Tyler the Creator, Lalah Hathaway, The Chosen Few Picnic, SZA, Lenny Kravitz and many others will dazzle the city this summer (Photo Credits: Facebook)
If you’re visiting us from another state, city or planet, just know that this isn’t your normal summer. This is Chicago summer.
So, rooftop by rooftop, block by block, we glow brighter than anywhere else on Earth. Nothing, and I mean nothing, tops #SummerTimeChi, not even New York—and I’m from there.
Our summers are culture, where the whole city is outside. And Black Chicago sets the tone.
Here’s your essential guide to #SummerTimeChi. Plan accordingly — and bring vibes.
Plenty.
All Summer Long
Free Outdoor Jazz Performances at Harper Court: Presented by the University of Chicago, this summer series features top local jazz talent under the stars in Hyde Park. All performances take place at 5235 S. Harper Court.
- June 6: Jeremiah Collier & The Re-Up Band
- July 11: Bethany Pickens
- August 8: Dee Alexander
- September 5: Tim Gant Project
Jazzin’ at the Shedd: Aquatic ambiance meets jazz every Wednesday night through August 27. A can’t miss for date nights.
Maxwell Street Market – May 11: Historic open-air market returns every second Sunday through October with food, art, music and culture.
Millennium Park Summer Music Series – June 26–Aug. 7: Free concerts every Thursday. Diverse lineups, iconic backdrops, and community vibes. The outdoor beauty of this venue alone, is something to behold.
Millennium Park Summer Workouts – May 17–Aug. 30: Free Saturday morning yoga, Zumba, and fitness classes in Millennium Park. Start your weekend with sweat and sunshine.
Pier 31 Restaurant: In the summer, this 31st Street Beach staple is like Steph Curry in Finals: it never misses. Soul, House, Hip-hop, Reggae, the DJs go to town.
Ravinia 2025: The summer lineup is nuts and it features more than 100 concerts and 40 artist debuts. Don’t miss performances by artists like Cynthia Erivo, Lenny Kravitz, Janelle Monáe, Morgan Freeman (Yes, that Morgan Freeman), and Earth, Wind & Fire, plus the 89th residency of the Chicago Symphony Orchestra with Ravinia Chief Conductor Marin Alsop.
Returning favorites include John Legend, Al Green, The Roots, Diana Krall, and Chicago, while Nas, Ray LaMontagne, King Gizzard & The Lizard Wizard are all making their Ravinia Festival debuts.
South Loop Farmers Market: Twice-weekly shopping with flavor and flair in the heart of the city.
Summer Jam 2025 at the Country Club Hills Amphitheater: Few venues match the charm of the CCH Amphitheater. This year’s lineup is stacked with stars including Lalah Hathaway, Robert Glasper & Avery Sunshine, Kem, Jeffrey Osborne, Sheila E., Dru Hill, 112, Shalamar, Terisa Griffin, Boney James, Jon B, and a comedy night with J. Anthony Brown, Sheryl Underwood, and more.
May-June
Millennium Park Summer Workouts – May 17–Aug. 30: Free Saturday morning yoga, Zumba, and fitness classes in Millennium Park. Start your weekend with sweat and sunshine.
Shakin’ the Mess Outta Misery – May 19–June 15 Pegasus Theatre revival exploring womanhood, memory, and community in 1960s Georgia. Held at Chicago Dramatists.
Memorial Day Wreath Laying Ceremony & Parade – May 24: Annual downtown tribute to U.S. military service members. Black veterans and community groups often lead the way.
The Weeknd: After Hours Til Dawn Tour – May 30: Stadium show with Playboi Carti and Mike Dean featuring tracks from The Weeknd’s latest trilogy and classic hits.
Invisible to Whom? at UChicago Regenstein Library – Through June 30: Photo exhibit of Robert A. Sengstacke’s iconic images reimagining Black visibility.
Tina – The Tina Turner Musical – June 3–8: Experience the inspiring life story and legendary music of Tina Turner at the Cadillac Palace Theatre. Runtime: 2 hours and 55 minutes with intermission. Recommended for ages 14 and up.
Grand National Tour: Kendrick Lamar and SZA – June 6: Kendrick and SZA take over Soldier Field for an epic stop on their Grand National Tour. Expect massive energy, unmatched artistry, and a night of pure lyrical power.
That’s What Friends Are For: Gladys, Dionne and Patti – June 7–July 27: Black Ensemble Theater stages a musical celebration of sisterhood and soul, honoring the legendary voices of Patti LaBelle, Dionne Warwick, and Gladys Knight. Enjoy unforgettable hits and heartfelt storytelling at 4450 N. Clark Street.
Chicago Blues Festival – June 5–8: Four days of soul-stirring blues at Millennium Park and the Ramova Theatre.
Jeremiah Collier & The Re-Up Band – June 6: Free jazz concert at Harper Court, Hyde Park. Presented by University of Chicago.
Maxwell Street Market – June 8: Come for the tacos, stay for the soul. Monthly Sunday market returns with vendors, food, and live music.
Taste of Chicago – Marquette Park – June 28: South Side edition of the city’s biggest culinary showcase. Food, performances, and neighborhood pride.
Tyler, the Creator at United Center – June 30 & July 1: The genre-bending visionary brings his latest project to the stage with signature flair and a can’t-miss live show. Two nights only at the United Center.
July
Millennium Park Summer Film Series – July 8–Aug. 19: Outdoor movies under the stars every Tuesday. Bring your blanket and your crew.
Bethany Pickens – July 11: Jazz pianist and Chicago treasure lights up Harper Court for a free performance.
Chicago Gospel Music Festival – July 12: Praise, power and community. Millennium Park becomes church for a day.
Chosen Few Picnic & Festival – July 12: House music’s biggest family reunion featuring Chosen Few DJs, guest performers and legendary vibes.
Maxwell Street Market – July 13: The summer market hits its stride. Don’t miss it.
Taste of Chicago – Pullman Park – July 19: Food trucks and family fun in historic Pullman.
August
Dee Alexander – August 8: The jazz vocalist brings her magic to Hyde Park as part of the free Harper Court series.
Steppin’ Under the Stars – August 8: Get your smoothest outfit and dancing shoes ready. This year’s 4th annual “Steppin’ Under the Stars” invites Chicagoans to step the night away under the open sky, with food trucks, adult beverages, and vibes courtesy of DJ Lavell C.
Taste of Chicago – Albany Park – August 9: Culinary delights and multicultural energy in Albany Park.
Maxwell Street Market – August 10: The summer edition of the iconic Maxwell Street Market.
Chicago Air and Water Show – August 16 & 17: Aerial stunts and lakefront thrills return to North Avenue Beach.
Chicago House Music Festival – August 22 & 23: The beat never stops. Celebrate the genre that put Chicago on the map.
September
Chicago Jazz Festival – August 28–Sept. 1: Millennium Park transforms into a jazz lover’s dream with artists from around the world.
Tim Gant Project – September 5: Smooth sounds in Hyde Park to close out the Harper Court summer jazz series.
Taste of Chicago – Grant Park – September 5–7: The main event. Downtown, diverse, and delicious.
Maxwell Street Market – September 14: The second-to-last market of the year. Stock up.
World Music Festival Chicago – Sept. 26–Oct. 5: Free concerts across the city featuring global rhythms and cross-cultural collaboration.
October–Not Summer But We’ll Count It
Maxwell Street Market – October 12: Final market of the season. Don’t miss your last chance for tacos, tunes, and treasures.
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