A Theater Lover's Guide to Chicago

Kroydell Galima (L) and Kamille Dawkins (R) in Pillars of the Community by Strawdog Theatre Company.
Kroydell Galima (L) and Kamille Dawkins (R) in Pillars of the Community by Strawdog Theatre Company. | © Heath Hays / Courtesy of Strawdog Theatre Company
Sarah Ashley

Chicago’s arts and culture scene is incredibly rich and ever-evolving. Impressive art museums, music festivals and exhibitions are available to experience every day. But, it’s the Windy City’s theater scene that may just be its most diverse and exciting avenue for entertainment. Theater-goers can experience everything from classic Broadway musicals and improvisational comedy, to bizarre vignettes and dramatic new works from local playwrights. In short, there’s a long list of spaces to visit and shows to see while staying in Chicago. If you love theater, you must check out the 10 on our list.

1. The Second City


The exterior of Second City comedy club with a curved marquee listing shows and events
© Bruce Leighty / Alamy Stock Photo
This Chicago institution is considered one of the most popular comedy clubs in the world. The Second City got its start with a group of young, driven University of Chicago students in 1959. Today, it is known for its hysterical sketch comedy and scathing political satire. With a growing number of performances and stages to choose from, audiences won’t be disappointed by the options Second City offers. The Mainstage and E.T.C. Stage shows are top-tier sketch comedies, though additional written pieces in the Up Comedy Club are sure to please. Many famous comedians got their start at Second City, including Tina Fey and Stephen Colbert, and these alums have been known to show up unexpectedly to play improv sets with the current cast. What could be more fun?

2. iO Chicago


© Kris Arnold / Flickr

Credited with being the home of long-form improvisation, iO (formerly Improv Olympic) has been a Chicago staple since its founding in 1981. Del Close, a world-renowned improv teacher and director, and his business partner, Charna Halpern, started the theater as a way to teach the art form and give performers a place to practice their craft. Improv is a unique theater form worth a watch for sure. Theater lovers should not miss the Improvised Shakespeare Company at iO. The incredibly talented cast performs a two-act improvised play in the style of William Shakespeare, complete with heightened language, rhyme and, of course, a slew of bizarre characters. The venue is known for training some of today’s most prolific comedians, including Amy Poehler, Jordan Peele and Bill Murray.

3. Black Ensemble Theater


© Black Ensemble Theater / WikiCommons

Jackie Taylor, an actress, playwright and avid producer, founded a community arts organization in 1976. By 2011, it had grown into a full theater and cultural center with a permanent home in Chicago’s Uptown neighborhood. The Black Ensemble Theater’s mission is to actively fight racism using the arts and educational programs for young people. The theater hosts world premieres of new musicals and plays and is known for being one of the most diverse theaters in the world. Its Five Play Season of Excellence puts up five plays every year written specifically for the Black Ensemble Theater and its performers. These plays must feature musical numbers, a positive story arc and historical perspective. Anyone and everyone who enjoys theater must take in one of these shows – and the company makes it easy by running 48 weeks out of the year.

4. Steppenwolf Theatre


Steppenwolf Theatre
© McDuff/WikiCommons | © McDuff / WikiCommons
The Steppenwolf Theatre in Old Town is perhaps the most well-known space for dramatic arts in the city. The established theater company has been performing continuously since the mid-1970s and is known for putting on riveting stage productions, as well as launching the careers of aspiring actors. The building has four stages, including LookOut, which often hosts dance performances. Past production honors include the National Medal of Arts and twelve Tony Awards. Current Artistic Director, Anna D. Shapiro, states that for the theater’s upcoming 2018/19 season, the goal remains to deliver productions to the public that not only allow us an opportunity to feel compassionately toward characters different from ourselves, but to celebrate the evolution of the world we live in. Tickets can be expensive, but matinee options are available for a lower price point and it’s always worth the money to see such extraordinary work.

5. Lookingglass Theatre


© Mike Burton / Flickr

Located in the historic Water Tower Water Works building on bustling Michigan Avenue, the Lookingglass Theatre focuses on bringing completely new works to the stage. After getting its start in 1988, thanks to several Northwestern University students, the venue won the 2011 Tony Award for Outstanding Regional Theater. The company puts collaboration first to create groundbreaking works of performance. Productions include everything from previously unknown dark comedies to well-known stories such as 20,000 Leagues Under the Sea. The company also boasts a Young Ensemble, which is a terrific place to see tomorrow’s stars flex their acting muscles on stage for the first time. Company members act, direct and write, which makes the Lookingglass Theatre a perfect place to see established artists explore their other talents.

