This study investigates the cinematic representation of city crime transactions in Chicago in the 1980s. The narrative nature of cinema provides an imaginative context for interpreting the physical and nonphysical dimensions of urban crimes. From a critical interpretive position, based on Peirce’s semiotics, this study uses “urban cinesemiotics” as the method to select image signs, identify their associated Chicagoan objects, and interpret their designoriented meaning. The theoretical roots of crime prevention through environmental design constitute the basis for the interpretation of movies. A total of 27 crime-related scenes from 9 Chicagoan movies made in the 1980s illustrate that most urban settings suffer from the lack of crime-preventive environmental design. In particular, natural surveillance (eyes on the street), encounter and enclosure, and border vacuums are major environmental factors that affect urban crimes in Chicago. Some crime scenes also depict why environmental design cannot influence individuals’ criminal intentions necessarily nor can they solve urban safety single-handedly.