The concept of chaos occupies a general place in F.I. Tyutchev’s poetic images system, however, its relationship with freedom as an ontological category, which is conceptualized in Russian philosophy, represented in this study by sophiology and personalism tradition, is still poorly reflected. It is proved that the appeal to the philosophical systems of Solovyov, Frank and Bulgakov is caused by the specifics of Tyutchev's legacy understanding and similarity in conception of chaos as the substantial principle of reality. The results of modern domestic and foreign philosophical researches on the chaos conception in its connection with poetry, mysticism and the concepts of Russian religious thinkers are analyzed. It is argued that the most productive way to comprehend the chaotic principle mystical aspect may be to compare its representation in Tyutchev's lyrics and N.A. Berdyaev's ontological epistemology. The interpretation of freedom concept as a key characteristic of the chaos generative basis underlying the personalistic existence is proposed. The connections of chaos, freedom and personality categories with Ungrund concept are revealed, the lines of Berdyaev and Tyutchev's thoughts divergence in understanding the nature of Deity, cosmic hierarchy, personal reality, the path of Eros and Thanatos are outlined. Berdyaev's philosophy of freedom main aspects overview and his method of interpreting the mystical principle, causality and substance as a tool for Tyutchev's philosophical poetry discursive analysis is given. It is concluded that the correlation of freedom and chaos as the sophiological and personalistic concepts is carried out in Russian philosophy through the creative principle mystical understanding, inspiration and intuitive stimulus of which is Tyutchev's poetry. © 2025 Elsevier B.V., All rights reserved.