This chapter examines the profound transformation of contemporary urbanism through Artificial Intelligence (AI), reframing its roles and values through a retrospective lens grounded in socio-technical history in the framework of urban development. By comparing the emergence of AI with prior waves of technological innovation since the modern era, this chapter critically examines how heuristic AI systems are redefining the discipline of urban design. The discussion underscores how AI cultivates a deeper, evidence-based comprehension of urban complexity, catalyzing inclusive urban renewal. By investigating AI’s foundational influence, the chapter positions AI as an ontological presence embedded across layers of urbanism Through systematic review along with case studies, three pivotal shifts in urban design model are identified: (1) From evidence-informed problem framing to human communication interaction (HCI); (2) data-informed urban design model shaped through collaboration with an expanded network of stakeholders; and (3) new typologies of urban form and transformation due to the materials and design focus shift. Collectively, these transformations contribute to the advancement of a more inclusive, adaptive, and intelligence-driven paradigm of AI-aided urbanism. Finally, by critically evaluating ethical challenges and data justice issues inherent in AI-aided urbanism, the chapter examines the risks and opportunities of AI as a collaborative agent in fostering more equitable, resilient, and opportunity-driven urban futures.