Chicago’s late-summer stage

Grammy Award-winning vocalist Dee Dee Bridgewater and acclaimed pianist Bill Charlap. (Photo credit: Joseph Sinnott)

Summer may be winding down, but festival season in Chicago is far from over! Be sure to check out these events in August and early September. From annual traditions to one-time performances, you won’t want to miss these Chicago events with a Jewish twist.  

Give my regards to Broadway…in Chicago! 

Each summer, some of musical theater’s greatest talents come together for Broadway In Chicago’s annual (and free) Summer Concert in Millennium Park. This year’s concert takes place on Aug. 10, at the Jay Pritzker Pavilion. 

The one-night-only event will feature performances from current and upcoming Broadway In Chicago productions. Music lovers can expect selections from The Notebook, The Outsiders, Waitress, Jekyll & Hyde, Dirty Dancing: The Musical, Operation Mincemeat: A New Musical, Jersey Boys, Maybe Happy Ending, and more!  

This annual tradition has a special connection to the greater Jewish community. Jewish composers and lyricists shaped Broadway’s Golden Age (1930s-1960s) and have inspired generations of composers since. When we think of Broadway, we think of the foundational works of individuals such as Irving Berlin, George and Ira Gershwin, Richard Rogers and Oscar Hammerstein II, Leonard Bernstein, and Stephen Sondheim. Beyond their beautiful music are the stories, which are relevant to the Jewish experience tales of identity, immigration, and social justice. 

Performing Aug. 10 at the Jay Pritzker Pavilion, 201 E. Randolph St., Chicago. For tickets, visit broadwayinchicago.com. 

Gregory Alan Isakov with the Chicago Philharmonic 

If you enjoy indie-rock and folk music, be sure to catch Gregory Alan Isakov’s upcoming performance with the Chicago Philharmonic on Aug. 19 at Ravinia Festival in Highland Park. Isakov—the grandson of a Lithuanian Jew who fled to South Africa during WWII—was born in Johannesburg, South Africa, and now calls Colorado home. A self-identified “horticulturist/musician,” Isakov’s music draws clear inspiration from the natural world. 

Since his debut album Rust Colored Stones in 2003, Isakov has established himself as an atmospheric storyteller. Proclaimed “Simple. Straightforward. Utterly evocative,” by The Associated Press, Isakov’s compositions are equally well-suited to concert halls and gorgeous outdoor venues like Ravinia. Isakov is internationally renowned for his lyric poeticism and hypnotic melodies. His 2019 album Evening Machines was nominated for a Grammy award for Best Folk Album. 

After two sold-out 2025 concerts, Isakov’s highly anticipated return to collaborate with the orchestra promises an evening of captivating music under the baton of Christopher Dragon. Performing Aug. 19 at Ravinia Festival, 200 Ravinia Park Rd., Highland Park. For tickets, visit www.Ravinia.org. 

Chicago Jazz Festival 

For more than 40 years, the Chicago Jazz Festival has drawn music lovers from around the world to celebrate the city’s rich jazz legacy. The free festival features a diverse lineup spanning legendary performers and emerging artists. Like other events at Millennium Park, attendees can relax beneath the iconic Jay Pritzker Pavilion or spread out with a picnic on the Great Lawn. 

Established in 1979 to honor Duke Ellington, the four-day event is the oldest of Chicago’s free lakefront music festivals. Chicago became a center of jazz during the Great Migration (1910–1970), when millions of African Americans moved north, bringing the traditions that transformed the city’s musical identity. 

Jewish artists and composers have also played a significant role in jazz history, from Benny Goodman and George Gershwin to many contemporary musicians. The festival regularly celebrates the Great American Songbook, whose enduring standards were shaped in large part by Jewish songwriters including Jerome Kern, Harold Arlen, and Dorothy Fields. 

This year’s festival features Grammy Award-winning vocalist Dee Dee Bridgewater with acclaimed pianist Bill Charlap, genre-defying pianist and producer Robert Glasper, M.E.B. (Miles Electric Band), and Grammy-winning clarinetist and saxophonist Paquito D’Rivera. 

Additional highlights include Joel Ross Good Vibes and Dr. Emma Dayhuff: Innovations & Lineage—The Chicago Project, featuring Dee Alexander, Corey Wilkes, Isaiah Collier, Michael King, and Jonathan Pinson.  

The 2026 Chicago Jazz Festival runs Sept. 3-6. Visit ChicagoJazzFestival.us for tickets and the full festival lineup. 

Jenna Cohen is a marketing and communications professional living in Chicago.