Black on the Block
Photograph: Courtesy Black on the Block | Black on the Block
Photograph: Courtesy Black on the Block

The best things to do in Chicago this weekend

With our guide to the best festivals, shows and cultural happenings across the city, consider your weekend plans covered.

Lauren Brocato
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We’re probably not alone in saying that the weekend is always on our minds here at Time Out Chicago HQ. Like you (probably), we spend the workweek daydreaming about the next restaurant to obsess over and obsessively updating our concert calendars. Whether you’re museum-hopping, plotting a day trip to escape the city, or ready to ghost your original plans for something spontaneous, you’ll find plenty of ways to make the most of your weekend in Chicago.

Updated August 26, 2026: It's a big week for music in Chicago. BTS is headed to Soldier Field for two nights; the Chicago House Music Festival is back; and Edgwater Music Fest returns to the North Side. Plus, the country's largest touring marketplace for Black-owned businesses, Black on the Block, is taking over Stadium Green at Soldier Field for the first time. Keep scrolling to discover more of the best weekend events across the city.

RECOMMENDED: The best things to do in Chicago today

Best things to do in Chicago this weekend

  • Music
  • Music festivals
  • Recommended

This annual fest and conference celebrating the iconic dance music genre born in Chicago brings a full day of DJ sets to Millennium Park. Acts this year are to-be-announced. The live music will be preceded by an open house and panel discussions, and the festival will wrap up with a chill-down session along the Riverwalk. For a full list of programming, visit the DCASE Chicago House Music Festival and Conference website.

  • Shopping
  • Markets and fairs
  • Museum Campus
  • Recommended

The country's largest touring marketplace for Black-owned businesses is headed to Chicago for the first time. Black on the Block, hosted by Taylor Bennett, is taking over Stadium Green at Soldier Field for a day with more than 100 Chicago businesses. Guests can also expect a food court and bars, live music performances, games, giveaways, a kids' zone and more.

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  • Music
  • Pop
  • Museum Campus
  • Recommended

A genuine international sensation, BTS from South Korea has topped the Billboard charts, performed on Saturday Night Live (the first Korean act to do so) and embarked on world tours that have taken them to every corner of the globe. The music of BTS doesn't stray far from the contemporary pop melting pot of hip-hop, EDM and R&B influences, though the group's willingness to address depression and LGBTQ rights (taboo topics in South Korea) in their lyrics separates them from their peers. After headlining two sold-out nights at Soldier Field in 2019 and a cancelled tour stop in 2020, the group's ARIRANG Tour brings it back to Chicago's biggest stadium for two more performances this summer that are sure to be jam-packed with screaming fans.

Tickets are sold out, but there are plenty of tickets on offer (for a hefty markup) through third-party services.

  • Things to do
  • Quirky events
  • River West/West Town
  • Recommended

Jeppson’s Malört is attempting to set the world record at its “Bad Decisions for Good Cause” event at Recess (838 W. Kinzie St.) on Sunday, August 30. The event kicks off at 5pm before the official attempt at 7:30pm. Malört will match $10 from every ticket sold to support Ravenswood Community Services, a nonprofit dedicated to providing food, housing and other supportive services to Chicagoans facing hunger and homelessness.

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  • Things to do
  • Festivals
  • River West/West Town
  • Recommended

Hip-hop organization Groundwaves, launched in 2018 by rapper MURS, is bringing the first Goodwaves Music Festival & Conference to the Salt Shed. Three days of programming kick off with live conversations and Q&As featuring speakers like Vic Mensa and Killer Mike, and culminate with an all-ages music fest at the Salt Shed Fairgrounds, headlined by Killer Mike, Snow Tha Product and more. All events are free; just be sure to secure a complimentary ticket in advance.

  • Things to do
  • Festivals

Edgewater Music Fest will be hosting over 35 musical acts—all curated by local promoter Kickstand Productions (known for booking music acts at Beat Kitchen, Subterranean, Bottom Lounge and more)—and 100 vendors for the inaugural Edgewater Music Fest. The fest is open to all ages, with a Kids' Zone activity area for the little ones.

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  • Art
  • Photography
  • Grant Park
  • Recommended

From model to battlefield correspondent—and with many other titles in between—Lee Miller was a complex figure, and this year, the Art Institute of Chicago is showcasing works from her career in an expansive exhibit titled Lee Miller: Fearless. The first comprehensive survey of Miller's photographs in more than 25 years, Lee Miller: Fearless will feature nearly 150 works and will explore her life and approach to creativity, both behind and in front of the camera.

  • Attractions
  • Ships and boats
  • Streeterville
  • Recommended

Set sail with Chicago Line Cruises for an evening of jazz on the river. On the last Sunday of each month through September, the cruise line is partnering with the Jazz Institute of Chicago for 90-minute cruises featuring live performances, an on-board bar, open-air decks and a prime view of the sunset.

