August is one of the busiest months of the year in Chicago, with blockbuster music festivals, can’t-miss concerts, world-class theater, neighborhood celebrations, major sporting events, and cultural experiences happening across the city and suburbs. Whether you’re catching Lollapalooza in Grant Park, spending an evening under the stars at Ravinia, exploring a new museum exhibition, or discovering a local tradition, these are the 31 best things to do in Chicago and the suburbs this August 2026.
Tag us in your summer adventures on Instagram @makeitbetter_foundation — we’d love to see where the month takes you.
August begins with the massive four-day music festival already underway in Chicago’s Grant Park. This year’s lineup includes headliners Charli XCX, Tate McRae, Lorde, Olivia Dean, hometown favorites The Smashing Pumpkins, returning to the Lollapalooza stage for the first time since 1994. A huge selection of aftershows also gives fans a chance to experience more intimate performances by their favorite artists. Tickets are nearly sold out but at time of writing some tickets types remain along with verified resale tickets.
Can’t make it in person? Livestream the festival at home on Disney+ and Hulu starting at 4 p.m. ET / 3 p.m. CT every day from July 30 through August 2. Get the full Lollapalooza livestream schedule here.
Celebrate Lollapalooza from the water aboard Tall Ship Windy at Navy Pier. For one week only, Chicago’s official tall ship is hosting special YUNGBLUD-themed sailings in honor of the Grammy-winning British musician’s Friday night festival performance.
The limited-time experience adds custom black sails inspired by YUNGBLUD to the iconic ship, plus themed drinks, exclusive giveaways while supplies last, and panoramic views of the Chicago skyline from Lake Michigan. Whether you’re heading to Grant Park for the show or looking for another way to soak up the energy of Lollapalooza weekend, these special sailings offer a memorable perspective of the city.
The FIFA World Cup may be over, but soccer/football fever continues when Liverpool FC and Leeds United bring Premier League action to Soldier Field. The preseason match offers fans a chance to see top-flight English football and some of the sport’s international stars as both clubs prepare for the 2026-27 Premier League season. Before kickoff, fans can also visit the free Fan Zone outside the stadium, featuring soccer-themed activities and entertainment. Get tickets.
What can 18th-century political cartoons teach us about modern satire? Inspired by the exhibition Ink & Outrage: 18th-Century Satirical Prints in London & Dublin at Driehaus Museum, a 2026 Make It Better Foundation Philanthropy Award winner, this panel brings together The Onion Head Writer Mike Gillis, The Onion Staff Writer Rob Knoll, and The New Yorker caricaturist Tom Bachtell to explore how satire has evolved and why it continues to shape public discourse. Moderated by University of Notre Dame historian Colin Barr, the discussion connects historical prints with today’s media landscape.
Tony Award winner Laura Benanti brings her acclaimed one-woman show Nobody Cares to Chicago’s Steppenwolf Theatre for the first stop on its national tour following runs at the Edinburgh Fringe, Off-Broadway, and London’s Underbelly Soho. A New York Times Critic’s Pick, the comedy blends candid storytelling, original songs, and Benanti’s signature wit as she reflects on motherhood, people pleasing, and getting older. Best known for her Broadway career and television roles in Younger, Nashville, The Gilded Age, and Supergirl, Benanti offers an intimate evening that is equal parts stand-up, cabaret, and confessional. Get tickets.
One of the country’s largest and longest-running LGBTQ+ street festivals returns to Chicago with three days of live music, comedy, drag, and nightlife in the heart of the city’s historic Northalsted neighborhood. This year’s lineup features Grammy winner Keri Hilson, Grammy winner Daya, RuPaul’s Drag Race winner Myki Meeks, comedian Jessica Kirson, singer-songwriter Dawn Richard, and entertainer Frankie Grande, along with dozens of additional performers across four stages. Beyond the entertainment, visitors can browse more than 300 vendors, food and drink booths, and community organizations at a festival that draws attendees from across the country and around the world each summer.
