The article analyzes the phenomenon of an innovative city from a cultural and philosophical perspective. The paper substantiates the characteristic features of an innovative city, namely: the tendency to move forward, dissatisfaction with the existing existence, the development of the category of opportunity from the point of view of assessing the innovative prospects of the city. The concept of "innovative city" in this study was compared with similar concepts of "ideal city", "city of the future", "fast city", "creative city". The distinction was made regarding the substantive, operational and dynamic aspects of the innovative potential of cities. In particular, for the concepts of "ideal city" and "city of the future", the most important is the substantive side of the innovation process, embodied in the ideal image of the city; while for the "fast city" the potential of innovation is associated with the idea of movement, trend, speed and multi-vector flow of change. The theoretical and methodological basis of the study is a phenomenological approach that substantiates the city as a semantic space-time construct with innovative development potential. The authors consider the substantive, operational and dynamic aspects of the concept of "innovation" in relation to urban transformation projects. Special attention is paid to the phenomenological aspects of the generation, implementation and translation of innovations to determine the strong semantic dominants of the "creative city", "fast city", "ideal city", "city of the future", innovative city as a whole. Analyzing the models of urban development, the difficulties of innovative programs related to the problem of determining the specific results of transformations, the lack of processality as such, inconsistency, utopianism, the predominance of the effect of the significance of mega-events over the practical results of innovation are emphasized. The methods of neutralizing the negative consequences of innovative strategies by maintaining a wide range of semantic alternatives that identify strong semantic dominants of the city; controlling the speed of changes that allow to "remove" the conflict between the anthropological and innovative dimension of the city; overcoming the ratio of innovativeness and trendiness, in favor of building the city's own unique imagery.