Urban systems have a number of factors (i.e., economic, social, and environmental) that can potentially impact growth, change, and transition. As such, assessing and managing these systems is a complex challenge. While, tracking trends of key variables may provide some insight, identifying the critical characteristics that truly impact the dynamic behavior of these systems is difficult. As an integrated approach to evaluate real urban systems, this work contributes to the research on scientific techniques for assessing sustainability. Specifically, it proposes a practical methodology based on the estimation of dynamic order, for identifying stable and unstable periods of sustainable or unsustainable trends with Fisher Information (FI) metric. As a test case, the dynamic behavior of the City, Suburbs, and Metropolitan Statistical Area (MSA) of Cincinnati was evaluated by using 29 social and 11 economic variables to characterize each system from 1970 to 2009. Air quality variables were also selected to describe the MSA's environmental component (1980-2009). Results indicate systems dynamic started to change from about 1995 for the social variables and about 2000 for the economic and environmental characteristics.