The best November 2025 events in Chicago

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.

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.

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.

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.

Check out galleries and artistic spaces around Wicker Park and Bucktown during this free monthly event that takes place the first Friday of each month. Venues will keep their doors open until 8pm so guests can meet gallery owners and artists, and explore a range of local art. Participating spots include Jackson Junge Gallery, Tom Robinson Gallery, SoNa Contemporary Art, Torque Ltd., Prism Spaces and more.

Now in its 31st year, the Gene Siskel Film Center's annual showcase of stories celebrating the Black experience takes place from November 7-16. As usual, there's also a series of robust short film programs, accompanied by panels and workshops. This year's film lineup is yet-to-be-announced. Visit the Black Harvest Film Festival website for a forthcoming schedule of screenings and ticketing options.

If you’re craving a deeper kind of calm (and really, who isn’t these days?), try a 75-minute yoga session inside the Peggy Notebaert Nature Museum’s Judy Istock Butterfly Haven. Here, your vinyasa flow finds quiet company among hundreds of fluttering butterflies and the occasional exotic bird. After class, wander through lush flora and tropical trees that will make Chicago feel half a world away—if only for a little while. Just remember to bring your own mat, a water bottle and a mind ready to drift someplace lighter.

The masterminds behind the irreverent long-running comedy show Drunk Shakespeare are unleashing their latest monster mash-up, “Drunk Dracula,” on the city during the month of October. The premise is simple, but no less hilarious: Dracula gets drunk, unsuspecting citizens fight for survival and Bram Stoker’s vampire classic gets a boozy makeover that’s equal parts unhinged and fun.

Founding frontman of the Talking Heads—and musical legend in his own right—David Byrne is returning to Chicago for a four-night stand with a new album in tow. Byrne’s forthcoming album, Who Is the Sky?, is his first release since 2018’s universally acclaimed album-turned-Broadway-show-turned-concert-film American Utopia. To celebrate the release of Who Is the Sky?, Byrne will travel around the globe with a band comprised of 13 musicians, singers, and dancers—all of whom will be mobile throughout the set.

Experience the Art Institute like never before by tagging along with Marielle Epstein, assistant director of Interpretation at the Art Institute of Chicago. “Mindful Looking” is a monthly program that teaches attendees how to use mindfulness practices to enhance their museum-going experience, encouraging reflection and contemplation. A close look at an artwork is followed by a discussion and a guided meditation around a theme presented in the session. No prior experience with meditation is required.