The 75 Funniest Jokes About Chicago That Will Make You LOL

Hey there, let me ask you something – do you fancy a good chuckle? I mean, who doesn’t? As someone who’s had the pleasure of living and exploring Chicago extensively, I can vouch for the city’s ridiculousness.

So much so that I’ve gone ahead and put together a list of 75 side-splitting jokes about Chicago that will undoubtedly make you LOL (that’s “laugh out loud” in case you’re not up with all the acronyms). Trust me when I say these quips are worth it.

List of Jokes About Chicago

1. Why did the hot dog blush? Because it saw the “windy” city!
2. What do you call a snowman in Chicago? A “Chilly-NOiseman”!
3. Why don’t Chicagoans tell secrets on the El train? Because they’re afraid the beans will spill!
4. How do you spot a tourist in Chicago? They’re the ones trying to catch a cab at rush hour!
5. What did one Chicago building say to the other? “High-rise” and shine!
6. Why don’t Chicagoans swim in Lake Michigan during the winter? They don’t want to get frostbite on their “Windy City”
7. What did the Chicago hot dog say to the ketchup? “You’re really squeezing the life out of me!”
8. Why did the tomato turn red when visiting Chicago? It saw the “Red Line” train coming!
9. What did the deep-dish pizza say to the thin-crust pizza? “I’m just a lot deeper than you!”
10. Why did the Chicagoan bring a ladder to the bar? Because the drinks were on the “rooftop”!
11. What do you call a group of Chicagoans stuck in traffic? A “congestion coalition”!
12. Why did the Chicago baseball team build a bakery? Because they needed a lot of “batter”!
13. What do you call a Chicagoan who doesn’t like deep-dish pizza? A “deep-diss” believer!
14. Why did the Chicagoan bring a flashlight to the comedy show? Because they wanted to “spotlight” the jokes!
15. What did the Chicago cat say when it saw a bird? “I hope it ‘hawks’ down a lot of mice!”
16. Why don’t Chicagoans eat doughnuts for breakfast? They prefer to “Dunkin’ the Bears”!
17. What did one skyscraper say to the other in Chicago? “I look up to you!”
18. Why did the Chicagoan start a gardening club? Because they wanted to “root” for the plants!
19. What did the Chicago firefighter say when asked about his job? “It’s always ‘blazing’ with excitement!”
20. Why don’t Chicagoans use umbrellas in the rain? They prefer to “go with the flow”!

21. What do you call a Chicagoan who can play the trumpet? A “Windy City” musician!
22. Why did the computer go to Chicago? It wanted to upgrade to the “Silicon Skyline”!
23. What did the Chicago tourist say after a long day of sightseeing? “I’m ‘Winded’ but still thrilled!”
24. Why did the Chicagoan bring a ladder to the beach? They wanted to “climb” up the sand dunes!
25. What did the Chicago bean say to the Chicago river? “Let’s make a ‘reflection’ on life!”
26. Why did the hot dog open a bakery in Chicago? Because it wanted to serve “Chi-dough-go” buns!
27. What do you call a Chicagoan who loves to dance? A “Windy City” twirler!
28. Why did the deep-dish pizza blush? It saw the “cheesy” skyline of Chicago!
29. What do you call a Chicagoan who’s always cold? A “Chill-inois”!
30. Why did the baseball team hire a Chicagoan as their coach? Because they knew they’d hit a “home-run”!
31. What did the Chicago tourist say after seeing the famous bean sculpture? “It’s quite a ‘refle-bean-tion’!”
32. Why did the Chicagoan bring a ladder to the concert? They wanted to get closer to the “high notes”!
33. What do you call a Chicagoan with a broken leg? A “Windy City” hopper!
34. Why did the Chicagoan become a gardener? Because they loved “growing” roots in the city!
35. What did the Chicago pizza say to the New York pizza? “I’ve got more ‘depth’ than you!”
36. Why did the Chicagoan bring a helmet to the beach? They were afraid of the “sand-pits”!
37. What do you call a Chicagoan who loves to read? A “Windy City” bookworm!
38. Why did the deep-dish pizza go to therapy? It had trouble handling all the “layers”!
39. What do you call a Chicagoan with a broken arm? A “Windy City” waver!
40. Why did the Chicagoan start a bakery on the beach? Because they wanted to make “sand-wiches”!

41. What did the Chicago bear say to the Chicago bull? “Let’s have a ‘bull’ish adventure!”
42. Why did the deep-dish pizza take a cooking class? It wanted to “rise” to the occasion!
43. What do you call a Chicagoan with a green thumb? A “Windy City” gardener!
44. Why did the Chicagoan bring a ladder to the library? They wanted to reach the “bookshelf”!
45. What did the Chicago train conductor say when asked about his job? “I’m always ‘on track’!”
46. Why did the Chicagoan become an architect? They loved “building” relationships with the city!
47. What do you call a Chicagoan who loves to sing in the rain? A “Windy City” crooner!
48. Why did the deep-dish pizza get a tattoo? It wanted to show off its “toppings”!
49. What do you call a Chicagoan with a broken nose? A “Windy City” sniffer!
50. Why did the Chicagoan open a gym on the beach? They wanted to offer “sand-wich training”!
51. What did the Chicago dog say to the Chicago cat? “Let’s chase our ‘tails’ together!”
52. Why did the deep-dish pizza write a novel? It had a lot of “story-topping” experiences!
53. What do you call a Chicagoan who loves winter? A “Windy City” snowflake!
54. Why did the Chicagoan bring a ladder to the theater? They wanted to “climb” the stage!
55. What did the Chicago skyline say to the moon? “Let’s have a ‘sky-high’ rendezvous!”
56. Why did the hot dog start a band in Chicago? It wanted to play “relish” tunes!
57. What do you call a Chicagoan who loves to paint? A “Windy City” artist!
58. Why did the deep-dish pizza go on a diet? It wanted to shed some “crust”!
59. What do you call a Chicagoan with a broken foot? A “Windy City” hopscotcher!
60. Why did the Chicagoan open an ice cream shop on the beach? Because they wanted to serve “sandy scoops”!

61. What did the Chicago lion say to the Chicago tiger? “Let’s have a ‘roaring’ good time!”
62. Why did the deep-dish pizza join a dance class? It wanted to learn some “spins”!
63. What do you call a Chicagoan who loves flowers? A “Windy City” bloomer!
64. Why did the Chicagoan bring a ladder to the art gallery? They wanted to “climb” to new perspectives!
65. What did the Chicago river say to the lake? “Let’s make waves in the ‘Windy City’!”
66. Why did the hot dog become a stand-up comedian in Chicago? It had a knack for “ketchup” lines!
67. What do you call a Chicagoan who loves photography? A “Windy City” shutterbug!
68. Why did the deep-dish pizza go on a road trip? It wanted to explore new “crust-inations”!
69. What do you call a Chicagoan with a broken hand? A “Windy City” high-fiver!
70. Why did the Chicagoan open a BBQ joint on the beach? Because they wanted to serve “sandy ribs”!
71. What did the Chicago bear say to the Chicago bull at the rodeo? “Let’s have a ‘bucking’ good time!”
72. Why did the deep-dish pizza become a comedian? It had a lot of “topping” material!
73. What do you call a Chicagoan who loves to swim in freezing water? A “Windy City” polar bear!
74. Why did the Chicagoan bring a ladder to the cinema? They wanted the best “viewing” experience!
75. What did the Chicago skyline say to the sun? “Let’s shine together in the ‘Windy City’!”

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