This article aims at critically investigating how urban aspirations, that is the capacity to collectively imagine and desire alternative spaces for the cities we live in, affect the construction of everyday children’s geographies. Drawing on Political Geography of Children, children are here considered as social actors that ceaselessly negotiate spatial practices and representations created and imposed by adults. Combining this theoretical framework with participatory action research methodologies, we analyze the activities carried out with children from San Giovanni Apostolo Onlus Association in the highly marginalized neighborhood of CEP (Palermo). More specifically, our emphasis is on the techniques of photo-walk and collective mapping along with the efforts of transforming the so-called field of via Calandrucci from a ‘disimagination zone’ into a space where children and young people can claim their right to aspire.