The best November 2026 events in Chicago

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 with bulbs that "sing" holiday songs. 

The circus is coming to town as Ringling Bros. and Barnum & Bailey presents a reimagined version of The Greatest Show on Earth from November 6-8. The new tour won’t have any animals, but instead features musical performances blended with aerial artistry, modern comedy and never-before-seen acts on highwire, trapeze, bicycles and more. Performers include The Navas Troupe on the Double Wheel of Destiny, unicyclist Weslley Williams, and trapeze group Flying Cáceres.

The Music Box Theater brings back its beloved annual Halloween tradition with five screenings of The Rocky Horror Picture Show. Each screening is paired with a shadowcast as actors perform in front of the screen during the film. It's a wonderfully weird tradition that's known to sell out.

“Rashid Johnson: A Poem for Deep Thinkers” is a major survey spanning the Chicago artist’s nearly three-decade career. Through photography, video, immersive painting and large-scale installation, the exhibition explores the fragility of the human psyche against the weight of historic forces. Centering freedom as his primary muse, Johnson draws inspiration from radical movements of the late 20th century, showcasing how individuals and communities resist established orders to carve out new paths through history.

This touring exhibition honoring one of the country's most significant sculptors of the 19th century stops at the Driehaus Museum. Known for major works like the Bethesda Fountain in New York City's Central Park, Stebbins' marble and bronze works are showcased in this career-spanning exhibition of sculptures, paintings, archival materials and more.

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.

Hosted at Stolen Saddle—one of Chicago's largest country bars—this annual Halloween-themed extravaganza features photo ops galore, plus an upstairs bar serving spooky cocktails like Freddy’s Tequila and Darcula's Blood. There’s no haunted house this go-around—but that doesn't mean Nightmare on Clark Street won't be serving up scares this Halloween season.

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.

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.

Every local thrifter worth one's salt knows that Vintage House Chicago is a treasure trove holding some of the city's best secondhand scores. The bimonthly vintage and handmade market showcases local makers and curators at rotating venues throughout the city. Each market features a new lineup, so you can plan on finding something new every time.