The best things to do in Chicago this weekend

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.

Whether you like your hot dogs dragged through the garden or topped with ketchup, this Portage Park fest has you covered. Local favorites, including Byron's Hot Dogs, Baked Cheese Haus, Chicago Doghouse, Frannies, Lee Concessions, Tikka Masala Dogs and Sausage Fest Food Truck, will compete to see who makes the best frankfurter, as voted on by fest-goers. In addition, there will be live entertainment, arts and craft vendors, a kids area, a top dog parade and a hot dog eating competition.

Three Chicago DJs are taking over a vintage design showroom for the weekend-long music series HeadRoom. Rather than a typical DJ show with rowdy crowds and chaos on the dance floor, guests arrive early, sit during the performance and see the headliner first. The nouveau DJ series encourages connection and a focus on the music. 

Kick off the start of summer festival season at Do Division, the street shindig with live music booked by Empty Bottle and Subterranean in West Town. Catch performances at two stages and check out food trucks, a fashion show, vendors for shopping and a Family Fun Fest area with kids activities, among other attractions.

Every local thrifter worth one's salt knows that Vintage House Chicago is a treasure trove holding some of the city's best secondhand scores. The bimonthly vintage and handmade market showcases local makers and curators at rotating venues throughout the city. Each market features a new lineup, so you can plan on finding something new every time.

Get ready for a roaring adventure at Brookfield Zoo Chicago! The Dino Dash Fun Run invites you to race, jog or casually stroll along a scenic 2-mile course that winds directly through the zoo’s world-class wildlife displays. Once you cross the finish line, you'll be celebrated with a commemorative Dino Dash medal to mark your achievement. The excitement doesn't end there, though; your registration also includes free admission to the zoo for the rest of the day, along with complimentary access to the Ferris wheel and carousel.

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.

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.

No, you haven’t stumbled into an early Oktoberfest—this is just how Lincoln Square welcomes street-festival season and the beginning of spring. Hoist a stein, grab a pretzel, watch some lederhosen- and dirndl-costumed dancers and embrace the neighborhood’s German heritage over the course of one fun-filled weekend.

The Midwest Film Festival proudly presents its 2026 season, “Midwest Royale,” an expansive celebration of cinema, culture and community. This landmark year honors more than two decades of the festival’s commitment to championing regional storytelling and elevating local creative talent. The season officially launches on May 31 at the Chicago Cultural Center with the Midwest Film Fair and the Best of the Midwest Winners Showcase. This opening event will feature screenings of the 2025 award-winning films alongside the highly anticipated announcement of the 2026 Best of the Midwest Awards (BMA) nominees.

Originally established in the late 1800s, the Maxwell Street Market brought vendors, musicians and cooks to an open-air flea market where shoppers could find just about anything they wanted. The market introduced the Maxwell Street Polish sausage, provided a venue for rising Chicago blues musicians and was immortalized in a scene in The Blues Brothers. These days, the market sets up on Maxwell Street, between South Halsted Street and South Union Avenue on Sundays, where visitors will find vendors hawking their wares, an abundance of delicious Mexican food and occasional performances by local bands and dance troupes. 

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.

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.

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.

Get ready to hunt for some new (and old) treasures! The beloved Randolph Street Market Festival is back with two days of curated, European-style vintage and antique shopping. Browse wares from hundreds of vendors, or grab a cocktail and bite to eat from local restaurants while tapping your toes to live music. 

Spin classes and weight lifting can wait for the winter. This summer, jump start your weekend with free cardio kickboxing, yoga, pilates and Zumba classes on Millennium Park’s Great Lawn and in Wrigley Square every Saturday from May through August.

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 Rhythem 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. 

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.

Immerse yourself in a new perspective on legendary artist Henri Matisse at this exciting new exhibition at The Art Institute of Chicago. Bedridden and unable to paint in the 1940s, Matisse turned to a new, more accessible medium: cut paper. Mining his memories of circuses, world travels, folktales and concerts in Parisian music halls, he produced a series of 20 maquettes that will be on display for the public to enjoy.

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. 

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.

Spanning two distinct periods of Alberto Aguilar’s career, “I just really want to tell you this one thing” explores the delicate themes of communication and translation. Rather than a static display, the exhibition serves as a collective offering by Aguilar and his collaborators for viewers seeking an active creative conversation. Mirroring Aguilar’s broader practice, this collection prioritizes the unique meaning that emerges only through exchange. 

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 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.

Following the tragic loss of his child in a confrontation with police, a grieving father is pressured by three strangers to take a cash settlement and disappear into a new life. He faces a devastating choice: accept the "hush money" and move on, or stay and be consumed by the ghosts of his past. The world premiere of this new work by Steppenwolf ensemble member Tarell Alvin McCraney is a lyrical, urgent exploration of grief and the corrosive power of the almighty dollar.

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.

To celebrate A Red Orchid Theatre’s 33rd season, join the Solidarity and Truth Summit—a gathering of the most “persecuted” and “misunderstood” people on earth. These self-identified Targeted Individuals believe they are victims of a vast, covert program of systematic surveillance and harassment by global powers. Over one whirlwind weekend in the woods, they will attempt to expose the Deep State, raise awareness for their plight and—despite their immense suffering—reclaim their humanity.

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.

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.

Thanks to a landmark donation from the family of Lee Kun-Hee, the late chairman of Samsung Group, Chicagoans will be able to view extraordinary Korean artworks once held in private collections. Spanning painting, ceramics and Buddhist sculpture, the exhibition includes 140 works that trace two millennia of artistic legacy—22 of which are officially designated National Treasures or Treasures by the Korean government.

Lifeline Theatre invites you to the greatest rock & roll show not on Earth! LOKI has arrived in Asgard, bringing chaos, comedy, and three (possibly) monstrous children in tow. As Loki tangles with Odin, Thor, and the mysterious Freya, secrets unravel and agendas collide. With the end of the world on the horizon, one question remains: In an “us vs. them” world, can we envision a new mythology?

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.

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.

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.

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.

DePaul Art Museum will be unfortunately closing this June, and they're going out with some of their finest curatorial work yet. Since the 1960s, Barbara Nessim has built a distinctive visual language that challenges traditional ideas about femininity and representation. One of the first women to gain prominence in the male-dominated world of commercial illustration, Nessim later became a pioneer of computer art in the 1980s. This exhibition—her first in Chicago—features paintings, drawings, digital works and a site-specific installation. It also highlights her famed sketchbooks, which the artist calls her “forever books,” a raw and unfiltered record of her creative process.

Experience Chicago through the eyes of artist Marvin Young at Intuit Art Museum’s latest exhibition. Since joining the Arts of Life studio in 2024, the lifelong South Sider has used vibrant mixed media to capture both imagined and remembered urban scenes. From large-scale portraits to detailed architectural landscapes, Young’s work brings the city to life with vintage walk-ups, classic cars and the energy of the streets. 

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. 

This sweeping exhibition examines the long legacy of dispossession across the Americas, tracking colonial conquest up to the present day. Bringing together more than 40 works by 36 artists from across Latin America, the show explores how land, culture and identity have been shaped by centuries of extraction and resistance. Organized around themes of Territory, Body and Cultural Heritage, the exhibition spans photography, sculpture, installation and video.