The Merriest Musical Events in Chicago This Holiday Season

Monday, December 9, 2019
The city sidewalks are dressed in holiday style and Chicago’s concert stages are getting in the spirit. When it comes to holiday concerts, the city has a festive sound for every music lover. Here are our favorites to see this season.
Photo courtesy of Ana Gasteyer/Facebook
Ana Gasteyer Saturday Night Live alum Gasteyer is bringing her new holiday album, Sugar & Booze, to town. She puts a jazzy, big-band swing on classic holiday hits as well as original songs. The festive performance also includes her signature comedic touch. Details: December 13, 7 p.m. and 9:30 p.m., at Space; $24–$48 Dave Koz Christmas Tour If you like your jazz smooth, don’t miss sax icon Koz and friends at the Chicago Theatre. Although he is Jewish, that hasn’t stopped him from spreading both Christmas and Hanukkah cheer at his holiday concerts. The Grammy-nominated musician is joined by special guests Jonathan Butler, Candy Dulfer, and Bill Medley for a contemporary take on classics and carols. Details: December 13, 8 p.m., at the Chicago Theatre; $60
Photo courtesy of Dave Koz/Facebook
Chicago Honky Tonk Presents: A Big Ole Holiday Matinee Saddle up for a rootin’-tootin’ holiday celebration at the Empty Bottle. Chicago Honky Tonk will feature a holiday matinee of 10 honky-tonk singers, all backed by Bottle regulars the Hoyle Brothers. Featured singers include members of Big Sadie, Wild Earp, the Family Gold, and more. The event also includes a holiday market and two-step dance lesson to help scoot in spirit. Details: December 15, noon, at the Empty Bottle; free Chicago Soul Spectacular Soul Xmas Party Evanston will get in the holiday groove with the second annual Chicago Soul Spectacular Soul Xmas Party. The show features Ava Chery, a former collaborator of David Bowie's and Luther Vandross's, as well as some of Chicago’s best musicians. Shake off the seasonal stress and dance to soul, funk, and Motown holiday classics. Details: December 15, 8 p.m., at Space; $15–$27
Photo courtesy of Jane Lynch/Facebook
Jane Lynch’s Swingin’ Little Christmas Step back to the Christmas parties of yesteryear with none other than Emmy- and Golden Globe winner Lynch. She indulges in the kitsch of Christmas with swinging arrangements, accompanied by Kate Flannery of The Office and Glee vocal arranger Tim Davis. The trio brings their Swingin’ Little Christmas album to life. Details: December 15, 5 p.m., at City Winery; $55–$78 Wilco’s Winterlude Hometown heroes Wilco returns to the stage in Chicago for the first time in two years. The band is celebrating the release of their latest album, Ode to Joy, with a four-night Winterlude residency at the Chicago Theater. Jeff Tweedy and company will offer a folk-fueled performance that’s a great early gift for music lovers. Details: December 15–19, 7:30 p.m., at the Chicago Theatre; $59.50–$80
Photo by Annabel Mehren/Courtesy of Pitch Perfect PR/Wilco
Do-It-Yourself Messiah If you prefer a DIY take on the holidays, indulge in a Chicago tradition since 1976. Chicagoans will join a world-class conductor, soloists, and a volunteer orchestra of musicians to perform Handel’s Messiah, complete with the “Hallelujah” chorus. The 44th annual event allows you to lend your voice to the holiday chorus. Details: December 16 and 17, 7 p.m., at Harris Theater; $15 First Annual Pop-Punk Xmas Do the holidays make you want to scream? Subterranean is encouraging you to belt some tunes before you see your family with the first annual Pop-Punk Xmas. Local pop-punk outfits Fluorescents, Invictus, Four Stars, the Kozmic Kicks, and Wolf Rd will lead you in letting it all out. Details: December 20, 8 p.m., at Subterranean; $8
Photo courtesy of Flourescents/Facebook
Tuba Christmas What’s more magical than the sound of 400 tubas? A Christmas tradition that began in 1974 in New York has made its way to one of Chicago’s most sumptuous hotels. Tuba musicians of all ages will fill the Grand Ballroom with holiday cheer under conductor Colonel Bryan Shelburne, a retired U.S. Army Band commander. Details: December 21, 12:30 p.m., at Palmer House Hilton; free to attend, participant registration is $10 Christmas for the Jews If you’re looking for an alternative to the traditional Christmas Day, celebrate with City Winery’s fourth annual Christmas for the Jews. Headliner Jason Suran will blow your mind with his abilities as a magician and mentalist. Comedians Sohrab Forouzesh and Joel Chasnoff will make spirits bright. A portion of proceeds from Chasnoff’s comedy and book sales is donated to his foundation, Project Elijah. Details: December 25, 6 p.m., at City Winery; $28–$35 CSO Merry, Merry Chicago! If you’re keeping it traditional, there’s no better musical celebration than seeing the Chicago Symphony Orchestra. Merry, Merry Chicago! features CSO members, the Chicago Symphony Chorus, and special guests in a family-friendly spectacular. Classics from “Joy to the World” to “Rudolph the Red-Nosed Reindeer” will come to life in Symphony Center. Details: December 15, 20, 21, 22, 23, showtimes vary, at Symphony Center; $64–$164