Arts & Entertainment

Caroling, Trees and the Christkindlmarket — Celebrate the Holidays With These Classic Chicago Traditions

From a mug of hot glühwein at the Christkindlmarket to a trip to the Walnut Room’s Great Tree, there are some Chicago activities that have become iconic holiday traditions. Read on for opportunities to shop, snack, carol and ride holiday trains.

Christkindlmarket

The beloved German-style market is returning to three locations in 2026 as it celebrates its 30th anniversary: Daley Plaza (Nov. 20-Dec. 24), Wrigleyville (Nov. 20-Dec. 31) and Aurora (Nov. 20-Dec. 24). Expect food, mulled wine and shopping opportunities with international vendors. Admission is free, but the markets can get crowded — weekdays tend to be a little less packed, especially earlier in the day.

For folks looking for a little something extra, the Daley Plaza and Aurora markets are hosting a number of special events this year.

At Daley Plaza, you’ll find scavenger hunts; tours before the market opens each day; a ‘Twas the Night Before Christkindlmarket preview event; and a Haus of Krampus day. Aurora brings Krampus Fest, a scavenger hunt and two children’s lantern parades.

The Walnut Room & Christmas Trees

Chicago’s official Christmas tree lights up for the season Nov. 20 with a ceremony at Millennium Park; you can expect seasonal treats and a fireworks display. Can’t make it? The tree will be illuminated through Jan. 10.

If you prefer your tree indoors, head to the Marshall Field’s Walnut Room at Macy’s on State Street. Reservations can be hard to get at the iconic restaurant — which has been drawing holiday revelers since 1907 — but a selfie spot allows any and all to see the 45-foot Great Tree (Nov. 7-Jan. 17), an annual attraction since the restaurant’s inception.

Chicago’s 2025 Christmas tree. (Walter S. Mitchell III / City of Chicago)

All Aboard!

For more than three decades, the CTA Holiday Train has brought holiday cheer to Chicagoans and visitors alike. Each train car is decorated with seasonal images and thousands of lights; Santa greets visitors from his sleigh on an open-air flatcar. A CTA Holiday Bus joined the fleet in 2014. The 60-foot bus is transformed into a winter wonderland; Santa greets people from the roof hatch. Rides are free and begin in late November; check back for the schedule.

Metra Holiday Trains (Dec. 5, 12, 13, 19) will run on six lines this season; tickets go on sale Nov. 16 and are expected to sell out quickly. Each train is decorated differently by Metra staffers including carpenters and electricians. The Metra Electric Line (Dec. 12, 13, 19) will take passengers to a winter wonderland at Millennium Station with games, treats and visits with Santa.

Caroling

There are a number of caroling options this holiday season. You can spend Friday nights at the Bean for the Millennium Park Holiday Sing-Along (Dec. 4, 11, 18). Songbooks and ASL interpretation will be available; admission is free.

Or swing by the Music Box Theatre for its annual Christmas Sing-A-Long & Double Feature (Dec. 5-24). For more than 40 years, the Lakeview theater has offered the chance to belt out carols and watch back-to-back Christmas classics: “It’s a Wonderful Life” and “White Christmas.” Santa now greets revelers, and lyrics are projected on the big screen.

And the Old Town School of Folk Music hosts the lively Songs of Good Cheer (Dec. 10-13) with a band of folk, country and jazz musicians. Songbooks are provided, and a portion of proceeds benefits the Greater Chicago Food Depository.

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