Callaway grew up in West Virginia, and hitchhiked to Chicago after dropping out of Ohio Wesleyan University in 1956. His arrival in Chicago with almost no money (and student loan debts) is a story he enjoyed telling, and he eventually was able to share it on the stage in "John Callaway Tonight" (in 2001).
His career as a journalist began in Chicago, a city he claimed he fell in love with instantly. He first worked in the City News bureau before joining Chicago's CBS station WBBM. He was named Vice President of CBS Radio in New York in 1968. But he was soon back in Chicago where he joined WTTW in 1975. "Chicago Tonight" was first broadcast on April 24, 1984, with an interview of Harold Washington.
"John Callaway through the years," Chicago Tribune photos (June 24, 2009).
"Journalist John Callaway dies," Chicago Breaking News Center (June 24, 2009).
"Ch.11 broadcast legend John Callaway dies," Chicago Sun-Times (June 24, 2009).
"John Callaway, Legendary Chicago Journalist, Dies at 72," Huffington Post (June 24, 2009) features the 1984 interview with Harold Washington.
Craig Kanalley, "Legendary local journalist John Callaway dies," Breaking Tweets Chicago (June 24, 2009).
Craig Wieczorkiewicz, "Legendary Chicago Journalist John Callaway dead," The Bread Line blog (June 23, 2009).
Charles Leroux, "Maximus John -- Master interviewer Callaway takes the stage to sing a song of himself," Chicago Tribune (March 16, 2001).