This research is dedicated to a comparative analysis of Alisher Navoiʼs work “Lison ut-Tayr” (“The Language of Birds”) and Geoffrey Chaucerʼs “Canterbury Tales”. These masterpieces of Eastern and Western classical literature are explored in terms of their narrative structure, artistic composition, as well as the similarities and differences in their social and moral ideas. The primary aim of this research is to investigate the correlation between Uzbek and English literatures by conducting a comparative analysis of these two works. Additionally, it seeks to analyze the philosophical and ethical perspectives of the authors through an examination of their narrative structures and symbolic imagery. In “Lison ut-Tayr”, Navoiy reflects the symbolic and philosophical essence of Sufi literature, while in “The Canterbury Tales”, Chaucer portrays medieval English society through realism. Both authors, drawing inspiration from previous literary traditions, skillfully express the social and spiritual issues of their time. The research examines the narrative structure, character development, artistic techniques, and thematic elements of the works, as well as the distinct and shared qualities of their symbolic and allegorical imagery. This study aims to provide a broader understanding of the significance and role of the literary heritage of these great authors in the cultural and literary development of their respective societies.