120 Chicago Instagram Captions for Windy City Trips

Did you know? About 30 million tourists visit Chicago… and that’s just from the United States! They don’t come for the sunshine and warmth, and yet, they inevitably fall in love with the Windy City to the point they at least casually dream about moving there.

If you’re lucky enough to take a trip to Chicago and sample all the city’s best sights and eats, you’ll have a camera roll full of amazing memories. All of them deserve engaging Chicago Instagram captions!

Not sure where to get started? Check out this list full of clever Windy City captions — and feel free to add any that float your boat right to your Instagram feed!

How to Write Memorable Chicago Captions for Instagram

No matter what initially appealed to you about Chicago, you’ll always find more reasons to love the city. So, you’re looking for the best way to write Chicago captions Instagram followers will react to with lots of likes and comments? Here are some tips to get you off to a good start. The rest of your captions will be a breeze!

• Wow your followers with clever Chicago Instagram captions filled with silly (but undeniably like-worthy) puns. Playful captions are always the best way to go if you have funny photos to share!
• If you want to tell your followers more about the famous sights you’re visiting, you can make your travel captions a little longer. Don’t overwhelm your followers, though. Perhaps share the one thing you liked best and add an intriguing comment.
• Use your captions to share the things your followers can’t see by looking at your striking photos. Talk about the smells, wind, temperature, sounds, and atmosphere. This will make your pictures come to life and immerse your Instagram audience in your travel experience.

Above all, have fun! If you’re writing Instagram captions for Chicago while you’re still enjoying your trip, don’t waste too much time coming up with the perfect one-liner. Share something interesting and put your phone away, because there’s so much more to discover!

Chicago Instagram Captions for Selfies

1. Came to Chicago, was totally blown away!
2. Chicago and all that jazz.
3. Came for the deep-dish pizza, stayed for the deep-dish pizza.
4. But first, let me take a selfie before the wind messes up my hairdo.
5. Gone with the wind.
6. Chicago really floats my boat.
7. Chicago has really thrown me for a loop.
8. City lights and windy nights.
9. I followed my heart, and it led me to the airport. Now I’m in Chi-Town.
10. Say Chi Chi Cheese!

Clever Chicago Instagram Captions

11. Bean there, done that.
12. Got 99 problems, but the Chicago wind will sweep them all away.
13. Came to get a tan. Was very disappointed.
14. Cruising along the Chicago River like there’s no tomorrow.
15. There’s nothing deeper than Chicago pan pizza.
16. Please keep me in the loop!
17. Let’s Chica-go!
18. Today’s smile? Courtesy of the Chicago skyline!
19. I’m in a good place today. Chicago. Oh, you thought emotionally? Yeah, that, too.
20. I got the Windy City blues…

Funny Chicago Captions for Instagram

21. I’m like a Chicago Bull to a red cloth.
22. What happens in Chicago never stays here, because the wind blows it all away.
23. Small town girl, big city dreams, head in the clouds. Yeah, literally. This is Chicago, after all.
24. Meet me in the city that always throws shade.
25. It’s bean totally cool, Chicago.
26. Chicago, because the cold never bothered me anyway.
27. Chicago calories don’t count, right?
28. Today’s forecast: 90% chance of wind, 100% chance of hot dogs.
29. Lost in Chicago, found by the lake with pizza in my hand.
30. Chicago has been a mind-blowing experience.

Cute Instagram Captions for Chicago

31. I lake you so much, Chicago.
32. Won’t you please come to Chicago just to sing?
33. I’ve bean waiting for you all my life.
34. Pizza? Oh, Chica-go on, then!
35. Shore, I’ll spend the day on the lake with you.
36. Hold onto your hat and wing it!
37. Meanwhile, in Chicago…
38. Keep calm and take a river cruise.
39. Putting the chic in Chicago, one selfie at a time.
40. Big city, small girl, huge dreams.

Chicago Instagram Captions for Couples

41. Just finding our Chi in Chicago.
42. Lost in Chicago, found in your arms.
43. The wind whispers secrets of romantic dates and deep-dish pizzas.
44. With our heads in the clouds and the wind beneath our wings.
45. Ready to be swept off my feet in Chicago!
46. Visiting the Magnificent Mile with a huge smile.
47. Chicago couple goals: Share a deep-dish pizza.
48. You’re the Symphony Orchestra to my heart.
49. You, me, and this hot dog stand. It was always meant to be.
50. Blues in our ears, love in our hearts.

Chicago Captions for Instagram with Friends

51. Oh, this scent? It’s called “Windswept Deep Dish,” and we’re happy to share.
52. Come get a slice of the fun!
53. Friends don’t let friends drink Chicago-style cocktails alone.
54. Meet us by the Willis Tower and hold onto your hat.
55. Young, wild, and free in Chi.
56. We’re on top of the world and in a windy state of mind.
57. Friends who shop in Chi-Town together slay together.
58. Radiate positive vibes and feel the wind in your hair.
59. Our idea of a balanced diet? One slice of pizza in each hand.
60. The best Chicago accessory? Beanies, of course. I guess that makes us a couple of beanie babies.

