September in Chicago brings major music and arts festivals, world-class theater, food events, museum exhibitions, author talks, comedy, and great opportunities to take advantage of warm weather while we still can. From biking a car-free Lake Shore Drive and hearing jazz in Millennium Park to seeing performances by Kyle MacLachlan, Patti Smith, Ilana Glazer, Eric Clapton, and some of the biggest names in punk and alternative music, these are the 30 best things to do in Chicago and the suburbs this September 2026.
Tag us in your September adventures on Instagram @makeitbetter_foundation — we’d love to see where the month takes you.
Sept. 3 – 6: Chicago Jazz Festival
One of Chicago’s signature free cultural events returns over Labor Day weekend, with performances at the Chicago Cultural Center and Millennium Park. This year’s lineup includes five-time Grammy winner Dee Dee Bridgewater with pianist Bill Charlap, Grammy-winning pianist and producer Robert Glasper, M.E.B. (Miles Electric Band) celebrating the Miles Davis Centennial, and Grammy-winning saxophonist and clarinetist Paquito D’Rivera. Admission is free.
Sept. 4 – 7: ARC Music Festival
Chicago’s house music legacy takes center stage at ARC Music Festival for four days at Union Park. The lineup spans house, techno, and electronic music, with artists including Anyma, Michael Bibi, Sara Landry, Underworld, Chase & Status, The Blessed Madonna B2B Lil’ Louis, Carl Craig, Moodymann, Stacey Pullen, Derrick Carter, DJ Heather, and Green Velvet. Get single or multi-day passes here.
Sept. 5 – Oct. 4: ‘The Attic: Things I’ve Seen While Lying on My Back’ at Goodman Theatre
Goodman Theatre, a Make It Better Foundation 2026 Philanthropy Award Winner, opens its 101st season with The Attic: Things I’ve Seen While Lying on My Back, a new theatrical memoir from Tony Award-nominated circus artist Shana Carroll. A co-founder of Montreal’s internationally renowned collective The 7 Fingers, Carroll draws on her own life and career as a trapeze artist for a production combining contemporary circus, dance, theater, and aerial performance. An international company of performers brings her memories to life in a deeply personal exploration of fear, courage, and the experiences that shape us.
Sept. 6: Bike the Drive
For one morning each year, cars disappear from DuSable Lake Shore Drive and thousands of cyclists take their place. The 25th annual Bike the Drive offers riders the rare opportunity to bike the iconic roadway with uninterrupted views of Lake Michigan and the Chicago skyline before gathering for a post-ride festival in Grant Park. The event benefits the Active Transportation Alliance, which advocates for safer walking, biking, and public transit throughout the Chicago area. Get info and register.
Sept. 7: Danny Elfman at Aragon Ballroom
Four-time Oscar-nominated composer and Oingo Boingo founder Danny Elfman kicks off his North American fall tour at Chicago’s Aragon Ballroom. One of the most distinctive composers in film and television, Elfman has scored more than 100 movies and spent more than 35 years collaborating with Tim Burton, creating the music for Batman, Beetlejuice, Edward Scissorhands, The Nightmare Before Christmas and many more. Beyond his work with Burton, his extensive credits include Spider-Man, Men in Black and the unmistakable theme to The Simpsons. The tour supports a forthcoming new album and features an all-star band whose members have played with Nine Inch Nails, Guns N’ Roses, Foo Fighters, A Perfect Circle and Dethklok. Get tickets.
Sept. 10: Harold Washington Literary Award Dinner Honoring Patti Smith
Musician, poet, and author Patti Smith will receive the 2026 Harold Washington Literary Award at the Union League Club of Chicago. Presented annually since 1989, the award recognizes authors whose work engages with contemporary life; past recipients include Isabel Wilkerson, Ta-Nehisi Coates, Rita Dove, Natasha Trethewey, and Scott Turow. The ticketed fundraiser serves as the official kickoff to Printers Row Lit Fest.
Sept. 10 – Oct. 4: The Humanities at Victory Gardens Theater
Victory Gardens Theater continues its long tradition of bringing new stories to the stage with the world premiere of The Humanities, a contemporary drama by acclaimed playwright and Northwestern University professor Zayd Ayers Dohrn. Directed by five-time Jeff Award winner Eddie Torres and featuring an all-Chicago cast, the play follows the fallout after a controversial speaker is invited to lecture at an elite American university, exploring questions of identity, race, campus protests, political violence, and the forces dividing the country. Performances begin Sept. 10, with the official opening Sept. 13. Tickets on sale now. Get 25% off all Adult and Senior tickets for performances on September 10, 11, and 12 with promo code PREVIEW.
Sept. 11 – 13: Evanston Folk Festival
The Evanston Folk Festival returns to the lakefront with two days of music at Dawes Park, headlined by Indigo Girls and Trampled by Turtles, with Josh Ritter, Sierra Hull, Valerie June, Mdou Moctar, Margaret Glaspy, Kathleen Edwards, and more. The weekend is bookended by two special shows at Cahn Auditorium: Punch Brothers kick off the festival Sept. 11, and Saturday Night Live alum Fred Armisen brings his Comedy for Musicians but Everyone Is Welcome show Sept. 13. The festival also features artist interviews, local food and drink vendors, and other programming.
