The spread and continued growth of urban areas presents a number of concerns for a sustainable future, particularly if cities cannot adequately address the rise of poverty, hunger, resource consumption, and biodiversity loss in their borders. Intended as a comparative illustration of the types of urban sustainability pathways and subsequent lessons learned existing in urban areas, this study examines specific examples that cut across geographies and scales and that feature a range of urban sustainability challenges and opportunities for collaborative learning across metropolitan regions. It focuses on nine cities across the United States and Canada (Los Angeles, CA, New York City, NY, Philadelphia, PA, Pittsburgh, PA, Grand Rapids, MI, Flint, MI, Cedar Rapids, IA, Chattanooga, TN, and Vancouver, Canada), chosen to represent a variety of metropolitan regions, with consideration given to city size, proximity to coastal and other waterways, susceptibility to hazards, primary industry, and several other factors.