The galloping urbanization of the world simultaneously transforms human society into a thoroughly urban society and dismantles the traditional “rural-urban” dichotomy. It is increasingly recognized in urban studies that human spatiality entails a complex pattern of settlements and dwellings. I propose a developmental-experiential theoretical framework for addressing what Stanley Milgram called the experience of living in cities. This framework particularly focuses on the atmosphere of living in cities. Founded on organismic-developmental axiomatic base introduced by Jacob von Uexküll, Heinz Werner, and Bernard Kaplan, and developed as cultural-developmental approach by Jaan Valsiner, the proposed framework centers on the experience of individual organismic relating to spatial environment. I draw on the work of Manuel Castells, Edward Soja, and Yi-Fu Tuan to conceptualize the emergence of meaningful places as the outcome of experiencing space. The concept of encounter introduced by Ash Amin and Nigel Thrift is used to locate the experience of the banal, everyday city life. Following Erving Goffman, the central question for the framework becomes the question of organization of experience. This question is tackled through Jaan Valsiner’s notions of semiotic mediation and regulation. I specifically focus on spatial signs that humans use to regulate the meaning-making process that creates as meaningful what Georges Perec called species of spaces, such as towns and cities. “The city,” from this standpoint, becomes one of the most important signs that mediate and regulate our experience of environments we inhabit. I discuss a number of theoretical and methodological directions in which this framework could be further developed to revive the urban, or settlement, psychology, which failed to develop as a viable subdiscipline despite the proposals of Georg Simmel and Nikolai Antsiferov in the early twentieth century, and the latter proposals of Milgram. This discipline should join efforts with settlement sociology and settlement geography to tackle the multiple challenges of urbanization by exploring its experiential dimension in its fascinating cultural diversity and intra- and interindividual variation.