He began his long broadcasting career when only eighteen, at Peoria radio station WMBD in 1934. Chicago radio station WGN hired him in 1940 to broadcast Cubs and White Sox games, largely on the recommendation of their top announcer, Bob Elson. His was the very first face shown when WGN-TV, Chicago's Channel 9, began broadcasting in 1948. This came after his U.S. Marine Corps service in World War II. Brickhouse missed the 1945 Cubs season, the only time in Brickhouse's long tenure that the Cubs would win the National League pennant. He announced White Sox games on WJJD in 1945. His only pennant as a broadcaster would belong to the White Sox in 1959, but neither the 1945 Cubs nor the 1959 Sox won the World Series.