Theater
Music Theater Works presents “Legally Blonde — The Musical,” based on the popular film, it’s the story of Elle Woods (Kayla Shipman) and her journey to Harvard Law School as she learns life’s important lessons. Mandy Modic directs. From Dec. 19-29 at North Shore Center for the Performing Arts, 9501 Skokie Blvd, Skokie. Tickets: $19.50-$106. Visit musictheaterworks.com.
In Daryl D. Brooks’ “Hitt Records,” vintage record store owners James and Charles Hitt use their vast knowledge of music to school their nephew and customers. Includes music from Curtis Mayfield, Phil Collins, Alexander O’Neil, Shalamar, Sister Sledge, Bob Marley and more. Brooks directs. From Dec. 21-Jan. 26 at Black Ensemble Theater, 4450 N. Clark. Tickets: $56.50-$66.50. Visit blackensembletheater.org.
Rick Schuler’s holiday show “Rocky Mountain High Experience, A John Denver Christmas,” features the singer-songwriters hits including “Rocky Mountain High,” “Sunshine On My Shoulders,” “Take Me Home Country Roads,” “Thank God I’m A Country Boy,” Aspenglow” and “Silver Bells.” From Dec. 19-22 at Broadway Playhouse at Water Tower Place, 175 E. Chestnut. Tickets: $45-$100. Visit broadwayinchicago.com.
Open Space Arts/Arts Judaica, in association with Her Story Theatre, present “The Berlin Diaries,” Andrea Stolowitz’s drama about her quest to learn about her extended Jewish family which was inspired by her great-grandfather’s journal kept after escaping Germany for New York in 1939. Izadorius Tortuga directs. From Dec. 20-Jan. 5 at Open Space Arts, 1411 W. Wilson. Tickets: $25. Visit openspacearts.org.
“Ayn Rand’s ‘It’s a Wonderful Life’ as Performed by the Conspirators Under the Direction of President Biden NO WAIT, Liz Cheney” is Sid Feldman’s comic retelling of the classic movie told through the eyes of libertarian Ayn Rand. Wm. Bullion directs. At 7 p.m. Dec. 20-22 at Otherworld Theatre, 3914 N. Clark. Tickets: $15. Visit conspirewithus.org.
Practical Theater Company presents “Weird,” a year-end sketch-comedy revue which blends elements of vintage radio shows of the 1940s with contemporary sketch comedy. At 8 p.m. Dec. 20-22 at Studio 5, 1934 Dempster, Evanston. Tickets: $35-$55. Visit studio5.dance/calendar.
Dance
Reggio “The Hoofer” McLaughlin presents his annual staging of “The Nut Tapper,” the holiday classic recreated with rhythms of tap, Spanish flamenco and Mexican zapateado. Also in the lobby is an exhibit of items from McLaughlin’s Tap History Archive. At 4:30 p.m. Dec. 22 at Old Town School of Folk Music, 4544 N. Lincoln. Tickets: $20. Visit oldtownschool.org.
Music
Jazz vocalist Samara Joy recently released a new studio album, “Portrait,” which NPR says is “the most jazz-literate album of her career so far.” And Joy just earned two Grammy nominations for her 2023 holiday EP, “A Joyful Holiday.” Songs from both are sure to make for a potent mix when Joy performs at 8 p.m. Dec. 20 at Chicago Theatre, 175 N. State. Tickets: $32+. Visit ticketmaster.com.
Over the years, the captivating sounds of the a cappella group Straight No Chaser have attracted a massive fan base. Find out why when the nine singers take the stage at 3 p.m. Dec. 22 at Chicago Theatre, 175 N. State. Tickets: $49+. Visit ticketmaster.com.
Inspired by 1920s jazz, klezmer and old-time music, the Squirrel Nut Zippers’ Christmas Caravan celebrates the season with heartwarming ballads, boisterous dance tunes and alternative holiday classics. At 7:30 p.m. Dec. 21 at Park West, 322 W. Armitage. Tickets: $55-$85. Visit jamusa.com.
The 34th annual Winter Solstice Sunrise Concerts return with Chicago-based musicians Hamid Drake and Michael Zerang welcoming the end of the year’s longest night at 6 a.m. Dec. 21 (sold out). Two more performances take place at 6 a.m. Dec. 22-23 at Links Hall, 3111 N. Western. Tickets: $38. Visit linkshall.org.