Photo by Frazer Harrison/Getty Images for Amazon Music
Rock & Roll Hall of Famers Foo Fighters bring their Take Cover Tour to Soldier Field this August. Led by Dave Grohl, the band continues the 2026 world tour with a Chicago stop that features Queens of the Stone Age and Mannequin Pussy as special guests. The concert marks one of the summer’s marquee stadium shows and one of the biggest rock events on Chicago’s 2026 concert calendar. Get tickets.
As Bad Bunny’s influence continues to spark national conversations about music, identity, and Puerto Rico, the Museum of Contemporary Art Chicago hosts a discussion with his collaborators and leading scholars of his work. The program features award-winning filmmaker Kacho López Mari, director of several of Bad Bunny’s most acclaimed music videos, alongside authors Petra Rivera-Rideau and Vanessa Díaz, whose new book, P FKN R: How Bad Bunny Became the Global Voice of Puerto Rican Resistance, explores the artist’s impact on culture and activism. A book signing follows the program. Get tickets.
For nearly a century, the Bud Billiken Parade has marked the end of summer and the start of a new school year, making it one of Chicago’s longest-running and most significant community traditions. The parade fills Bronzeville with marching bands, floats, dance teams, youth organizations, and community groups before culminating in the Bud Billiken Back-to-School Festival in Washington Park. Over the decades, the event has welcomed notable participants including Oprah Winfrey, President Harry S. Truman, Duke Ellington, and Barack Obama before he became president, underscoring its enduring place in Chicago history.
Chicago’s own Chance the Rapper makes his Ravinia debut Aug. 8. The performance follows the release of STAR LINE, the Grammy-winning artist’s first album in six years. Fellow Chicago rap pioneer Twista joins the evening as a special guest, adding another hometown connection to one of Ravinia’s most anticipated concerts of the season. Fellow Chicago rap pioneer Twista joins the evening as a special guest, bringing together two influential eras of Chicago hip-hop. Get tickets.
Tony, Emmy, and Grammy Award winner Hugh Jackman makes his Ravinia debut on Aug. 9 alongside Chicago Philharmonic, a 2026 Make It Better Foundation Philanthropy Award winner, for an evening celebrating his acclaimed career on stage and screen. Best known worldwide as Wolverine in the X-Men franchise and for starring roles in The Greatest Showman and Broadway productions including The Music Man and The Boy from Oz, Jackman will perform songs spanning musical theater and film in a concert showcasing the acting, singing, and dancing talents that have made him one of today’s most versatile entertainers.
Tori Amos brings her In Times of Dragons tour to the Auditorium Theatre Aug. 14. The Grammy-nominated singer-songwriter has spent more than three decades earning acclaim for her genre-defying music, virtuosic piano performances, and deeply personal songwriting. Her latest album, In Times of Dragons, is “a metaphorical story about the fight for Democracy over Tyranny.” Get tickets.
More than a million spectators are expected along Chicago’s lakefront as the Chicago Air and Water Show returns for another weekend of military and civilian flight demonstrations. The nation’s largest free air and water show will be headlined this year by the U.S. Air Force Thunderbirds, whose six F-16 Fighting Falcons take over from the U.S. Navy Blue Angels, which are absent because of a scheduling conflict. The lineup also includes the U.S. Army Golden Knights, U.S. Navy Leap Frogs, and civilian aerobatic performers. If you’d rather avoid the largest crowds, the Aug. 14 rehearsal offers a chance to catch many of the same practice flights before the weekend begins.
Grammy-winning rock band Alabama Shakes comes to Ravinia with founding members Brittany Howard, Heath Fogg, and Zac Cockrell. The group’s debut album, Boys & Girls, earned multiple Grammy nominations and was followed by performances at the White House and Saturday Night Live. Chicago-born singer-songwriter Liam Kazar opens the evening. Get tickets.
