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Dozens of people skate around the McCormick Tribune Ice Rink in Millennium Park ahead of the city's annual tree lighting ceremony.

Dozens of people skate around the McCormick Tribune Ice Rink in Millennium Park ahead of the city’s annual tree lighting ceremony.

Tyler Pasciak LaRiviere

Your Chicago holiday season bucket list: 33 festive things to do, from lights to live shows

Chicago’s most festive season is upon us, and the city is brimming with holiday cheer. It can be overwhelming to navigate all the events happening this time of year, so we combed all of the offerings and put together this curated, holiday bucket list for you with contributions from WBEZ and Chicago Sun-Times reporters.

Whether you’re a live theater lover or just want to stroll through some twinkling light displays, we have a suggestion for you.

The Joffrey's Nutcracker

The Joffrey’s Nutcracker is set against a backdrop of 1892 Chicago.

Photo by Todd Rosenberg / Courtesy of the Joffrey Ballet

Catch a Nutcracker performance

Seeing a performance of the Nutcracker is certainly a holiday season classic, and luckily, there is no shortage of options here in Chicago. If you’re looking for a more traditional staging, the Joffrey Ballet’s rendition offers spins, twirls and Tchaikovsky with one twist: It’s set in Chicago in 1892, just months before the opening of the World’s Fair. Lyric Opera House, 20 N. Wacker Drive; Tickets from $36.

The show has also been infinitely re-imagined. The Nut Tapper at the Old Town School of Folk Music features Spanish flamenco and Mexican zapateado. 4544 N. Lincoln Ave.; $20.

Dancers in white tutus perform onstage.

The A&A Ballet’s ‘Art Deco Nutcracker’ evokes the 1920s.

Courtesy of A&A Ballet

From A&A Ballet Chicago, The Art Deco Nutcracker draws inspiration from 1920s America. Athenaeum Center, 2936 N. Southport Ave.; tickets from $22.

Or, for adult audiences, The Buttcracker — A Nutcracker Burlesque puts a saucy spin on the story. Greenhouse Theater Center, 2257 N. Lincoln Ave.; tickets from $22.

There’s even a Nutcracker that is as much about the music as the dance. Sugar Hill puts the jazz in Nutcracker, building the story around the collaborative prowess of Duke Ellington and Billy Strayhorn and setting it in 1930s Harlem. Auditorium Theater, 50 E. Ida B. Wells Dr.; tickets from $44.

Finally, families can check out The Immersive Nutcracker – A Winter Miracle, which introduces children to the story through a 30-minute immersive experience. Lighthouse ArtSpace Chicago, 108 W. Germania Place; tickets from $29.99.

Even more Nutcracker options can be found here.

Mariah Carey performs in Dubai in 2019. The

Mariah Carey performs in Dubai in 2019. The Queen of Christmas will return to Chicago for a United Center concert in December.

Kamran Jebreili

Take in some live music, from blues to Mariah Carey

It’s peak concert season, no matter your style. Hometown standouts Mavis Staples and Andrew Bird stage performances that will be a draw. Grammy-winner Staples is holding “A Concert for Justice” on Dec. 1 at Cahn Auditorium in Evanston. 600 Emerson St., Evanston; Tickets from $59.

Andrew Bird and his violin return to Fourth Presbyterian Church for the artist’s annual Gezelligheid concerts happening Dec. 7-15. 126 E. Chestnut St.; tickets from $56.

The Queen of Christmas is coming to town. Mariah Carey performs on Dec. 3 at the United Center. 1901 W. Madison St.; tickets start at $82.

For blues fans, Alligator Records presents “A Blues Christmas” on Dec. 15 in the Aon Grand Ballroom on Navy Pier. 600 E. Grand Ave.; free. Jazz and blues lovers will find a deep list of local talent at the Delmark Records holiday all-star showcase at Thalia Hall on Dec. 20. 1807 S. Allport St.; tickets from $30. Or, close out the holiday season with the Trans-Siberian Orchestra on Dec. 28 at Allstate Arena. 6920 Mannheim Road, Rosemont; tickets from $49.75.

