Grant Park Music Fest CEO to step down

Paul Winberg, president and chief executive officer of the Grant Park Music Festival, announced Wednesday that he will retire in spring 2026.

Winberg, 63, is credited with tripling the festival’s annual contributions, bolstering its administrative infrastructure and overseeing a key change in artistic leadership last year. Under his watch, the festival has become one of the country’s foremost free classical music series.

“It was my goal all along to make sure we were financially in a really strong position and artistically in a place where we can continue to grow, and to make sure we had a board and staff that I could hand off to the next leader, and they could just run with it,” he said.

Winberg began discussing his departure inside the organization some 18 months ago but waited until Giancarlo Guerrero completed his first summer as the festival’s artistic director as principal conductor before making his announcement.

“I am very in awe of his leadership. Paul has done an amazing job,” said Jeffrey Haydon, president and chief executive officer of the Ravinia Festival in Highland Park, the summer home of the Chicago Symphony Orchestra.

In 2004, the Grant Park festival, a free, summer classical-music series featuring the Grant Park Orchestra and Chorus, took a transformational leap forward. It moved from the rudimentary Petrillo Music Shell in Grant Park to Millennium Park’s Pritzker Pavilion, a sleek, sprawling amphitheater designed by renowned architect Frank Gehry, but kept its well-recognized name.

Winberg arrived seven years later after serving nearly eight years as executive director of the Eugene (Ore.) Symphony Orchestra.

According to Haydon, he played a major role in the 10-week festival capitalizing on its new performance home and significantly boosting its profile both locally and nationally. “He increased the stature and professionalism of it and made it more of America’s urban classical music festival,” the Ravinia leader said.

Winberg, a Brainerd, Minn., native who once served as an intern with the festival, returned to find an organization that was artistically vibrant but needed stronger administrative support. He fortified the staff and board and boosted fundraising, including doubling the size of the organization’s endowment to $30 million during the past three years.

Overall, the festival’s annual budget has almost doubled from $4.7 million in 2011 to $9 million in 2025 and the staff has grown to 16 year-round staff members (14 full time and two part time), about twice the number when Winberg arrived.

Haydon praised Winberg’s ability to navigate Chicago’s unusually competitive summer classical scene. “He’s been collaborative about it,” the Ravinia leader said, “but he’s also helped the organization chart its own identity and path in a way that anchors and supports everything else around it.”

In that collaborative spirit, Winberg has made taking the festival beyond its main Millennium Park venue a top priority, including neighborhood concerts as part of the Chicago Park District’s Night Out in the Parks. “He has always had a great focus on: How can the music festival relate to the many communities of Chicago?” Haydon said.

The festival’s fellowship program, which began in 2013 as a collaboration with the Chicago Sinfonietta to promote equity and inclusion, has provided 70 to 80 emerging musicians and singers a chance to perform with the Grant Park Orchestra and Chorus and gain valuable experience. “It’s helped advance this need in the symphonic and choral fields to create a more diverse orchestra and chorus that is more reflective of the city in which we are operating,” Winfield said.

Another of Winberg’s accomplishments was shepherding the search for a replacement for Carlos Kalmar, who stepped down in 2024 as Grant Park’s artistic leader after 25 seasons. Guerrero was chosen as his successor from an initial list of 150 candidates.

Winfield was “really nervous” about how audiences would accept Guerrero after Kalmar’s long tenure, but he said the transition went off without a hitch. “He produced some mind-blowing performances this past summer,” the festival president said. “He took what Carlos Kalmar built and truly took it to the next level.”

The search for Winberg’s replacement will begin immediately, and the organization hopes to have someone in place by the time he steps aside. What kind of traits would Winberg like to see in his successor?

“First and foremost,” he said, “they have to have be someone who truly loves what the Grant Park Music Festival stands for in this city. This is a civic and cultural treasure for the city, but it’s also one that is artistically important [in the broader field] as well. So, someone who really understands that and cares for that and continues to nurture that is going to be really important.”