Hubbard moved to Chicago in the mid-1940s. He worked at WIND-AM and hosted stage shows at the big Loop theaters. He also played the ukulele, performing at lounges around Chicago on weekends. In 1956, he joined WGN as a personality. In addition to his regular duties, that included hosting the morning drive time show until 1965, he appeared on the Saturday night "Barn Dance" show. He wrote some of TV scripts for Hawaiian Eye and Love, American Style.