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  • Sports and fitness
  • Running
  • Uptown

Local no-kill animal shelter PAWS hosts its 26th annual 5K race at Montrose Harbor, where humans and dogs can make their way through a lakefront course while raising money to support the organization's work. Once you cross the finish line, you'll be able to enjoy live entertainment for humans and pups alike, including a dog agility course and a "doggy oasis" outfitted with pools for cooling off. Don't have a four-legged friend to bring along? Not to worry—there will be plenty of adoptable doggos for you to pet.

  • Ukrainian Village
  • Recommended

Sportsman's Club's Sunday BBQ series is back for another glorious year, bringing local restaurants to the bar's patio to cook a meal that's usually paired with a beverage. For the uninitiated, the takeovers are first-come, first-served, with the featured chef holding court over the bar's grill and menu. This year's lineup includes Bar Bambi, Pizz'amici, Milli by Metric, Kimski, Mister Tiger, Diego and more.

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  • Things to do
  • Classes and workshops
  • Millennium Park
  • Recommended

Get ready to bust a move because Chicago SummerDance is back with free dance classes. The instructor-led classes are completely free and open to dancers of all ages and experience levels. This year's lineup is packed with beginner-friendly classes across dance styles, all informed by the city’s rich cultural landscape. From ballroom and Bollywood to Brazilian samba and Chicago steppin’, there’s something for everyone—even those who claim to have two left feet.

  • Musicals
  • Sheffield & DePaul
  • Recommended

A Gen Z version of Grease takes the stage at the Apollo Theater this season. Vape! The Grease Parody is an Off-Broadway spoof of the iconic 1978 musical, complete with playful takes on the original storylines, modern references and, yes, vapes instead of cigarettes.

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  • Things to do
  • Streeterville
  • Recommended

Navy Pier's former Crystal Gardens space is transforming into a retro roller skating rink this summer. Grab your skates and hit the rink for some of the best views in the city, plus an arcade, drinks and groovy disco tunes. At night, the Skate After Dark party turns up the energy for the 21+ crowd with DJ sets on select nights throughout the summer.

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  • Things to do
  • Wicker Park

If dozens of vendors aren't enough of a draw for you to come to the lively Sunday market at this West Town neighborhood’s namesake park, maybe the weekly complimentary market programming—which includes free yoga, meditation and storytime for kids—will be. The market is also committed to sustainability, with plastic-free vendors and composting.

  • Things to do
  • Streeterville

Enjoy outdoor live music all summer long at the Navy Pier Beer Garden. The free series will feature local, regional and national acts performing countless genres and musical styles every weekend. Check the official Navy Pier website for the full lineup and schedule.

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  • Things to do
  • Fireworks
  • Streeterville
  • Recommended

During the summer, the Chicago attraction hosts twice-weekly fireworks shows (on Wednesdays at 9pm and Saturdays at 10pm) from Memorial Day weekend through Labor Day weekend, with stunning views available from across the pier's public spaces. During the winter months, the pyrotechnics return for a much-needed encore. If you're feeling weary of crowds, you can also take in the show from nearby beaches or while cruising along the Lakefront Trail.

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  • Things to do
  • Walks and tours
  • Loop
  • Recommended

Ready to explore Chicago's amazing architecture while floating on the river? The Chicago Architecture Center River Cruise takes place aboard a First Lady boat, transporting guests on a 90-minute tour that traverses three branches of the Chicago River and explores the stories behind more than 50 buildings that make up the city's iconic skyline.

What separates the Chicago Architecture Center River Cruise from similar tours are the knowledgeable Chicago Architecture Center docents that lead each excursion. You'll be able to chat with experts who know the nitty-gritty details of Chicago architecture and are eager to help you learn more about the structures surrounding you—something that makes this attraction appealing to tourists and longtime residents.

All tours depart from the First Lady dock on the Chicago Riverwalk, located just down the stairs from the northeast corner of Michigan Avenue and Wacker Drive. If you want to continue learning about Chicago's buildings after your tour, you can add a Chicago Architecture Center ticket for just $5—and it's good for seven days after you board the boat.

  • Things to do
  • Exhibitions
  • Museum Campus

Whether you’re parenting a pint-sized Pokémon devotee or a nostalgic millennial still clinging to a holographic Charizard card for its “possible resale value” (guilty), the Pokémon Fossil Museum is designed to surprise and delight. Making its U.S. debut at the Field Museum in spring 2026, the international exhibition invites visitors to compare Fossil Pokémon like Tyrantrum and Archeops with real-world fossils—including SUE the T. rex. Expect Pokémon models, real fossil excavation tools and immersive soundscapes throughout.

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  • Things to do
  • Exhibitions
  • River North
  • 3 out of 5 stars
  • Recommended

Part art installation, part psychological gauntlet, Theater of the Mind is David Byrne and Mala Gaonkar’s newest exploration of the self. Tucked inside a 15,000-square-foot office, the experience invites small groups of 16 or less to navigate a sensory-bending labyrinth. But the real variable isn't the set design; it’s the audience. Group participation is a central element of the show, which can be exhilarating but also sometimes awkward; the instructions are sometimes muddled, and the responses of the group can affect the narrative in ways that don’t always cohere. Ultimately, your enjoyment of Theater of the Mind may hinge on the group you’re there with—and on your own state of mind.

