The monograph is devoted to understanding the spatial and semantic “labyrinths” of (post)postmodern urban culture from the perspective of digital humanities, in particular the concept of fractality. The concepts of “fractal”, “fractal pattern”, “multifractal”, “attractors” and “strange feedback loops” in their cultural aspects make it possible to see fractal shapes of history and culture in urban everyday life, in the sociocultural practices of the festive and night metropolis. Streets and city blocks, monuments and sculptures, mannequins and street performers, advertising billboards and museum artifacts, libraries and shopping centers, fire extravaganzas and art projects - like the city as a whole - create endless fractal "patterns" of local and world culture. The book is designed to a wide range of readers, including specialists in cultural studies, philosophy, social and cultural anthropology, teachers and students of humanities universities, everyone interested in urban culture and new angles of its research.