10 Sidesplitting Chicago Comedy Shows To Tickle Your Funny Bone

Charli Renken Charli Renken

10 Sidesplitting Chicago Comedy Shows To Tickle Your Funny Bone

Comedy gold is mined right here in Chicago!

With so many star comedians coming out of Chicago– Bill Murray, John Mulaney, Cameron Esposito, Hannibal Buress, etc.– it’s no surprise how big the city’s comedy scene is. While not all of them have Belushi-level fame (yet), we think these 10 comedy shows are hilarious ways to spend your Saturday night.

1. Drunk Shakespeare at The Lounge At The Lion

Drunk Shakespeare Chicago Theatre

The Shakespeare-themed comedy show is exactly what it sounds like. One of five classically-trained actors takes five shots and then (over-confidently) performs the lead in a Shakespearean play. The other four sober actors attempt to keep the play moving, while their drunk co-star inevitably makes a number of surprising character choices. Each show is different depending on who’s drinking what, but the result is always an unforgettable, gut-busting 90 minutes of the Bard as you’ve never seen him performed before. Buy tickets here.


2. The Buttcracker: A Nutcracker Burlesque at The Den Theatre

Photo by Matthew Gregory Hollis

The Buttcracker: A Nutcracker Burlesque returns to the Den Theatre Dec 5 for a fourth year of Christmas-themed debauchery. A sexy twist on the classic tale, the live performance is filled with burlesque, magic, sword balancing, circus, dance, and more! This body-positive show is quickly becoming a favorite among Chicago comedy-lovers. Tickets for this raunchy, holiday spectacle are on sale now.


3. 55th & Heartbreak at The Revival

The Revival’s improv show 55th & Heartbreak is a fast-paced, hysterically funny show presented by Chicago’s best comedians. Inspired by today’s headlines and current events, the show features a variety of music, improv, and sketch comedy. Don’t miss your last chance to see 55th & Heartbreak this Sat, Nov 23. Tickets are available here. 


4. Twisted Broadway at LIPS Chicago

While this isn’t strictly a comedy show, Twisted Broadway certainly makes us laugh with its outrageous takes on Broadway classics. This drag show makes for a hilarious evening for any musical theatre fan. Buy tickets here and receive a three-course prix fixe dinner and a free frozen cosmo!


5. Strip Joker at Mary’s Attic


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Another body-positive comedy show, Strip Joker is a monthly stand up showcase at Mary’s Attic. The show is entirely LGBTQ+ produced by five Chicago comedians with a concept that’s exactly what it sounds like; stand up comedians tell jokes while stripping off one garment at a time to promote body-positivity. It’s sexy, it’s hilarious, it’s our favorite queer comedy show! Find out more on the show’s Facebook page.


6. The Second City


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It would be ridiculous not to include this famous Chicago improv spot on our list of best comedy shows. Known for its famous alums– Steve Carell, Tina Fey, Joan Rivers just to name a few– Second City has some of the country’s best comedy classes and puts on incredible shows multiple times a week. A few upcoming shows include Do You Believe in Madness?, Grinning From Ear to Ear, and the holiday parody Deck the Hallmark. Find out more about Second City and it’s shows and classes on their website. 


7. The iO Theater


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The iO Theater has been home to some of Chicago’s most popular comedy show for over three decades! A prime spot for improv, iOS has a number of great shows including Improvised Shakespeare, The Harold, Cool Aunt, Dreamboat, and more! Similar to Revival and Second City, iO Theater also gives improv classes and has a great open mic for aspiring comedians! Find out more on their website.


8. Annoyance Theatre & Bar


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Located in Lakeview, Annoyance Theatre & Bar has a variety of shows that are bound to make you giggle. The long-running comedy spot features original plays, improv, sketch comedy, and more. They also have a great bar and are located just off the Belmont Red line stop. A few current shows include Shit Fyre, a musical about the failed festival, the interactive comedy show Trigger Happy, and Hitchcocktails, a murder mystery improv show. Find out more on the theater’s website.

9. Laugh Factory

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This list wouldn’t be complete without Laugh Factory. Ever since the SoCal comedy club expanded to Chicago in 2012, Laugh Factory has hosted the best of local stand up comedians several nights a week. They even occasionally bring in big-name headliners and have two awesome open mics! Check out more here.

10. Wait, Wait, Don’t Tell Me by NPR


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This long-running radio show is shot live in Chicago every week, which means you can either listen to it from the comfort of your home or catch a live show! During the hour-long show, panelists and contestants are quizzed in hilarious ways about the week’s news. The Webby nominate show is the perfect show for newsy with a funny bone. Learn more on NPR’s website.

Feature photo: Shutterstock.

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