Structurally resilient and functionally sound pavements should withstand excessive water run-off. Permeable pavement systems (PPS) may be used to reduce runoff, improve effluent water quality, and/or achieve psychosocial, societal, and sustainability benefits. The recent advances in pavement material and construction techniques, structural and hydraulic designs, drainage, and new approaches to measure filtration present an opportunity to quantify the environmental benefits of PPS. This paper presents the environmental impacts of integrating PPS in urban areas, including the effects on life cycle assessment, sustainability, and resiliency. The outcome is presented from case studies in the USA (Oregon, Missouri, Minnesota, Louisiana, Wisconsin, New Jersey, and Georgia), as well as international case studies (China, Australia, The Netherlands, and UK). Some of the case studies include conventional impervious surfaces for comparison. Based on these case studies, it is evident that the implementation of PPS in cityscapes could offer several benefits.