The production of urban futures significantly influences public policies and decision-making. Futures emerge from a diversity of visions that are continually updated. However, amid this diversity, many urban actors share an institutionalization of futures. The institutionalization of futures contributes in a certain way to the anticipation of cities understood as an inherent property of complex systems. This chapter aims to demonstrate how anticipatory systems can be applied to cities. This anticipatory property of cities is neither homogeneous nor static in the various subsystems that make up cities. In this chapter, the notion of anticipation is decomposed into two dimensions: (a) the future disposition and predictive capacity of the systems and (b) the transformative or updating capacity of the system as a response to possible evolution. Because of their complex nature and decentralized system, cities present a diversity of complementary future and anticipatory regimes, and the diversity of future and anticipatory regimes of cities are shared among urban actors, forming urban anticipatory communities.