Written by: Danielle Bluford


If you didn’t know, the Windy city of Chicago is the place the best and brightest future comics come to try their hand at stand up, improv, and sketch comedy. Most have indeed heard of Second City, but did you know there are other numerous venues that serve up a tasty batch of laughs each and every night here in this fine city? Let’s attempt to name only a few today, because its quality and not quantity we’re after.

1.) CIC Theater –  When you come to CIC, expect to be greeted by any number of staff that all truly care about this place and the people in it. With improv and sketch shows Wednesday through Sunday evenings. there is always something different and unique to experience. House teams of consistent performers and newbies putting on one of a kind shows are all welcomed and encouraged. CIC lets audiences experience shows that come from a place of heart, truth and silliness.

Show Faves: Married on Thursday nights (an improv show about real connected relationships with heart) and the always funny Saturday night Showcase– its always a hit (and a hoot).

P.S.: If you want to brush up on your improv skills after seeing their shows, check out a Dabble class on Improv For Self Expression or an Intro to Improv Workshop and you won’t be dissapointed!

CIC Married


2.) Annoyance Theater  – You can feel the energy the moment you walk in the space. The open front bar is filled with people, their energy created by a community of people hungry for cutting edge entertainment that is special and unique. Many supportive alums, including Stephen Colbert, have supported the construction and existence of the new beloved space. This new East Lakeview spot was a relocation for the theater last year when they moved from their long time home in Uptown. You can always see something good at the Annoyance, whether a consistent, long running show fave (Messing with a Friend) , uniquely organic improv (Trigger Happy) or a sweet rotation of solo shows (Hideous) that showcase more personal works and points of view.



3.) iO Chicago — This Chicago staple has been around for decades and kicked off the careers of the greats such as Chris Farley, Tina Fey, Amy Poehler, Neil Flynn, and Mike Meyers. Here, you can see shows with a variety of themes, veteran performers as well as newer talent, and even Shakespearean themed improv. The only thing you need here to have a good time is a willingness to experience something new.

io Chicago 2

Show Faves: Improvised Shakespeare, The Heraldo (Spanish improv that is filled with flavor) and Revolver (SNL’s Vanessa Bayer’s team) on Friday nights.

P.S.: If you wanted to practice your Spanish before heading out to see the Heraldo (Spanish improv show), check out this Dabble class on Spanish Language Immersion + Cooking!


4.) The Shit Hole — This place is a true gem that you may only ever hear of by word of mouth. Until recently, you haven’t been able to Google ‘The Shit Hole’ so easily, or like them on Facebook, as this is how they like it. Recently Chicago Reader reviewed and recommended, this space is one that invites curiosity, a willingness to experience comedy, music and sometimes darker topics from inside an attic converted theater space. All by donation, the team of guys that run The Shithole (including but not limted to: Zach Bartz, Kevin Gerrity, Loren England and Dan Wilcop + more greats) just ask that you contribute in some way: either donate money for beer or sign your name on their art covered walls. A more supportive house you will never ever find. This place is the tops (literally).


The Shit Hole

Show Faves: Sunday and Thursday nights at 8 PM are the regular showcases, but sometimes they do Friday night special shows at 8 PM as well. Location is roughly near Honey Butter Fried Chicken, but its best to private message founder, Zach Bartz, on Facebook for the rightful address. Trust us, its worth the extra step!

P.S.: While you’re at it and already trying something new, check out Dabble’s Harp playing class. Hey, if you get good enough, maybe you’ll want to perform at The Shit Hole too!