Noon | Be Merry at Christkindlmarket in Daley Plaza

The smell of cinnamon-roasted nuts and fresh bratwursts will draw you into Christkindlmarket, a free open-air Bavarian Christmas market in Daley Plaza. Vendors from Germany, Poland, Peru, Ukraine, Nepal, and other countries from around the world sell handmade holiday gifts like 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 souvenir mug—before heading a few blocks east to do some shopping on State Street. 

3 p.m. | See the Macy’s Christmas Windows 

Seeing shoppers clustering in front of the Macy’s on State Street? Go 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 come to life with mechanical elves, toy ballerinas, and miniature lights. Head inside with the kids to wander through Dickens Village and Santaland, where Santa waits to hear what each child wants for Christmas.

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. | Enjoy 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, which is often dressed with a glorious array of ornaments and other festive decor.

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 named one of the 15 Best Ice Skating Rinks in the U.S. Skaters can practice their best forward crossovers 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 the 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. The details of this festival change annually, but in years past, it’s featured a towering 42-foot-tall tree, an indoor tubing hill, and a skating rink. The rides have been a blast, too: kids have been able to spin in giant hot-cocoa cups and whirl around on a reindeer-festooned carousel.

1 p.m. | SEE Christmas Around the World at the Museum of Science and Industry

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 traditional ornaments found in countries from Europe to Oceania. The Hyde Park museum started this tradition in the 1940s to honor soldiers fighting in World War II during the holidays. You’ll learn a Belizean tree features wooden doves, while Estonians like to decorate their tree with apples.

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

Finish your Christmas in Chicago by spending some time in Bedford Falls. If you’ve never seen It’s a Wonderful Life or White Christmas on the big screen, head to the Music Box, a beloved art-deco cinema, for its Annual Christmas Show (select dates, December 12–24), which screens both films. At intermission, Santa Claus himself leads a sing-a-long of popular holiday tunes. If you can’t make the double-feature, keep an eye on the theater’s calendar for other seasonal movies, as the Music Box has been known to show Die Hard, Gremlins, and Elf in the past.