Melissa Etheridge usually performs with musicians well-versed in the rhythms of rock ’n’ roll. But for her next appearance in Chicago, the iconic rock star has chosen as her backing band a group of musicians more familiar with the intricacies of Beethoven and Brahms.

Joined by members of the Chicago Symphony Orchestra, Etheridge will appear June 16 for the Chicago Symphony Orchestra Association’s 25th annual Corporate Night. Sean O’Loughlin will be the guest conductor.

If you’ve ever wondered how Etheridge’s many hit songs would sound if backed by an orchestra, you’re about to get your answer. Always ready for a challenge, Etheridge admits it’s a pairing that many rock artists would not want to try, but she’s confident it will be a “very memorable evening.”

Etheridge, 53, is the first to acknowledge that she’s never done anything like this. She and her management team were looking for a way to try something different. So she first spent the month of April on the road performing solo acoustic shows. Now in addition to an additional run of solo shows, she’ll sprinkle in a few concerts with orchestras. Her concert with the CSO, will be followed by performances with the Boston Pops and the San Francisco Symphony. Between the tour dates, she married her partner, film/television producer Linda Wallem (“Nurse Jackie”), on May 31 in California.

“I’ve always loved classical music but I’m not an avid follower and have only a passing knowledge,” Etheridge says. “Yet I have a great admiration and respect for the history of classical music and the musicians who play it.”

Etheridge now ponders the difference between the process of creating a rock song and developing a complex orchestral piece. “When you create music like I do, you know it comes from that pairing of words and music in your head that no one can hear but you,” Etheridge explains. “And then you realize all these great composers pulled all of this complex music out of their heads. This ability to create all this timeless music, just music, we’re not talking words here, that conveys so much emotion is astounding.”

Though working with her band remains “a blast,” she is intrigued by the challenge of working with a much larger orchestra. Plus, it gives Etheridge a new way of approaching her classic songs; new arrangements/charts of the songs have been written for this tour. Etheridge also will play guitar and piano during the concert.

“I’ve played ‘Bring Me Some Water” for 25 years and ‘Come to My Window’ for 20,” she says, laughingly referring to two of her biggest hits. “So, yes, this is a very fresh, beautiful way to express the songs. I have to be open to new thoughts in the songs when working with the arranger, and that’s been a very interesting process. Both the solo tour and the orchestra shows actually help me grow as an artist.”

At 8 years old, Etheridge picked up the guitar and then began playing in local bands in her teens. “It’s all I’ve ever wanted to do,” she says. After completing high school, she attended Boston’s Berklee College of Music, but left after only one year to make her way as a performer in Los Angeles,where her bluesy vocal style and riveting stage presence earned her a loyal following. Legend has it that after a chance encounter with music industry legend and Island Records founder Chris Blackwell at a small club in Long Beach, Calif., she was signed on the spot, leading Blackwell to confess that he felt “the future of rock ’n’ roll has a female face.”

Etheridge knows must dedicate a portion of each concert to her hits; the fans expect it. But new music is always on her mind. She’s spent the last six months writing and recording a batch of new songs, some of which will be included on her next album, “This Is Me,” her first independent record due out in the fall. “One of the reasons it’s called that is because it’s a varied group of songs that feature a lot of my influences,” Etheridge says. “Rock to pop to folk, soul and R&B. All of it’s there, and it’s been a blast creating it.”

But like many singer-songwriters of her generation, Etheridge faces a music world that difers significantly from her heyday in the late 1980s to mid-1990s, when she released five albums, sold a collective 12 million discs and had a half-dozen Top 10 hits. But she feels now is the “best it’s ever been for artists” and that “the playing field has been leveled.”

“I think the environment today gives choices to the fans and allows artists to reach fans directly,” she says. “And I think that makes live music more important, more valuable than ever. The music business may have changed but people’s love of music never will.”

Mary Houlihan is a Chicago-based arts writer and reviewer.