Sept. 11 – Oct. 18: Play On! at Chicago Shakespeare Theater
Shakespeare gets the jazz treatment when Play On! opens Chicago Shakespeare Theater’s 40th Anniversary Season. Inspired by Twelfth Night and set to Duke Ellington classics including “It Don’t Mean a Thing” and “Don’t Get Around Much Anymore,” the three-time Tony-nominated jazz musical returns with original director Sheldon Epps and a newly updated book by Cheryl L. West. Broadway veterans lead the cast, including Hailee Kaleem Wright (Moulin Rouge!, SIX), Krystal Joy Brown (Merrily We Roll Along, Hamilton), and Edred Utomi, who recently played Alexander Hamilton in Hamilton on Broadway. A special Black Creativity Night on Sept. 22 will celebrate Black excellence, brilliance, and joy across music, dance, and art with a pre-show gathering featuring cocktails, music, and an artistic conversation. Get tickets.
Sept. 12 – 13: Printers Row Lit Fest
The Midwest’s largest free outdoor literary festival returns for its 41st year, bringing free literary programming in the historic South Loop neighborhood. Authors, booksellers, publishers, and literary organizations gather for conversations, readings, panels, book signings, and more. Highlights this year include Newbery Medalist Christopher Paul Curtis, New York Times bestselling author Dolen Perkins-Valdez, Pulitzer Prize winner Heather Ann Thompson, playwright and author Zayd Ayers Dohrn, and Veep actor and comedian David Pasquesi. Events are free, with seating for programs available on a first-come, first-served basis.
Sept. 12 – 13: El Grito Chicago
El Grito Chicago returns to Grant Park after last year’s event was cancelled in response to ICE operations in Chicago. The annual celebration of Mexican Independence Day brings two days of Mexican music, dance, food, art, family activities, and more. The weekend culminates Sunday evening with the El Grito Civic Ceremony led by the Consul General of Mexico in Chicago, commemorating the historic call for Mexican independence. Get tickets online.
Sept. 14 – 20: Chicago Exhibition Week
More than 50 galleries and creative spaces across the city participate in the fourth annual Chicago Exhibition Week, spotlighting Chicago’s visual arts scene through exhibition openings, artist talks, gallery tours, performances, receptions, and other special events. Participating institutions range from galleries and independent art spaces to Make It Better Foundation 2026 Philanthropy Award Winner Art Institute of Chicago, The Arts Club of Chicago, Graham Foundation, and Studio Gang.
Sept. 15: Hubbard Street Night at Wrigley Field
Hubbard Street Dance Chicago celebrates its 49th season with its second annual Hubbard Street Night at Wrigley Field as the Chicago Cubs take on the Atlanta Braves. The evening brings Hubbard Street supporters together for a night of baseball while supporting the contemporary dance company’s artists and education programs. Hubbard Street is a 2026 Make It Better Foundation Philanthropy Award winner, and qualifying gifts made by Aug. 31 will be matched dollar-for-dollar by the Foundation, up to $10,000. Get tickets.
Sept. 16: Tisha Campbell: The A Word
Actress Tisha Campbell, best known for Martin, My Wife and Kids, and the House Party films, comes to the South Shore Cultural Center for a conversation and signing tied to her new memoir, The A Word: A Mother’s Journey Through Autism and Love. Campbell will discuss motherhood, family, advocacy, autism, and her decades-long career in television and film.
Sept. 17 – Nov. 1: Topdog/Underdog at Steppenwolf Theatre
Pulitzer Prize winner Suzan-Lori Parks’ acclaimed Topdog/Underdog opens Steppenwolf Theatre Company’s new season with Tony Award-winning director Kenny Leon at the helm. Steppenwolf ensemble members Glenn Davis and Namir Smallwood star as brothers Lincoln and Booth in the darkly funny examination of sibling rivalry, resentment, race, and survival.
Sept. 17: Liz Phair and Sleater-Kinney at Salt Shed
Chicago-born singer-songwriter Liz Phair shares the stage with influential rock band Sleater-Kinney at one of the city’s best music venues, The Salt Shed Outdoors, as part of their Flannel and The Fury 2026 tour. Phair was part of Chicago’s early-’90s indie-rock scene, and her landmark 1993 debut Exile in Guyville took aim at the male-dominated culture she encountered within it.
Sept. 17 – 27: The Joffrey Ballet’s Liliom
The Joffrey Ballet launches its new season with a Chicago premiere that brings ballet, theater, and live jazz together on the Lyric Opera House stage. Choreographer John Neumeier reimagines Ferenc Molnár’s 1909 play Liliom, which also inspired Rodgers and Hammerstein’s Carousel, as the story of a troubled carnival barker given a final chance at redemption. The Joffrey becomes the first U.S. ballet company to stage the work, accompanied by the Lyric Opera Orchestra and a 16-piece jazz ensemble performing Michel Legrand’s score live onstage.
