Dexter Walker & Zion Movement perform at the 2021 Millennium Park Holiday Sing-Along (previously “Caroling at Cloud Gate”) at Cloud Gate in Chicago's Millennium Park; December 2021.
Photograph: Patrick L. Pyszka/City of Chicago
Photograph: Patrick L. Pyszka/City of Chicago

The best Christmas concerts and shows in Chicago for the holiday season

’Tis the season for caroling, The Nutcracker, jingle bells and oodles of holiday music.

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Last updated November 19, 2025: Baby, it's cold outside! When you're not shopping at Christkindlmarket or taking a spin on local ice skating rinks, warm up this holiday season with the help of some festive live music. Whether you're hoping to test your caroling skills with a sing-along at Millennium Parkcatch a guitar-centric tribute to A Charlie Brown Christmas or watch the Joffrey Ballet's classic production of The Nutcracker, you'll find plenty of ways to celebrate Christmas in Chicago thanks to these holiday concerts spanning a wide variety of musical genres. 

RECOMMENDED: Check out even more things to do for Christmas in Chicago

Top Christmas concerts in Chicago

  • Things to do
  • Loop
  • Recommended

This holiday season, The Joffrey Ballet celebrates the 10th anniversary of two-time Tony Award®-winning choreographer Christopher Wheeldon’s interpretation of The Nutcracker. Accompanied Tchaikovsky's classic score, The Nutcracker is a fantastical adventure engaging merging Chicago's rich cultural heritage and the wonder of the season. 

  • Drama
  • Loop
  • Recommended

The Goodman Theatre’s annual holiday production of the Charles Dickens classic returns to the stage, with Christopher Donahue and Austin Tichenor taking on the role of Ebenezer Scrooge. The play has been a staple of the Goodman's calendar for more than 40 years, allowing returning attendees and new generations to see the quintessential Christmas story unfold before their eyes. Prepare to be visited by three spirits—and don't be suprised if A Christmas Carol's touching tale of redemption makes you shed a few tears.

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  • Things to do
  • Performances
  • Loop
  • Recommended

There’s no better place in Chicago for holiday cheer than under Millennium Park’s Cloud Gate (a.k.a. “The Bean”), where like-minded songbirds delight in shared songs amidst the twinkling lights of the city Christmas tree and the sounds of laughter from nearby ice skaters. With some hot cocoa in your hand, join local choirs and bands as they lead attendees in a powerful sing-along of joyful holiday carols. This year, the series takes place Fridays at 6pm from December 5–19, with a different choral group highlighted each week.

  • Lake View

Experience the holiday classic, It's a Wonderful Life, as a 1940s-style live radio play this holiday season at The Athenaeum Center. Set in the venue's Paradiso space, every seat guarantees an intimate experience of George Bailey's renewal of faith in himself, his family and his community. Whether you're returning as part of a cherished holiday tradition or discovering the story's magic for the first time, this production is sure to lift your spirits.

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  • Movies
  • Family and kids
  • Wrigleyville
  • Recommended

For the 42nd year, Southport Corridor’s favorite historic theater brings three weekends of Christmas singing followed by a double feature of classic holiday films to Chicago’s North Side.  Sit back in plush theater seats with snacks and drinks as you belt “Rudolph the Rednosed Reindeer” and “It's Beginning to Look a Lot Like Christmas,” and just when you’ve worn yourself down, stay for a showing of White Christmas and It’s a Wonderful Life.

  • Music
  • Classical and opera
  • Loop
  • Recommended

The Loop’s National Historic Landmark Orchestra Hall is ornate enough to dazzle year-round, but shines extra bright for the Chicago Symphony Orchestra’s Merry, Merry Chicago! holiday concert conducted by Alastair Willis. On a stage decked with—literally—boughs of holly, larger-than-life red bows and wreaths, the acclaimed instrumentalists play tunes ranging from beloved holiday favorites to Christmas in Chicago, a local treasure. Before the show and during intermissions, you’ll even hear pop-up performances from Chicago school choirs and community ensembles throughout the halls.

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  • Children's
  • West Loop

Pinkies up! Little ones and their families are invited to ring in the holiday season in style during The Beatrix Potter Holiday Party, an annual trunk and puppet show at the Chicago Children's Theatre that brings Potter's beloved stories to life with whimsy and humor. The play's young viewers get to interact with characters like Tom Kitten, Jeremy Fisher and Peter Rabbit throughout the 60-minute production, which features live music alongside narration and puppetry. 

  • Things to do
  • Printers Row
Tim Warfield's Jazzy Christmas
Tim Warfield's Jazzy Christmas

If your motto is the more saxophone the better, soak up the smooth sounds of Tim Warfield’s Jazzy Christmas show. Joined by a talented band of piano, trumpet, vocalists and more, the American saxophonist embraces the holiday classics you love with new interpretations. Sip a warming cocktail and enjoy the atmosphere at Jazz Showcase, one of Chicago’s most historic clubs. 

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  • Music
  • Rock and indie
  • Suburbs

Holiday prog-rockers Trans-Siberian Orchestra make their annual trip to Rosemont, arriving just before Christmas with an all-new, over-the-top light show set to overwrought versions of seasonal songs. If you're still not tired of hearing the band's inescapable high-octane rendition of "Carol of the Bells," snag a seat and warm yourself in the glow of searing pyrotechnics and gleaming lasers at one of TSO's Allstate Arena gigs.

  • Things to do

Chicago’s favorite German-style outdoor holiday market is more than just a delightful place to snack on stinky cheese (technical term: raclette), shop for European-made trinkets and warm up with glühwein. Each year, Christkindlmarket also features heartfelt performances by various children’s choirs and Phenix Trio, a group famed for getting audiences to sing with them. So sing along, smile and enjoy the cheer amongst the sparkling holiday decor.

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