The Chicago Holiday Season Bucket List

Family. Friends. Lots of shopping. Eating. Drinking. General merriment. 

The holiday season really does involve everything we love. The holidays in Chicago are no different. In fact, there are a few can't-miss December activities that make it one of the best cities to celebrate in. 

There's no wrong way to celebrate the holidays. (As long as it's respectful. That's all we ask for, people.) However, we thought we'd throw out a few of our favorite must-dos, too. Now it's time to get all holly jolly with yourself.

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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 24. You can also catch a secondary location in Wrigleyville's Gallagher Way space and Milwaukee. 

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.  

Indie Holiday Shopping

If you don't have everyone on your shopping list checked off, consider Chicago's local vendors and markets as your best options for finding a meaningful gift. There are dozens of indie holiday markets happening throughout town showcasing local handmade artisans with clothing, jewelry, baking accessories, wall art, toys, whozits, whatzits and more on sale. 

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 Millenniumm Park to visit the city of Chicago's official tree—a 55-foot blue spruce decorated and on display until January 6th. 

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. 

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See 'A Christmas Carol' at The Goodman Theatre

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. 

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ZooLights At The Lincoln Park Zoo

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). 

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Tree Lights at The Morton Arboretum

The Morton Arboretum's annual tree lighting display, "Illumination," projects beautiful hues onto the mile-long walking stretch through January 5th. Wintry activities like marshmallow roasting also abound here. 

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Take A Trolley Tour

Walking is great and all, but let's not forget that December is kind of cold. Stay warm(er) with the Chicago Trolley & Double Decker Co.'s holiday lights tours—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!  

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Go Ice Skating At Millennium Park

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 changeup. 

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Watch The Joffrey Ballet's Performance Of 'The Nutcracker'

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 13th and 14th. 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. 

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Caroling At Cloud Gate

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. 

The Music Box Theater's Annual Christmas Double Feature & Sing-A-Long

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.  

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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. Hawthorn Mall hosts a morning of family-friendly activities including crafts, dreidel spinning and more. The Bernard Horwich JCC hosts a bash on December 22. Try your hand at Chicago Botanic Garden's Hanukkah cooking class if you're feeling adventurous! For a lighter take on the holiday, check out Graystone Tavern's "8 Crazy Nights" pop-up open through January! 

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Navy Pier's Winter WonderFest

Navy Pier's Festival Hall gets decked out in holiday spirit again this year. Hundreds of trees, thousands of ornaments and a full-sized ice skating rink make up this family fun zone. You can also fill the day with activities like cookie decorating and themed obstacle courses. Who knows? You might even spot Santa!

Get lit at Butch McGuire's 

Sure, a lot of bars around town put up seasonal decorations. But what about 45,000 Christmas lights? Yep, Butch McGuire's in the Gold Coast has that—along with hundreds of other decorations and holiday knick-knacks hung throughout the bar. 

Christmas Around The World At MSI

The Museum Of Science and Industry's yearly holiday celebrations "Christmas Around The World" and "Holiday Of Lights" are back through January 5th. More than 50 holiday displays representing cultures and traditions from around the globe are on display now with special performances happening every weekend!

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Winterland At 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! Get there before Winterland packs up and heads back to the North Pole on February 16th. 

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Holiday-Themed Pop-Up Bars

It's all the rage! Temporary bars themed around your favorite holiday movies, stories and traditions are sprouting up all over town. Step in for spirited food, drinks and an Instagram-worthy experience. 

Happy holidays, Chicago! Make this season count.