This essay studies and compares characters in The Canterbury Tales from four perspectives: with regard to the 14th century social conditions, religious beliefs, aesthetics, and narration. Sociologically speaking, the characters show a significant relationship with historical, economical, and social events such as the spread of bourgeoisie, the spread of rural life, social corruptions, and peasants’ revolt. Secondly, different religious ideas among pilgrims signify the contrast between people’s religious tendencies and Church, facing failure as to political power. From an aesthetic point of view, characters signify contradictory sensations such as fear from God’s punishment; suffering and aggression, similarly depicted in Gothic art, in one hand, and courtly love, tendency to worldly beauties, and sin, on the other hand. Thus, the change of social values in a transitory society is perceived. Fourthly, the application of vulgar language, frame stories, dialogic viewpoints, and ignorance of time and place at the end of pilgrimage signify narrations based on freedom of speech and confession leading to new ideas such as individuality, people’s social rights, and women’s rights in the Middle Ages. Therefore, the research shows realities of thoughts and minds in a critical period of human history, which could not have been recorded by historians.