The Best Theater in Chicago

By Robert Glaze

Chicago is a theater town with many actors choosing to stay here and work rather than moving to New York or other cities. There are purportedly over 200 theater companies in the area. The Goodman, Chicago Shakespeare, Steppenwolf, Lookingglass and Court Theatre have all received the Tony Award for Best Regional Theater. Many productions start in Chicago and then move to Broadway after successful runs here.

My top recommendations include:

Make a beeline for the Writer’s Theatre, in Glencoe, on the North Shore at 325 Tudor Ct. Terry Teachout, of the Wall Street Journal, in the past said that this is one of the best regional theaters in the country. Their productions are outstanding!!!  I saw Sondheim’s Into The Woods in 2019 and in 2023 went up to see the musical Once and it was a wonderful production. Their new theater designed by architect Jeanne Gang is beautifully done. The Metra train can get you there easily from the Chicago Loop and it is a block walk to the theater. 

Goodman Theatre: A Tony Award Winning Regional Theater with great productions. Founded in 1922, it has been at its current location since December 2000. There are two theaters, the Owen and Ivan, named after the Goodman Brothers. The Owen is the main stage and the Ivan the smaller of the two with often newer plays. 170 N. Dearborn. My last show was a brilliant production of the musical The Who’s Tommy last August. It opens on Broadway in NYC next month.

Steppenwolf Theatre: Try to see a performance at this Tony Award winning regional theater, located at 1650 N. Halsted in Lincoln Park. In the past it sent August: Osage County to New York which went on to win the Tony for best play. Its current ensemble members are active in movies and theater around the country. In 2016, they opened the new 1700 Theater and Front Bar off the lobby.

In 2021, they opened and expanded into a 50,000 sq. ft. building next door which includes the Ensemble Theater and Liz and the Eric Lefkofsky Arts and Education Center, also known as The Loft. There is also a wine bar and sidewalk lounge.

TimeLine Theatre Company: Located 615 Wellington just west of Broadway, this is a theater company that continually gets great reviews for its productions. It is celebrating its 27th season and has presented 90 productions, including 13 world premieres and 41 Chicago premieres. I have seen four plays in the last few years and the quality is really outstanding! I went last Sunday to see the production of Notes from the Field written by Anna Deavere Smith. They are in process of moving to a larger and new permanent venue at 5033-5035 N. Broadway Ave. in Chicago’s Uptown neighborhood.

Chopin Theater: A small theater, at 1543 W. Division St., they offer plays by several small theater companies along with literary, music, film and social events. The historic building opened in 1918.

Court Theatre: Head south to Hyde Park and the University of Chicago for excellent productions. It has been a Chicago institution for almost 70 years.

Chicago Shakespeare Theater: Despite being on the very touristy Navy Pier, this is an excellent theater company that not only produces the best of Shakespeare but features musicals and other dramas from Sondheim to those from other countries like Ireland, Italy and South Africa. Their productions of Follies and Sunday in the Park with George were excellent.

On St. Patrick’s Day 2019, I had a great experience when I saw the play Two Pints from Dublin’s Abbey Theatre in the theater bar. With 50 people in the audience, it was about two guys drinking in a bar in Ireland. It was so fun!!

The theater just opened a great new performance space called The Yard. I just went to my first performance and the space is stunning. I saw the musical SIX which premiered in Chicago before it went to Broadway. It is a wonderful musical! I also saw the premier of The Notebook, a new musical, in 2022 before it opens next month on Broadway. 800 E. Grand Ave. Discounted parking is available. They have a special section in the Navy Pier garage for theater patrons.

Theo Ubique Cabaret Theatre: For fans of cabaret and musicals, head to Evanston to their new facility at 721 Howard St. In the past I have seen the productions of The Light in the Piazza and Aspects of Love. A 3-course prix fixe dinner is available before curtain time, by reservation.

A Red Orchid Theatre: A small theater in Old Town, this is a quality company with ensemble members including founding member Michael Shannon. 1531 N. Wells.

