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

The best December 2025 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 2025 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

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.

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.
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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.

City of Chicago Christmas Tree

  • Things to do
  • Millennium Park
  • Recommended
City of Chicago Christmas Tree
City of Chicago Christmas Tree
Photograph: Patrick L. Pyszka
Every year, Millennium Park is adorned with an epic Christmas tree that remains on display until the beginning of the new year. The larger-than-life attraction is festooned with twinkling lights and crowned with an illuminated star. Spectators can check out the festive tree near Washington Street and Michigan Avenue through early January. Want to see the tree light up for the first time this season? The annual Christmas Tree Lighting Ceremony returns this year on Friday, November 21.
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Chicago Architecture Biennial

  • Things to do
  • Festivals
  • Recommended
Chicago Architecture Biennial
Chicago Architecture Biennial
Photograph: Luis Urculo, Courtesy of Chicago Architecture Biennial
Every two years, Chicago becomes a global hub of architecture and design during the Chicago Architecture Biennial. This edition’s theme is SHIFT: Architecture in Times of Radical Change, bringing together over 100 projects by architects, artists and designers from 30 countries—each piece engaging with the cultural, social and environmental fluxes transforming our world. Not sure where to start? Check out our first-timer's guide to the exhibition. Stay up-to-date by visiting the Chicago Architecture Biennial website.

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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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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Lightscape

  • Things to do
  • Exhibitions
  • Suburbs
Lightscape
Lightscape
Photograph: Alex Hewitt
The Chicago Botanic Garden hosts this annual (and quick to sell out) display of festive lights, giving guests a host of shimmering reasons to visit the forest preserve during the holiday season. Set along an illuminated path, the after-dark experience features a series of installations to explore, including a 110-foot tunnel made up of 100,000 lights and a group of trees festooned in bulbs that “sing” holiday songs. 
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Adler at Night

  • Museums
  • Museum Campus
Adler at Night
Adler at Night
Photograph: Courtesy Adler Planetarium
Escape the planet with exhibits about the first lunar missions, the solar system and more, plus immersive shows in the dome theater. Stationed just a stone's throw away from the Adler, the Doane Observatory is also home to the largest public telescope in the area and gathers 7,000 times more light than the human eye. Every Wednesday, the Adler stays open late from 4pm-10pm so that folks can visit after work or school. And best of all, admission is free on those nights for Illinois residents.
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Christmas Around the World

  • Things to do
  • Exhibitions
  • Hyde Park
  • price 2 of 4
Christmas Around the World
Christmas Around the World
Photograph: Heidi Peters
Every year, the Griffin Museum of Science and Industry puts up its four-story Grand Tree and surrounds the towering pine with more than 50 trees that represent Chicago's various communities and their respective holiday celebrations. Visitors will be able to take in even more seasonal cheer at the accompanying Holidays of Light exhibit, which recognizes the traditions of Chinese New Year, Diwali, Kwanzaa, Ramadan, Hanukkah, Visakha Puja Day and St. Lucia Day. Admission to Christmas Around the World and Holidays of Light is included with a regular Museum of Science and Industry 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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