Chicago Jokes That Will Make Light of Everything

This is a compilation of Chicago jokes, all fit in one article. Chicago, the city of blues and business. The city known for its cold winters and unforgiving attitude is a source of pride and inspiration to thousands of people. 

Here are some funny jokes, puns, stories, and one-liners about the city that never fails to make you laugh.

Chicago Jokes That Will Make You Laugh Out Loud

  • Of course, all Chicagoans know that the White Sox play at Comiskey Field.
    • Or is it the U.S. Cellular Field?
  • Chicago Cubs baseball games won’t serve beer for the rest of the year.
    • They lost the opener.
  • Is there a difference between a Chicago Bears fan and Marty McFly?
    • Eventually Marty McFly stopped going back to 1985.
  • What is the best way to get to Carnegie Hall?
    • Practice. 
  • What is the best way to get to Navy Pier?
    • Take your theater degree and the 66 bus.
  • Why don’t you want to hang out with someone from Chicago?
    • Because ‘Illinois you!
  • What do you do to keep a bear out of your backyard?
    • Put up a goal post.
  • Man A: I just returned from the islands.
    • Man B: Oh, the Caribbean?
    • Man A: No. Goose Island, Stony Island and Blue Island.
    • Man B: Does dis bus go todaLoop?
    • Man B: No, it goes “beep-beep.”
  • What is the difference between Chicago-style jazz and New Orleans-style jazz?
    • About a thousand miles.
  • What’s the most common elementary school essay in Chicago?
    • What I want to be *IF* I grow up.
  • What is the name of a song about people who love Chicago style pizza?
    • Truly, Madly, Deep Dish Pizza.
  • What is the only thing that grows in Chicago’s South Side? 
    • The Crime Rate!

Related Jokes: Miami Jokes, Indiana Jokes, American Jokes

Hilarious Chicago Puns and Stories

  • What is the best way for a Chicagoan to apologize?
    • “I’m so-ree for the deep-dish pizza puns!”
  • The Cubs fan brought a ladder to the game for what reason?
    • Because they heard the seats were in the nosebleed section!
  • What is the best way to make a Chicago-style hot dog?
    • Start with a regular hot dog, and then put absolutely everything on it!
  • In Chicago, why was the computer so cold?
    • Because it left its Windows open!
  • When it’s windy in Chicago, what do you call it?
    • Wednesday!
  • The Chicago tourist brought a raincoat for what reason?
    • Because they heard it’s always “Chi-rainy!”
  • A Chicago-style pizza was just ordered.
    • It started shooting as soon as I opened the box.
  • Speeding tickets are no longer issued by the city of Chicago.
    • Instead, to deter speeders, they are giving away Cubs tickets.
  • Visitors often wonder why Chicagoans drink so much.
    • They wonder if we’re alright.
    • They ask, ‘Do you guys ever drink water?’
    • I say, ‘We eat a lot of hot dogs, is that drinking water?’
  • In Chicago, we know it will stop raining within minutes if it’s raining.
    • If it’s hot, a chilling breeze will whip up soon.
  • This man is frank and earnest with women.
    • In Fresno, he’s Frank and in Chicago he’s Ernest.
  • If you’ve never met a University of Chicago student, I’ll tell you a bit about him.
    • If you give him a glass of water, he says, “This is a glass of water. But is it a glass of water?
    • And if it is a glass of water, why is it a glass of water?”
    • And eventually he dies of thirst.
  • Some people in New York said,
    • “Gee, I’m enjoying the crime and poverty, but it’s just too cold. Let’s go west.”
  • Welcome to Chicago…
    • It’s a place where the weather’s made up and the seasons aren’t important. 
  • Chicago: 
    • Home of the El Train which is Spanish for… The Train.
  • Man A: Where are you from? 
    • Man B: Illinois
    • Man A: Where is Illinois?
    • Man B: Des Plaines
    • Man A: Ohh ok what’s that by?
    • Man B: Rosemont, Skoki, Niles, etc
    • Man A: Um where?
    • Man B: Chicago…I’m from Chicago. I live in Millenium Park. I am the bean. 

Crazy Chicago One-Liners

  • Chicago stole a pizza of my heart.
  • A day at Lake Michigan buoys my spirits!
  • I love Chicago, but I’m ready to get the L out of here.
  • Chicago floats my boat.
  • What you talkin ’bout Willis Tower?
  • There are only two seasons in Chicago: winter and police brutality.
  • Two jumbo hot dogs with the works is what we call salad in Chicago.
  • My comedian friend told me yesterday he was home sick for Chicago, so I shot him.
  • I went to Chicago for the food, but stayed because the weather forced me to hibernate.
  • The Chicago Police Department replaced all sirens with the National Anthem to force suspects to stop running and take a knee.

One-Liners You’ll Love Too:

The Chicago Trivia Showdown

Author’s Note

Chicago is a great place and the people there love their city and take pride. Chicago also has a long and rich history and that makes it the perfect city to poke fun at. 

I hope you enjoyed these Chicago jokes today. Let us know if we missed any hilarious jokes about the city in the comments section. Be playful and make light of anything negative. Visit our website for more fun and jokes.

Find out these funny facts about the people and city of Chicago.

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About the author

Megha Sharma

Megha is the heart of - When waking up in the morning, her first thought always is how to create a smile on someone's face before breakfast. Her passion are jokes for the youngest and about animals.

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