This documentary takes the viewer on a journey along Halsted Street, from the southern tip of Illinois, north through various Chicago neighborhoods, to the end of the road at Broadway in Chicago's Lakeview neighborhood.

The nom d'art 'Tommy Chicago' reflects independent filmmaker Tom Palazzolo's unique status within the Chicago film community. Since 1967, Palazzolo has filtered all aspects of the Windy City through his audacious lens. This documentary captures the artist at work and play on his latest film: we see him engage street urchins in the service of his vision, teach his son that you CAN buy love, and drive cast and crew to the brink of artistic chaos. Colorful and fast-paced, the tape illuminates the vital interplay between Palazzolo's brash personal style and his filmic art.