Prairie Avenue is a north–south street on the South Side of Chicago, which historically extended from 16th Street in the Near South Side to the city's southern limits and beyond. The street has a rich history from its origins as a major trail for horseback riders and carriages. During the last three decades of the 19th century, a six-block section of the street served as the residence of many of Chicago's elite families and an additional four-block section was also known for grand homes. The upper six-block section includes part of the historic Prairie Avenue District, which was declared a Chicago Landmark and added to the National Register of Historic Places.

The Near North Side is the eighth of Chicago's 77 community areas. It is the northernmost of the three areas that constitute central Chicago, the others being the Loop and the Near South Side. The community area is located north and east of the Chicago River. To its east is Lake Michigan, and its northern boundary is the early 19th-century city limit of Chicago, North Avenue. In 2020 the Near North Side had 105,481 residents, surpassing Lake View as the largest Chicago community area by population. It is also the most densely populated community area and has the second most skyscrapers, after the Loop. With the exception of Goose Island, the Near North Side is known for its extreme affluence, typified by the Gold Coast, Magnificent Mile, Navy Pier, and skyscrapers.