This article explores how preschool children perceive the urban environment and how urban space influences the development of their autonomy. Drawing on interdisciplinary perspectives from urban planning, environmental psychology, and child development, the study analyzes the ways young children interact with and interpret their everyday urban surroundings. A mixed-methods research design was employed, combining qualitative and quantitative approaches, including semi-structured interviews, children’s drawings, and content and cluster analyses. The empirical study was conducted with a sample of 130 preschool children aged 4-6 years living in the central districts of Baku. The findings demonstrate that children’s urban experiences are largely shaped by interactions with parents and close relatives, while environmental awareness is strongly influenced by intergenerational factors, particularly the role of grandparents. Limited opportunities for independent interaction with urban objects and spaces lead many children to compensate through imaginative constructions of an idealized, fairy-tale city. Children’s perceptions reveal early sensitivities to environmental problems, social behavior in public spaces, and the availability of safe and accessible areas for play and communication. The results highlight that children’s views of the city serve as an important indicator of how urban environments support or constrain cognitive, emotional, and social development. The study emphasizes the necessity of incorporating children’s perspectives into urban planning and social policy, offering practical implications for the design of inclusive, child-friendly, and sustainable urban environments.