The best October 2025 events in Chicago

This annual fall street festival returns to Lincoln Square for one apple-filled weekend. Shop autumnal goods at the festival's marketplace, munch on apple-stuffed tamales and apple doughnuts from local restaurants, sip cider and apple-flavored beer, catch live music performances and bring the kids for seasonal activities. For more fall fun, check out our guide to the best orchards for apple-picking near Chicago.

Explore music from around the globe during this annual festival, now in its 24th year, which brings a wide array of performers to venues across the city for free musical performances. Experience sounds and subgenres from regions like Brazil, South Korea, Senegal and more. For a full list of performances, visit the festival's website. 

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.

Want to get a free, behind-the-scenes look at the Chicago Board of Trade Building, Walt Disney's birthplace home, Orchestra Hall at Symphony Center and more iconic buildings throughout the Chicago area? You’ll have a chance to do so when the Chicago Architecture Center’s annual festival Open House Chicago returns to the city, opening up more than 170 architectural wonders across the city for free tours. 

Take an autumnal stroll through Chicago’s Northalsted neighborhood and indulge in a culinary adventure. For four blissful hours, you’ll have the chance to savor bites from more than 20 of the area’s top restaurants and bars, including El Taco Cart, The Villa Toscana, Kit Kat Lounge & Supper Club, Elevate Coffee, Big Gay Sal’s Pizza, Roscoe’s Tavern, GoodTimes Brewery and more. A $30 ticket will get you unlimited tastings, including samples of a variety of beers, spirits and cocktails. 

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. 

Want to drink a beer underneath Máximo the titanosaur in the Field Museum’s Stanley Field Hall? You'll be able to sample creations from more than 65 breweries when the Chicago Beer Festival returns to the beloved institution. Each attendee receives 40 tasting vouchers that can be exchanged for pours from 3 Floyds, Revolution, Half Acre and other breweries from Chicagoland and beyond. 

Every October, more than 45,000 runners hit the streets of Chicago and take a 26.2 mile tour of the city by foot. While it's too late to enter the race (and complete weeks of grueling training), you can join tens of thousands of spectators on the city's streets to cheer on participants as they make their way through the course. The start and finish line in Grant Park isn't open to the public, but you can head to neighborhoods like Pilsen, Chinatown, Boystown and Lincoln Park to join crowds of onlookers toting handmade signs, blaring music and encouraging all of the runners as they whiz by, or meet your runner at the reunite area of Grant Park starting at 9:30am. 

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.