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.

Every local thrifter worth one's salt knows that Vintage House Chicago holds some of the city's best thrift scores. The bi-monthly 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.

Returning to a two-acre plot of land just west of Goose Island, Jack's Pumpkin Pop-Up saves you a trip to the suburbs by bringing a huge corn maze, more than 10,000 pumpkins, axe throwing, carnival games, food trucks, twinkling orange light displays and more fall fun to the city. A general admission ticket nets you access to the pop-up, but you can also opt for add-ons that let you take home a pumpkin, grab a drink at one of bars or go axe throwing.  When is Jack's Pumpkin Pop-up? The pop-up opens September 18 and runs through November 2. How do I get tickets to Jack's Pumpkin Pop-up? Timed-entry tickets can be purchased via Jack's website. Prices vary based on time and ticket type.

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. 

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.

Keep a music venue at the top of its game for as many years as a vinyl record spins at RPMs, and you'll find a very cheeky anniversary to celebrate. The venerated Empty Bottle has long stood as a high water mark for indie bands, a haven for experimental acts and a welcoming watering hole for Chicagoans writ large—not to mention the home of Peg, the venue's bar cat-turned-mascot. In celebration of its 33 ⅓rd anniversary, the Bottle is hosting a series of concerts that welcome the return of memorable acts from the venue's storied past, like psych-pop sensation Cindy Lee, twangy soul outfit Whitney and dream pop quad The Pains of Being Pure at Heart. 

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.