The best October 2025 events in Chicago

The masterminds behind the irreverent long-running comedy show Drunk Shakespeare are unleashing their latest monster mash-up, “Drunk Dracula,” on the city for one month only. 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.

An unforgettable evening of thrills, chills and specialty drinks awaits for guests ages 21 and over at Zoo After Dark: BOOs & Brews. This adults-only evening features seasonal brews and cocktails, a costume contest with coveted prizes, music by DJ Nurotic, up-close encounters with Animal Ambassadors and more.

The first-ever Haunted House Party at Shedd Aquarium brings together house music and Halloween for a night to remember. Despite the event's name, there will be no scares here—the event's vibe is decidedly more “house party” than “haunted.” Guests are invited to come dressed in their finest costumes and dance the night away to sets by Chicago’s own Dee Jay Alicia and DJ Loria Branch. 

Step aboard City Cruises’ Seadog for a fun-filled journey through Chicago's history of ghosts, spirits, scandals and sins. As guests cruise along the Chicago River for 45 spooky minutes, expert—and costumed—docents weave stories of Chicago's darker side while cruising through the city's most iconic architecture. The cruise is BYOB, so be sure to bring a bevvy of your choice. 

More than 115 emerging artists will be selling their work at Saatchi Art's touring art fair, which takes place this year at Artifact Events. Prices for art start at around $100, making this the perfect opportunity for burgeoning collectors to start their very own gallery wall without spending an arm and a leg. 

A terrifying story set in the world of the Paranormal Activity film franchise, Felix Barrett (Sleep No More) and Chicago playwright Levi Holloway's latest endeavor promises chills and thrills. Here's what you need to know: James and Lou flee from Chicago to London in hopes of escaping the past, but they soon discover that it's not the city that was haunted—it's them. 

Some of the latest and greatest movies to hit the festival circuit arrive in the Midwest during the Chicago International Film Festival, which typically presents a lineup of around 100 dramas, documentaries, comedies and foreign films, plus 60 short film programs. In addition to CIFF's home base at AMC Newcity 14, the fest offers viewing opportunities across the city, with screenings at the Music Box Theatre, the Gene Siskel Film Center and more. Learn about other programming on the Chicago International Film Festival website.

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 latest 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.

Make your Halloween a little BOO-zier (get it?) during the Ravenswood Costume Crawl, which invites costumed attendees to stroll along a route stocked with local desserts, snacks and drinks samples on Montrose and Ravenswood Avenues. Come dressed to impress—one lucky person will also win a bottle of Malört.

Southport Corridor is going all-out this Halloween, on Southport from Belmont to Irving Park. The block will be packed with family-friendly activities, beer from Corridor Brewery, wines curated by Galleria Liquors, a pumpkin patch, photo ops, inflatables from Lakeshore Sport and Fitness, trick-or-treating at local businesses and more.