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A large Christmas tree and crowds at Winterland at Gallagher Way
Photograph: D TATUM
Photograph: D TATUM

The best December 2024 events in Chicago

Find the best holiday activities in Chicago, including free things to do and picks from theater, music and pop-ups.

Jeffy Mai
Edited by Jeffy Mai
Editor, Time Out Chicago
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The arrival of December sends the holiday season into full swing—prepare yourself for a jam-packed roster of glittering Christmas lights, festive holiday pop-ups and plenty of glühwein to be sipped at Christkindlmarket locations in both Daley Plaza and Aurora. As the month draws to a close, bid adieu to 2024 at New Year's Eve events and parties happening at Chicago hotels, clubs and other hotspots, where you'll find Champagne towers and other special ways to welcome 2025 in style. So make the most of the final month of the year with our guide to the best events in Chicago this December.

RECOMMENDED: Check out our 2024 Chicago events calendar

Time Out Market Chicago

Time Out Market Chicago

Time Out Market Chicago
Photograph: Jaclyn Rivas for Time Out

We've rounded up the best chefs in the city to join us at Time Out Market Chicago, a culinary and cultural destination in the heart of Fulton Market featuring more than 15 kitchens, three bars and one drop-dead gorgeous rooftop terrace—all spread across three floors.

Best Chicago events in December 2025

The Paper Machete

  • Comedy
  • Uptown
  • Recommended
The Paper Machete
The Paper Machete
Photograph: Sarah Larson
This weekly “live magazine” is a cavalcade of culture, politics and wit featuring journalists, actors, comedians and musicians offering idiosyncratic reports on the news of the day. Head to Uptown’s iconic Green Mill for drinks, hot takes and laughs; the longstanding Saturday afternoon edition tends to run about two and a half hours.

ART on THE MART

  • Art
  • Film and video
  • Recommended
ART on THE MART
ART on THE MART
Photograph: Courtesy of ART on THE MART
Displaying a 25-story-tall video installation on the side of THE MART, ART on THE MART is the largest permanent digital art projection in the world, with programming that changes seasonally. ART on THE MART's array of 34 digital projectors show the creations after dusk every evening. Running Thursdays through Saturdays beginning at 7:30pm, it’s best viewed from the section of the Chicago Riverwalk between Wells Street and Franklin Street.
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360 Sky Yoga

  • Sports and fitness
  • Yoga & Pilates
  • Streeterville
  • price 2 of 4
  • Recommended
360 Sky Yoga
360 Sky Yoga
Photograph: Courtesy 360 CHICAGO
Head to 360 Chicago on Saturdays for yoga with a killer view. Instructor Britta Eumann will lead an hour-long class on the 94th floor of 875 North Michigan Avenue (formerly the John Hancock Center) that’s suitable for all ages and skill levels—you just need to bring your own mat and arrived properly dressed. Registration is $55 and includes a cocktail or coffee, plus admission to the observation deck so you can stick around and snap some photos after you're done striking poses on the mat.
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Drunk Shakespeare Chicago

  • Things to do
  • Performances
  • Loop
  • price 2 of 4
Drunk Shakespeare Chicago
Drunk Shakespeare Chicago
Photograph: Mike Sause
You’ve probably seen a Shakespeare play before, but never like this. Five professional actors come together for each performance of Drunk Shakespeare. The twist? One of them has had five shots before the show and is trying to stay on track while the other four actors do their best to hold the performance together.
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Vintage House Chicago Market

  • Things to do
  • Lincoln Park
Vintage House Chicago Market
Vintage House Chicago Market
Photograph: Shutterstock
Every local thrifter worth one's salt knows that Vintage House Chicago holds some of the city's best thrift scores. The bimonthly vintage and handmade market showcases local makers at rotating venues throughout the city. Each market features a new lineup, so you can plan on finding something new every time.