The world’s largest urban triathlon returns to Chicago as more than 8,000 athletes compete in Supertri Chicago, the largest triathlon in North America. Participants tackle a swim in Monroe Harbor, a bike course through downtown, and a run past landmarks including Buckingham Fountain and Soldier Field, while spectators line the lakefront to watch the action. Race options range from a kids event to SuperSprint, Sprint, Olympic, and the endurance-focused Enduro challenge, with the weekend also raising funds for pediatric cancer research at Lurie Children’s Hospital of Chicago. Register.
More than a dozen of Chicago’s leading dance companies, including Make It Better Foundation Philanthropy Award Winner The Joffrey Ballet, Hubbard Street Dance Chicago, Giordano Dance Chicago, Trinity Irish Dance Company, Deeply Rooted Dance Theater, and Ensemble Español Spanish Dance Theater, come together for the 35th anniversary of Dance for Life, one of the city’s signature cultural fundraisers. Held at the historic Auditorium Theatre, the annual performance celebrates Chicago’s internationally respected dance community while raising money for the Chicago Dance Health Fund, which supports the health and wellness of dance professionals. The milestone event includes a world premiere finale by choreographer Randy Duncan, whose credits include the film Save the Last Dance starring Julia Stiles and Yale’s production of The Winter’s Tale starring Oscar winner Lupita Nyong’o, while honoring the event’s origins as a response to the HIV/AIDS crisis that profoundly impacted the dance community. Get tickets.
The Chicago Black Dance Legacy Project returns to the Harris Theater, a 2026 Make It Better Foundation Philanthropy Award Winner, for a one-night-only performance, Dancing the Archive: Embodied Histories, Collective Power. The program brings together 10 Black dance companies representing styles from ballet and tap to African and contemporary dance, including Deeply Rooted Dance Theater, Muntu Dance Theatre, M.A.D.D. Rhythms, and Joel Hall Dancers & Center. Along with repertory works, the evening features world premieres created to honor 10 Chicago Legacy Bearers, celebrating the artists, educators, activists, and civic leaders whose contributions have helped shape the city’s cultural landscape. Get tickets.
The Taste of Greektown festival returns for its 36th year with the city’s largest celebration of Hellenic cuisine and culture, along Halsted Street from Adams to Van Buren. The neighborhood’s acclaimed Greek restaurants are the stars of the show, but Taste of Greektown also offers plenty of live music and entertainment, Greek dancing, unique shopping and retail, and family activities. For more information, visit GreektownChicago.org.
Celebrate the 26th anniversary of the PAWS Chicago 5K Walk/Run for Their Lives, Chicago’s largest dog-friendly charity event. Thousands of participants and their four-legged companions gather at Montrose Harbor for a morning of walking, running, agility courses, entertainment, giveaways, and fundraising to support homeless pets. Whether you’re racing, strolling, or cheering from the sidelines, the event offers one of the city’s biggest celebrations for animal lovers while benefiting the lifesaving work of PAWS Chicago.
If you’ve been meaning to see Iceboy! or The Completely Untrue Story of How Eugene O’Neill Came to Write “The Iceman Cometh,” now is the time. The world premiere musical recently became Goodman Theatre’s best-selling production of all time, drawing more than 53,000 audience members and surpassing previous attendance records held by War Paint and The Who’s Tommy. Starring Megan Mullally, Nick Offerman, and Grey Henson, the production has been extended for a third and final time through Aug. 16, marking one of the final highlights of the Goodman’s Centennial Season. Get tickets at Goodman Theatre, a Make It Better Foundation 2026 Philanthropy Award Winner.
For more than 90 years, the Grant Park Music Festival has brought free performances by the world-class Grant Park Orchestra and Grant Park Chorus to audiences across Chicago. Most concerts take place at Millennium Park’s Jay Pritzker Pavilion, where visitors can spread out on the Great Lawn with a blanket or picnic and enjoy live classical music against the backdrop of the Chicago skyline, while additional performances are held at neighborhood venues throughout the city. Free lawn seating is available on a first-come, first-served basis, with reserved seating also offered for select performances. The final weeks of the 2026 season, which concludes Aug. 15, include Gershwin’s An American in Paris, Mozart’s Requiem, Dvořák’s New World Symphony, Beethoven’s Symphony No. 9, and a performance by acclaimed pianist Garrick Ohlsson.
