This paper focuses on the concept of a sustainable city and its theoretical implications for the urban system. Urban sustainability is based on positive interactions among three different urban sub-systems : social, economic and physical, where social well-being coexists with economic development and environmental quality. This utopian scenario doesn’t appear. Affluent economy is often associated with poverty and criminality, labour variety and urban efficiency coexist with pollution and congestion. The research subject is the analysis of local risk and opportunity conditions, based on the application of a special definition of risk elaborated and made operative with the production of a set of maps representing the multidimensional facets of spatial organisation in urban sustainability. The interactions among the economic/social and environmental systems are complex and unpredictable and present the opportunity for a new methodology of scientific investigation : the connectionistic approach, processed by Self-Reflexive Neural Networks (SRNN). These Networks are a useful instrument of investigation and analogic questioning of the Data Base. Once the SRNN has learned the structure of the weights from the DB, by querying the network with the maximization or minimization of specific groups of attributes, it is possible to read the related properties and to rank the areas. The survey scale assumed by the research is purposefully aimed at the micro-scale and concerns the Municipality of Milan which is spatially divided into 144 zones
