In this article, we examine the imaginative geographies of the new millennium through a critical reading of cyberfiction. This fiction, we argue, through its use of estrangement and defamiliarization, and its destabilization of the foundational assumptions of modernism, provides a cognitive space in which to contemplate future spatialities given the present postmodern condition – a cognitive space which is already providing an imaginal sphere in which present-day individual and institutional thought and practice are partially shaped. Using a detailed reading of 34 novels and four collections of short stories, we illustrate the utility of this cognitive space, and its appropriation, through an exploration of fictional visions of postmodern urbanism in the early twenty-first century. We assess the viability and utility of these visions by comparing them to academic analyses of the sociospatial processes shaping present-day urban form and spatiality.