Adler Planetarium
Photograph: Courtesy Adler Planetarium
Photograph: Courtesy Adler Planetarium

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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The weather may feel like summer, but the events calendar in Chicago is celebrating all things autumnal and Halloween-themed. If you’re ready to embrace spooky season, look no further than Music Box Theatre’s monthlong horror movie marathon “Music Box of Horrors: Dead and Loving It!” or Island Party Hut’s Fall Fest on The Riverwalk. For the booze enthusiasts, there’s no shortage of bevvy-themed events this week: Chicago Beer Festival, Lincoln Park Wine Fest and more are on the docket. If you’re looking for a more low-key weekend, catch an artist talk at the Chicago Humanities Festival, pet some pooches at Chicago Canine Rescue Barktoberfest or catch up-and-coming artists at Avondalia Art Show: In Chorus & Cohesion.

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

Time Out Market Chicago

Best events in Chicago this week

  • Things to do
  • Festivals
  • Lincoln Square

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. 

  • Music
  • Latin and world
  • Loop

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. 

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  • Things to do
  • Lake View

Chicagoans are invited to bring their pup and join the Chicago Canine Rescue Barktoberfest, a festive, dog-friendly event raising funds for Chicago Canine Rescue. Guests can take part in the Sam Adams Human Stein Hoisting Contest and cheer on their furry friends in the Dog Pup Cup Holding Contest. Other event highlights include raffles benefiting Chicago Canine Rescue, free pup cups for all dogs, a German-style buffet and drink specials.

  • 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. 

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  • 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. 

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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. 

  • 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
  • Festivals
  • Museum Campus
  • Recommended

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. 

  • Kids
  • Lincoln Park

Get your fall feels on at Lincoln Park Zoo's annual free festival. You can snag a photo with a giant pumpkin, watch master gourd carvers at work, enjoy live music and see all kinds of animals. The festival also includes several ticketed experiences such as carousel rides, a bounce house, harvest maze, a slide and more. 

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  • Things to do
  • Festivals
  • Sheffield & DePaul

Looking to learn a little more about wine? Head to Jonquil Park for the annual Lincoln Park Wine Fest, where sommeliers and brand ambassadors will coach you through a two-hour tasting session. Each general admission ticket comes with a sample of 12 varietals of wine and a commemorative tasting glass; spring for a VIP ticket for an expanded tasting that includes five additional specialty wines to taste. Either way, you'll be able to watch live music performances while you sip. 

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  • Things to do
  • Performances
  • Loop

The masterminds behind the irreverent long-running comedy show Drunk Shakespeare are unleashing their latest monster mash-up, “Drunk Dracula,” on the city just in time for spooky season. 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.

  • Things to do
  • Festivals
  • Andersonville

For two decades, Andersonville’s artistic community has been gathering once a year for a weekend of creative celebrations, showcasing work from local artists in businesses and galleries throughout the neighborhood. The weekend's activities also include self-guided art walks and a fall wine walk, where guests are invited to sip vino at participating businesses as they stroll around the district.

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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. 

  • Things to do
  • Festivals

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. 

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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.

  • Art
  • Contemporary art
  • Hyde Park

Join the University of Chicago's Smart Museum of Art as they celebrate “Unto Thee,” Theaster Gates's first solo museum exhibition in his hometown of Chicago. Known for his installations merging sculpture, performance and social practice, Gates has become a driving force in the contemporary art world and beyond. “Unto Thee” embodies the relationships Gates has fostered throughout Chicago, underpinning his belief that art has the capacity to connect and transform communities.

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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.

  • Things to do
  • Festivals
  • North Center

Go for a spin on a carnival ride, catch a set from a local band, enjoy tasty German fare or sip brews in the St. Ben’s Parish courtyard at this family-friendly party. Admission is free, but you'll need to buy tickets for Bavarian food, beers and rides on the carnival attractions. Prost!

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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.

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