The purpose of this chapter is to explore understandings of autonomy in the context of urban life and emerging notions of the autonomous city enabled though the use of AI (artificial intelligence). A review of the research and practice literature for autonomy is provided in relation to urban life and AI, enabling formulation of a conceptual framework for autonomy, urban life, and urban AI. Guided by the framework, an exploratory methodological approach is used to further probe the challenges and opportunities surfaced while conference-based polling serves to enrich findings. Insights and limitations are provided along with future directions for study and exploration, concluding with a note on the significance of this chapter.