Birds of prey are becoming increasingly common occupants of urbanized settings, but the comparative benefits or detriments they experience in urban environs compared to exurban areas are poorly understood. We examined the reproductive success and phenology of Mississippi Kites (Ictinia mississippiensis) nesting concurrently in urban and exurban areas in west Texas during the 2010–2012 and 2014 breeding seasons. Our objective was to better understand the reproductive advantages or disadvantages that kites may experience by nesting in urban areas rather than exurban areas. We calculated annual productivity, estimated daily survival rates of nests, and estimated hatch dates. Kites produced 0.52 fledglings per urban nesting attempt and 0.33 fledglings per exurban nesting attempt. We found no difference in the mean number of young that fledged from successful urban (1.06) and exurban (1.07) nests, but kites in urban areas had greater nesting success within years than those in exurban areas. Both heat and drought were associated with low productivity and success in both areas, but the urban landscape appears to have provided some buffer to their effects. These factors may have had direct (e.g., exposure) or indirect (e.g., negative influences on prey availability) influences on reproductive success. Counter to previous studies of urban raptors, we found that exurban kites nested significantly earlier than urban kites. This may be linked to differences in environmental conditions and prey availability between the areas. Our results suggest that urban areas provide a reproductive advantage for Mississippi Kites in terms of facilitating an overall higher nesting success, but this does not translate into increased productivity for successful pairs. Further, our data suggest that, although urban areas may buffer species from drought or heat, that buffer can be breached during severe conditions.