The Good, the Bad and the Ugly of Chicago’s Notorious Theatre Scene

Chicago: where all the funny people go to become even funnier and be discovered for fame and fortune. This is a stressful career track for these actors, but a traveler’s inexpensive dream. The amount of comedic and theatrical venues, overflowing with opportunities to see the next Tina Fey or Bill Murray onstage at an extremely reasonable price, can almost be overwhelming. Never fear – Jackie is here!

My catalyst for moving to Chicago was to pursue a casting career. The recommendations I am about to unleash are from first-hand experiences of immersion, either being on the stage directly, or sitting in the audience supporting and critiquing acts. I will debrief a multitude of theatres and comedy locations—not necessarily the best or the most expensive, but some off the beaten path. This shall include “The Good,” “The Bad,” and most certainly “The Ugly” because, let’s admit it, “The Ugly” is as entertaining as “The Good” as a traveler.


Where better to start than the Goodman Theatre. Located in Chicago’s downtown loop by the Daley Plaza, it is Chicago’s oldest active, non-profit theatre. This award-winning regional theatre boasts two stages. First, the Albert Theatre, which highlights main-stage performances of historical, well-known and remounted plays. It also allures the likes of famed stars such as Nathan Lane, Diane Lane, and Brian Dennehy to the stage. Sometimes controversial, such as its 2011 Camino Real (American Flags burning in the name of art), if you’re looking for something family-friendly, the Goodman annually mounts The Christmas Carol, which should not be missed. The Owen Theatre is the Goodman’s Blackbox space, which can be reconfigured into numerous displays, molding to the set designer’s vision. Performances here are typically new works or workshops. Tickets are cheaper and the plays are grittier for this tourist- attracting theatre.

Other theatres similar to the Goodman: Steppenwolf, Lookingglass Theatre, and Chicago Shakespeare.

Tickets typically run between $25 and $200 (depending on the show, seat, and stage). But, a little secret: always type in “INDUSTRY” in the Promo Code section for weekday performances. You may land yourself a free pair of tickets to the hottest show in town.


Chicago boasts a plethora of off-loop theatres, which is exactly how it sounds. These theatres are not in the downtown loop, but are nestled in the neighborhoods of Chicago. They are enclosed and set in intimate locations, ignited with passion-driven performances. Since the actors, directors and designers are not being paid for their artistic contribution (or paid very little), the stage is ripe with their blood, sweat and tears. They’re doing this solely for the love of theatre. You’ll get some hits and some misses, of course, but how can you not enjoy a performance at Red Tape Theatre (off the Belmont stop). Here, the innovation of this small theatre company re-imagines their theatre space—an old Church gymnasium—to present daring, avant-garde pieces every time. Thursdays is “pay what you can,” and ticket prices are never more than $10. Buy a drink at the bar and sit on the wooden bleachers. For a moment, you’ll be transported back to high school.

Other companies similar to Red Tape Theatre: Red Moon Theatre, Red Twist Theatre, (Chicago likes the color Red), Collaboraction, the Neo-Futurists, Victory Gardens, and The Den Theatre.


The world over has heard of the Second City. Most travelers will go to a Main Stage performance, usually displaying the talents of the next Saturday Night Live (SNL) cast member. I advise you to instead, go to Improv Olympic on Clark Street, next to Wrigleyville Stadium. You’ll see the same performers for half the cost. Improv Olympic isn’t sketch material, but in fact, is the birthplace of long-form improvisation. You can check out TJ and Dave—a two-person, totally improvised 30-to-45-minute set – for your first time. If you’re more daring to sit through the up-and-comers, buy a $5 ticket to the Cabaret Theatre on a Monday night, and watch them perform on Harold Teams. For all Lady Improv, watch the Virgin Daiquiris Wednesdays at 8 p.m. These veteran comedic actresses aren’t shy about their vulgar material or periods. However, my advice is to pay the $15 for either Thursday or Friday night to see the Improvised Shakespeare Company, an all-male team who improvises in—you guessed it—the style of the immortal Bard, William Shakespeare. I have seen these phenomenal players perform eight times. Who knows? You might get lucky the night you go. Sir Patrick Stewart has been known to make guest appearances.

Other improv locations: The Annoyance Theatre, The Second City, and The Second City Training Institution, Stage 773.

For off-the-beaten path improv: PH Comedy Bar, Studio B, The Den Theatre, and The Upstairs Gallery


Interested in wading through the feces-infested Nile River to potentially come out with a diamond? You’ll pay next to nothing, if not nothing, to watch some pretty horrific theatre and comedy at the amateur level, yet potentially walk away having witnessed a performance that the most established actor couldn’t dream of delivering. Trust me – THE UGLY in Chicago – will provide stories for ages.

Gorilla Tango Theatre in Wicker Park off of the Western Blue Line has established itself as ‘burlesque theatre central.’ Want to see Batman Burlesque? Go Gorilla. Want to see Republican Party Burlesque? Go Gorilla Tango. Want to see a one-woman show in which the actress can impersonate every Simpson’s character flawlessly? Go Gorilla. It has an ever-changing schedule, so predicting the level of the night is impossible. At most, you’ll pay $10. It’s worth it.

The Play Ground Theatre and Studio BE: This improv and sketch blackbox theatre allow Chicago’s comedians to perfect their not-so-mainstream comedy. Obscenities are often thrown around, and on any given night, a dance party with the audience will ensue after the shows. It’s BYOB for both theatres, and Wednesday nights at the Play Ground is ‘Gimme Five’ a solo-comedy act where actors test out their impersonations, characters, and jokes. It’s often weird, sometimes Ugly—as I’m referring to the time I saw a girl make out with a rotisserie chicken—but always rewarding. Plus, it’s $5.

Bar-prov is also a happening thing. In hundreds of bars throughout Chicago, wandering in to have a drink may lead to watching an indie improv team play together in front of a fireplace. This is growing in popularity, as more and more comedians saturate Chicago.

Some bars that have bar-prov: The Atlantic Bar and Grill, The Black Rock Pub and The Blarney Stone. Go for a milk stout and get a free laugh.


Not so much a secret anymore, a traveling group of actors and improvisers are perfecting the art of word-of-mouth theatre. The Backroom Shakespeare project is one of my favorite experiences. The premise: a group of actors decide on a Shakespearian play. They rehearse once. Commit the lines to memory as much as possible, and rendezvous in the back of a bar, small park or alcohol warehouse to perform their play. Gender roles are often mixed. Admission is free as long as you buy a drink. Games are played before. And, the onslaught of jarring performances from classical trained and unknown actors renders you speechless. Occasionally, the Improvised Shakespeare Company will perform after the first show.

About the author

Adventura is Jackie’s second middle name. Originally a farm girl from the great state of Kansas, after traveling throughout Mexico, Costa Rica, Panama, and Ecuador, one could say she’s caught the Spanish influenza. Currently residing in Madrid working as an English Professor and taking clown classes at night, Jackie’s expertise in intellect remains to be heard, but her experience in travel is extremely diverse. Watch out Europe and Africa. Jackie plans to reverse colonize you.

Jackie graduated with a BA in Theatre Peformance and a BA in Spanish from the University of Kansas. She's road tripped across half of the United States by herself to live in Washington D.C. and Chicago, where she worked for several theatres and casting agencies. In her spare time, Jackie's favorite thing to do is eat jamón (ham). #jamon

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