Family. Friends. Shopping. Eating. Drinking. Merriment.
No, this isn't a greatest-hits list of what life has to offer - it's a description of the HOLIDAY SEASON! A time of year that encompasses pretty much everything we love and throws a tidy little bow on it. Chicago's no slouch when it comes to can't-miss December activities, so we got to work on compiling the best of the best of 'em on this page.
Photo via Facebook.com/Christkindlmarket
Sipping hot mulled wine out of a boot-shaped mug is a Chicago tradition if there ever was one. This German-inspired open-air market has been bringing holiday joy to locals since 1996. Its flagship location sets up shop in Daley Plaza every winter and runs through December 24th.
Even if you've already wrapped up your holiday shopping for the season, Christkindlmarket's food and drink options still make it a fun place to wander with someone you're sweet on.
Walk The Magnificent Mile & Check Out The Macy's Window Displays
Chicago's Magnificent Mile, the stretch of Michigan Avenue between Oak Street and the Chicago River, always looks especially stunning during the holidays, with tons of lights, store window displays and carriages lining the streets. It makes for a beautiful nighttime stroll. Don't forget to make a stop at Millennium Park to visit the city of Chicago's official tree, a 55-foot blue spruce decorated and on display until January 8th.
Keep heading south past the river and pop over to State Street for more of the city's longest-running holiday traditions. The Macy's window displays are always extravagant and always dazzling. Once you're done posting to Instagram, you can snag more double-tap-worthy pics inside the department store's restaurant. The Great Tree, a 100+ year tradition, towers 45 feet above the dining room and is on display through early January.
Photo via Facebook.com/Goodmantheatre
The story of A Christmas Carol is a classic in any city, but the Goodman's production is a longstanding favorite and 40+ years into its annual run.
Image via Facebook.com/Lincolnparkzoo
We're always down to hit up Lincoln Park Zoo and hang with snow monkeys and sloths and penguins, but what about when they're illuminated by 2.5 million holiday lights?! It's even better. Plus, there are family-friendly activities scheduled throughout the month (and adult beverages for sale, too).
Image via Facebook.com/Mortonarboretum
The Morton Arboretum's annual tree lighting display, "Illumination," projects beautiful hues onto the mile-long walking stretch through January 3rd. Wintry activities like marshmallow roasting also abound here.
Image via Facebook.com/Chicagotrolley
Take A Trolley Tour
Walking is great and all, but let's not forget that December is kind of cold. Stay warm(er) with a trolley holiday lights tour, bussing you to all of the best displays. Or see Chicago's holiday lights like never before with a nighttime helicopter ride around the city courtesy of Chicago Helicopter Experience!
Image via Facebook.com/Maggiedaleypark
Go Ice Skating In The Loop
The McCormick Tribune Ice Rink is one of the most picturesque rinks in the city, surrounded by twinkling skyscrapers and nestled under The Bean. Let's not forget that admission is also free! (However, skate rentals do cost between $12 and $14.) Thanks to the Maggie Daley Park Skating Ribbon, you now have another ice skating option nearby if your tradition needs a slight change-up.
Image via Facebook.com/Thejoffreyballet
We've come to expect a fresh take on old classics from The Joffrey Ballet and they continue to prove us right with the company's production of The Nutcracker, retold with a Chicago twist.
Celebrate The Spirit Of Kwanzaa
Prepare for your Kwanzaa celebration at the Africa International House's Pre-Kwanzaa Marketplace happening December 20th. You might also visit some of Chicago's cultural institutions such as the DuSable Museum of African American History or the Bronzeville Children's Museum to further learn about the holiday's traditions and history.
Photo via Cityofchicago.org
Does anything scream "so Chicago" as much as bundling up in the middle of December and singing holiday songs in front of The Bean? I mean, come on! It's so cute it's almost annoying.
It's exactly what you think it is. The Music Box's annual holiday extravaganza features White Christmas and It's A Wonderful Life. Each screening starts with Santa Claus himself, along with the theater's organist, leading the audience in renditions of beloved carols before the film begins.
Image via Transitchicago.com
Catch The Holiday CTA Train & Bus
It's the only time of year you'll race to catch a certain train for reasons other than running late to work. The Chicago Transit Authority's holiday train and bus are back and more decked out than ever. Follow along with the schedule (aka Santa tracker) here.
Celebrate Hanukkah On The North Side
For the area's best Hanukkah celebrations, you'll need to head just outside of the city proper. For a fun take on the holiday, celebrate Hanukkah with Chicago's favorite drag bubbe, Merriam Levkowitz at Graystone Tavern. Find some laughs for the whole family at Greenhouse Theater Center for Hannukah Shmanukkah!
Photo via NavyPier.org
Navy Pier's Festival Hall gets decked out in holiday spirit again this year. Hundreds of trees, thousands of ornaments, giant nutcrackers, and plenty more wintery whimsy. Complete the day with hot cocoa and hot apple cider. Who knows? You might even spot Santa!
The Museum Of Science and Industry's yearly holiday celebrations "Christmas Around The World" and "Holiday Of Lights" are back through January 6th. More than 50 holiday displays representing cultures and traditions from around the globe are on display now with special performances happening every weekend!
Photo via Facebook/Gallagher Way
When the Cubs aren't in season, Santa comes out to play. Gallagher Way at Wrigley Field has transformed into a winter playground complete with an ice skating rink, curling classes, free holiday movies screenings and more!
Updated November 2025
Happy holidays, Chicago! Make this season count. Did we miss your favorite thing to do? Let us know!
