A Halloween celebration at Central Park Bar
Photograph: Courtesy of Central Park Bar
Photograph: Courtesy of Central Park Bar

The best things to do in Chicago this week

Find the very best things to do in Chicago this week, including cultural events, festivals and shows.

Shannon Shreibak
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Last updated October 27, 2025: It happened: We’ve reached the final week of spooky season—a bittersweet pocket of time before fake cobwebs are replaced by string lights and crisp fall breezes yield to punishing sleet and snow. So, before the city slips into a yuletide tizzy, squeeze in a few of the best (mostly Halloween-themed) things to do this week. If you’re looking to embrace all things spooky and scary, there’s no shortage of events for you: Haunted Halsted Halloween Night Parade marches through the Northalsted neighborhood, the Shedd Aquarium transforms into a haunted house and Weegee’s Lounge becomes David Lynch’s Twin Peaks. There are plenty of things to do for the Halloween abstainer, too: the Vimeo Staff Picks Screening brings some of the platform’s best short films to the big screen, La Carrera de los Muertos winds through Pilsen and The Other Art Fair returns to Artifact Events this week.

RECOMMENDED: Discover the best things to do in Chicago in October 2025

Time Out Market Chicago

Best events in Chicago this week

  • Museums
  • Museum Campus

Every Wednesday, the Adler stays open late from 4–10pm so that folks can visit after work or school—best of all, admission is free for Illinois residents. Escape the planet with exhibits about the first lunar missions, the solar system and more, plus sky shows in an immersive dome theater. 

  • Experimental
  • Uptown

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.

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  • Art
  • Film and video
  • Recommended

Displaying a 25-story-tall video installation on the side of THE MART, ART on THE MART is the largest permanent digital art projection in the world, with programming that changes seasonally. ART on THE MART's array of 34 digital projectors show the creations after dusk every evening. Running Thursdays through Saturdays beginning at 7:30pm, it’s best viewed from the section of the Chicago Riverwalk between Wells Street and Franklin Street.

  • Comedy
  • Uptown
  • Recommended

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.

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  • Sports and fitness
  • Yoga & Pilates
  • Streeterville
  • Recommended

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 levelsyou 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.

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