Chicago Pride Parade
Photograph: Jordan Avery
Photograph: Jordan Avery

June 2026 events calendar for Chicago

Jump into summer in Chicago with our picks for the best festivals, fairs, exhibits and events.

Jeffy Mai
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Is there anything better than June in Chicago? The days are long, summer festival season has arrived and cold weather finally feels like a distant memory, giving us ample opportunity to enjoy afternoons at Chicago beaches and evenings spent sipping frozen cocktails at the city's best rooftop bars. As always, you'll find plenty of seasonal events to keep busy, from big summer music festivals like the Chicago Blues Festival and the Lyrical Lemonade Summer Smash to charming neighborhood art fairs. Plus, don't miss the numerous Pride events happening. Say hello to summer with our list of the best things to do in Chicago this June.

RECOMMENDED: Events calendar for Chicago in 2026

The best events in Chicago this June

  • 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.
  • Things to do
  • Exhibitions
  • Grant Park
  • 4 out of 5 stars
  • Recommended
To know Matisse is to know Jazz—or at least the vivid images that make up the book, which gathers some of his most iconic works of the 20th century. After a lifetime spent wrestling with the tension between color and line—a struggle that often seemed fruitless—an emergency surgery and the long, bedridden recovery that followed led Matisse to experiment with cut paper shapes, the very forms he is now synonymous with. The result of that creative breakthrough was Jazz, a book of 20 vibrant plates, now on display at The Art Institute of Chicago alongside several of his other pursuits in painting, printmaking, textiles and beyond. While you may feel well-acquainted with Matisse’s work through pop culture osmosis—Icarus, for instance, emblazoned on the cover of The Body Keeps the Score, a trauma text that has achieved an unusual level of mainstream popularity—“Matisse's Jazz: Rhythms in Color” recontextualizes these familiar, often misread images. Icarus, for example, is not surrounded by stars but by bursting artillery shells, a subtle yet unsettling trace of fascist anxiety creeping into Matisse’s vision. Jazz itself occupies only a small atrium within this multi-room exhibition. Elsewhere, the galleries open onto Matisse’s experiments across mediums: woodcuts, graphite sketches and lesser-known sculptures, each offering a different angle on his restless practice. The exhibition ultimately stands as a testament to the idea that life can begin at 70. As we watch other artists...
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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.
  • Museums
  • Museum Campus
Escape the planet with exhibits about the first lunar missions, the solar system and more, plus immersive shows in the dome theater. Stationed just a stone's throw away from the Adler, the Doane Observatory is also home to the largest public telescope in the area and gathers 7,000 times more light than the human eye. Every Wednesday, the Adler stays open late from 4pm-10pm so that folks can visit after work or school. And best of all, admission is free on those nights for Illinois residents.
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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.
  • 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. Every corner is crafted to ignite curiosity and inspire a sense of awe we, whether you’re a kid seeing it all for the first time or an adult who forgot what it feels like to play.
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  • Things to do
  • Exhibitions
  • Hyde Park
How are some of the most iconic costumes of the past century made? Costume designer Paul Tazewell pulls back the curtain in this behind-the-scenes exhibition. Highlights include costumes from Wicked, Janelle Monáe’s MET Gala looks and Steven Spielberg’s West Side Story. Sketches, videos and narration reveal how imagination becomes wearable art.
  • 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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  • Sports and fitness
  • Yoga & Pilates
  • Streeterville
  • price 2 of 4
  • 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 levels—you 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.
  • 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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