John Callaway (August 22, 1936 – June 23, 2009) was an American journalist, who appeared on radio and television as a host, interviewer and moderator. He was the original host of Chicago Tonight, a nightly news program broadcast on the Chicago, Illinois television station WTTW, serving in that role from 1984 to 1999.
John Callaway was born and raised in New Martinsville, West Virginia, in 1936. While growing up John's father owned a weekly newspaper. After his father became ill, hospital bills left him unable to help pay for college. Callaway had already accrued $800 in loans and a job as a dishwasher could not cover his expenses. He dropped out of Ohio Wesleyan University after a little more than a year in college, telling the dean that he was dropping out of school temporarily and was hoping to earn enough money at the steel mills in the Chicago area to pay for the remainder of his college studies. The dean gave him $50, almost all of which was spent until he had only 71 cents left. He hitchhiked to Chicago through Ohio and Indiana, and was given a train ticket on the South Shore Line, arriving at Randolph Street Station on February 6, 1956, with the 71 cents in his pocket and immediately fell in love with the city.
He worked in a series of odd jobs, and was told that the steel mill idea wouldn't work out. He took acting classes at night, which lasted until his instructor told him "Callaway, you're the worst actor I've ever had the pleasure of working with." He went on to tell him about a position that would fit with his father's career, where reporters could enjoy the free food available at political dinners.
This led Callaway to his first media job, at Chicago's City News Bureau, where he was employed as a police reporter. He was hired in 1957 by WBBM-TV and its associated radio stations, a CBS affiliate, as a reporter and documentary producer. There he won several national awards for The House Divided, a 13-segment documentary on the civil rights movement in the United States. As WBBM's News Director, he oversaw the station's 1968 conversion to an all-news radio format. He came back to Chicago in 1973 after being employed in New York City as a vice president of CBS Radio, and became the WBBM-TV lead reporter.