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The Ravinia Jazz Mentors are eight of Chicago’s finest jazz artists, working with Ravinia’s Reach Teach Play to not only give school performances and master classes but actively train an auditioned group of top Chicago Public High School student musicians in skills for future professional studies and music careers. The ensemble (and the Jazz Mentor Program) is led by saxophonist Pat Mallinger, who for nearly three decades led regular late-night sets at the Green Mill, and joined on winds by 2016 Chicagoan of the Year trumpeter Pharez Whitted and former longtime Chicago Jazz Ensemble lead trombonist Audrey Morrison. The rhythm section includes Ernie Adams, who has drummed with a who’s-who ranging from Al Jarreau and Dianne Reeves to Joe Zawinul and Arturo Sandoval, and twice Grammy-nominated Latin percussionist Eric Hines, plus Chicago Jazz Orchestra bassist Dennis Carroll; pianist Richard Johnson, who has been a member of two Marsalis ensembles and the Jazz at Lincoln Center Orchestra; and guitarist Bobby Broom, who co-led the Deep Blue Organ Trio and currently fronts a namesake trio and Organi-Sation.

Since 2011, Civitas Ensemble has combined the outstanding collaborative musicianship of multiple top Chicago Symphony Orchestra string chairs with a thirst for interdisciplinary exploration of new and traditional chamber music, including pairings with dancers, visual artists, and poets. Their Alla Zingarese project, released on Cedille in 2018, leaped to the whirlwind crossroads of Western classical and Romani folk traditions, creating “a trip through history … and a venture into new musical territory with surprises aplenty” (Chicago on the Aisle). In their first appearance at Ravinia as Civitas—though all veterans of the festival’s stages—the core trio of CSO Asst. Concertmaster Yuan-Qing Yu, CSO Asst. Principal Cellist Kenneth Olsen (an early 2000s alum of Ravinia’s Steans Institute), and Chicago College of Performing Arts Piano Program Head Winston Choi bring a program of Turina and Tchaikovsky headed up by a picturesque recent work by longtime Chicagoan Stacy Garrop.

While people Jahari Stampley’s age may be quipping about staving off quarter-life crises, the 25-year-old Chicago-native pianist is understandably more focused on cultivating virtuosities. A year ago, he released his debut album, Still Listening, and a couple months later played the final round of the Herbie Hancock Competition, a prominent proving ground for young jazz artists. “I’ve heard some of the best pianists in the world. In a sense, he really challenges them,” Hancock said, awarding Stampley the top prize, “I’ve never heard anybody play quite like that. … I was thinking, ‘Maybe I should study with him.’ ” The New York Times was equally effusive: “Stampley’s style arrived like a lightning bolt … unforced, as if powered from an internal engine.”

WindSync embraces classics from across centuries of music writing, using their vibrant “fourth wall”-breaking approach to performance to make standard repertoire a fresh experience. Whether originally written for wind quintet instruments or specially arranged for them, WindSync combines familiar favorites and folk music songbooks and traditions with an actively growing body of freshly inked works, threading it all together to tell compelling stories about music history and human selves. On the heels of All Worlds, All Times, their debut album that “will make you want to get up and dance” (The WholeNote), the quintet hit number-one on the Billboard Classical chart with the works of Miguel Del Aguila, recorded in the famed Studio Two at Abbey Road.

A kaleidoscopic string trio that “fully inhabits the spirit of the works they are playing in the moment, with as ardent a flame as if they had written it themselves” (Fanfare), Black Oak Ensemble returns to Ravinia with the grand reveal of their latest laser-fine focus. “O Britannia”—also due to be released as their latest Cedille album—highlights works by living women composers in the United Kingdom, including new pieces by Shirley Thompson OBE and Errollyn Wallen CBE, who was recently named Master of the King’s Music to succeed Dame Judith Weir and become just the second woman to hold the honorary role.