Charlotte Perkins Gilman’s The Yellow Wallpaper and Kate Chopin’s The Awakening, published in 1892 respectively 1899, portray two women’s fight against patriarchal society and for individual freedom. From leading a life as the submissive wife of Léonce Pontellier, Edna in The Awakening starts breaking the rules patriarchal society has determined, and tries to create a life of her own. The unnamed protagonist of The Yellow Wallpaper, suffering from post-natal depression, is brought by her husband to a mansion in the countryside to recover. Her husband, also functioning as her physician, forbids her to do any kind of work he believes is exhausting to her (including even writing and daydreaming). One of the few ways she can fight against the patriarchal system which surrounds her, and one of the few ways she can feel free, is by writing a secret journal. The purpose of the essay is to examine symbols of patriarchy, captivity, and freedom in The Yellow Wallpaper and The Awakening. It is argued that the authors use specific symbols to represent the patriarchal system which surrounds the heroines. Furthermore, it is argued that symbols are used to reinforce the sense of captivity the protagonists experience in their daily lives, as well as to portray the freedom the protagonists try to obtain.