  • Things to do
  • Exhibitions
  • Grant Park

“Willem de Kooning Drawing” is the first exhibition to explore the full scope of the artist's drawing practice, framing it as the foundation of his boundary-breaking career. Featuring more than 200 artworks—including rarely seen drawings alongside paintings, sculptures and prints—this exhibition offers an unprecedented opportunity to experience seven decades of his graphic production while shedding light on his constant experimentation with various materials, tools and techniques.

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  • Circuses & magic
  • Streeterville
  • Recommended

Chicago's opulent new magic lounge, The Hand & The Eye, is introducing a limited-edition series dubbed Summer Friday Magic. Through Labor Day, a limited number of guests can enjoy a truncated, 45-minute show in the venue's Vault Theatre without having to commit to the typical full evening of programming.

  • Art
  • River West/West Town

Intuit Art Museum joins the national Handwork 2026 celebration with an exhibition investigating Henry Darger’s relationship to traditional American paper crafts. Drawing on research by art historian Dr. Mary Trent, the exhibition demonstrates how Darger adapted common practices—such as making paper dolls and scrapbooks—into a complex, mixed-media narrative style. By showcasing Darger’s source materials alongside his final works, the exhibition highlights how he reclaimed these institutionalized hobbies to express the interior lives and struggles of the marginalized.

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  • Museums
  • History
  • Loop
  • Recommended

In honor of America's 250th anniversary, the American Writers Museum presents a pop-up exhibition titled "Declarations: 250 Years of Writing Toward Independence." An 1832 William Stone print of the Declaration of Independence, a 1776 British edition of Thomas Paine's Common Sense, which advocated for the independence of U.S. colonies, and more artifacts will be on view. Visitors can also explore works related to the Declaration by Abraham Lincoln, Frederick Douglass and other historical figures, as well as edit the document into their own words through interactive activations.

  • 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.

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  • Art
  • River North

As the Driehaus Museum’s first artist-in-residence, Brendan Fernandes will transform the Murphy Auditorium into a dynamic site for sculpture, movement and sound. Inspired by the Judson Dance Theater, Fernandes’ Scores for the Murphy Auditorium will unfold as an episodic residency throughout 2026, with performances and public programs announced over time.

  • Things to do
  • Exhibitions
  • Loop

"Flyway City: Architecture for a Flourishing Ecosystem," designed by Studio Gang and led by world-renowned architect Jeanne Gang, explores solutions to prevent the estimated one billion annual bird-glass collisions in the U.S. Through a variety of architectural models, interactive media and local artifacts, the exhibition demonstrates how urban design can coexist harmoniously with nature. 

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  • Music
  • Music festivals

Looking for free concerts near Chicago? Hop on the Blue Line to Rosemont's Parkway Bank Park for Thursday night performances—with a few holiday and weekend dates sprinkled through the summer—including performances by Atomic Punks, Live the Who and Rhythm of the Rocketman, complete with a fireworks show at the end of the night. Beverage tents will be located on site, but we won't fault you if you prefer to pre-game with a fishbowl-sized spiked punch from nearby Sugar Factory. For a full schedule of shows, visit the Parkway Bank Park website

  • Things to do
  • Exhibitions
  • Avondale

With soundstage-sized pieces like horned sculptures emitting soap bubbles, inflated spheres bedecked in abstract squiggles and surreal faceless figures hovering in space, “EmotionAir” reimagines the humble balloon as any other artistic medium—a conduit for creativity and emotion. 

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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 arrive 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.

  • Things to do
  • Exhibitions
  • Streeterville

This first-of-its-kind exhibition at the Museum of Contemporary Art Chicago explores the visual, political and spiritual histories of dancehall and reggaetón through contemporary art. Once grassroots scenes, both genres have become globally influential movements tied closely to sexual and political liberation. The show features works by more than 35 artists, including Jean-Michel Basquiat, Edra Soto, supakid and Lee “Scratch” Perry.

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  • Things to do
  • Performances
  • Loop

You’ve probably seen a Shakespeare play before, but never like this. Five professional actors come together for each performance of Drunk Shakespeare. The twist? One of them has had five shots before the show and is trying to stay on track while the other four actors do their best to hold the performance together.

  • 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 every time you show up to see it.

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  • Things to do
  • Exhibitions
  • Hyde Park

This immersive exhibition recreates the Secret Annex where Anne Frank, her family and four others hid during the Nazi occupation of the Netherlands. Chicago is only the second U.S. city—and the first in the Midwest—to host the experience, which includes rarely seen artifacts from Frank’s life. Visitors can walk through the reconstructed hiding place while learning about Anne’s childhood, the rise of Nazi Germany and the Frank family’s years in Amsterdam. The exhibition offers a powerful look at the risks, courage and daily realities of those who lived in hiding. Admission is free on Friday, June 12 in honor of what would have been Anne's 97th birthday. Guests can also enjoy the exhibit for free with the purchase of a general admission ticket for the rest of the weekend.

  • 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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  • 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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