Cities are a major source of intellectual creativity and political engagement. We have not finished, and we will never finish, understanding the transformation of cities and the impact of this transformation on society and culture at large. The focus for this chapter is what I would call the great twenty-first century urban paradox—an urban world without cities. Let me try to explain first, and then go into the details of the analysis. I would say that cities have been throughout history sources of cultural creativity, technological innovation, material progress and political democratization. By bringing together people of multicultural origins and by establishing communication channels and systems of cooperation, cities have induced synergy from diversity, dynamic stability from competition, order from chaos. However, with the coming of the information age cities as specific social systems seem to be challenged by the related processes of globalization and informationalization. New communication technologies appear to supersede the functional need for spatial proximity as the basis for economic efficiency and personal interaction. The emergence of a global economy and of global communication systems subdue the local to the global, blurring social meaning and hampering political control traditionally exercised from and by localities. Flows seem to overwhelm places as human interaction increasingly relies on electronic communication networks. Therefore, cities as specific forms of social organization and cultural expression, materially rooted in spatially concentrated human settlements, could be made obsolete in the new technological environment. Yet, the paradox is that with the coming of the techno-economic system, urbanization— simply understood as spatial concentration—is in fact accelerated. We are reaching a predominantly urban world, which before 2005 will include for the first time in history at least 50 per cent of the planet’s population in cities. Core activities and a growing proportion of people are and will be concentrated in multimillion metropolitan regions. This pattern of social–spatial evolution could lead to what I call urbanization without cities. As, on the one hand, people concentrate in spatial settlements, at the same time suburban sprawl defuses people and activities in a very wide metropolitan span.