Chaos theory (or complex systems science, CSS) has made considerable inroads across a range of social science disciplines, including criminology. However, little has been done to assess the relevance of chaos theory for advancing a philosophical criminology. This task is significant because it tells us something about where, how, and why most modernist theories of crime are of limited utility when advancing the interests of justice and humanism in society. Accordingly, this article outlines the essential features of a philosophical criminology, including its commitments to ontology, epistemology, aesthetics, and ethics. Moreover, the contexts in which several key chaos theory principles such as iteration, sensitive dependence on initial conditions, bifurcations, attractors, fractal space, and dissipative structures function to promote a philosophical criminology are explored. A number of implications stemming from this analysis for purposes of critical theory building in law, crime, and justice studies are provisionally delineated.