From medieval city views to contemporary urban imaginaries, imagination has always played a major role for outlining human understandings of urban life. Just recently, urban studies, urban planning, and artistic research have re-discovered imaginary approaches to urban lifeworlds as viable stimuli for urban transformation and social critique. In order to find pathways for sustainable development, creative strategies and imaginations of collective utopia have become a vital source of inspiration for urban planning and architecture. Interdisciplinary, inclusive approaches to create urban utopia have become central to thinking and writing about the urban as a shared imaginary matrix for collective sensemaking. This article provides a selective overview of the role of urban imaginaries from the Middle Ages, to the 20th century, and on to contemporary perspectives on urban spaces. In this brief tour d’horizon the potentials of images, imaginations, and utopian perspectives on urban life are sketched out for exploring and ultimately designing places of urban cohabitation. As an introduction to this journal issue on the role of urban imaginaries for creating liminal spaces for social change and critique, this article also aims to describe the use of creative strategies and urban imaginaries for urban studies, urban transformation projects, and artistic interventions in urban spaces. The articles in this issue demonstrate the multifaceted nature of urban imaginaries in contexts as diverse as exhibition design, visual anthropology, urban studies, and virtual/augmented reality. Adopting different imaginary perspectives ultimately paves the way for understanding urbanization as a utopian project, a collective struggle, and a manifestation of collective will, which continuously produces tangible and intangible outcomes. Processes of planetary urbanization, therefore, also inspire us to reflect on social, economic, and cultural co-evolution and participation on a global scale. This way, urban imaginaries become blueprints for social change, critique, and societal innovation.