Theater for winter 2023: Our 10 picks for promising upcoming shows downtown, at Lookingglass and more

After a rocky 2022 with fewer productions, widespread leadership turnover and at least one historically important theater, Victory Gardens, facing dissolution, Chicago theater regroups for 2023. The new year always brings optimism and hope, and a reason or 10 to turn off the boring video streams and get out of the house. So here are some especially promising upcoming shows to warm up your winter months.

“Boulevard of Bold Dreams,” TimeLine Theatre: This new play by LaDarrion Williams is set on the night in 1940 when Black actress Hattie McDaniel won an Academy Award. It looks at race and class during the so-called Golden Age of Hollywood. But there’s a twist very much in line with the thinking of today’s young artists: What if McDaniel had decided not to accept her Oscar? Malkia Stampley directs. Feb. 1 to March. 19 at TimeLine Theatre, 615 W. Wellington Ave.; tickets $29-$62 at 773-281-8463 and timelinetheatre.com

“Cabaret,” Porchlight Music Theatre: Among the first out of the gate in the new year, the highly experienced directing and choreographic team of Michael Weber and Brenda Didier say “Willkommen” with a new production of the famed musical about living and loving in Berlin, even as the world fell apart. Erica Stephan plays Sally Bowles with Gilbert Domally as Clifford Bradshaw and Josh Walker as the Emcee. Jan. 14 to Feb. 12 at the Ruth Page Center for the Arts, 1016 N. Dearborn St.; tickets $25-$77 at 773-777-9884 and porchlightmusictheatre.org

“Describe the Night,” Steppenwolf Theatre Company: Structured as a mystery, this new play by ensemble playwright Rajiv Joseph stars Steppenwolf co-artistic director Glenn Davis and ensemble members Caroline Neff, Sally Murphy, James Vincent Meredith, Yasen Peyankov and Karen Rodriguez. It’s the story of the Russian writer and journalist Isaac Babel, who was arrested and executed by Josef Stalin. The widely beloved Austin Pendleton directs. March 2 to April 9 at Steppenwolf Theatre, 1650 N. Halsted St.; tickets $42-$66 at 312-335-1650 and steppenwolf.org

“Into the Woods,” Paramount Theatre in Aurora: Stephen Sondheim’s beautiful musical about life’s fears and journeys has been a big hit on Broadway this fall. Aurora’s Paramount Theatre won’t be repeating the minimalism of that production but offering a new, fully staged version of the beloved show, ideal for all the family. Jim Corti and Trent Stork codirect with Larry Yando appearing (for the first time in Aurora) as the narrator and with a cast of Chicago all-stars including Stephen Schellhardt as the Baker, Sarah Bockel as the Baker’s Wife and Hannah Fernandes as Cinderella. Feb. 1 to March 19 at Paramount Theatre, 23 E. Galena Blvd., Aurora; tickets start at $28 at 630-896-6666 and paramountaurora.com

“Les Miserables,” Cadillac Palace: The waif logo is back, along with the musical that many people think of as the GOAT, hosted by Broadway in Chicago. This is a union production of a long-proven tour, in contrast with many of the reprise engagements on offer downtown this winter, including nonunion tours of “Chicago” and “Cats” that spend most of their time in much smaller cities. “Les Miserables” will surely be the fully produced show you remember with a stellar cast. Feb. 15 to March 5 at the Cadillac Palace Theatre, 151 W. Randolph St.; tickets start at $31.50 at 800-775-2000 and broadwayinchicago.com

“Once,” Writers Theatre in Glencoe: After much too long a break, Writers Theatre returns to the production of musicals with a local staging of Enda Walsh’s luminescent “Once,” one of my favorite tuners of the last 20 years. It’s based on the beloved movie about a friendship between a Czech immigrant to Dublin and an Irish street musician. Katie Spelman directs and choreographs a show starring Matt Mueller and Dana Saleh Omar. Feb. 16 to March 26 at Writers Theater, 325 Tudor Court, Glencoe; tickets $40-$85 at 847-242-6000 and writerstheater.org

“the ripple, the wave that carried me home,” Goodman Theatre: This new, emotionally intense drama from the impressively poetic writer Christina Anderson had its well-received world premiere at the Berkley Repertory Theatre this fall (Berkeley Rep commissioned the play), and the shared debut production arrives in Chicago this winter. Anderson’s drama is set in Kansas in the 1960s and follows the daughter of a family of activists, working to integrate public swimming pools and teaching Black kids how to swim. Jan. 13 to Feb. 12 at the Goodman’s Owen Theatre, 170 N. Dearborn St.; tickets start at $15 at 312-443-3800 and goodmantheatre.org

“The Threepenny Opera,” Theo Ubique Theatre: In the early years of Theo Ubique Theatre, long Chicago’s leading producer of intimate musicals, Kurt Weill revues were common. And thus in honor of this important company’s 25th anniversary, the artistic director Fred Anzevino stages a new production of Bertolt Brecht and Weill’s most famous satirical work. Anzevino’s return to the company he loves is most welcome. March 10 to April 30 at Theo Ubique Cabaret Theatre, 721 Howard St., Evanston; tickets $35-$50 at 773-939-4101 or theo-u.org

“Villette,” Lookingglass Theatre Company: Finally, a new show at the Lookingglass Theatre! In February, this essential company stages a dramatization of Charlotte Brontë's 1853 novel “Villette,” as adapted by Artistic Associate Sara Gmitter and directed by Tracy Walsh. It’s the rather gothic story of a young Englishwoman named Lucy Snowe who leaves her countryside home to travel to a fictional French-speaking city to teach at a girls’ school, where she finds adventure, romance and maybe her own destiny. Feb. 8 to April 23 at Water Tower Water Works, 821 N. Michigan Ave.; 312-337-0665 or lookingglasstheatre.org

“Wuthering Heights,” Wise Children at Chicago Shakespeare Theater: In a welcome return of major international productions to Navy Pier, the British director Emma Rice’s widely acclaimed adaptation of Emily Brontë's novel features (among other innovations) a singing and dancing chorus embodying Bronte’s beloved Yorkshire moors. It’s the work of Rice’s renowned Wise Children company and a coproduction of Britain’s National Theatre, Bristol Old Vic and York Theatre Royal; the highly conceptual show is in the middle of a five-stop U.S. tour. Jan. 27 to Feb. 19 at Chicago Shakespeare Theater at Navy Pier; tickets $59-$106 at 312-595-5600 or chicagoshakes.com

Chris Jones is a Tribune critic.

cjones5@chicagotribune.com