The holiday season is here once again, and what better place to celebrate than Chicago? The Windy City is hosting its fair share of festivities this year, from holiday lights and music at the zoo, to a giant tree lighting ceremony, to a traditional European Christmas market, and everything in between. So if you’re in the mood to plan some holiday fun, we have the perfect list for you.

Of course, it’s important to be safe this holiday season too. Be sure to bundle up in warm clothes when you attend these events, especially the outdoor ones, as the holiday season in Chicago can be extremely cold. And be sure you’re safely covered with auto insurance before you hop in your car to drive to one of these events. Here is our top list of the best things to do in Chicago this holiday season with your friends and family.

Lion statue in Chicago, IL
Imagevia Flickr by Licensed CC BY 2.0

Christkindlmarket: A German Christmas Market in Chicago

International travel may still be slowly opening up, but you can experience the buzz of an authentic German-style Christmas market right here in Chicago. The Christkindlmarket offers free admission and open air, spread throughout the Daley Plaza from Nov. 19 to Dec. 24. The market’s expansive offerings of local and international vendors will entice you with bratwurst, hot spiced wine, roasted nuts, arts and crafts, gift ideas, holiday music, and more.

Marketed as the most authentic traditional holiday market outside of Europe, Christkindlmarket is definitely worth a visit this holiday season. So bundle up and gather your family and friends, jump in your car, and head to the market for shopping and festivities.

Millennium Park Christmas Tree

Chicago’s “official” Christmas tree will be erected from Nov. 19, 2021 (don’t miss the tree lighting ceremony at 6:30 p.m.), to Jan. 9, 2022. This year’s lighting ceremony will feature entertainment from Dreezy Claus and Sister Claus, music by DJ Selah Say, Mariachi Herencia de Mexico, Brian McKnight, and Chicago Soul Spectacular, as well as performances by Kenwood School of Ballet, the Chicago Opera Theater, and Cirque du Soleil. Concessions will be available throughout Millennium Park.

The tree will remain illuminated through the new year, so even if you miss the big event, you can plan an evening to see the lights. Be sure to check out some of the other attractions in the Millennium Park area, such as the neighboring ice skating rinks or museums. Another holiday event in Millennium Park is the Holiday Sing-Along (aka Caroling at Cloud Gate). Every Friday at 6 p.m. from Nov. 20 to Dec. 17 (and Sunday, Dec. 12), join other festive folks to sing along with traditional and modern holiday tunes.

Ice Skating at McCormick Tribune Ice Rink

Nothing adds to the allure and magic of Christmas lights quite like lacing up some ice skates and spinning around an outdoor rink. To even further enhance the whimsical experience, McCormick Tribune Ice Rink is placed just in front of Cloud Gate (aka The Bean), so the twinkling lights and joyful visitors are reflected in its shining surface.

To add to the experience, see if you can arrive on a snowy day. There’s nothing like skiing at the holidays with snow falling all around. Be sure to grab a cup of cocoa after at one of the nearby cafes. Admission to the ski rink is free, but you do need reservations in advance (book online). Bring your own skis or rent from their facilities.

ZooLights at Lincoln Park Zoo

You might not be able to spot Santa’s reindeer, but you can still see animals this Christmas season at the Lincoln Park Zoo! The historic zoo will put on an impressive display, incorporating over 2.5 million lights and synchronized music, from Nov. 21, 2021, to Jan. 2, 2022.

This year’s ZooLights at Lincoln Park Zoo has new and upgraded exhibits, including an 18-foot Christmas tree and a new lights show on the South Lawn. Other activities include photos with Santa, Snowy’s Spirits & S’mores pop-up bar, spiced wine, beer, and themed cocktails, snacks, and shopping. Tickets are just $5, but there is also free entrance on Mondays and Tuesdays. Note that admission is limited, so be sure to arrive early to enjoy this festive event.

Holiday Movies and Holiday Shows 

Bundle up and head to the iconic Gallagher Way for classic holiday movies outside every Thursday in December. This year’s line-up includes some favorites: “National Lampoon’s Christmas Vacation,” “Home Alone,” “Elf,” and “A Christmas Story.” There are also plenty of other activities to keep you busy nearby, including ice skating, Santa’s workshop, a Hanukkah celebration, and the Wrigleyville Christkindlmarket (same organizer but different venue from the other market featured on this page).

Music and performances abound this holiday season in Chicago. Local Chicago theaters have a great lineup of Christmas and holiday-themed shows this year. On Dec. 7 you can catch the Jingle Ball at All State Arena, featuring acts like the Black Eyed Peas, Doja Cat, and Lil Nas X. Or catch a live production of the lovable holiday favorite, “How the Grinch Stole Christmas,” at the James M. Nederlander Theatre. If you’re a fan of dazzling rock music, be sure to catch the Trans-Siberian Orchestra on Dec. 23 at the Allstate Arena.

Have a Safe and Festive Holiday Season in Chicago

Chicago will host almost endless holiday festivities this year. From Christmas lights to heart-thumping musical performances, ice skating to traditional Christmas markets, there’s something to entertain every member of the family this holiday season. So bundle up in your favorite tacky holiday sweater, grab your friends and family, and head to one of the events on this list. To stay safe as you drive from event to event this year, be sure you’re covered with excellent auto insurance from American Auto.

We know there are plenty of amazing holiday events in Chicago, and it’s difficult to fit everything in one list. Did we miss any of your favorite holiday events? Let us know!


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