Abstract: The object of this research is the city viewed as a multilayered semantic phenomenon. The needs of transdisciplinary nature determine the vector of its analysis in light of the possibility of application of diagnostic approach, which incorporates the theoretical and practical aspects, cognitive and transformative sides. The goal consists in the development of diagnostic model of the city as a cultural phenomenon. The position is defended on the limitation of classical diagnostic search applicable to the so-called city. The prospects of its research correlate with the nonclassical interpretation of diagnostics, which views it as methodology of cognition. The basic method of this research is modelling. The development of diagnostic model of the city is founded on M. M. Bakhtin’s concept of chronotope. Namely chronotope is determines as the basic parameter underlying its construct. Incorporating the spatiotemporal parameters of the city and their cultural meanings, it allows recording the temporal-topos configurations in city motion, which reflect various qualitative states of its existence, set by the past, present and future. The author offers a ternary model of the city, consisting of historical-cultural, eventful, and innovative chronotopes. The formulated conclusions indicate that the proposed chronotopes can be viewed separately or following the principle of complementarity, which allows assessing the city from the perspective effective arrangement of urban space, as well as the presence of problematic fields therein.