December 2017 events calendar for Chicago

Find the best holiday activities in Chicago, including free things to do, and picks from theater, art and music
Photograph: Jaclyn Rivas Christkindlmarket

We know you're tempted to hide from the cold in your apartment, but there's just so many things to do in Chicago in December. The holiday season means Chicago is buzzing with winter events, great (though sometimes stressful) shopping as well as wonderful shows and concerts. Whether you’re lacing up your skates at Millennium Park or hiding away with a hot cocktail at a cozy bar, there are tons of reasons to make the most of December in Chicago. 

RECOMMENDED: Events calendar for Chicago in 2017

Featured events


Randolph Street Market Festival


More than 200 vendors hawk their antique housewares, furniture, ephemera, clothing and more at this indoor-outdoor festival. Stop in for vintage clothes and jewelry, a vinyl swap meet, a fancy food market and global goods bazaar or bring your own items for appraisal. This event typically occurs on the last weekend of each month. During the warm-weather months of May–September, the market adds an outdoor area, offering even more vintage shopping and a beer garden.

Christmas in Chicago


December concerts

Thom Yorke
Photograph: Courtesy Nasty Little Man
Music, Dance and electronic

Thom Yorke + Oliver Coates

icon-location-pin Loop

After bringing Radiohead to the United Center for a pair of shows earlier this year, Thom Yorke will return to Chicago in December for a special concert in support of his 2014 solo album, Tomorrow's Modern Boxes. Joined by longtime Radiohead producer Nigel Godrich and backed by live visuals created by Tarik Barri, Yorke will dig into the glitchy, electronic sounds he's created as a solo artists, as well as with Atoms For Peace. Don't expect to hear any Radiohead songs—Yorke's recent performances have served as deep dives into his own catalog, complete with renditions that expand upon his work in interesting ways. Experimental cellist Oliver Coates supports.

lollapalooza 2018, travis scott
Photograph: Neal O'Bryan
Music, Rap, hip-hop and R&B

Travis Scott + Sheck Wes + Trippie Redd + Gunna

icon-location-pin United Center

After celebrating the release of his latest album, ASTROWORLD, at Lollapalooza this summer, Travis Scott returns to Chicago on his WISH YOU WERE HERE tour. The Houston rapper and Kayne West protege presides over a cavalcade of famous friends on his recent record, trading verses with Drake, harnessing the psychedelic production of Tame Impala’s Kevin Parker and making way for guitar riffs provided by John Mayer. While you probably won’t see an of ASTROWORLD’s most prominent guests at the United Center, Scott is bringing New York emcee Sheck Wes, SoundCloud rapper Trippie Redd and “Phase” rapper Gunna along for the ride.

December comedy shows

iO Theater
Photograph: Anthony Soave
Comedy, Improv

Whirled News Tonight

icon-location-pin River North

  Now in its 15th year, Whirled News Tonight has become an institution at the iO Theatre, hence its prime time slot. Improvised scenes are based on news articles from that week, which audience members post to the back wall of the stage. The show boasts alumni including Jordan Klepper (The Daily Show, The Opposition with Jordan Klepper), Sarah Haskins (Trophy Wife), Arnie Niekamp (Hello From the Magic Tavern) and more. 

Photograph: Byron Hatfield
Comedy, Sketch shows

Bye Bye Liver: The Chicago Drinking Play

icon-location-pin Lake View

"Bye Bye Liver" combines two robust Chicago traditions: comedy and heavy drinking. The show opened ten years ago for a three-week run, then kept getting extended. It centers on common party situations most Chicagoans can relate to, and incoroprates interactive audience games like "Would You Rather." If you're looking to get drunk, quick, and have a great time doing so, "Bye Bye Liver" is always a solid bet. 

December theater shows

Theater, Children's

That's Weird, Grandma: Holiday Stories

icon-location-pin Uptown

Want to look cool to your favorite pipsqueak (and adult friends, too)? Introduce them to Barrel of Monkeys' joyously long-running public show. The troupe conducts writing workshops with CPS grade school students by day, then transforms the kids' stories into hilarious or heartfelt skits and songs, performed with abandon by a spirited ensemble. The show goes holiday-themed for performances from December 4 through 23.

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