She served as chief of staff to Chicago Mayor Richard M. Daley, and helped lead the city's bid for the 2016 Olympics.
She also organized the NATO and G8 summits and served as chief executive of McCormick Place and Navy Pier.
The former mayor was among those in attendance at Tuesday morning's outdoor remembrance at Women's Park and Garden on South Indiana Avenue in the South Loop.
"She was the best," Daley said.
Obama Foundation Chief Executive Valerie Jarrett was among the speakers.
"If there was a big job that needed to get done, Lori was always everyone's obvious choice," Jarrett said.
Healey died last week from pancreatic cancer at the age of 65.
She's survived by her son and daughter.
Most recently, she worked as an executive at the Obama Foundation, where she oversaw construction for the presidential center in Jackson Park.
Tuesday's event was a who's who of Chicago's movers and shakers: Past and present gathered to pay tribute.
"She knew her way through bureaucracy. She knew her way around egos. She knew the way to 'yes' when everyone else was stuck at 'no,'" said state Rep. Kam Buckner, a Democrat who represents the 26th District.
Healey was a major player in the public and private sector, putting her stamp on major city projects. Patrick Daley spoke on behalf of his dad and sisters.
"She reminded me so much of my mother, not just in her capabilities, but in her character, the quiet strength, unwavering integrity and that ability to make everyone in a room feel valued and heard," Daley said.
Former Mayor Lori Lightfoot said, when she was elected, she immediately reached out to Healey.
"Anybody who was smart as a mayor, you wanted to have Lori Healey on speed dial," Lightfoot said.
Father Tom Hurley joked that Healey must have had a hand in naming the pope.
"For all those who think Bob Prevost became Pope XIV because of a bunch of cardinals, I think it was actually Lori Healey that made Chicago a pope," he said.
Healey was described as tough, pragmatic, a visionary, strategic, warm funny and humble, someone who found inspiration in the ability to create opportunity for others.
But, all of Healey's friends say her biggest accomplishments were her two children and grandchildren.
"Whenever we had our family events or weekends in Michigan, she didn't pick up the phone. She didn't pick up a computer; she was present for us," son Ramsey Al-Abed said.