Chicago’s 1893 World’s Columbian Exposition continues to haunt the public and literary imagination. A temporary but massive “city” built in a single park, the Fair was part of a larger sociocultural trend of nineteenth-century exhibitions. This chapter focuses on some of the fiction set at the Chicago Fair, those contemporaneous works written and published around 1893, often by authors who attended the Fair themselves. The temporal proximity of this literature to the event itself provides a useful way to gain insight into the quotidian experiences of tourists to the Fair. Many scholars have looked at these literary works in depth, but my own entanglement with the literary fair is framed by my 2007 and 2008 archaeological survey and excavation of Chicago’s Jackson Park, the former site of the Fair. Although some of the physical remains of the Fair linger into the present, albeit in ruined or heavily modified forms, novels from the Fair addressed the reality that the Fair, though immense, was designed to be temporary. Finally, a look at a more recent wave of literature on the Fair points to the continued interest in and expressive power of the Fair into the twenty-first century.