The arrival of December brings a flurry of holiday magic to the Windy City, with locals and tourists bundling up and heading out to enjoy the season despite the cooler temperatures. Chicago local Kirsten Maxwell of Kids Are A Trip shares some of the holiday season’s highlights you won’t want to miss.

The holidays in Chicago are a wonderful time to visit. There’s a chill in the air and snow on the ground, and the city becomes a winter wonderland dressed in its holiday finery, beckoning visitors and locals to come together and enjoy the season. Holiday events start right around Thanksgiving and run through the first week of the new year, so there is plenty of time to join in the fun. Here are some of the best events to celebrate the holidays in Chicago.


This market in Chicago’s Daley Plaza is every bit as authentic as the ones in Germany. There are vendor stalls with nutcrackers, chocolate-covered fruit, and beer steins too. The smells of potato pancakes, pretzels, and glühwein fill the air as visitors stroll past the handicrafts for sale. The market is free, but it is very crowded on weekends. There’s also a sister Christkindlmarket in the suburb of Naperville that’s equally festive. Both markets are open through December 24th.

Best Events to Celebrate the Holidays in Chicago - Christkindlmarket - Travelocity

Photo credit: Christkindlmarket Chicago

Caroling and Ice Skating in Millennium Park

A visit to Millennium Park is wonderful any time of year, but it’s magical during the winter. It is home to Chicago’s official Christmas tree and the McCormick Tribune ice-skating rink. Admission is free, so bring your own skates or rent them at the rink (open through mid-March). After spinning around, why not enjoy hot cocoa and snacks at the Park Grill Café or head to Michigan Avenue for a heavier meal? Adjacent to the rink at Cloud Gate (aka The Bean), there is caroling every Friday night by various choirs. These free performances put everyone in the holiday mood. Santa also stops at Millennium Park, but be sure to check the schedule. Bring your own camera for photos, and tell Santa what’s on your holiday wish list!

On the other side of Millennium Park, don’t miss the ice-skating ribbon at Maggie Daley Park, where a ribbon of ice winds its way through the playground and trees. Admission is free; bring your skates or rent them on site. Definitely something unique to Chicago—and the Chicago skyline provides a stunning backdrop.

Best Events to Celebrate the Holidays in Chicago - Millennium Park Skating

Photo credit: Choose Chicago

The Joffrey Ballet’s Nutcracker

The Nutcracker has been a Chicago tradition for over 30 years, but in 2016, the company will present the premiere of choreographer Christopher Wheeldon’s version. The audience discovers the magic of Chicago’s mysterious 1893 World’s Fair through the eyes of a child in this new spin on a holiday classic. The entire production is breathtaking.

Illumination: Tree Lights at the Morton Arboretum

It may be cold in December, but that doesn’t stop people from bundling up and heading out to see the spectacular decorations at the Morton Arboretum in Lisle, about 30 miles southwest of downtown. The Arboretum decorates the vegetation in thousands of sparkling and dancing lights that interact with visitors as they make their way along the Illumination Trail. Some of the trees respond to touch and sound, music plays, and visitors can stop at fire pits and hot cocoa stands to warm themselves along the way. It’s a magical way to spend an evening.

Museum of Science and Industry: Christmas Around the World and Holidays of Lights

Since 1942 the Museum of Science and Industry has welcomed visitors with its gigantic four-story themed holiday tree, surrounded by more than 50 trees from around the world. Each smaller tree represents a specific country or culture and its traditions. On weekends there are global holiday performances (such as Irish dancers or an Austrian chorus), photos with Santa, and indoor snow showers to make the holiday experience complete.

Best Events to Celebrate the Holidays in Chicago - MSI

It’s A Wonderful Life: Live! in Chicago

This fabulous production at the Greenhouse Theatre re-creates a 1940s radio broadcast of Frank Capra’s holiday classic It’s a Wonderful Life, bringing the entire town of Bedford Falls to life. In addition to performing the timeless classic, the production features 1940s-style commercials from local sponsors, Christmas carols, and interactive opportunities for the audience, and after the show, everyone is invited to join the cast and crew for milk and cookies. Sounds like a wonderful life indeed.

Window-Shopping and Making Time for Holiday Tea

Chicago stores love to join in the holiday fun, and amazing decor can be found at the Macy’s on State Street with its holiday windows and 45-foot Christmas tree, the dazzling centerpiece of their famous Walnut Room. Stores along the Magnificent Mile also have a large variety of decorations, so whether you’re window-shopping or checking gifts off your list, you’ll enjoy taking a walk in the city.

Another fun event is taking holiday tea at one of the downtown hotels. Favorites include The Peninsula, The Drake, and The Ritz. They offer a perfect stop to enjoy delicious sandwiches and holiday music after a long day of shopping along Michigan Avenue.

Chicago sparkles during December, so we've found the best events to celebrate the holidays in Chicago.

Photo credit: Choose Chicago

Kirsten Maxwell is an official Travelocity Gnational Gnomad. Gnational Gnomads is an exclusive group of high-profile travel and lifestyle experts who offer tips and inspiration on behalf of Travelocity. For more information on the Travelocity Gnomads, visit

Travelocity compensates authors for their writings appearing on this site; such compensation may include travel and other costs.

Pin It on Pinterest

Share This