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Christmas in Chicago: A 48-Hour Holiday Itinerary

BY: Lisa Farver | Dec 3, 2014

Horse-drawn carriages ferry shoppers down State Street, tiny wooden shops sell mulled wine, and kids ice-skate the night away under a mirrored skyline—there’s a traditional holiday magic to Christmas in Chicago. The city’s modern attractions get into the act, too, with Willis Tower turning the lights on its spires red and green.

Locals have long known Chicago rivals New York City as a premier holiday destination, but for those uninitiated to the Windy City’s wintery charm, we’ve curated a two-day itinerary to spotlight some of the most festive activities for the season. Even Chicago’s easily navigable public transit system gets into the spirit: take the CTA’s Holiday Train, or—for the first time ever in Chicago—the CTA’s Holiday Bus, to get around during your visit.  


Day 1: Downtown and the Loop

Noon | Browse Christkindlmarket in Daley Plaza

The smell of cinnamon-roasted nuts and fresh bratwursts will draw you into Christkindlmarket, an open-air Bavarian market in Daley Plaza, where admission is free. Vendors from countries including Germany, Poland, Peru, Ukraine, and Nepal sell handmade holiday gifts such as cuckoo clocks, hand-blown glass ornaments, and wooden nutcrackers. Fill up on potato pancakes and warm up with gluhwein—a toasty mulled wine that comes in a signature mug—before heading a few blocks east to do some shopping on State Street.  

3 p.m. | See the Macy’s Christmas Windows while Shopping on State Street

If you see shoppers clustering in front of the windows of the Macy’s on State Street, join them! They’re admiring the dioramas in each window, a tradition that began in the 1890s when the storefront was the flagship Marshall Field’s.The display’s theme changes each year, but past dioramas have included mechanical elves, toy ballerinas, and miniature lights.

While you’re on State Street, check your holiday list twice while using coupons for Macy’s, Sephora, the Disney Store, and other shops.

5 p.m. | Have Dinner at the Walnut Room

On the 7th floor of Macy’s, take part in another century-old tradition—dinner at the Walnut Room, named so for its handsome wood paneling. Try the restaurant’s signature chicken pot pie and sneak a few pictures of the main attraction: the 45-foot tall Christmas tree, strung with 5,000 lights.

7 p.m. | Go Ice Skating by the Bean

Festive holiday lights and the glow of skyscrapers illuminate the McCormick Tribune Ice Rink  at Millennium Park, which Fodor’s calls one of the nation’s top ice-skating rinks. Skaters can practice their best triple salchow jump in the reflection of Anish Kapoor’s Cloud Gate sculpture, affectionately known by locals as “The Bean” for its legume-shaped design.

Day 2: Beyond the Loop

10 a.m. | Bring Kids to Winter WonderFest at Navy Pier


Entering Winter WonderFest at Navy Pier feels like you’ve been transported to the North Pole, except with pleasant indoor temperatures. A towering 42-foot-tall tree shares space with an indoor tubing hill and a skating rink inside this winter dreamland. The rides are a blast for kids: they’ll spin in giant hot-cocoa cups, take a spin on a reindeer-festooned carousel, and bounce around in an inflatable bounce house shaped like a 30-foot-tall snowman.

Buy discounted tickets to Winter WonderFest at Navy Pier on Groupon.

1 p.m. | Explore Christmas Around the World and Holidays of Light at the Museum of Science and Industry

Christmas Around the World @ the Museum of Science and Industry, Chicago Photo: JB Spector, Museum of Science and Industry, Chicago

Ever wonder how families in other countries decorate for the holidays? The Museum of Science and Industry has the answer, trimming more than 50 trees with the traditional ornaments found in countries ranging from the Netherlands to the Philippines. The South Side museum started this tradition in the 1940s to honor soldiers fighting in World War II during the holidays. Don’t miss the museum’s Grand Tree, which sparkles with more than 30,000 lights and LEGO-themed trinkets.

6:30 p.m. | Watch Festive Movies at Music Box Theatre

Christmas-in-Chicago-48-Hour-Holiday-Itinerary-Music-Box-Theatre_600c360 Photo courtesy of Music Box Theatre

Christmas in Chicago can sometimes mean spending Christmas in Bedford Falls. If you’ve never seen It’s a Wonderful Life or White Christmas on the big screen, head to the North Side for the Music Box’s Annual Christmas Show (select dates, December 10–24). The city’s beloved art-deco theater screens these holiday classics for two weeks. At intermission, Santa Claus himself leads a sing-a-long of popular holiday tunes. You can also catch the theatre's alternative double-features of Die Hard and Gremlins or Elf and Love Actually (select dates, December 12-20).