Imagining the future of cities is often an exercise that is based upon the imagining of future transport infrastructure. The article explores this connection historically by drawing parallels between London, Paris and Shanghai since c.1851. It focuses on the role that symbols and mythmaking play in the process of envisioning future transport and future cities. It raises questions about the continuities between contexts that are distant across space and over time and the extent to which such continuities might provide some insights into the many connections between cities, transport and mobilities.