Navy Pier new year's eve fireworks
Photograph: Courtesy Navy Pier | Navy Pier's fireworks show
Photograph: Courtesy Navy Pier

The best things to do in Chicago this weekend

Find the best things to do in Chicago this weekend with our guide to concerts, exhibitions, festivals and more.

Shannon Shreibak
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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.

Last updated May 18, 2026: Hunting for the best weekend plans in Chicago? From dedicated planners to last-minute adventurers, we’ve got you covered. This week’s highlights include Chicago's annual Memorial Day Parade, the return of Navy Pier's fireworks show and a whole slew of music festivals, with programming ranging from reggaeton to indie. We’ve also rounded up some of the best free events in Chicago, too, for good measure. Scroll down to discover the best events across the city!

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The best things to do in Chicago this weekend

  • Things to do
  • Loop
  • Recommended
Memorial Day Parade
Memorial Day Parade

After a wreath is laid at the eternal flame in Daley Plaza at 11am in remembrance of those who died serving in the U.S. armed services, Chicago's annual Memorial Day Parade marches down State Street (from Lake to Van Buren streets) beginning at noon. Crowds line the street waving flags and paying their respects as part of this Chicago tradition, which dates all the way back to 1870.

  • 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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  • 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
  • Festivals
  • North Center

Ravenswood Corridor neighbors Dovetail and Begyle return this year for their annual Memorial Day weekend street fest on Malt Row, where attendees can sip beer from both breweries and grab bites from Beard and Belly, Donerman, Happy Lobster and more. Catch live music and consider tossing in a donation, which will benefit neighborhood food pantry The Friendship Center. 

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  • Music
  • Music festivals
  • Millennium Park
  • Recommended

Started in 2022, this two-day extravaganza returns to Grant Park over Memorial Day weekend. Taking place on a single stage in Grant Park's Hutchinson Field, Sueños will feature headlining sets from Kali Uchis, Fuerza Regida, J Balvin and more. In addition to two days of music, you can try food from some of Chicago's best Latin restaurants, a host of art installations and experiential activations, and a Ferris wheel in the park that you can ride between (or during) sets. 

  • Things to do
  • Festivals
  • Lake View

Love cover bands? Head to Lakeview (right by the Belmont Red Line station) for three days of music, featuring an eclectic lineup of local acts. Kill time between sets by shopping for wares from local artisans and makers. Plus, you'll find beer, wine and plenty of neighborhood vendors to browse while you hang out on the street.

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  • Sports and fitness
  • Running
  • Museum Campus

You may never get to take enter the gridiron with the Chicago Bears, but you can take off on a 10-mile run from the team's home turf. The Soldier Field 10-Mile begins and ends at the stadium, sending participants on a scenic jaunt down the Lakefront Trail. Everyone who registers receives a Chicago jersey tee and a stadium blanket, and finishers get a medal memorializing their achievement. Stick around afterwards for a beer at the post-race tailgate.

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  • Music
  • Music festivals
  • River West/West Town

Returning for its second year, The Salt Shed’s flagship music festival promises a weekend of left-of-center sounds and alternative icons. This year’s lineup features Aussie singer-songwriter Courtney Barnett, electronic luminary Toro y Moi, and noise-pop pioneers The Jesus and Mary Chain. Beyond the music, attendees can explore the quirky Oddball Market and a studio sale curated by the Chicago nonprofit Arts of Life.

  • Sports and fitness
  • Millennium Park

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.

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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 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

  • 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
  • Exhibitions
  • Grant Park
  • 4 out of 5 stars
  • Recommended

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.

  • 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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  • 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
  • Loop

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. 

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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 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
  • 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.

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  • Drama
  • Lincoln Park

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.

  • 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.

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  • Drama
  • River West/West Town

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.

  • 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
  • Exhibitions
  • Grant Park

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.

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  • Musicals
  • Rogers Park

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?

  • 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.

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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.

  • 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
  • Exhibitions
  • Sheffield & DePaul

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.

  • Art
  • River West/West Town

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. 

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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. 

  • Things to do
  • Exhibitions
  • Lincoln Park

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.

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