The Ultimate Guide to Seeing an Improv Comedy Show in Chicago

Second City: The highest honor for a Chicago improviser is to perform for Second City. This theater has catapulted the careers of too many comedy legends to name, including Bill Murray, Tina Fey, Chris Farley, Alan Arkin, Amber Ruffin, Keegan Michael-Key and many more.

iO Theater: Formerly called the Improv Olympic (before the Olympics, well, sued them), iO is the theater where long-form improvisation was created. To see a long-form show, check out a Harold show.

ComedySportz: See teams of quick-witted comedians compete for points in this popular improv show.

The Annoyance Theater: The Annoyance is another staple in the Chicago improv scene, and it’s where performers can really let their freak flags fly. The Holy F**k Comedy Hour is a free show at midnight on Fridays and it’s always a good time. Also of note is this theater’s great bar and proximity to the night life of Chicago’s Boys Town neighborhood.

Baby Wants Candy: An improvised musical where the players aren’t just making up the plot, but the songs as well.

HitchCocktails: A cast of whip-smart improvisers make up an entire Hitchcock film on the spot…while slowly getting drunk.

Drunk Shakespeare: Located inside a hidden library cocktail bar, actors attempt to perform a Shakespeare play after one of their numbers takes (at least!) five shots of whisky.

TJ and Dave: To Chicago improvisers, this is the best improv show. A team of two season players, TJ Jagodowski and Dave Pasquesi make up a two-man show where they play all the characters. This show is becoming a rarer and rarer occurrence, so if it's playing while you’re in town, see it.

The Armando Diaz Experience: One of iO Chicago’s staples. Improvisers make up a set based on a guest monologist’s stories.

Improvised Jane Austen: A team of improvisers don their finest Georgian garb and improvise a Jane Austen story based on an audience suggestion.

Ale House: Consistently named the best dive bar in Chicago. Ale House was a favorite of Anthony Bourdain and Roger Ebert (who once called it “the best bar in the world that I know about”). But mostly, this is where the employees and cast members of Second City go to drink. Old Town Ale House is not for the faint of heart. The walls are covered in obscene paintings of celebrities and politicians, including a nude photo of Rob Blagojevich being sentenced in court.

Nookies: Nookies is one of Old Town’s most beloved staples. A diner with cozy comfort food right down the street from Second City, and therefore a favorite of its cast members.

Corcoran's: An Irish pub with good fare and a great patio across the street from Second City.

The Fudge Pot: Chocolatiers down the street from Zanies and Second City. Buy delicious handmade chocolates shaped and molded into almost anything you can imagine.

1959: The bar and restaurant is located inside Second City, and is in fact named after the year the theater was founded. It has great cocktails and food, and many aspiring comedy performers work there before becoming cast members themselves.

Utopian Tailgate: A rooftop bar in the same building as Second City, this place is pumping with energy. Aiming to emulate the fun and games of going to camp, there are swings, corn hole lanes and even a giant Jenga game.

Elaine's Coffee Call: A cozy coffee shop inside Hotel Lincoln, this place serves delicious coffee and pastries. It’s directly across from Lincoln Park and down the street from Second City.

The J. Parker: The rooftop cocktail bar located atop Hotel Lincoln. Absolutely stunning views of Lake Michigan, Lincoln Park and the Chicago skyline. Best enjoyed at sunset.

Orso's: Italian restaurant in Old Town, a local favorite.