Chicago Sinfonietta’s holiday concert features performances of “Greensleeves,” “Appalachian Carol,” “O Holy Night,” “I Saw Three Ships,” “Winter Wonderland,” “Go Tell It on the Mountain” and more. At 6:30 p.m. Dec. 19 at Auditorium Theatre, 50 E. Ida B. Wells. Tickets: $27-$67. Visit auditoriumtheatre.org.
Kentucky born singer-songwriter Chris Knight taught himself John Prine songs at 15 and began writing his own songs at 26 after hearing Steve Earle perform. Now at 64, he’s among the tried and true masters of Americana. At 7:30 p.m. Dec. 22 at Robert’s Westside, 7321 Madison, Forest Park. Tickets: $30. Visit robertswestside.com.
Singer-songwriter Michael McDermott’s annual Mischief & Mistletoe residency features three nights filled with original tunes and holiday classics. At 7:30 p.m. Dec. 21-23 at City Winery, 1200 W. Randolph. Tickets: $32-$45. Visit citywinery.com.
Cellist-singer Ian Maksin, known as a “one-man orchestra,” transforms his cello into an entire symphonic experience combining classical and world music. At 7 p.m. Dec. 22 at Epiphany Center for the Arts, 201 S. Ashland. Tickets: $30, $35. Visit epiphanychi.com.
Museums
“Framed Views” is a photography show which includes images taken during this year’s Open House Chicago. The Chicago Architecture Center hosted a photo competition inviting people to take photos while exploring the city’s architectural sites during the weekend event. Out of more than 1,300 submissions, the finalists and winners are featured in the exhibit. To June 1 at 111 E. Wacker. Admission: $14, children 5 and under free. Visit architecture.org.
For a winter break road trip head downstate to Springfield for “Freedom in Form: Richard Hunt,” an exhibit highlighting the work of the Chicago artist whose massive sculptures can be seen around the state and country. Over his 70-year career, Hunt, who died last year, gave form to the pain and the hopes of African Americans striving for true equality. To April 20 at the Abraham Lincoln Presidential Library and Museum, 212 N. 6th St., Springfield. Admission: $6-$15, children 4 and under free. Visit presidentlincoln.illinois.gov.
Movies
Be Kind, Rewind is a series of 13 films from the past year including Francis Ford Coppola’s “Megalopolis,” Alice Rohrwacher’s “La Chimera,” Kelly O’Sullivan’s “Ghostlight,” Edward Berger’s “Conclave,” Sean Baker’s “Anora” and more. From Dec. 20-Jan. 2 at Gene Siskel Film Center, 164 N. State. Tickets: $14.50. Visit siskelfilmcenter.org.
John Cusack hosts a screening of one of his most popular films — Cameron Crowe’s “Say Anything.” In his four-star review of the 1989 film, Roger Ebert writes, the film “exists entirely in a real world, is not a fantasy or a pious parable, has characters who we sort of recognize, and is directed with care for the human feelings involved.” A Q&A with Cusack follows. At 7:30 p.m. Dec. 20 at Auditorium Theatre, 50 E. Ida B. Wells. Tickets: $39+. Visit ticketmaster.com.
Holiday Fun
Winterland features a 360-degree immersive experience, a kaleidoscope of colors and winter scenes. Plus there’s photo ops with giant Christmas trees and Nutcracker soldiers, a children’s play area, a craft station, hot beverages and more. To Jan. 5 at Navy Pier, 600 E. Grand. Tickets: $12.50-$22.50. Visit winterlandchicago.com.
Stay cozy and warm in your car and enjoy Light of Christmas, the city’s only holiday drive-through experience featuring more than one million synchronized lights that dance to the sounds of the season. To Jan. 5 at Guaranteed Rate Field, 3326 S. Wentworth. Tickets per vehicle: $20.99-$54.99. Visit lightofchristmas.com.
The Chicago Botanic Garden’s enchanting Lightscape fills the garden grounds with light, art and music. This year’s edition features an all-new path with transformed vistas and dazzling installations from around the world. To Jan. 5 at 1000 Lake Cook Rd., Glencoe. Admission: $19-$39, ages 2 and under free. Visit chicagobotanic.org.