High Quality Content by WIKIPEDIA articles! Prairie Avenue is a north–south thoroughfare on the South Side of Chicago, which historically extended from 16th Street in the Near South Side community area of Chicago in Cook County, Illinois, United States, 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.