This chapter presents readers with an opportunity to engage with the concept of uncertainty through the lens of cities and urbanism. Operating within an environment of profound uncertainty relating to the future of humanity, contemporary cities present divergent narratives of hope and despair. They are chronically underfunded and over-burdened, home to deeply divided communities and decrepit infrastructure, and struggling with chaotic unplanned growth and chronic pollution. Yet they have the capacity to assemble social, material and technical actors and relations in novel, experimental and collaborative ways so as to respond to these emergent challenges. These insights lead us to the question, what can we learn from cities about living with, planning and governing uncertainty? The contributing authors answer this question by presenting five perspectives on urban uncertainties. Ranging from looking at the street level and ordinary uncertainty to looking at the governing of uncertain technological futures, to discussing the ethical outcomes of governmental solutions to climate change, the authors excavate the varying ways in which uncertainty stimulates experimental forms of urban development and governance, and with what social and political implications. They conclude with optimism: if a progressive, equitable and ethical socio-political milieu is fostered in cities, it is possible to effectively tackle urban challenges in uncertain cities.