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 close to 200 small theater companies in the area. The Goodman, Chicago Shakespeare, Steppenwolf and Lookingglass have all received the Tony Award for Best Regional Theater.
Make a beeline for the Writer’s Theatre, in Glencoe, on the North Shore. Terry Teachout, of the Wall Street Journal, says 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. The Guildhall restaurant, at nearby 694 Vernon, is a great spot for a pre-theater or post-theater meal.
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. I went to a brilliant production of the musical The Who’s Tommy in August 2023. It opened on Broadway in NYC in March 2024. In July 2024 I really enjoyed the new musical Midnight in the Garden of Good and Evil. I expect it to open on Broadway as well. 170 N. Dearborn.
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 are active in movies and theater around the country. In 2016, they opened the new 1700 Theater and Front Bar off the lobby.
The 1700 Theater is used in partnership with other local theater companies. In August 11, 2024 I went to the production of Kokandy Productions, Out of Focus, at the Chicago Musical Theatre Festival in the 1700 Theater. It is a wonderful venue with cabaret seating at tables.
In 2021, they opened an expanded into a 50,000 sq. ft. building next door which includes the Ensemble Theater and Liz and Eric Lefkofsky Arts and Education Center, also known as The Loft. There is also the Tap Bar.
TimeLine Theatre: Located at 615 Wellington, just west of Broadway, this is a theater company that continually gets great reviews for its productions that present stories inspired by history. I have been several times. The quality of the plays is really outstanding!
I went last in February 2024 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. One of the theater companies is Kokandy Productions. On August 11, 2024 I went to one of their productions Out of Focus, at the Chicago Musical Theatre Festival at the Steppenwolf Theatre. It was excellent. I hope to see another one of their prouctions at the Chopin Theater.
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 opened on Broadway in March 2024. 800 E. Grand Ave. My last performance was Judgement Day staring Jason Alexander in May 2024. It was a great comedy.
Discounted parking is available. They have a special section in the Navy Pier garage for theater patrons.
Before or after a performance, I recommend you enjoy a meal at celebrity Chef Art Smith’s new family-friendly restaurant, Reunion. It features Southern comfort food including fried chicken, fried catfish, fried green tomatoes, biscuits, mac & cheese and collard greens. I really enjoyed my shrimp and grits before my Sunday matinee. They also have large outdoor patio. I went back again and loved the fried green tomato eggs benedict with grits for brunch before my last performance.
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 outdoor in a Chicago 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 along with matinee of Anything Goes in February 2024. I also loved seeing the concert version of Sunday in the Park with George, downtown, at the historic Studebacker Theater in the Fine Arts Building in May 2024.
Lookinglass Theatre: This is a great Chicago-based theater company located in the old Water Tower Pumping Station directly across from Water Tower Place. After a process of a transformation after COVID, they returned to the stage in January 2025. 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 a number of bars, restaurants and coffee shops nearby for you to enjoy before or after a performance.
I went back in May 2024 for a wonderful production of The Choir of Man which originated at the Edinburgh Fringe Festival in 2017 and opened on the West End in London in October 2021. I really like th venue.
The Broadway Playhouse at Water Tower Place features plays and musicals through Broadway in Chicago. It is at 175 E. Chestnut. In February 2024 I went to the matinee of the comedy, Golden Girls – The Laughs Continue. Prior to that in October 2023, I saw the Tony Award winning play, The Lehman Trilogy produced by Timeline Theatre. In August 2024, I enjoyed SAVOR After Hours with dancers from Dancing With The Stars.
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.
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. I went recently 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.
Silk Road Rising and Lifeline are other great options.
The Lyric Opera of Chicago presents a Broadway musical at the end of their opera season. I loved 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.