June 2026 events calendar for Chicago

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.

Chicago Pride Fest brings two days of music, drag, vendors and LGBTQ-friendly event to Northalsted in celebration of Chicago Pride Month. Swing by to catch headlining sets from major chart-topping and local artists. Plus, browse arts and crafts from more than 150 vendors and don't miss out on the Proud Pet Parade at noon on Sunday. Once you've had your fill, head to one of the best gay bars in Chicago to keep the party going.

In June 2026, the Chicago Symphony Center commemorates the United States’ 250th anniversary with a curated season reflecting the nation’s rich and evolving cultural landscape. Featuring the Chicago Symphony Orchestra alongside elite guest artists and jazz ensembles, these performances honor American resilience and creativity. From the seminal works of Copland, Gershwin and Ives to the cinematic grandeur of John Williams’ Star Wars: A New Hope score performed live to film, the season celebrates the enduring spirit of American music.

Dragon boat teams paddling to the beat of a drum face off against one another on the South Branch of the Chicago River at this annual event, racing all afternoon to raise money for local schools and literacy organizations. Back on land, attendees can watch the races, visit vendor booths and take in live entertainment (including dancers and musicians) throughout the afternoon.

The oldest juried craft fair in Hyde Park features paintings, sculptures, jewelry and ceramics from nearly 200 artists. The event also features blues and jazz acts, presented by Buddy Guy's Legends, as well as a family-friendly activity area and various food vendors. Attendees can shop for artwork created in a variety of mediums, including glass, jewelry, leather, photography, printmaking, painting, sculpture, wood, ceramics or fiber.

On June 13, teams of two will bring their custom-built bicycles to Chicago for the Red Bull Spin Off, a high-energy challenge requiring balance, brains and bravery to navigate a floating race track without falling in. This quirky athletic challenge will showcase 40 teams from across the country; they'll be judged on creativity, showmanship and race time.

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.

Take a stroll and browse the work of more than 200 artists on the streets of Old Town at this annual two-day art fair. Attendees can also take a self-guided tour of more than 50 local gardens, enjoy live music from local performers and explore a selection of food and drinks provided by area restaurants and vendors. Admission is free, but donations are encouraged.

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 reinvent themselves in their so-called later years—Kim Gordon, or even David Bowie in his final creative chapter—it’s refreshing to encounter this same sense of possibility at the edge of age.

Still, the show doesn’t fully cohere. Jazz—arguably the gravitational center—feels slightly under-scaled relative to its cultural weight, and the surrounding works, while compelling, at times read more like satellites than a tightly woven narrative. It’s a rich and worthwhile exhibition, but one that stops just short of transcendence.

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.