The wave of “digital age” featuring digital information is coming. Digital technology is profoundly changing the societal development direction and evolution paths. It also has significant bearing on production modes, social interactions and lifestyles. With regard to urban design, a system of knowledge about the creation and adaptation of material space forms that integrate humanities, art, technology and materials, digital technology has provided it with a brand-new and revolutionary scientific impetus for its evolution. The result of this evolution is “digital urban design paradigm based on human-computer interaction”, i.e., the urban development is moving toward “pan-dimensionality” and “individual ubiquity”. The future of urban design will construct a new approach to urban research and engineering, which is more complex, capable of accommodating and compatible with multiple goals of “instrumental rationality” and “value rationality”. Such a new approach shall be led by the probabilistic theory of “gray scale thinking”, reflecting quaternary synergetic view of “scientific rationality, ecological rationality, cultural rationality and technical rationality” to realize the cognitive progress of “engineering for the benefit of mankind”.