Callaway worked for ABC7 between 1981 and 1983 as a critic at-large.
His long career set the standard for excellence in journalism.
"I really want to learn. I want to bring people with me to learn and so you get up in the morning and you're engaged," said Callaway during an interview with ABC7.
His simple philosophy led to a highly respected career; he was considered by many colleagues to be the best interviewer in the business.
He was known for his in-depth interviews and the breadth of preparation.
Callaway hosted 'Chicago Tonight' for 15 years before retiring in 1999. He still hosted the weekly 'Friday Night Show,' in which he spoke with newsmakers from around the world.
He enjoyed in-depth conversations with politicians, athletes and entertainers on WTTW's "Chicago Tonight." His exhaustive research and professionalism earned him the admiration of his fellow journalists.
Phil Ponce now hosts 'Chicago Tonight.' He said Callaway lived for the art of conversation.
"John always honored the person he was interviewing. He honored them by preparing, by listening. He was the best interviewer in the country," said Ponce.
"It came from extreme curiosity and a dogged pursuit of all the information that one can have about the person he was about to interview," said Bruce DuMont.
Callaway was also a member of the ABC7 family; he worked as an at-large critic between 1981 and 1983.
"He came out of a journalism family, himself, so he grew up around the tables with his mother and father debating political issues," said Bruce DuMont, founder Museum of Broadcast Communications and Callaway's producer.
Born in West Virginia, Callaway is the son of a newspaper editor who moved to Chicago as a college dropout. He started in journalism at the City News Bureau, moved on to WBBM Radio and on to WTTW. He would rise to become one of the dominate voices in news in the city.
His work won him more than 60 awards, including seven Emmys and a Peabody.
Callaway continued to work in the final months of his life. According to his wife, Callaway was conducting interviews and mediating panels; he had recently moderated a panel at an Iron and steel industry conference in St. Louis.
"Just a great all around guy and an understanding man who really was one of the best journalists I think I've ever met," said John Hultman, WBBM Radio.
"Most people think John is from a serious, dour, insightful person. But he was really one of the funniest people I knew," said Dumont.
Callaway is survived by two daughters, who are accomplished cabaret singers.
He was 72 years old.