Here are all the shows you need to see for Chicago Theatre Week 2025

On the last night of Frida Kahlo’s life, viewers of Frida…A Self Portrait are transported to La Casa Azul, the famous Mexican artist’s home. The one-woman production is written and performed by Vanessa Severo, and sees the artist reminisce about her life. Throughout the 75-minute play, Severo connects her own life’s experience to the famed artist’s, and explores Kahlo’s works, addiction, physical limitations and romances. The play is running at Writers Theatre, a non-profit theatre company, in suburban Glencoe.

At a motel in the Mojave Desert, two lovers, or fools as the play would suggest, meet up and clash. With just three main cast members, Fool for Love is a haunting drama that explores the deeply complex relationship between the trio. The play was written in 1983 by noted playwright Sam Shepard, whose works also include A Lie of the Mind and Buried Child, for which he won the Pulitzer Prize for Drama in 1979.

Betrayal isn’t structured like a traditional play. The events move in reverse chronological order, showcasing the demise of an affair and going back in time as it occurred and ultimately to the beginning. The play stars Academy Award- and Emmy Award-winner Helen Hunt as Emma, who is having an affair with Jerry, her husband’s friend and coworker. Betrayal, which is playing at the Goodman Theatre, was first written by British playwright Harold Pinter in 1978.

A musical based on the 2007 film of the same name, Waitress follows Jenna, a waitress at a cafe who’s in an abusive relationship with her husband, Earl. After becoming pregnant, Jenna starts an affair with her doctor and enters a pie-baking contest, hoping to win the grand prize in order to fund her escape.

You’ve probably seen Hamlet. Now it’s time to see Fat Ham, a reimagining of the Shakespeare tale. The Pulitzer Prize-winning and Tony-nominated play by James Ijames tells the story of Juicy, a queer Black man whose widowed mother has married his uncle. When his father’s spirit shows up for revenge during a backyard cookout, Juicy must grapple with his identity. Fat Ham is showing at the Owen Theatre, part of the Goodman Theatre in the Loop.

There’s a good chance that you’ve heard of A Raisin in the Sun. If you’re a fan of theatre, maybe you’ve even seen it or read it. The play, written by Lorraine Hansberry, depicts the experience of a black family on Chicago’s South Side as they try to improve their financial circumstances after the death of the family’s patriarch. The plot deals with still-relevant issues, like housing discrimination and racism. A Raisin in the Sun is being performed at Court Theatre in Hyde Park, the professional theatre of the University of Chicago.

Sam Shepard is one of the most highly-regarded American playwrights for good reason—his works are a masterclass in writing about bleak situations and infusing them with black comedy, like in A Lie of the Mind. The play, which is also a part of Chicago Theatre Week at the Raven Theatre, is centered around spousal abuse and how it impacted two families.

Chicago Theatre Week isn’t just about plays and musicals. There are numerous types of performances highlighted in the discounted shows, including dance. During the week-long celebration, Hubbard Street Dance offers an opportunity to see its winter series, which features four performances—Into Being by FLOCK, Within the Frame by James Gregg, Black Milk by Ohad Naharin and IMPASSE by Johan Inger.

Some of the Chicago Theatre Week offerings are only available to see for a short time, but that’s not the case for The Infinite Wrench—the longest-running late-night show in Chicago. The performance is actually 30 different brief plays, all packed into one hour. Even if you’ve seen The Infinite Wrench before, you’re still in for a treat as the plays change weekly.

During its original Broadway run in 2015, Fun Home won seven Tony Awards, including Best Musical, Best Original Score and Best Leading Actor in a Musical. Now, the award-winning musical has moved on from New York and is playing in Chicago during Chicago Theatre Week. Fun Home was based off of the graphic novel memoir of the same name written by Alison Bechdel. Both the novel and musical follow Bechdel as the writer comes of age: Bechdel’s experience of coming out as a lesbian and her relationship with her father, who was a closeted gay man.

You’ve probably seen a Shakespeare play before, but never like this. Five professional actors come together for each performance of Drunk Shakespeare. The twist? One of them has had five shots before the show and is trying to stay on track while the other four actors do their best to hold the performance together.

The song “Three Little Birds” by Bob Marley and the Wailers is almost 50 years old but its enduring message lives on, most recently in the children’s musical Bob Marley’s Three Little Birds, which is playing at The Greenhouse Theatre Center. The reggae classic is just one of many Bob Marley hits featured in the production, which centers around Ziggy and his three avian friends. The musical is inspired by the children’s book Every Little Thing, written by Marley’s daughter Cedella.