While a large body of research has established a clear association between structural conditions of urban youths’ residential neighborhoods and their involvement in delinquent behavior, how specific sociobehavioral and community contexts outside the home are associated with delinquency remains unclear. Research to date sheds limited light on the characteristics of the places where urban youth spend their time, both within and outside their residential neighborhoods, and how those settings might be associated with delinquent behavior. This study advances place-based delinquency scholarship by examining three key aspects of the places where urban youth spend time—i.e., surrounding community context (e.g., crime), social and behavioral features (e.g., adult supervision), and distance from home—using cross-sectional data gathered from a sample of 296 minority youths ages 13 to 17 residing in high-burden urban neighborhoods in Chicago. The study has three specific aims; first, the study examines the characteristic of settings where urban youth report spending time during a typical week. Second, the study examines whether involvement in delinquent behavior is associated with characteristics of these settings. Third, the study evaluates whether youths’ evaluations of risk and safety are associated with various aspects of activity space and whether these associations vary by delinquent behavior. The following key set of findings emerged from the study: Urban youths spend much of their time in locations geographically removed from their homes, although usually within the same general area of the city. Furthermore, indoor settings located within high-risk community contexts exhibit protective proximal features, particularly adult supervision, adult presence, and goal-oriented activities. Delinquent youths were less likely to spend time in settings characterized by higher levels of adult supervision and youth engagement in goal-oriented activities compared to nondelinquent youths. Limited evidence was found to indicate that features of the surrounding community context were associated with delinquent behavior. The study is unique in that it is the first to integrate these three key aspects of urban youths’ activity settings. Second, the project is the first contextual analysis of delinquent behavior focusing on the association between where and how urban youth spend their time and engagement in delinquent behavior. These research aims have received little attention in the literature and merit scientific investigation given the little we know of the daily settings where urban youth spend time and how they relate to health and behavior.