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.

Joffrey at the Harris: Matters of the Heart features new works by two of today’s leading female choreographers: Chanel da Silva and Annabelle Lopez Ochoa. Drawing on themes of love and resilience, The Joffrey Ballet will perform the world premiere of da Silva’s Wabash & You, a love story set in Chicago and featuring live on-stage accompaniment by Indiana-based funk band The Main Squeeze. Wabash & You will be followed by the Midwest debut of Lopez Ochoa’s Broken Wings (2024), a work inspired by Frida Kahlo's life and accompanied by the Chicago Philharmonic.

SANCTUM returns for another weekend of dark music, dancing and community at Thalia Hall and its piano lounge Tack Room. SANCTUM prides itself on standing head and shoulders above other music festivals, bringing in extra sound support from Big Audio, decking the room with curated decor and offering an “ALL VIP” ticketing concept that grants all attendees the same level of access. This year's lineup includes Lebanon Hanover, Qual, Male Tears, Beau Wanzer and more.  

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.

Check out all sorts of cool trinkets, wares and eats at this indoor market highlighting artisan makers from Chicago’s South Side. Taking place on the second floor of the Promontory, the family-friendly event features new and returning vendors, a cocktail bar, lounge areas and tunes by DJ Sean Alvarez of We Love Soul.

This annual festival assembles luminaries from the fields of politics, journalism and the arts for a multi-week series of programming across the city, with events ranging from lectures and discussions to screenings and musical performances. Not sure which events to hit? Some of this season's biggest speakers include Kate McKinnon, Margaret Atwood, Salman Rushdie and Nick Offerman. You can see a full schedule of programming on the Chicago Humanities Festival website.