Chicago Instagram Captions About Nightlife

61. Chicago sunsets and old style beer. That’s the dream.
62. Dance to the rhythm of the Chicago blues.
63. Endless Chicago nights and pizza bites.
64. Let the beat of the Windy City set you free.
65. You had me at craft cocktails.
66. Shredding the dance floor, Chi-Town style.
67. With butterflies in her stomach and wind in her hair.
68. Chicago doesn’t break. It bends. So hit the dance floor.
69. Living the Chicago dream.
70. Life ain’t perfect, but a night out in Chicago definitely can be.

Chicago Captions for Instagram About Food

71. Me + Chicago Pizza = Yes!
72. My love for Chicago really isn’t that deep.
73. Chicago-style hot dogs? I’m never having anything else, ever again.
74. I think I’m in deep-dish heaven.
75. We go together like the caramel and cheese in Chicago popcorn.
76. Juicy meat and hot pickles. I love Chicago’s Italian beef sandwiches.
77. Coming to Chicago was no mis-steak.
78. Chicago is a slice of heaven, and I’m never going home.
79. Jibarito dreams and riverside walks.
80. Pizza, Italian beef sandwiches, and jibarito. Is there anything else I need in life? A diet as soon as I go back home, I suppose.

Chicago Instagram Captions for Famous Sights

81. Having a Wrigley Field day here!
82. The Lincoln Zoo: Where entry is free, and the animals are cute.
83. You’re not done with Chicago until you’ve seen American Gothic in person.
84. I like big boats, and I cannot lie.
85. Lakefront trails and crazy winds. I’m ready for a big adventure!
86. Rising like a Phoenix in Jackson Park.
87. Cruising through life on the Chicago River.
88. These Chicago folks are leading me up the garden path in the botanical garden!
89. Waterfront restaurants and riverside walks. What could be better?
90. If you’re ready to succumb to pier pressure, meet me on the Navy Pier.

Fantastic Quotes for Chicago Instagram Captions

91. “It really wasn’t about picking Chicago. I feel like Chicago picked me.” — Alex Weisman
92. “Chicago is an October sort of city, even in spring.” ― Nelson Algren
93. “Chicago’s neighborhoods have always been this city’s greatest strength.” — Jane Byrne
94. “I’m impressed with the people from Chicago. Hollywood is hype. New York is talk. Chicago is work.” —Michael Douglas
95. “Chicago ain’t no sissy town.” — Hinky Dink Kenna
96. “Chicago is incredibly gracious. People here have so much pride.” — Giuliana Rancic
97. “Let me tell you something. I’m from Chicago. I don’t break.” ― Barack Obama
98. “Chicago will give you a chance. The sporting spirit is the spirit of Chicago.” — Lincoln Steffens
99. “Chicago’s one of the rare places where architecture is more visible.” — Frank Gehry
100. “I miss everything about Chicago, except January and February.” — Gary Cole

Short Chicago Captions Instagram Followers Will Love

101. Chicago is calling out, and I have to go.
102. Everything is a breeze in Chicago.
103. Chicago is my love language, and deep dish pizza is the way to my heart.
104. When life gives you lemons, trade them for a plane ticket to Chicago.
105. I’m the CEO of Riverside Walks.
106. Windy vibes and pizza slices.
107. Crushing hard on these deep-dish crusts.
108. Left my heart in the Windy City. Please DM me if you find it.
109. Chicago, you’re the wind beneath my wings.
110. Chicago, I love you.

Creative Writing Prompts for Chicago Instagram Captions

Did you enjoy our Instagram captions for Chicago, but would you like to write your own captions, too? Great! Let’s keep the momentum going. Follow along with these prompts! Because we’ve already started the sentences, finishing them will be a breeze!

111. Dreaming of deep-dish pizza and…
112. They don’t call it the Magnificent Mile for nothing. Today, I discovered…
113. Chicago sights and…
114. I’m just going with the flow, letting the wind…
115. After this trip, I’ll always think of… when I hear “Chicago.”
116. Chicago, where every winding path uncovers a new…
117. My idea of a perfect day in Chicago? …
118. Chicago’s streets are alive with…
119. Came for the boat tour, stayed for the…
120. I’m feeling the Chicago blues and…

FAQ About Chicago Captions for Instagram

How long should my Chicago Instagram captions be?

Unless you’re using your Instagram page as a travel journal (which is a great idea!), you’ll probably discover that shorter captions get more likes and comments. If you aim for captions with a length of between 140 and 220 characters, your followers will better understand the context of your photos, without being distracted by a wall of text.

What are the best emojis to add to my Chicago captions for Instagram?

Our favorite Chicago-related emojis include 🎶, 🍕, ⛵️, 🏙️, 🌬️, and 🚶, but you have plenty of other great choices. Whatever you do, don’t overwhelm your followers with a long string of unrelated emojis. Choose carefully, and try to limit yourself to no more than three per caption.

Can you recommend some good hashtags to include in my Chicago Instagram captions?

No problem! Some of your safest bets include #windycity, #chitown, #chicagoeats, and #chitecture. Always include hashtags related to the exact sight you’re enjoying as well, and feel free to choose some hashtags that show your mood.