10 Fantastically Festive Things To Do This Holiday Season In Chicago (2023)

The holiday season in Chicago is in full swing and there is so much festive fun to be had. We've rounded up some must-do Christmas activities in Chicago.

Elliot McGowan

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During this time of year, the city shines particularly bright with lights illuminating every corner you turn. From sipping cocktails on one of Chicago’s many winterized rooftops to basking in the spectacle of one of Chicago’s exhilarating light shows—here are 20 of the most festive things happening this holiday season in Chicago!

1. Go ice skating at Maggie Daley Park

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Of all Chicago’s holiday season shenanigans, there are few as iconic as ice skating in Chicago’s many amazing ice rinks, and there are few as unique at the Maggie Daley Park Ice Rink.

Offering an “alpine in the city” experience skating down Maggie Daley Park’s quarter-mile rink in the heart of Chicago has to be one of the activities we most associate with the festive season.

The winding ribbon of ice curves up and down around a 40-foot climbing wall with the city’s stunning skyline in the backdrop. It’s a must for your Christmas checklist. It’s also free with your own pair of skates all time slots Monday through Thursday!

More information about the Maggie Daley Park Ice Rink can be found here.

2. Ride the CTA Holiday Train

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One of Chicago’s most cherished Christmas events is back for the season. Santa’s holiday train trip around Chicago is always one of the most eagerly anticipated activities providing affordable fun for all Chicago families.

The Chicago Transit Authority’s train and bus are decorated inside and out with festive decorations and thousands of lights to make them glow as they glide and glimmer around Chicago.

Now in its 31st year of operation, the Allstate CTA Holiday Train and the Allstate CTA Holiday Bus began lighting up Chicago on Friday, November 25th and will be whizzing around all 8 lines through Monday, December 19th.

The CTA Holiday Train and Holiday Bus schedules plus more information can be foundhere.

3. Sip Glühwein at Christkindlmarket

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Chicago’s German-inspired annual Christmas market is another extremely popular Christmas event. The beloved Christmas market returned on Friday, November 18th, and will run through to Christmas.

This year both The Christkindlmarket Daley Plaza and The Christkindlmarket Wrigleyville are welcoming guests into villages to peruse handmade gifts whilst enjoying German food and beverages beneath the snowflakes and glistening lights.

Enjoy the smell of roasted nuts, fresh pretzels, bratwurst, hot spiced wine, and the magic of festive music all in the coziest of atmospheres!

More information about Chicago’s Christkindlmarket can be found here.

4. Check out a holiday light show or three

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Chicago’s many light shows are some of our most treasured winter traditions. In 2020 all light show experiences turned to drive-thru events or were heavily adapted hindering the real light show experience and making us all realize just how much we took them for granted.

Gorgeous natural backdrops, cutting-edge light art installations, and festive cheer all combine providing some of Chicago’s most magical multi-sensory events and we’ve rounded up the best of them all.

  • Lightscape at Chicago Botanic Garden
  • Illumination: Tree Lights at The Morton Arboretum
  • ZooLights at Lincoln Park Zoo
  • Holiday Magic at Brookfield Zoo
  • AMAZE Light Festival at Odyssey Fun World

The full list with all you need to know about Chicago’s winter light show experiences can be found here.

5. Be captivated by a Christmas Candlelight Concert

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Step into Chicago’s most exquisite spaces to experience some of the most treasured holiday classics. From Christmas concerts to tribute performances, the beloved Candlelight series is bringing talented musicians to perform at venues, illuminated with hundreds of candles this season. Here are some of our favorite festive concerts taking place this month:

See the full list of candlelight concerts taking place in Chicagohere.

6. Cozy up in a rooftop igloo

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Cocktails, cozy blankets, and igloos? Winter wonderlands at bars and rooftops are some of our shining lights in the winter months. It’s officially cozy season, so what better way to celebrate the colder weather than by running away from it and sheltering under one of Chicago’s enchanting igloos?

Many of Chicago’s rooftops and patios have erected igloos for the holiday season so you can enjoy cocktails in your own personal snowglobes beneath the stars. Godfrey Hotel’s winter wonderland is one of our favorite Chicago winter hideouts and a great place to revel in Christmas cheer during the holiday season in Chicago.

More information about Godfrey Hotel’s winter wonderland can be found here.

7. Host your own winter games at the Gwen Hotel luxury rooftop

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Another unique winter experience can be had up on The Gwen Hotel’s luxury rooftop. While you won’t find lavish igloos here you’ll instead be able to enjoy the hotel’s annual Curling & Cocktails experiences. The hotel kits out its rooftop with not igloos, not ice skating, but an outdoor curling rink high in the sky.

Curling sessions come with a complimentary round of cocktails meaning you can sip away on your favorite tipple while going toe to toe with your friends on the state-of-the-art curling rink.

More information about the Gwen Hotel’s curling and cocktails can be found here.

8. Indulge in the exorbitance of Chicago’s Christmas pop-ups

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Each year various bars and restaurants across Chicago transform their spaces and decorate themselves head to toe in an exorbitant amount of holiday decor.

While the boozy milkshakes and Christmas-themed cocktails can at times border on the obscene, if there is one time of the year to indulge yourself, we all know it is Christmas time in Chicago.

One of our top picks from the array of Christmas pop-ups in Chicagoland has to be the immersive Santa Baby Pop-Upthat takes over Deuce’s Major League Bar in Wrigleyville every year.

Here you’ll find a wide selection of decadently garnished drinks and mouth-watering cocktails as well as a food menu from ‘Santa’s Snack Shack’ providing more than 20 different Christmas-themed bites.

More information about the Santa Baby Pop Up can be found here.

9. Catch an Art on the MART winter projection

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Of all Chicago’s public art pieces, Art on the MART is certainly one of the most spectacular. We’ve been treated to many months of stunning art spectacles on the facade of the Merchandise Mart since they returned earlier in 2022 for a climate change-themed spring program in collaboration with Shedd Aquarium.

Now the “largest permanent digital art projection in the world” has begun showing some sensational new shows for its winter program. “Chicago Design Through the Decades” by Daria Tsoupikova, Sharon Oiga, and Guy Villa Jr and The Nutcracker by Joffrey Ballet of Chicago will light up the 2.5-acre river façade at 7:30 & 8 pm nightly, changing from the 8.30 and 9 pm summer and fall showing times.

More information about Art on the MART’s winter projections can be found here.

10. Check out Chicago’s Harry Potter experience

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It’s the most magical time of the year and what pop-up could be more magical than one that allows you to revel in the wizarding world?Witches, wizards (and even muggles!) can finally embark on an incredible journey to Hogwarts™ at the worldwide premiere of Harry Potter™: Magic at Play, exclusively in Chicago.

The massive Harry Potter™: Magic at Play experience has finally arrived in Chicago, taking over three floors at the Water Tower Place on Michigan Avenue, where guests of all ages can interact, explore, play, and climb their way through the most iconic moments at Hogwarts™.

Don’t miss this magical adventure for wizards, witches, and even muggles (gasp!)—Accio tickets!

[Featured image from Shutterstock]

See more: A Chicago Winter Bucket List: 10 Essential Wintertime Experiences In Chicago

Tags:christmas, winter

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