6. CIC Theater


CIC Theater
© CIC Theater

This unassuming improv theater showcases some of the best improv comedy in Chicago – which is saying a lot, since the Windy City is home to some of the world’s most prolific comedy institutions. Players at the CIC Theater perform long-form improv with exuberance, inhibition and expertise. Also a training center, the venue has a full bar and offers shows Wednesday through Sunday. The best performance to check out is Saturday’s 10:30 p.m. lineup; three excellent improv teams get wild on stage, each with a unique personality and form. What makes CIC (which stands or Chemically Imbalanced Comedy) stand out is its encouragement to performers to push themselves to try innovative methods of improv and styles of play. Most teams at this theater build their own forms, which means the multiple shows an audience can see in a single night will each have a different structure, arc and pace.

7. Broadway in Chicago


Oriental Theater
© bradleypjohnson / WikiCommons

Founded in 2000, Broadway in Chicago hosts the biggest and best musicals and plays at five spectacular theaters downtown Chicago. Audiences at the Auditorium Theater, the Broadway Playhouse Theater, the Cadillac Palace Theatre, the CIBC Theater and the Oriental Theater are riveted weekly with outstanding shows. The group makes up the Chicago Theater District in the Loop. Perfect for musical theater lovers, Broadway in Chicago offers hits including Miss Saigon, The Book of Mormon, Hamilton, Tootsie, Pretty Woman the Musical and many more. You can also sign up for tours of the theater spaces, if a behind-the-scenes look is what you’re after. Many productions offer rush tickets at discounted prices, too, to make enjoying Broadway-caliber shows a little more affordable.

8. Edlis Neeson Theater

Theater, Museum

© Jeremy Atherton, 2006 / WikiCommons

The Museum of Contemporary Art in Chicago’s Streeterville neighborhood is home to the Edlis Neeson Theater. The MCA Stage series hosts local and internationally recognized talent in this state-of-the-art performance space. With only 300 seats and walls covered in exquisite oak panels, the Edlis Neeson is both intimate and stunning. Audiences over the years have been delighted by dance performances, film screenings, panel discussions, live theater and more. Performances typically push the envelope of what traditional theater looks, feels and sounds like, incorporating dance, film, song and spoken word into a single production. Most works are only available for short periods of time and the line-up changes frequently, so visitors should do research ahead of time to know what shows will be available on desired dates. Audiences can also expect many of the MCA Stage series shows to tackle difficult topics currently affecting our world, like prison reform and underground political movements. A must-see for theater lovers from all backgrounds.

9. The Neo-Futurists


The Neo-Futurists
© Evan Hanover / Courtesy of The Neo-Futurists
This theater and its company fuse a spectacular array of sport, spoken word and performance together to generate some of Chicago’s most unique shows. Audiences viewing performances in The Neo-Futurists’ 150-seat space in the Andersonville neighborhood can expect live theater with twists of Dada and Surrealist art. Their current production, Infinite Wrench, consists of a string of two-minute-long plays that range in style from horror to comedy, satirical to inspirational, and beyond. The only certainty is that no two shows are alike. In keeping with this vibe, ticket prices are based on the roll of a dice at the door and only cash is accepted. Lines are often long, stretching down the block for the Neo-Futurists’ shows Fridays through Sundays, but have no fear! Performances run 50 weekends out of the year. This is truly the best place to see experimental theater in Chicago – and perhaps the country.

10. Strawdog Theatre Company


Strawdog Theatre Company
© Heath Hays / Courtesy of Strawdog Theatre Company

Founded in 1988, the Strawdog Theatre Company delivers outstanding performances with a focus on ensemble-based work and a collective environment. For 30 years, the company has devoted itself to both producing never-before-seen works and reviving old classics, constantly seeking out fresh ways to inspire and entertain audiences in their storefront space in North Center. Some seasons in the past delivered up to seven plays, while others focused on just three or four. In their current season, which happens to be their 30th and the start of an era at a new address, the Strawdog Theatre Company explores what it means to write one’s own story and “determine one’s own identity” through three brand new plays. This is a terrific choice for theater lovers looking for a local, storefront theater with impactful productions.

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