1 Evoking the Golden Boy

The Siskel Film Center hosts a monthlong Robert Redford retrospective honoring the ultimate movie star. Screenings include The Sting, All the President’s Men, and Quiz Show.
Dec. 2–31. siskelfilmcenter.org

2 Sing Out, Ms. Cleaves!

The half dozen wives of Henry VIII belt their way through beheadings and divorces when the pop-rock musical Six returns on tour. Dec. 2–14. broadwayinchicago.com

3 What’s Not to Love?

Native son John C. Reilly expands the Great American Songbook with his vaudeville-inspired show, Mister Romantic. Dec. 4–6. steppenwolf.org

4 Discomfort Zone

Emmy-winning comedian Jerrod Carmichael, who dissects his interracial queer relationship in his most recent HBO special, Don’t Be Gay, settles in for six nights of standup. Dec. 6–11. thedentheatre.com

5 Sleigh Me

The Aimee Mann & Ted Leo Christmas Show, an evening of songs and sketches anchored by the beloved indie musicians, skates into the Irish American Heritage Center. Dec. 11–12. oldtownschool.org

6 Porn This Way

The kinky film fest Hump!, curated by sex advice columnist (and native Chicagoan) Dan Savage, screens twice at the Music Box. Dec. 11. musicboxtheatre.com

7 Projecting Good Cheer

Created during the pandemic, Manual Cinema’s Christmas Carol reimagines Dickens’s classic through the lens of skeptical Aunt Trudy, who hosts a Zoom holiday gathering. Dec. 12–28. fineartsbuilding.com

8 The Faux Nepo Babies

Though not related to the Piano Man, local comedians-turned-rockers Billy Joel Jr. have nurtured that joke into a burgeoning fan base. Dec. 18. emptybottle.com

9 Drums of Lore

Tsukasa Taiko’s annual MCA concerts, Taiko Legacy and Reduction, are a December treat. This year, Reduction ties into the Yoko Ono exhibition with jazz-fusion covers of the Plastic Ono Band. Dec. 19–20. airmw.org

10 Outsider Architecture

Iconoclastic 20th-century architect Bruce Goff championed fantastical shapes. The Art Institute delves into his Material Worlds with this retrospective. Dec. 20 – March 29. artic.edu