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.

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. 

The eighth annual Destinos: Chicago Latino Theater Festival returns to Chicago with a four-week lineup of live theater performances at venues throughout the city and Northwest Indiana. As usual, this year's lineup revolves around Latino-driven storylines, including several world premieres: Teatro Inovarte (a musical blending mariachi, ballet and queer love), Concrete Content (an immersive sketch show reimagining Latin futures via fake movie trailers) and more. You can view a full lineup of plays on the fest's website. 

Every two years, Chicago becomes a global hub of architecture and design during the Chicago Architecture Biennial. This edition’s theme is SHIFT: Architecture in Times of Radical Change, bringing together over 100 projects by architects, artists and designers from 30 countries—each piece engaging with the cultural, social and environmental fluxes transforming our world.

Not sure where to start? Check out our first-timer's guide to the exhibition. Stay up-to-date by visiting the Chicago Architecture Biennial website.

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. This month's highlights include a conversation with Kate McKinnon, a performance with Angela Davis and Nicole Mitchell's Black Earth Ensemble and a discussion with Harvard professor Stephanie Burt on the genius of Taylor Swift.

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.