Other concert ideas.

The Chicago Sinfonietta

Chicago Sinfonietta presents its ‘Holidays of Light’ on Dec. 15 at the Auditorium Theatre.

Courtesy of the Chicago Sinfonietta

Revel in rich classical orchestrations

Something about classical music and the holidays just go hand in hand. For one night only, the classical label Cedille Records will present “Miracles of Miracles: Music for Hanukkah” on Dec. 7 at Temple Har Zion. 1040 N. Harlem Ave., River Forest; tickets from $38.

Chicago Sinfonietta presents “Holidays of Light” on Dec. 15 at the Auditorium Theatre. Conductor Chelsea Tipton will lead a showcase that ranges from Christmas classics to traditional Jewish and Latin-American music. 50 East Ida B. Wells Dr.; tickets from $25.

The Chicago Symphony Orchestra will present “Merry, Merry, Chicago!” Dec. 15-17 and 22-23 with Thomas Wilkins conducting and vocalist Ashley Brown as soloist. The orchestra will present crowd-pleasing classics like “Joy to the World” and “I’ll Be Home for Christmas.” 220 S. Michigan Ave.; tickets from $45.

CSO will also perform Handel’s “Messiah,” under the direction of the acclaimed conductor Sir Andrew Davis at Symphony Center from Dec. 21-23. Tickets from $55.

Additional classical music performances.

Manual Cinema's Christmas Carol

Manual Cinema’s spin on the ‘Christmas Carol’ brings Dickens into the digital age.

Courtesy of Writers Theater

Take a trip to the theater for a show

From classics to new shows, Chicago’s theaters are booked with holiday performances. The Goodman Theatre’s Christmas Carol has been going 46 seasons strong for a reason. Larry Yando again reprises the starring role as Ebenezer Scrooge. 170 N. Dearborn St.; tickets start at $25.

For a more modern take on the Dickens classic, Manual Cinema’s Christmas Carol starts with a family Zoom call. Then the puppets take over. Writers Theater, 325 Tudor Court., Glencoe; tickets from $40.

A new theatrical adaptation of Jim Henson’s beloved 'Emmet Otter's Jug-Band Christmas' runs through the end of the year.

A new theatrical adaptation of Jim Henson’s beloved ‘Emmet Otter’s Jug-Band Christmas’ runs through the end of the year.

Photo by Michael Brosilow

There’s no Scrooge in sight at the Studebaker Theatre, where a new theatrical adaptation of Jim Henson’s beloved tale, Emmet Otter’s Jug-Band Christmas, just opened. The show follows Ma and Emmet Otter, who risk what they have to make each other’s holiday dreams come true. 410 S. Michigan Ave.; tickets from $43. Or, over at Cadillac Palace, How the Grinch Stole Christmas! The Musical is on stage until Dec. 31. 151 W. Randolph St.; tickets from $35.

Strawdog Theatre Company presents Hershel & The Hanukkah Goblins, in partnership with the Chicago Loop Synagogue, from Dec. 2-23. The show, which is an adaptation of Eric Kimmel’s book by the same name, tells the tale of a troupe of traveling actors who visit a town where no one is celebrating Hanukkah, so they spring into action to save the holiday. Chicago Loop Synagogue, 16 S. Clark St.; free, suggested $15 donation.

More theater.

Cinnamon-and-sugar coated almonds at Christkindlmarket

Christkindlmarket in Daley Plaza serves up festive favorites such as cinnamon-and-sugar coated almonds.

Pat Nabong

Get into the festive spirit at Christkindlmarket

Through Christmas Eve, Christkindlmarket serves up mulled wine, German fare and holiday cheer in Daley Plaza. The annual market, and its collectible mugs, have become quite popular, so this year, there’s a new fast-entry pass that allows visitors to skip the line for $25. Otherwise, the market is free to enter and peruse. 50 W. Washington St.

Don’t want to deal with downtown? There are also Christkindlmarket locations in Wrigleyville and west suburban Aurora. Free.

