7 Comedians on Their Favorite Jokes About Chicago

You will laugh at these jokes and like it

November 10, 2017 9:00 am

Our favorite Chicago one-liner in recent memory, as recently told to us by local comedienne Zoe Schwartz:

“Chicago only has two seasons: winter and police brutality.”

Harsh? Yes. But between the weather, gun violence and, hell, the Bulls’ management, it’s no wonder Chicagoans are bitter.

So we asked our favorite Chicago-bred funnypeople to share their best jokes about the city.

Because if you can’t laugh here, get ready to suffer.

Pat McGann
Twitter: @mcgannpat

“Midway is the best; a little airport in the middle of a neighborhood. I love when I take a cab there. The driver always asks, ‘What airline?’ It’s like, just drop me off. There are two doors. I’m good.”

“Who designed the Eisenhower? Ever been on I-290? What a treat. Just like, ‘Hey, we’re sick of these exits on the right … what do you say we throw some up on the left, too? When we get to Harlem, bring the ramp machine over here and let’s give it a go for a few.’”


Pat McGann is a longtime Chicago comic. He created and hosted the Emmy-nominated show “The Chicago Stand Up Project,” and his comedy album “Sounds Good” is available on Spotify. www.patmcganncomedy.com


Danielle Puterbaugh
Instagram: @puterbaughdani

“How do you get to Carnegie Hall? Practice. How do you get to Navy Pier? Take your theater degree and the 66 bus.”

“People visiting Chicago wonder why we drink so much. They wonder if we’re OK. They ask, ‘Do you guys ever drink water?’ I say, ‘We eat a lot of hot dogs, is that drinking water?’”


Danielle Puterbaugh is one half of The Puterbaugh Sisters, a sister comedy duo. They produce the hilarious variety show “Entertaining Julia,” which ran for eight years in Chicago and is now in its ninth season in L.A. www.puterbaughsisters.guns.beer


Martin Morrow
Twitter: @martinmorrow

“A lot of people get mad about the gangs in Chicago and the murder rate as if we haven’t dedicated whole tours, museums and movies to white gangsters like Al Capone and Bugs Moran. Maybe Lil Gunshot is trying to take his place in history, too, and it’s on the city for normalizing it.”


Martin Morrow is a former ensemble cast member on the Second City Touring Company and  a recent alumnus of the Second City Mainstage, appearing in “The Winner … Of Our Discontent.”  www.martinmorrowcomedy.com



Beth Stelling
Twitter: @BethStelling

“I rode my bike through the winters in Chicago. It was so cold I would have to bundle up completely. One day I pulled up to a stop sign and an old man leaned over to me to ask, ‘Excuse me, sir? Is the bus coming?’ And I looked at him and said, ‘I’m a girl!’ And then I rode away. So the rest of that winter I was just wearing my bra on the outside of my coat.”


Beth Stelling came up through the Chicago stand-up scene and studied improv at The Annoyance Theater. Her Netflix stand-up special is out now. She now lives in L.A. www.sweetbeth.com


Sean Flannery
Twitter: @sean_m_flannery

“Chicago’s affinity for nicknames runs so deep it nicknamed its own highways, which makes traffic reports impossible to decipher if you’re not from the area. It’s never I-90 or -290 or -55, it’s an odd collection of bishops and presidents fighting each other. It sounds less like a traffic report and more like an explanation of how the Vietnam War started.”

“A Chicago bicyclist is what you get when you take all the aggression and recklessness of a Chicago car driver, then add the entitlement of thinking you’re saving the planet.”


Known as one of Chicago’s “loudest comics,” Sean Flannery is known around the city for his barroom humor. He hosts the Blackout Diaries, a comedy show in which Chicago’s best comics tell true drinking stories. www.worldsdumbestman.com


Peter-John Byrnes
Facebook: @PeteByrnes

“The shame of every Chicagoan isn’t Capone: It’s Styx.”

“Chicago to the English dictionary: ‘Jeet?’ As in, ‘I am inquiring as to whether you have dined.’”

“Having two jumbo hot dogs with the works is what we in Chicago call ‘salad.’”


A comedy scene stalwart who’s been at it since 1985, local legend Peter-John Byrnes has probably done more open mics than his health allows. www.peterbyrnes.com


Adam Burke
Twitter: @atpburke

“Chicago’s ketchup fatwa is weird. It’s odd that there are 900 rules about what can and can’t go on your meat and zero rules about what goes IN the meat. That frankfurter is made of cow lips and monkey toes; Heinz isn’t the issue. That Polish is tied off with a human colon. Condiments are the problem.”

“When I ask tourists what they most like about the city, they sometimes say the Bean. Which is the most narcissistic answer you can give. What do you like most about our historic, multi-cultural city? I liked the giant fucking mirror. I liked where I could see myself and it’s all weird looking.”


Originally from the UK, Adam Burke has been performing comedy in Chicago and throughout the U.S. for over ten years and is a regular panelist on NPR’s Wait Wait Don’t Tell Me. www.adamburkecomedy.com

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