Urban areas provide organized, engineered, sociological and economic infrastructure designed to provide a high quality of life, but the implementation and management of urban infrastructure have been a continued challenge. Increasing urbanization, warming climate, as well as anthropogenic heat emissions that accompany urban development generates “stress.” This rapidly growing ‘urban stress’ affects the sustainability of cities, making populations more vulnerable to extreme hazards, such as heat. This talk focuses on modeling and impact assessment relevant at appropriate scales (~km to m scales) for heterogeneous urban built and natural environment within Chicago metropolitan area. I will discuss some fundamental science questions related to removing uncertainty in urban climate modeling and understanding urban processes with an aim to capture meteorology, evaluate energy consumption, and assess air quality. This talk will also discuss solutions and strategies to mitigate urban heat-related challenges in vulnerable neighborhoods of the Chicago metropolitan area by combining social vulnerability indices (a function of exposure, sensitivity and adaptive capacity) with green roofs implemented in a climate model as a potential urban heat mitigation strategy.