This chapter explores the writing of Aleksandar Hemon, Dmitry Samarov, and Erika L. Sánchez as a process of carving out a personal space in the city. Their diverse literary output exemplifies the complexities of immigrant identity and its myriad dialogues with home, boundaries, and space. Hemon’s literature reveals a nuanced spatial-temporal sensitivity that establishes a multilayered and overlapping experience of Chicago and his native Sarajevo. Russian-born Samarov encounters Chicago through the window and rearview mirror of his taxi, observing the city and its inhabitants close-up yet from the sidelines. His unique perspective encompasses the immigrant outsider stance alongside an intimate insider knowledge, facilitating his tersely articulated and poignant vignettes of Chicago’s city- and human-scapes. Sánchez, second generation Mexican, boldly crosses restricting boundaries in her work, challenging constraints of family, community, neighborhood, and nation. By straddling a mixture of cultures, languages, genres, and themes, she cultivates her own distinctive space. Taken together, the writers offer a literary panoply of what it means to be an immigrant in Chicago today.