The article is dedicated to the analysis of the idea of flight in fiction and the scope it provides for the representation of a person’s real vision or the symbolic designation of psychological states and understanding. The interpretation of one’s perspective as a personal quality and a property of space or time is also considered. The comparison of literary works is focused on the expressive approach аin the scholarly heritage of the 20th-century outstanding philosophers and aestheticians M. Bakhtin and A. Losev. The novel Aviator by Evgeny Vodolazkin, a representative of modern Russian prose, is analyzed in detail. The ideas and interpretations of flight in the works of R. Bach, A. de Saint-Exupery, and other famous writers of the past century are compared. The dependence of the destinies of those who strive for flight on the historical turns of their time is demonstrated. The main value of the concept of flight for these authors lies in the breadth of human horizons, in the “vigilance of the heart” and “touch to the soul.”