Long a fan of The Divine One, vocalist Ann Hampton Callaway offered an even more tangible homage to the great jazz vocalist with a live tribute album titled, “From Sassy to Divine: The Sarah Vaughan Project” (2014).

“Among vocal jazz’s female holy trinity,” wrote Christopher Loudon in JazzTimes, “Billie Holiday and Ella Fitzgerald have been lionized most but Sarah Vaughan has been feted best, via such fine salutes as Carmen McRae’s ‘Sarah: Dedicated to You’ and Dianne Reeves’ ‘The Calling.’ What, then, can an artist like Ann Hampton Callaway add? Plenty, it turns out.”

Because of that album and the recognition it gained, as well as Callaway’s own standing as a jazz singer, the Chicago native was invited to join Dee Alexander and René Marie as vocal soloists for the Chicago Jazz Orchestra’s “A Tribute to Sarah Vaughan,” which will be presented May 20 as part of the Symphony Center Presents Jazz Series. The event, led by the orchestra’s director, Jeff Lindberg, will mark Callaway’s debut in Orchestra Hall and her first time performing with Alexander and Marie. Among the selections she is scheduled to perform are “How High the Moon,” “Lullaby of Birdland” and “Send in the Clowns,” all using Vaughan’s original jazz orchestra transcriptions. “It’s very important to put your own stamp on these songs, so every song I do I arrange myself in my way,” Callaway said. “What does the lyric say to me? But I have to say that Sarah Vaughan’s approach to singing was very sensual. She made love to a song. She used words, she used sounds, she conjured beautiful orchestral qualities in her voice. She taught me a lot about the voice as an orchestra, bringing out the cellos and the flutes and the trumpets for various types of songs. Some of my singing is directly influenced by what I learned from Sarah Vaughan, but my approach is still very much my own.”

Sarah Vaughan was a big influence on her own vocal style, says Ann Hampton Callaway.

Sarah Vaughan was a big influence on her own vocal style, says Ann Hampton Callaway.

The idea of doing a Vaughan tribute first emerged after Callaway released an album in 1996 titled “To Ella With Love” (re-released on the Shanachie label in 2005). Afterward, her father, John Callaway, a celebrated Chicago broadcast journalist and a jazz buff who was an important inspiration for her singing career, told her that he thought her vocal texture and sensibility might be better suited to Vaughan’s works. “So that sort of stayed with me,” she said. Then when she was planning to do a show devoted to Vaughan at Dizzy’s Club Coca-Cola under the auspices of Jazz at Lincoln Center, her label approached her about turning that engagement into a live album.

“When I knew it was going to be a record,” Callaway said, “I was particularly careful about doing an extensive amount of research and really trying to choose songs that painted a portrait of her and that were arranged to give a real sense of story about who she was a person and as an artist.”

One telling song, for example, is Stephen Sondheim’s “Send in the Clowns.” During her research for the program, Callaway realized that she had been in attendance for Vaughan’s final appearance at the Blue Note in 1989, right after the vocalist learned that she had lung cancer. That night, the esteemed singer performed the melancholic standard with particular profundity. “The energy she had on that song was just chilling,” Callaway said. During her Vaughan tribute, Callaway tells the story of that night, and then proceeds to sing a version of “Send in the Clowns,” which she arranged in a minor instead of its normal major key. “It’s a theatrical moment, because people suddenly put themselves in her shoes,” Callaway said. “What was it like to know that you’re singing in public and none of your friends know you are dying?”

Born in Chicago in 1958, Callaway lived there for 10 years before moving with her family to New York when her father was hired as a vice president of CBS Radio. When she was 10, her father gave her a rhyming dictionary, and she has been writing songs ever since. “It was just a natural part of who I am,” she said. The family returned five years later, in time for her to attend New Trier East High School in Winnetka, which had an extensive performing arts program that helped set her on an artistic path. “That was a very formative time,” she said. After attending college for two years at the University of Illinois, she left for New York to try her hand at show business, and she’s never looked back.

Though Callaway has enjoyed a highly varied career that has carried over to Broadway and television, she has always been rooted in jazz and cabaret. “I am my own brand,” she said. “I think of myself as a pop-jazz singer. Cabaret is a style of performing that involves intimacy and relating to an audience in a more personal way. I think a lot of times that people who are steeped in the cabaret tradition are always putting the lyric first. We’re always putting the storytelling first. It’s not just dazzling music, it has to be dazzling music with a purpose and intention.”

Whatever she is singing, she likes to put a jazz twist on it. A good example is her program, “The Streisand Songbook,” which she debuted in 2012 with the Boston Pops and continues to perform with orchestras nationwide. It features such Streisand signature tunes as “Funny Girl,” “A Star Is Born” and “The Way We Were,” all done with Callaway’s own jazzy touch. “I have the jazziest arrangements of Barbra Streisand songs that you would imagine,” she said. “So I’m putting my own jazz spin on classics from pop to Broadway to the various forms of music that Barbra sang.”

Jazz even followed Callaway to the Great White Way, where she was nominated for a Tony Award for her performance in “Swing!,” a musical that ran for more than 450 performances in 1999-2001. A celebration of the Swing Era, it featured standards by such well-known bandleaders as Duke Ellington, Count Basie and Benny Goodman.

Throughout her career, Callaway has been an advocate of what has become known as the Great American Songbook, a collection rooted in the timeless tunes of such composers as George Gershwin, Cole Porter and Richard Rodgers, along with contemporary works in the same vein. “There’s a level of storytelling and beauty and humanity and charm and wit in the Great American Songbook that’s a whole world of music that deserves to be nurtured and presented in new ways,” she said. “It’s just a part of our history and our identity that needs a little a bit of preservation and care that not everybody can give it.”

At the same time, Callaway has written more than 250 songs of her own, including the theme to the popular television series “The Nanny.” Three of her songs are featured on seven of Streisand’s many albums, and they have also been recorded and performed by such artists as Karrin Allyson, Barbara Carroll, Michael Feinstein, Carole King, Patti LuPone and Liza Minnelli. Callaway is hoping to record the first album of her own original songs in the next year or two.

Jazz cruises, symphony halls, intimate cabarets and Broadway stages. Streisand hits, jazz classics and original songs — Callaway revels in the variety of it all. She loves to share the wonderfully diverse world of music whenever and wherever she can.

Kyle MacMillan, former classical music critic of the Denver Post, is a Chicago-based arts journalist.