Making its North American debut at the Field Museum, Pokémon Fossil Museum pairs beloved Pokémon with real-world paleontology in an exhibition that encourages visitors to see both through a new lens. Interactive displays compare fossil-inspired Pokémon such as Tyrantrum and Archeops with actual prehistoric specimens, including the museum’s iconic SUE the T. rex, highlighting the connections between science, discovery, and imagination. Developed in collaboration with Japan’s National Museum of Nature and Science and The Pokémon Company, the exhibition runs through April 11, 2027 and is expected to be one of Chicago’s most in-demand museum experiences of the year. Tickets are limited and subject to availability.
Theater of the Mind, co-created by Academy, Grammy, and Tony Award–winning artist David Byrne and writer and investor Mala Gaonkar and directed by Andrew Scoville, is an immersive theatrical experience at Goodman Theatre that unfolds as a guided journey through a series of sensory environments. In groups of 16, audiences move through interconnected rooms over 75 minutes, engaging sight, sound, taste, and touch in experiences inspired by neuroscience that challenge how we perceive and construct reality. The run has been extended through Sept 27.
Political cartoons and biting social commentary aren’t just products of the internet age. Ink & Outrage: 18th-Century Satirical Prints in London & Dublin explores the golden age of caricature through works by James Gillray, Thomas Rowlandson, Isaac Cruikshank, and other influential artists who used humor and exaggeration to critique politics, power, and society. The exhibition at Driehaus Museum, a 2026 Make It Better Foundation Philanthropy Award winner, also examines how Dublin publishers adapted and reimagined London’s satirical prints, revealing how ideas, art, and dissent circulated across Britain and Ireland on the eve of revolution and reform. Get tickets.
Making its Midwest debut at EXP Rosemont, Minecraft Experience: Villager Rescue brings the video game into the real world in an escape-room-esque interactive attraction through seven Minecraft-inspired environments on a mission to save a village from a zombie attack. Using handheld interactive devices, participants collaborate to complete challenges, gather resources, and encounter iconic friends and foes from the game. Designed for players and non-players (a great crash course for unfamiliar parents), the limited-run experience combines immersive environments with the creativity and problem-solving that have made Minecraft the best-selling video game of all time. Learn more and get tickets.
Celebrating the 100th anniversary of Route 66, this year’s Summer Screenings series highlights classic road movies from around the world. Cinema/Chicago’s annual free film program spotlights a different country’s national cinema each week throughout the summer. Visit Cinema/Chicago — a 2026 Make It Better Foundation Philanthropy Award Winner — online for the film lineup and free ticket information.
Brookfield Zoo Chicago’s Dinos! exhibition features life-size dinosaur models, interactive climbing areas, fossil-themed activities, and educational exhibits throughout the zoo. Included with general admission, the seasonal experience offers hands-on opportunities for families while exploring the zoo grounds. Details online at Brookfield Zoo.
Willem de Kooning Drawing is the first major exhibition to examine the artist’s expansive drawing practice, and the first solo presentation of his work at the Art Institute since 1969. Drawing features more than 200 works, many of which have never been shown together before. Get tickets.
The MCA’s annual Tuesdays on the Terrace concert series continues this month with free performances on the Anne and John Kern Terrace Garden, featuring artists spanning pop, soul, R&B, jazz, and more. Food and beverages are available for purchase, and guests are invited to bring their own food and non-alcoholic beverages. Entry to Tuesdays on the Terrace is complimentary, but limited. Tickets are released every Wednesday at noon for the following week’s performance; MCA Members get priority access to tickets. Get tickets and learn more online at Tuesdays on the Terrace.
The Griffin Museum of Science and Industry’s Crafting Characters: The Costumes of Paul Tazewell showcases the work of the Academy Award-winning costume designer behind Wicked, Hamilton, West Side Story, and more. Original costumes, sketches, photographs, and behind-the-scenes materials offer a closer look at Tazewell’s creative process. The exhibition remains on view through Sept. 7.
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