The Top 9 Best Things to do in Chicago During the Holidays

Christmas in Chicago is a simply the most wonderful time of the year as the city transforms into a winter wonderland filled with festive events and celebrations.  From caroling and Christmas lights to strolling Christkindlmarket or skating the ribbon, these beloved traditions help make the holiday season a little brighter.  

Magnificent Mile Lights Festival

Ring in the holiday shopping season at this two-day festival that takes place on Michigan Avenue. The fun begins on Friday, November 22, when Pioneer Court hosts family-friendly activities (including a visit from Santa Claus) and treats from Garrett Popcorn, Frango and Eli’s Cheesecake. On Saturday, November 23, stores on the Magnificent Mile will offer special experiences and offers throughout the day, before Michigan Avenue hosts a two-hour tree-lighting parade led by Grand Marshals Mickey Mouse and Minnie Mouse, which sets off from Oak Street at 5:30pm.


You haven’t experienced the holidays in Chicago until you’ve stepped into this giant open-air market inspired by a similar seasonal tradition in Nuremberg, Germany. At Christkindlmarket, guests can shop handcrafted items like nutcrackers, cuckoo clocks, beer steins and glass ornaments. When hunger strikes, nibble on potato pancakes, hot pretzels, schnitzel, döner and chocolate-covered treats. And no trip to Christkindlmarket is complete without a steaming mug of Glühwein, a traditional hot spiced wine (there’s also hot cocoa for the kids).


If you enjoy Christmas lights, ZooLights at Lincoln Park Zoo is for you.   Featuring over 2.5 million twinkly lights, ice sculpture carving, caroling, as well as live performances and other special events all season long.  Special events include visits from Santa, a holiday market (Dec 3), an adults-only night (Dec 5), a live performance of music from A Charlie Brown Christmas (Dec 15) and a Zoo Year’s Eve celebration (Dec 31).

Illumination: Tree Lights at Morton Arboretum

When the weather gets cold, the trees at Morton Arboretum light up in a sea of color at this popular winter event. Guests at Illumination stroll down a one-mile path watching the tress and fauna come to life as holiday music pipes in the background.  Visitors can stop by crackling fires to warm up, make s’mores, as well as sip on hot cocoa. 

Caroling at Cloud Gate

Nothing gets you into the holiday spirit faster than listening (or singing) traditional holiday classics.  Meeting every Friday from November 29 through December 20, enjoy Christmas caroling, led by the likes of the Sounds Good! Choir (Nov 29), Mark Hubbard and The Voices (Dec 6), the Chicago Children’s Choir (Dec 13) and the Wicker Park Choral Singers (Dec 20). It’s free to attend and it’s just a short walk to the McCormick Tribune Ice Rink.

Ice Skating in Millennium Park

Skate under the Chicago skyline and within eyeshot of the Chicago Christmas Tree at the McCormick Tribune Ice Rink in Millennium Park. Admission to the rink is free, and you can rent skates for $13–$15. The most popular time to hit the rink is in the evening, so show up earlier if you don’t feel like waiting in line for your chance to slide around. Take advantage of free skating lessons on Fridays at 11am and Saturdays and Sundays at 9am. If it seems too warm to skate, call ahead—this rink is open through March 8, weather permitting.

Christmas Around the World & Holiday of Lights

Since 1942, the Museum of Science & Industry has continued the tradition of celebrating the holidays by featuring trees representing different cultures from around the world.  What started as a single tree has turned into a breathtaking display of over 50 trees surrounding the four-story Grand Tree in the main hall.   In addition to the trees and lights, special performances and events take place throughout the season. 

Winter WonderFest

Throughout the month of December, Navy Pier transforms into Winter WonderFest. This festival inside is decorated with trees and candy canes and activities include an indoor ice skating rink, an indoor Ferris Wheel, a zip line, inflatable slide, a carousel, spinning cups, and a train ride. Santa is also there waiting to listen to Christmas wishes. 

Holiday Lights Tour

What better way to get into the holiday spirit than by taking a tour to see Chicago’s holiday lights!  Now in its second year, Gray Line Chicago is offering a tour that includes seasonal favorites with stops at ZooLights and Christkindlmarket plus views of the Chicago Christmas tree, Magnificient Mile, and Macy’s holiday windows. 

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