Rapid population growth and urban sprawl have expanded built-up areas, affecting flood patterns in cities. Sustainable urban drainage systems (SUDS) have gained significant attention by attempting to replicate natural pre-development drainage conditions. This paper presents a new transdisciplinary methodology for assessing the potential feasibility of 12 different SUDS typologies by considering physical restrictions and six types of contextual barriers. The approach integrates input from academic and non-academic actors, fuzzy logic, geographic information system tools, and multi-criteria decision analysis. A neighborhood in Bogotá, Colombia, was selected as the unit of analysis, framing a relevant case study for highly urbanized areas. The findings demonstrate the differential impact of local context constraints and emphasize the importance of comprehensive approaches to SUDS planning that consider criteria other than technical. The methodology is a tool to support architects, engineers, urban planners, and urban water decision-makers in the planning of sustainable and flood-resilient cities.