Lady Gaga performing in Las Vegas
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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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There really is something for everyone on this week's event calendar, whether you’re a punk rocker, a wine enthusiast or a Labubu collector. With rain in this week's forecast, it doesn't hurt to have some indoor plans—like Reeling Film Festival, Chicago Architecture Biennial or Hyde Park Handmade Artisan Bazaar—on the docket. If inclement weather doesn't faze you, cheer on the brave athletes at the Chicago River Swim, break out your boots for Wrigleyville Country Fest or drink your way across the riverfront at the Riverwalk Oktoberfest Pub Crawl.

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

Time Out Market Chicago

Best events in Chicago this week

  • Things to do
  • Suburbs

Just when you thought the state's largest mall couldn't surprise you anymore, Woodfield Mall announces WONDRA, a sprawling new immersive experience. Inside, you’ll wander through enchanted meadows that respond to the sound of your voice, stumble across bioluminescent landscapes and drift into crystal caves and celestial gardens that blur the line between digital spectacle and raw wonder. 

  • Things to do
  • West Loop

As if you needed an excuse to spend golden hour at Time Out Market Chicago's rooftop bar—we're hosting a very special happy hour until the cold snap arrives. Sip on vibrant spritz drink specials crafted for summer lounging, complete with a live DJ spinning feel-good vibes all evening long. Whether you're here to dance, chill or just toast to the moment, this is your chance to savor the season.

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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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  • Things to do
  • Loop

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. Not sure which events to hit? Some of this season's biggest speakers include Kate McKinnon, Margaret Atwood, Salman Rushdie and Nick Offerman. You can see a full schedule of programming on the Chicago Humanities Festival website

  • 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 8:30pm, it’s best viewed from the section of the Chicago Riverwalk between Wells Street and Franklin Street.

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  • 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.

  • Movies
  • Loop
  • Recommended

Founded in 1981 and organized by Chicago Filmmakers, Reeling is the second-oldest LGBTQ film festival in the U.S., featuring a lineup of features, shorts and documentaries highlighting the diversity of queer stories and filmmakers from around the world. The fest will show dozens of feature and short films this year in a mixture of in-person and virtual screenings. For a full schedule of films and other events, visit the festival's website.

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  • 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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