captions for Instagram

134. “I’ve bean thinkin’ about you Chicago.”

135. “Chicago, it’s bean real!”

136. “Chicago, where have you bean all my life.”

137. “Cool beans.”

138. “I’ve never bean to Chicago before.”

139. “Chicago: Bean there, done that.”

140. “Chicago’s frozen bean.”

141. “You haven’t bean to Chicago unless you’ve bean here.”

Chicago best photo spots instagrammable places

Interesting Facts About Chicago Captions For Instagram

142. Feeling on top of the world at the Willis Tower! On a clear day, you can see four states: Illinois, Michigan, Indiana and Wisconsin.

143. The world’s first skyscraper was built in Chicago in 1885.

144. Walt Disney, Robin Williams, Harrison Ford, Michelle Obama, Hugh Hefner, Jennifer Hudson, Bill Murray, Hillary Clinton and Tina Fey were all born in Chicago.

145. The Deep Dish pizza and the brownie were created in Chicago.

146. The Chicago River is the only river in the world that permanently flows backwards. The reversal of the river flow was done to divert the sewage away from Lake Michigan’s water supply and prevent water borne illnesses in the late 1800’s, and it is one of the greatest engineering achievements in the world.

147. Chicago has more moveable bridges than any other city in the world.

148. I’m off on another adventure. Can you guess where I’m going? All I have to say is… deep dish pizza.

149. The Ferris wheel was invented in Chicago.

150. 5 parks you must visit when in Chicago:

  • Millenium Park
  • Lincoln Park
  • Grant Park
  • Jackson Park
  • Garfield Park

Chicago best photo spots instagrammable places

Chicago Captions For Instagram Summary

Chicago is really a great city for culture and for getting some great photos for your Instagram! Hopefully you got lots of ideas and inspiration in this list of 150 Chicago captions and quotes for Instagram.

You can find a caption that’s perfect for any photo, whether it is a beautiful or meaningful quote or a hilarious funny pun about Chicago.

Do you know any more captions or interesting facts about Chicago that would go perfectly with an Instagram photo? Let me know in the comments below!

Travel quotes inspire us all right? If you are looking for some more inspirational quotes check these out:
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