By Choose Chicago
(See Part I: Holiday Lights here, Part II: Holiday Markets here, and Part III: Christmas-y Things To Do here.)
There’s truly no time like the holidays in Chicago.
Each winter, the city is full of bustling excitement and seasonal celebrations. You can admire twinkling light displays, go ice skating with skyline views, shop for gifts in a charming neighborhood boutique or pop-up market, catch a holiday show in a stunning downtown theatre, and so much more.
See the Chicago Christmas Tree
Don’t miss one of Chicago’s biggest and brightest holiday traditions — the City of Chicago’s official Christmas Tree, a local tradition for more than 100 years. Don’t miss the annual Christmas Tree Lighting Ceremony in November, which includes live performances and a fireworks display.
The massive tree, which will light up the center of iconic Millennium Park, is adorned in twinkling lights and makes the perfect holiday photo opp. The tree shines brightly near the intersection of Michigan Avenue and Washington Street through January. Make sure to stop by one of the magical ice skating rinks while you’re there.
Holiday Shopping in Chicago
Pick up some gifts for loved ones (and maybe something for yourself) in Chicago’s many shopping districts. The Magnificent Mile, one of the world’s most iconic retail destinations, is a good place to start. You’ll find famous department stores, luxury showrooms, and favorite chains — plus tons of holiday lights twinkling from the trees that make the whole area feel merry and bright.
A few blocks away, State Street is another shopper’s paradise where you’ll find the iconic Macy’s on State Street. Stroll around the building to admire their annual Holiday Windows, adorned with intricate themed displays, and step inside to dine beneath the Great Tree at the historic Walnut Room.
And if you’re looking for something truly unique, don’t miss Chicago’s many neighborhood boutiques. That’s where you’ll find a treasure trove of one-of-a-kind gifts, like custom-made leather goods, artisan crafts, vintage finds, and locally crafted clothing. Check out these top neighborhoods for unique holiday shopping.
Explore more: Find the perfect gifts with our guide to holiday shopping.
Plan A Special Holiday Meal
It doesn’t get much more festive than a meal at the Walnut Room. Located inside Macy’s on State Street, the historic spot is the the first restaurant ever opened in a department store and an essential holiday destination. The stately interior is adorned with elegant decor and sparkling chandeliers, with the towering Great Tree in the center of it all. Make sure to try Mrs. Hering’s chicken pot pie, an original recipe from the 1890s. And don’t miss the famed holiday window displays that line the exterior of the landmark building.
Spot the Chicago Holiday Train
A beloved Chicago tradition for more than 30 years, the CTA holiday train will once again make its way through the city this December. Marvel at the six-car train decorated with holiday scenes and thousands of sparkling lights, then hop on board to meet the elves handing out candy. Don’t forget to wave to Santa, whose sled replaces the head car. There’s also a holiday bus that will traverse the city streets, bringing holiday cheer to neighborhoods throughout Chicago.
