Data for this study were collected in Chicago as part of a larger, nine-site, longitudinal study of the effects of terminating the SSI/DA&A program on former benefit recipients. Chicago was used as the sample site because it was the only site that collected all three primary sources of information used in this study: standardized psychiatric and substance use diagnoses, urine samples for drug testing, and arrest histories. The final analytical sample consisted of 187 participants (73 percent of the baseline sample) who provided complete self-report information at baseline, psychiatric diagnoses at the 12-month interview, SSI status and income at their final interview, and testable urine samples for at least one or more of the 12-, 18-, and 24-month interviews. Eighty-four of the participants completed all five interviews. Cox regression survival models were used to analyze the relationships between demographic characteristics, SSI status, psychiatric diagnosis, and drug use and time-to-arrest over the 2-year follow-up period. The findings suggest that both substance use disorders and psychiatric disorders are related to criminal activities and that the relationships vary among crime categories; however, substance use and psychiatric illness do not uniformly increase the chances of arrest among these crime categories. Rather, arrests for different types of crimes are related to specific psychiatric and substance use disorders. For this sample, gender was not significantly associated with the chance of arrest and only reached statistical significance for crimes in the other category. The research findings are preliminary and suggestive due to the small number of participants and the limited number of diagnostic and drug categories used in this study. Future studies are recommended. References and 2 tables