Amadeus at Steppenwolf

  • Drama
  • Lincoln Park
Amadeus at Steppenwolf
Amadeus at Steppenwolf
Photograph: Courtesy of Steppenwolf Theatre Company
Peter Shaffer's 1979 masterwork brings to life the rivalry between composers Antonio Salieri (Ian Barford) and Wolfgang Amadeus Mozart (David Darrow). Salieri is the Court Composer and the established standard of the day—his compositions are palatable, albeit restrained. Enter Mozart, a wild child prodigy with climbing notoriety and the ability to make music like no one has ever heard. Mozart's music moves Salieri to tears, but also awakens a destructive jealousy that compells him to supress Mozart at every turn. 
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The Nutcracker

  • Dance
  • Ballet
  • Loop
  • price 3 of 4
  • Recommended
The Nutcracker
The Nutcracker
Photograph: Lauren Quinn, Courtesy of Joffrey Ballet
Having retired cofounder Robert Joffrey's production of The Nutcracker after nearly 30 years, the Joffrey Ballet debuted a brand-new version in 2016, set in Chicago against the backdrop of the 1893 World's Columbian Exposition. This year's production will be staged in the Civic Opera House (where the Lyric Opera also resides), featuring music performed by the Lyric Opera Orchestra and the stunning choreography of Tony Award winner Christopher Wheeldon. The Chicago-inspired iteration of the classic Christmas ballet will have you humming “Dance of the Sugar Plum Fairy” for days after you leave the theater.
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Christkindlmarket

  • Things to do
  • Markets and fairs
  • Loop
  • Recommended
Christkindlmarket
Christkindlmarket
Photograph: Jaclyn Rivas for Time Out
The iconic German-inspired holiday market at Daley Plaza brings just over a month of Christmassy celebrations to the Loop. Browse stalls stocked with handmade gifts, German food and plenty of hot beverages to keep you warm while you wander around and soak in the festive atmosphere. Don't leave without trying spiced glühwein, a German hot wine concoction that's best enjoyed in the market's famous boot mugs.
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The Infinite Wrench

  • Experimental
  • Uptown
  • price 1 of 4
The Infinite Wrench
The Infinite Wrench
Photograph: Joe Mazza
For more than 30 years, the Neo-Futurists have been delighting late-night crowds with performances that pack 30 miniature plays into a 60-minute show. The company's signature show is more unpredictable than ever these days, with a handful of compact new plays premiering every week. Within the span of 10 minutes, you may be treated to a poignant monologue about everyday life or an irreverent diatribe delivered by a pantsless member of the cast—all inspired by the experiences of the performers on stage. Always changing and evolving, it's the rare show that truly offers something different everytime you show up to see it.
Buy ticket

Show & Tell for Grown-Ups

  • Comedy
  • Storytelling
  • Logan Square
Show & Tell for Grown-Ups
Show & Tell for Grown-Ups
Photograph: Sarah Larson
Wanna relive the thrill of punishing a captive audience like you did during grade school show-and-tell? Then Show & Tell for Grownups is the place for you! Once a month, comedians, storytellers and everyday passionate folks gather to share their quirky, heartfelt or downright fascinating interests. Each presenter gets five minutes on the clock to wax philosophical about their obsession, then it’s the audience’s turn with a quick Q&A. Think of it like falling down a Reddit rabbit hole—only live, and way more fun. Feeling especially brave? Sign up for your five-minute show-and-tell slot here.
Buy ticket
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Best Chicago events in December 2024

The Infinite Wrench

  • Experimental
  • Uptown
The Infinite Wrench
The Infinite Wrench
Photograph: Joe Mazza

For more than 30 years, the Neo-Futurists have been delighting late-night crowds with performances that pack 30 miniature plays into a 60-minute show. The company's signature show is more unpredictable than ever these days, with a handful of compact new plays premiering every week. Within the span of 10 minutes, you may be treated to a poignant monologue about everyday life or an irreverent diatribe delivered by a pantsless member of the cast—all inspired by the experiences of the performers on stage. Always changing and evolving, it's the rare show that truly offers something different everytime you show up to see it.

Read more
Buy ticket

The Paper Machete

  • Comedy
  • Uptown
  • Recommended
The Paper Machete
The Paper Machete
Photograph: Sarah Larson

This weekly “live magazine” is a cavalcade of culture, politics and wit featuring journalists, actors, comedians and musicians offering idiosyncratic reports on the news of the day. Head to Uptown’s iconic Green Mill for drinks, hot takes and laughs; the longstanding Saturday afternoon edition tends to run about two and a half hours.

Read more
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