The research presented in this paper is a work in progress. It provides linkages between the author’s earlier research under the sustainable land planning framework (SLP) and emergent ideas and planning and design strategies, centered on the (landscape) ecological dimension of cities’ sustainability. It reviews several concepts, paradigms, and metaphors that have been emerging during the last decade, which can contribute to expand our vision on city planning and design. Among other issues, city form—monocentric, polycentric, and diffused—is discussed. The hypothesis set forth is that cities can improve the pathway to sustainability by adopting intermediate, network urban forms such as polycentric urban systems (PUS) under a broader vision (as compared to the current paradigm), to make way to urban ecological regions. It discusses how both the principles of SLP and those emergent ideas can contribute to integrate PUS with their functional hinterland, adopting an ecosystemic viewpoint of cities. It proposes to redirect the current dominant economic focus of PUS to include all of the other functions that are essential to urbanites, such as production (including the 3Rs), recreation, and ecology in a balanced way. Landscape ecology principles are combined with complexity science in order to deal with uncertainty to improve regional systems’ resilience. Cooperation in its multiple forms is seen as a fundamental social, but also economic process contributing to the urban network functioning, including its evolving capabilities for self-organization and adaptation.