For musical fans, head to Porchlight Music Theatre which has had a focus on musical theater since 1996. They now perform at the Ruth Page Center for the Arts at 1016 N. Dearborn. You might also like their new series, Porchlight Revisits, which presents lost or forgotten productions for two nights only and their New Faces Sing Broadway, offered several times a year. I have been to several productions and have thoroughly enjoyed each one. In 2021, I went to my first performance outdoors in Washington Square Park which is part of the summer series, Broadway in your Backyard. It was excellent! In 2022 I went to their annual fundraiser which featured the music of Stephen Sondheim and another Broadway in your Backyard in Wicker Park. I enjoyed seeing the families and children engaged with the music.

Recent productions that I have enjoyed include A Chorus Line, Sunset Boulevard and Cabaret in 2023. This afternoon I am attending the matinee of Anything Goes! I can’t wait as it is getting great reviews.

Lookingglass Theatre: This is a great Chicago-based theater company located in the old Water Tower Pumping Station directly across from Water Tower Place. They are in the process of a transformation and will be returning to the stage this year. If you see a play on the schedule directed by Mary Zimmerman, don’t miss it. 821 N. Michigan.

The Apollo Theater was built in Chicago’s Lincoln Park neighborhood in 1978. Located at 2540 N. Lincoln Ave., the Apollo has 440 seats and a lobby featuring art exhibits and a full bar. I recently went back again for a performance after several years and loved the experience. There are several bars, restaurants and coffee shops nearby for you to enjoy before or after a performance.

The CIBC Theatre, Cadillac Palace Theatre and the James M. Nederlander Theatre are the venues of Broadway in Chicago which provide pre-Broadway and post-Broadway plays and musicals. Many productions start in Chicago before heading to the Great White Way. My last production was the Louis Armstrong musical A Wonderful World.

The Broadway Playhouse at Water Tower Place features plays and musicals through Broadway in Chicago as well. It is at 175 E. Chestnut. I went on Wednesday to the matinee of the comedy, Golden Girls – The Laughs Continue. Prior to that, last October, I saw the Tony Award winning play, The Lehman Trilogy produced by Timeline Theatre.

I was sad to learn that during the pandemic in 2020/21 that the Mercury Theater at 3745 N. Southport Ave. was permanently closing. But in late 2021, I was thrilled to learn that it was reopening and would continue to play a prominent role in musical theater in Chicago. It has been a popular venue for its homegrown productions such as Avenue Q and Spamalot, which I saw there in its larger Mainstage Theater. I was recently back for two Mainstage productions of the musicals Priscilla, Queen of the Desert and Big River.

In addition, they have a smaller and more intimate Venus Cabaret Theater, where I have really enjoyed recent productions of Company, An Unforgettable Nat King Cole Christmas Show and Lady Day at Emerson’s Bar & Grill, a one-woman musical about Billie Holiday. I hope you will go and support this important local venue!

Athenaeum Theatre:  Located south of the Music Box and Mercury Theatre, the Athenaeum is an historic theater, and for over 100 years and is Chicago’s oldest continually running off-loop theater. With a large main stage and three smaller studio theaters, it is home to a number of theater companies, dance companies, comedians and concerts. Make sure to check out their website for the current schedule. In the past I went to an excellent contemporary opera presented by the Lyric Opera. Street parking is available, but they also have two nearby lots they share with a neighborhood church. 2936 N. Southport.

The Lyric Opera of Chicago presents a Broadway musical at the end of their opera season. I have enjoyed Jesus Christ Superstar and West Side Story.

For great a great small theater experience, check out the schedule for the productions at Stage 773, a performance venue at 1215 W. Belmont. I have seen several productions there. Next door at 1229 W. Belmont is Theater Wit. I went to my first production a few years ago that was excellent. They have three performance spaces.

In 2023 I attended my first performance in the DePaul Theatre School, at 2350 N. Racine. It is an attractive, contemporary building with several performance spaces that was designed by the internationally renowned architect César Pelli, and his firm Pelli Clarke Pelli Architects and opened in 2013.

There are several productions staged and performed by the students throughout the school year. I was very impressed with the quality of the performance. I already have a ticket for an upcoming production of A Midsummer Night’s Dream in May 2024.

I hope you enjoy local theater as much as I do and that you will continue to support these companies as they emerge from the struggles due to COVID-19 the last four years.


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