Sept. 17: Irish Fellowship Club 125th Anniversary Celebration
The Irish Fellowship Club of Chicago marks 125 years of Irish-American civic, cultural, and philanthropic history with a celebration at Theater on the Lake featuring former Irish Taoiseach Enda Kenny. Founded in 1901, the organization has raised millions of dollars for scholarships, grants, and Irish cultural organizations and has longstanding ties to prominent political leaders in both the U.S. and Ireland, including John F. Kennedy and former Chicago mayors Richard J. and Richard M. Daley, both past Club presidents. The evening also features the Shannon Rovers, themselves celebrating 100 years, along with Tom Gleason, the Chancey Brothers, Jimmy Moore, and fireworks over Lake Michigan.
Sept. 17 – 27: Reeling: The Chicago LGBTQ+ International Film Festival
The second-longest-running LGBTQ+ film festival in the world returns for its 44th edition with 11 days of queer cinema, including more than 40 feature films and 50 shorts from around the world. Reeling opens Sept. 17 at the Music Box Theatre with Cannes winner La Bola Negra from directors Javier Calvo and Javier Ambrossi, starring Penélope Cruz, Glenn Close, Miguel Bernardeau, Lola Dueñas, and Julio Torres. Founded in 1981, the Chicago Filmmakers festival showcases LGBTQ+ narrative features, documentaries, shorts, and experimental films at theaters across Chicago.
Sept. 18 – 20: Riot Fest
One of the largest independently run music festivals in the country, Riot Fest returns to Douglass Park with more than 100 artists over three days, including Twenty One Pilots, Iggy Pop, Tool, Morrissey, Nas, Pierce the Veil, Alanis Morissette, Elvis Costello & The Imposters, and Patti Smith and Her Band. Beyond the music, Riot Fest supports the surrounding North Lawndale and Little Village communities year-round through its Beyond the Fest program, with initiatives including local hiring, paid internships and scholarships, small-business support, free tickets for neighborhood residents, and investments in Douglass Park.
Sept. 19 – 22: Chicagohenge
One of Chicago’s most photogenic natural phenomena returns around the fall equinox, when the rising and setting sun aligns with the city’s street grid, creating dramatic views framed by downtown buildings. Chicago’s streets run almost perfectly east to west, allowing the sun to line up with them around the spring and fall equinoxes. This year’s fall Chicagohenge is visible around sunrise and sunset Sept. 19–22. Learn more about Chicagohenge and when and where to see it from the Adler Planetarium.
Sept. 20: Chicago River Swim
Five hundred swimmers take to the Chicago River for one- and two-mile courses through the heart of downtown. The event begins and ends along the Chicago Riverwalk, sending swimmers beneath historic bridges and through a stretch of the city that would have been nearly unimaginable as an open-water course decades ago. The Chicago River Swim is a program of A Long Swim, which raises funds in support of ALS research.
Sept. 19 – 20: Chicago Live! at Navy Pier
More than 100 performing arts organizations and artists take over five stages throughout Navy Pier during Chicago Live!, the Midwest’s largest free performing arts festival. This year’s lineup includes Anthony Rapp, Nico Segal, The Second City, Chicago Philharmonic, Hubbard Street Dance Chicago, Joffrey, Giordano Dance Chicago, Deeply Rooted Dance Theatre, and RuPaul’s Drag Race stars Denali and Utica, alongside dozens of additional Chicago performers and companies.
Sept. 27: 2026 Illinois Rock & Roll Hall of Fame Induction Ceremony
The Illinois Rock & Roll Hall of Fame brings its annual induction ceremony to Chicago for the first time, honoring a 2026 class that spans rock, blues, soul, jazz, and radio. This year’s inductees include Survivor, Koko Taylor, Curtis Mayfield, Kevin Cronin, The American Breed, and longtime WXRT personality Terri Hemmert, with live performances by Plain White T’s, The Flock, Hot Mix 5, and a reunion of The Boyzz. WGN Radio’s Bob Sirott hosts the celebration at the Harris Theater, a Make It Better Foundation 2026 Philanthropy Award Winner. The induction ceremony is the largest annual fundraiser for the Joliet-based Illinois Rock & Roll Museum on Route 66. Get tickets.
Sept. 30: Kyle MacLachlan: Fictional Selves
From Twin Peaks and Blue Velvet to Dune, Portlandia, and Sex and the City, Kyle MacLachlan has spent more than four decades creating memorable characters on film and television. The actor comes to the Athenaeum Center for Thought & Culture for a Chicago Humanities conversation tied to his new memoir, Fictional Selves, reflecting on his career, acting, and his longtime creative partnership with filmmaker David Lynch.
Ongoing
Through April 11: Pokémon Fossil Museum
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.
Through Oct. 25: Theater of the Mind
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.
Learn more about Theater of the Mind in our interview with David Byrne.
Through Sept. 13: Ink & Outrage: 18th-Century Satirical Prints in London & Dublin
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.
Learn more by reading our interview with exhibition curator Silvia Beltrametti.
Through Oct. 10: Minecraft Experience: Villager Rescue
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.
