The notion of transparency in urban life is explored in this chapter in the context of artificial intelligence (AI), through a review of the research and practice literature. Using an exploratory methodological approach, challenges and opportunities surfaced during the literature review are further explored, guided by a conceptual framework formulated in this chapter for urban life, transparency, and AI. Key elements pertaining to transparency and urban life in relation to AI are identified and organized into categories that include collaboration, smart citizens, and trust explored in terms of tensions and complications as challenges and opportunities. This chapter provides an overview of insights emerging from the explorations pertaining to the complexities, possibilities, and evolving of the transparency concept in the context of AI environments, now and going forward, while acknowledging the presence of various limitations.