Cities, which were the capital cities of ancient civilizations, reflect the lifestyles, cultural and spiritual values of societies with their architectural and monumental structures. Orhan Okay, who is an original intellectual and scientist with his thoughts on history, society and civilization as well as his scientific studies in the field of Modern Turkish Literature, had the opportunity to get to know Eastern and Western civilizations closely and analyse them from many aspects. Evaluating both civilizations with their cities of historical and cultural significance, Okay's attention to Paris and Istanbul focuses on symbol values and history; culture, art, architecture, religion and social life are reflected as the concrete embodiment of these values. In his literary works entitled Bir Başka İstanbul and Bir Başka Paris, Okay's critique and interpretations of the degeneration that took place in cities as a consequence of the modernization process are important in terms of culture, civilization and social history. In this study, based on the abovementioned literary works, Prof. Dr. Orhan Okay's perspective on Paris and Istanbul will be determined in the context of culture, civilization, art and social life.