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
Englewood Village Market
Select Saturdays: June 14 & 28, July 12 & 26, Aug 9, 23 & 30, Sept 27, Oct 11 & 25 | 9 a.m.–1 p.m. | Englewood Village Plaza, 58th & Halsted
Now in its sixth year, Grow Greater Englewood’s signature open-air market connects residents with Black-owned businesses, fresh produce, local eats, and cultural programming rooted in Black culinary and land traditions. Expect wellness workshops, arts activities, and a strong sense of community at this vibrant Saturday morning gathering. Free to attend.
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 to Oct. 12 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 Where House, hip-hop, soul, and people meet. The 31st Street Beach staple stays lit.
Ravinia Festival Ravinia’s 2025 summer lineup features more than 100 concerts and 40 artist debuts. Don’t miss performances by artists like Cynthia Erivo, Lenny Kravitz, Janelle Monáe, Maren Morris, Lang Lang, Beck, “Weird Al” Yankovic, Lindsey Stirling, Morgan Freeman, and Earth, Wind & Fire, plus the 89th residency of the Chicago Symphony Orchestra with Ravinia Chief Conductor Marin Alsop.
Returning favorites include Heart, John Legend, James Taylor, The Black Crowes, Al Green, The Roots, Diana Krall, and Chicago, while Kygo, Juanes, Nas, Sutton Foster, Ray LaMontagne, King Gizzard & The Lizard Wizard, and The Mohan Sisters are all making their Ravinia Festival debuts.
Highland Park’s music sanctuary brings out legends. Watch for The Roots, Glasper, TLC, and more.
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.
Chicago Greeter Neighborhood PopUp Series Join the Chicago Greeter Neighborhood PopUp Series for FREE guided walks through the city’s vibrant neighborhoods – led by friendly local volunteers! Every Saturday at 11:30 AM & 1:00 PM from Memorial Day through Labor Day Weekend. A new neighborhood each time — come explore like a local. Full schedule at www.chicagogreeter.com.
Chicago’s Soul: The Words and Music of Gwendolyn Brooks and Curtis Mayfield – July 26 Sherman (John) Park, 1301 W. 52nd St. | 5 p.m. A moving, multidisciplinary performance that blends the poetry of Pulitzer Prize-winner Gwendolyn Brooks with the music of soul legend Curtis Mayfield. Featuring narration by NPR’s Cheryl Corley and music by Lucy Smith and her band. Part of the Chicago Park District’s Night Out in the Parks series. Free.
The Color Purple at Goodman Theatre – Extended run through August 3 Directed by Lili-Anne Brown with a powerhouse cast including Brittney Mack as Celie, Aerie Williams as Shug Avery, and Shantel Renee Cribbs as Nettie, this Tony Award-winning musical adaptation of Alice Walker’s classic novel has added six performances by popular demand. Experience a stirring story of resilience and hope brought to life with vibrant choreography, music, and heart. Tickets available at GoodmanTheatre.org/Purple or 312.443.3800.
That’s What Friends Are For: Gladys, Dionne and Patti at Black Ensemble Theater – Extended run through August 10 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.
July
Keyshia Cole – The Way It Is 20th Anniversary Tour – July 5 United Center | 7 p.m. Celebrate two decades of R&B truth and power with Keyshia Cole and a stacked supporting lineup.
Zo! and Tall Black Guy – July 5 City Winery Chicago | 7:30 p.m. (Doors at 6 p.m.) City Winery presents Zo! and Tall Black Guy live for one night only. Known for their innovative takes on R&B that blend classic soul with progressive production, the duo brings their acclaimed joint album “Abstractions” to life in an electrifying performance that pushes the genre forward while honoring its roots.
Glenn Jones – July 6 City Winery Chicago | 7:00 p.m. (Doors at 5:30 p.m.) Grammy-nominated Chicago native and R&B soul legend Glenn Jones returns to City Winery. With new hits like “Love By Design” featuring Regina Belle and a catalog that spans decades, this live show brings powerhouse vocals and heartfelt soul to an intimate stage.
Raekwon & Ghostface Killah Meet-and-Greet – July 7 Village Dispensary Bucktown, 1850 W Webster Ave | 1:00–2:30 p.m. Celebrate the 30-Year Anniversary of Only Built 4 Cuban Linx with legends Raekwon and Ghostface Killah. This exclusive meet-and-greet event offers fans a rare opportunity to connect with the Wu-Tang Clan icons in an intimate setting.
Wu-Tang Forever: The Final Chamber – July 7 United Center | 8 p.m. Hip-hop history live on stage. Wu-Tang Clan reunites for their farewell tour.
RnB After Dark – July 7 City Winery Chicago | 7:30 p.m. (Doors at 6 p.m.) An intimate evening of soul, showcasing some of the most talented vocalists in the scene.
Bethany Pickens – July 11 Jazz pianist and Chicago treasure lights up Harper Court for a free performance.
