Top Chicago Jokes, Chicago Puns, Chicago Dad Jokes & More

In this very funny joke compilation, we have come up with the best chicago jokes, chicago puns and chicago dad jokes to make you laugh.

The Windy City Laughs: Top Chicago-Style Jokes Guaranteed to Make You Chuckle

1. Why did the tomato turn red when it visited Chicago? It saw the big ketchup bottle in Millennium Park!
2. What do you call a Chicago hot dog with no toppings? A plain wiener.
3. Why did the scarecrow win an award in Chicago? Because he was outstanding in his field!
4. What did the Chicago deep dish pizza say to the thin crust pizza? “I’m a little deeper than you.”
5. Why did the Chicago Bears fan bring a ladder to the game? They heard the seats were up high!
6. Why did the Chicago musician get arrested? They were caught for playing too much sax in the Loop.
7. What did the Chicagoan say when the pizza delivery guy arrived late? “You’re cutting it close!”
8. Why did the coffee file a police report in Chicago? It got mugged.
9. What do you call a group of dancers from Chicago? The Windy City Ballet.
10. Why was the math book sad in Chicago? It had too many problems.

Gotta Love that Second City Humor: Hilarious Chicago Jokes That Will Have You in Stitches

1. Why did the Chicago politician go to the dentist? To fill in a cavity – in their campaign promises!
2. How do ghosts from Chicago travel? They take the “L” train.
3. What do you call a comedian from Chicago who can’t make anyone laugh? A Chi-larious jokester.
4. Why did the Chicagoan bring a ladder to the comedy show? To reach the Second City!
5. What do you call a group of Chicago improv actors? The Windy Wit ensemble.
6. Why did the Chicago chef switch to cooking hot dogs? They wanted to relish in a new career.
7. What’s a Chicagoan’s favorite type of humor? Deep dish jokes.
8. Why did the comedian refuse to perform in Chicago during the winter? They heard the audience could be frosty.
9. How do Chicagoans stay warm during the winter? By laughing at ice-cold jokes!
10. Why was the Chicago crime scene investigator always laughing? They had a great sense of “crimedy.”

Chicago Puns Galore: The Funniest Jokes About the City of Big Shoulders

1. Why did the salsa move to Chicago? It wanted to salsa-dance in the city that never sleeps.
2. What’s a Chicagoan’s favorite type of book? Windy tales!
3. Why was the Chicago chocolate factory so successful? They had a great team that didn’t take breaks – they were always on a Kit-Kat!
4. How do Chicagoans handle stress? They sausage it out with a deep dish pizza.
5. Why did the Chicago coffee shop close down? It couldn’t espresso itself properly.
6. What did the Chicago architect say when designing a new building? “I’m building this up from the ground up!”
7. Why did the Chicago math teacher go to the beach? To get a “tan-gent” on triangles.
8. What’s the key to success in Chicago? A deep understanding of the city’s architecture.
9. Why did the Chicago musician only play in the Loop? They didn’t want to be a flat note.
10. What’s a Chicagoan’s favorite vegetable? The Big Shoulders of corn!

Laughing Your Way Through the Loop: Side-Splitting Jokes About the Heart of Chicago

1. Why did the Chicago dog walker bring an umbrella to work? There was a drizzle in the Loop!
2. What did the Chicago plumber say when fixing a leaky faucet? “Looks like we’re all washed up here.”
3. Why did the Chicago jazz musician get kicked out of the band? They kept tooting their own horn.
4. How do Chicagoans know it’s summer? The snow cone stands in the Loop open up.
5. What did the speeding ticket say to the Chicago driver? “You’re going too fast, slow down in the Windy City!”
6. Why did the Chicago tourist get lost in the Loop? They couldn’t find their way out of the comedic traffic.
7. What’s a Chicagoan’s favorite type of sandwich? The “loop-de-loop” sandwich – a classic Chicago creation.
8. Why did the Chicago detective get a promotion? They had a real knack for solving “loop-holes.”
9. Why did the Chicago comedian become a surgeon? They were great at making people laugh – and stitch up wounds!
10. What’s a Chicagoan’s favorite field of study? Windy Science – the study of laughter in the Loop!

From Deep Dish to Deep Laughs: The Best Chicago Jokes to Brighten Your Day

1. Why did the Chicago cat get lost in the alley? It was chasing the tail-lights in the Loop!
2. What do you call a Chicagoan who’s obsessed with puns? A real deep dish joker.
3. Why did the Chicago bartender get a new job? They heard there were gin-uinely funny customers in the Loop.
4. How do Chicagoans greet each other in the morning? With a deep-dish smile and a side of humor!
5. Why did the Chicago ghost stay in the Loop? They heard it was full of spirit.
6. What’s a Chicagoan’s favorite type of music? Windy City tunes – the soundtrack of laughter in the Loop!
7. Why did the Chicago chef put on a comedy show during dinner service? They wanted to dish out laughter with their dishes.
8. What did the Chicago weather report say? It’s going to be sunny with a chance of deep dish laughs.
9. Why was the Chicago marathon runner always laughing? They had a real “runner’s high” from all the humor in the city.
10. What’s a Chicagoan’s favorite way to relax after a long day? A deep-dish laugh in the Loop with friends and family!