In my essay I investigate Mexican-American writer Sandra Cisneros’s autobiographically inspired novels, The House on Mango Street (1984) and Caramelo (2002) with a focus on the representation of native Mexican and Mexican-American women characters selected to study. The aim of my essay is to explore transitions between the characters’ cultural identity by examining whether the characters obtain cross-cultural identity; to what extent they are able to accept the Mexican and the American culture as a part of their identity. I classify the characters into three groups on the basis of their stage in constructing their cross-cultural identity. The first group involves the “pilgrims,” Cisneros’s multicultural characters. The second group embraces the “tourists,” the native Mexican characters. The third group includes the “mestizas,” the youthful, multicultural protagonists of the novels. To elaborate on the pilgrim and the tourist characters, I rely on Zygmunt Bauman’s essay, “From Pilgrim to Tourist – or a Short History of Identity” (1996), and I use Gloria Anzaldúa’s Borderlands/La Frontera (2007) to analyze the mestiza characters. Within each group the characters stand on the same stage in their cross-cultural identity; however, among the groups I argue that transitions can be observed; there are not only generational differences between them, but the characters have a different approach towards the Mexican and the American culture, therefore the processes in their identity result in different relationship and attitude towards the cultures. In my essay, I argue that only the mestiza characters are able to construct a cross-cultural identity and transcend the limitations of the patriarchal Chicano culture.