This chapter examines the two Chicago-set graphic novels of Chris Ware entitled Jimmy Corrigan: The Smartest Kid on Earth (2000) and Building Stories (2012), as well as Lost Buildings (2004), Ware’s “on-stage radio & picture collaboration” with Ira Glass for National Public Radio. The chapter argues that Ware’s body of work explores how various human networks engage with the storied history and urban geography of his adopted city, and that it does so in endlessly experimental ways that have continued to redefine the expressive potential of the comics form. In these works, Ware creates complex visual narratives in which the city and its ever-changing urban landscape is often as much of a character as the people inhabiting it, and his meticulously drawn pages are thus an attempt not only to depict and make sense of Chicago but also to create a visual index of the relationship between its spatial and emotional lives. Despite his untraditional choice of form, this approach places him in a lineage of Chicago writers that reaches all the way back to the earliest recorders of life in the city.