Thousands gather for the tree lighting in downtown Chicago on Nov. 17, 2023.

Thousands gather for the annual Christmas tree lighting in downtown Chicago on Nov. 17, 2023.

Tyler Pasciak LaRiviere

Check out the twinkling seasonal lights around town

The Christmas tree in Millennium Park is officially lit for the season and will remain illuminated through early January. But that downtown display is just one place to see twinkling holiday lights. Randolph Street and Michigan Avenue.

ZooLights at Lincoln Park Zoo features both new and familiar displays. 2001 N. Clark St.; tickets from $7, free on Mondays. And Brookfield Zoo’s Holiday Magic event sparkles with a display of more than two million LED lights. 8400 31st St., Brookfield; tickets from $20.95.

The Morton Arboretum also has a dazzling display, Illumination: Tree Lights, along a one-mile tree lined path. 4100 Illinois Route 53, Lisle; tickets from $12.80.

Through Jan. 3, Light of Christmas Drive Thru illuminates Sox Park with more than one million lights for viewing by car. 3326 S. Wentworth Ave.; tickets from $24.99 per vehicle.

An ice skater twirls at the Millennium Park public rink.

An ice skater twirls at the Millennium Park public rink, which is now open for the season.

Tyler Pasciak LaRiviere

Take a twirl on skates

Strap on your skates and hit the ice. Newly opened for the season, the Ice Skating Ribbon in Maggie Daley Park offers a picturesque path to glide along amid the skyscrapers of downtown. $5 with your own skates on select dates, $16-$22 for skate rentals.

There’s also ice skating in Millennium Park, near the Bean. Free with your own skates, $16-$20 for skate rentals. The rink at Wrigley Field reopens this week as part of the game-filled “Winterland.” Gallagher Way, 3635 N. Clark St.; $5 for admission.

The Chicago Park District will open its popular neighborhood ice skating rinks starting Friday, Nov. 24, including in McKinley, Midway Plaisance, Mt. Greenwood and Warren Park. $7 for skate rental.

The Drake Hotel peeks through a snowy landscape after a winter storm in 2021.

The Drake Hotel peeks through a snowy landscape after a winter storm in 2021. The hotel hosts a popular holiday tea.

Pat Nabong

Indulge a bit with a tea party

Take a trip back in time with a holiday tea party in The Drake Hotel’s Palm Court. There are even caroling performances on select days.140 E. Walton Place; tickets from $35.

For younger kids, the Chicago Children’s Theatre hosts The Beatrix Potter Holiday Tea Party. The event features a trunk and puppet show with four classical tales, followed by a tea party with chocolate milk and cookies with the cast and puppets. Best suited for children 8 years old and younger. 100 S. Racine St.; tickets from $42.25.

Take in a holiday movie with the score played live

There’s something magical about a movie with a soundtrack played live by an orchestra. This year brings a few options. On Nov. 25, Elf in Concert at Auditorium Theatre will show the 2003 movie, while a live orchestra plays the score. Tickets from $45.

The Chicago Symphony Orchestra will play the score to the suburban-set Home Alone on Dec. 8-10 at Symphony Center. Tickets from $99.

See fireworks at Navy Pier

New this year, Navy Pier brings back its fireworks show for the winter. Bundle up with the whole family and enjoy the spectacle on Saturdays from Nov. 25-Dec. 23 and on New Year’s Eve. Free.

Santa Claus waves at a crowd.

Santa Claus will pop up in locations around the city, including the Hyde Park Holly-Day on Dec. 2.

Pat Nabong

Find Santa

Kris Kringle can be found across Chicago for pictures and wish making. Catch Santa at Hyde Park Holly-Day on Dec. 2 (53rd Street and Harper Avenue) or downtown at Macy’s Santaland (111 N. State St.) or 900 North Michigan Shops until Dec. 24.

Santa will also make appearances at Brookfield Zoo, Rosemont’s Sparkle Light Festival, Lincolnwood Town Center and on the trolley at Westfield Old Orchard.

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