It’s beginning to look a lot like Christmas on Southport Avenue. The historic Music Box Theatre is bringing back one of Chicago’s favorite holiday traditions: its 43rd Annual Christmas Sing-A-Long & Double Feature, running December 5–24, 2026.
This year’s celebration features two beloved films, It’s a Wonderful Life and White Christmas, with a festive sing-along and a visit from Santa before each screening.
Two holiday classics return
Frank Capra’s It’s a Wonderful Life (1946), starring James Stewart and Donna Reed, follows George Bailey as he discovers the extraordinary impact of an ordinary life. It’s a movie about community, friendship, and the people who make life worth living.
White Christmas (1954), starring Bing Crosby, Danny Kaye, Rosemary Clooney, and Vera-Ellen, brings Irving Berlin’s music, lavish dance numbers, and old-Hollywood holiday charm to the big screen.
The sing-along is part of the magic
The Music Box Christmas experience is about more than watching a movie. Each screening begins with a roughly 25-minute holiday preshow featuring a cartoon, Christmas carols accompanied by organist Dennis Scott, and Santa Claus. It’s the kind of communal experience that can’t quite be recreated in a living room.
A Southport Avenue tradition
Opened in 1929 at 3733 N. Southport Avenue, the Music Box Theatre remains one of Lakeview’s most distinctive cultural landmarks. While so many neighborhood movie houses have disappeared, the Music Box continues to draw Chicagoans for classic films, special programming, and experiences like this annual Christmas celebration.
Make a night of it: enjoy dinner at a Southport Corridor restaurant, browse the neighborhood’s shops, and settle into the theater for a little holiday nostalgia.
2026 dates, tickets and details
- When: December 5–24, 2026
- Where: Music Box Theatre, 3733 N. Southport Avenue, Chicago
- Films: It’s a Wonderful Life and White Christmas
- General admission: $17 for a single feature or $25 for a double feature
- Members: $14 single feature or $21 double feature
- Children under 13: $10 single feature or $15 double feature
According to the theater’s event information, member online ticket sales begin October 23 at noon, general online sales October 26 at noon, and advance box office and telephone sales October 29 at 4 p.m. Check the theater’s schedule for individual showtimes and availability.
View the official Music Box Christmas Sing-A-Long schedule and tickets.
What are your Music Box Christmas memories?
For some Chicago families, this is a tradition spanning generations. Have you attended the Music Box Christmas Sing-A-Long? Tell us your favorite memories in the comments.