32nd African/Caribbean International Festival of Life (IFOL) – July 11–13 Park 540, 2401 S. Federal St., Chicago South Loop | 12–10 p.m. daily A cultural celebration spotlighting the music, food, arts, and lifestyles of the Caribbean, Africa, and beyond. Presented by Martin’s International, the 32nd annual IFOL features Reggae, Afrobeat, R&B and more, alongside crafts, cuisine, and vibrant community vibes. A summer staple for cultural pride and unity.
Chicago Gospel Music Festival – July 12 Praise, power and community. Millennium Park becomes a 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.
Shop Black Fest Chicago – July 12 Midway Plaisance Park, Hyde Park | 2–7 p.m. Celebrate Black culture, community, and entrepreneurship at this one-of-a-kind outdoor festival. Featuring 40+ Black-owned vendors, delicious food, live DJ sets, line dancing, and a bounce house for the kids, Shop Black Fest offers an energizing afternoon in the heart of Hyde Park. Free and open to all ages.
Maxwell Street Market – July 13 The summer market hits its stride. Don’t miss it.
Luv Locz Experiment & AKiVA the Band – July 13 The Wild Hare Rooftop | 7 p.m. (Doors open) Reggae on the Rooftop with live bands, DJs, and unbeatable sunset vibes.
V103 Summer Block Party – July 14-15 Huntington Bank Pavilion at Northerly Island R&B lovers, get ready for the fourth annual V103 Summer Block Party! This signature Chicago event brings the heat with a star-studded lineup featuring Keith Sweat, Ne-Yo, Ja Rule, Ashanti, and Tank. An essential night for fans of classic and contemporary R&B, all set on the lakefront at one of the city’s most scenic venues.
Alabama Shakes – July 16 The Salt Shed Outdoors | 7 p.m. Brittany Howard returns with the Shakes for their first tour in eight years.
Taste of Chicago – Pullman Park – July 19 Food trucks and family fun in historic Pullman.
Tacos y Tamales Festival – July 18–20 Pilsen, Chicago A three-day explosion of Latin food, music, dance, and culture in the heart of Pilsen.
Roscoe Village Burger Fest – July 18–20 Belmont Ave. from Damen to Oakley This festival returns for its 18th mouth-watering year with two stages of rockin’ music, arts & crafts, and the action-packed “Kids Zone.” Sizzling hot is the only way to describe this wildly popular Windy City food and music street happening. Visitors even have the opportunity to vote for Chicago’s Best Burger! A $10 suggested fest donation benefits the invaluable programs and services of the Lakeview Roscoe Village Chamber of Commerce.
Wicker Park Fest – July 25–27 Celebrate 21 years of indie spirit with music, food, art, and community in one of Chicago’s most iconic neighborhoods.
IBUKUN Hip Hop Art & Culture Fest – July 26 Zhou B Art Center, 1029 W. 35th Street A one-of-a-kind celebration of Black music, art, fashion, and community. Featuring headliner Rapsody, special guests Wood Harris, Cynthia McWilliams, Ta’Rhonda Jones, and more. Includes live performances, a Black art gallery, panel discussions, fashion showcase, and the prestigious Dr. Christian Adeyemi Akiwowo Legacy Award presentation.
Lollapalooza 2025 – July 31–Aug. 3 Grant Park The ultimate music fest returns. Headliners include Olivia Rodrigo, Tyler, the Creator, Sabrina Carpenter, Rüfüs du Sol, Luke Combs, Twice, A$AP Rocky, Korn, Gracie Abrams, and Doechii.
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.
ChiCarnival Weekend 2025 – August 15–17 Various Locations (TBA) Chicago’s Caribbean Carnival Weekend returns with 3 days, 4 epic events, and nonstop vibes. Hosted across the city by ChiCarnival Experience, the weekend includes Soca on the Seas (Boat Party), Soca Insanity (Saturday Night After Party), Call to Dutty (Paint, Powder, Water Day Fête), and Last Lime (Sunday Night Wind Down). Featuring top Soca artists, DJs, and Caribbean flavor from around the globe.
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.
African Festival of the Arts – August 30–Sept. 1 Washington Park After a one-year hiatus, the African Festival of the Arts returns for its 35th year, transforming Washington Park into a vibrant celebration of African diasporic culture. From legendary performances to drum circles, food, and local vendors, AFA remains one of the South Side’s most treasured traditions. Hosted by Africa International House USA, Inc., this Labor Day weekend festival honors a legacy of culture, creativity, and community.
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 – Sept. 5 Smooth sounds in Hyde Park to close out the Harper Court summer jazz series.
Taste of Chicago – Grant Park – Sept. 5–7 The main event. Downtown, diverse, and delicious.
Harold Washington Literary Awards Dinner – September 4 The prestigious HWLA returns to honor acclaimed author Sandra Cisneros. This annual literary gala celebrates diverse voices and kicks off the Printers Row Lit Fest. Past honorees include Isabel Wilkerson, Ta-Nehisi Coates, and Natasha Trethewey.
Printers Row Lit Fest – September 6 & 7 One of Chicago’s most beloved literary events returns to South Dearborn Street. From 10 a.m. to 6 p.m. each day, enjoy author talks, readings, book vendors, and more—all FREE and open to the public. Come rain or shine!
Maxwell Street Market – Sept. 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.
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