Winter has arrived right alongside 2025 and at least you can count on Chicago’s busy new theater season to keep you out of the cold.
Here’s a look at 10 of the most interesting productions opening between now and the end of March, listed in alphabetical order. I’ve not yet seen most of these shows, of course, so there is always the caveat that some may not live up to expectations. And given the quantity of openings, I may also have missed a few gems. Those you will have to find on your own.
“Betrayal”: Harold Pinter’s famously taut 1978 drama charts the multi-year affair between Jerry and Emma, with Jerry as the best friend of Emma’s husband, Robert. The play unspools in reverse order. In the first scene, you witness the end of Jerry and Emma’s affair. In the last scene, you see the inspiring seduction. Billed as a major revival and directed by the still-new artistic director Susan Booth, the Goodman Theatre’s production will star Helen Hunt, the well-known actress who won an Academy Award for her work in “As Good as It Gets” and achieved TV fame in the 1990s with “Mad About You.” Robert Sean Leonard and Ian Barford will play the men compelled by Hunt’s Emma. Feb. 8 to March 16 in the Goodman’s Albert Theatre, 170 N. Dearborn St.; 312-443-3800 and goodmantheatre.org
“Circus Quixote”: The much-loved Lookingglass Theatre, long enough in hiatus as to worry us all, finally returns to full, original productions in its city-owned theater on the Magnificent Mile this winter with “Circus Quixote,” a piece penned by Kerry and David Catlin that’s based on Miguel de Cervantes’ “Don Quijote of La Mancha.” Longtime collaborator Sylvia Hernandez-DiStasi is in charge of the circus component and the show will star Michel Rodriguez Cintra. Hopefully, the piece will remind us that idealism still has a place in our overly mercurial world. Jan. 30 to March 30 at Lookingglass Theatre in Water Tower Water Works, 821 N. Michigan Ave.; 312-337-0665 and www.lookingglasstheatre.org
“Fool for Love”: The late, great playwright Sam Shepard was crucial to the Steppenwolf Theatre Company building its international relationship and, thanks to memorable productions of “True West,” “Buried Child” and “Curse of the Starving Class,” no writer has been more closely associated with the Steppenwolf aesthetic. Reason indeed to anticipate the coming Steppenwolf production of “Fool for Love,” one of Shepard’s most powerful plays. Director Jeremy Herrin’s production will star the ensemble members Cliff Chamberlain, Tim Hopper and Caroline Neff. Jan. 30 to March 16 at Steppenwolf Theatre, 1650 N. Halsted St.; 312-335-1650 and www.steppenwolf.org
“Hamlet”: This show from the much-admired Teatro La Plaza of Lima, Peru, fuses the iconic Shakespearean tragedy with what are described as personal stories from the lives of a cast made up of eight young performers with Down syndrome. Both the text (the show is performed in Spanish with English surtitles) and direction are by Chela De Ferrari. Seen at the Edinburgh Festival this past summer, this particular “Hamlet” was admired by critics for how well it linked Shakespeare’s most famous and alienated outsider with an experience not uncommon for those with Down syndrome. March 13-23 at Chicago Shakespeare Theater at Navy Pier, 800 E. Grand Ave.; 312-595-5600 and chicagoshakes.com
“Jaja’s African Hair Braiding”: The title tells you what you need to know: this comedy is set in the titular salon in Harlem and, structurally speaking, the play is not unlike “Steel Magnolias” in that it celebrates (and pokes some fun at) a community centered on a salon that serves both as a gathering place and a cultural touchstone. I enjoyed it a lot on Broadway and this is much the same production. Jan. 14 to Feb. 2 at Chicago Shakespeare Theater at Navy Pier, 800 E. Grand Ave.; 312-595-5600 and chicagoshakes.com
“The Listeners”: This new opera, part of the Lyric Opera’s spring season, was created by the composer-lyricist team of Missy Mazzoli and Royce Vavrek and follows a schoolteacher named Claire who is driven mad by the constant presence of a low-frequency hum in her ears. Her family doesn’t understand but Claire, it turns out, is not alone in hearing the sound. It’s worth noting that the opera is not entirely fictional. “The Listeners” is a Lyric co-commission with the Philadelphia Opera and first was seen at the Norwegian National Opera in 2022. March 30 to April 11 at Lyric Opera of Chicago, 20 N. Wacker Drive; 312-827-5600 and www.lyricopera.org
“A Raisin in the Sun”: Lorraine Hansberry’s drama, inarguably the greatest play ever written about Chicago and a poetic masterpiece, was born on Chicago’s South Side. So in a sense, the story of the Younger family with the simple dream of moving to a house they can call their own in a neighborhood of their choice is coming home when Court Theatre mounts a new production, just a few blocks from where Hansberry grew up. Gabrielle Randle-Bent directs a cast that includes such Chicago talents as Shanésia Davis, Brian Keys, Kierra Bunch, Martasia Jones and Eliott Johnson. Jan. 31 to March 2 at Court Theatre, 5535 S. Ellis Ave.; 773-753-4472 and www.courttheatre.org
“Shucked”: If your cure for the winter blahs is laughter, look for the corncob poster ’cause “Shucked” is your show. When I saw it on Broadway, I giggled and tittered all night at this gag-heavy musical penned by Robert Horn and staged by the rascally Jack O’Brien. “Shucked” is a politically incorrect breath of fresh air when it comes to pretentious Broadway musicals and about nothing whatsoever except one-liners. In some ways. “Shucked” is like a live version of “Hee Haw” as if written by Mel Brooks. Through Jan. 19 at the CIBC Theatre, 18 W. Monroe St.; www.broadwayinchicago.com
“Titanique”: This very funny off-Broadway show is an affectionate spoof of both the “Titanic” musical, in all of its glorious excess, and the iconic Canadian singer Celine Dion, in all of her glorious excess too. Expect much campery and emoting, interspersed with mega-power ballads. It was all great fun in New York, where “Titanique” played to packed houses downtown every night. This new Chicago production produced in partnership with Porchlight Music Theatre is expected to play for several weeks and is directed by the original director, Tye Blue — but with an all-Chicago cast playing Rose, Jack and the crew of the doomed steamship. March 25 to May 18 at Broadway Playhouse at Water Tower Place, 175 E. Chestnut St.; www.broadwayinchicago.com
“Waitress”: The very reliable Paramount Theatre in Aurora has snagged the regional premiere of this tuneful, warm-centered Sara Bareilles musical where the titular small-town server narrates her complicated life through the names of the pies she serves: the Key Lime to Happiness Pie, the Betrayed By My Eggs Pie and the My Husband is a Jerk Chicken Pot Pie. First starring Chicago’s own Jessie Mueller as an adaptation of Adrienne Shelly’s 2007 movie, “Waitress” is as sweet as it is unpretentious. Michelle Lauto will be the star of director Katie Spelman’s production. Feb. 12 to March 30 at Paramount Theatre, 23 E. Galena Blvd., Aurora; 630-896-6666 and www.paramountaurora.com
Chris Jones is a Tribune critic.
cjones5@chicagotribune.com
