The History of Woodlawn

Learn about the long history of one of Chicago's South Side Neighborhoods

The Woodlawn neighborhood was originally a small community of Dutch farmers who settled the area in the mid-nineteenth century. Although Chicago did not annex the neighborhood until 1889, Woodlawn farmers maintained a relationship with the nearby city through the sale of produce. Prior to the late nineteenth century, the population of Woodlawn never quite exceeded 1,000 residents. However, that changed when the decision was made to host the World’s Columbian Exposition of 1893 in the neighboring community of Jackson Park. With the subsequent influx of entrepreneurs, residents, and tourists, Woodlawn saw a boom in development and population. The World’s Columbian Exposition of 1893 is also what spurred the creation of the Midway Plaisance.

Following the World’s Columbian Exposition of 1893, Woodlawn faced economic hardship. It was a painful reminder of the temporary development that resulted from the Exposition. To combat this depression, two commercial centers were introduced into the otherwise residential neighborhood: the Washington Park Subdivision, and the development of 63rd (which, due to its proximity to the L, attracted many people from around Chicago). The racetrack associated with the Washington Park Subdivision was replaced with apartment buildings in the early twentieth century. Additionally, Woodlawn began to attract middle-class Black families who could afford to purchase property outside of the Black Belt (the “Black Belt” was a term used to describe a host of South Side neighborhoods where the majority of residents were Black and brown people). With so few commercial attractions, the economic conditions in Woodlawn declined once again, with the severity of the decline increasing during the Depression. Additionally, the shifting racial demographics promoted a bout of white flight, despite the efforts of Woodlawn businessmen, landlords, and University of Chicago officials to forestall the influx of Black residents. In the 1920s and 30s, local landlords working with the University of Chicago exploited restrictive covenants, keeping Woodlawn predominantly white and insular until after World War II. At that point, activists fought against the restrictive covenants, which were eventually deemed illegal. Black families began moving to Woodlawn in earnest in the 1950s; many were Black migrants from the south or Black Chicago residents attempting to avoid redevelopment efforts. Opportunistic landlords capitalized on the limited housing available to Black families, illegally dividing apartments into cramped units, known as ‘kitchenettes’. In addition to being crowded into subdivided apartments, limited housing available to Black residents allowed landlords to charge them higher rents. By the middle of the twentieth century, approximately 89% of Woodlawn’s population was Black. The effects of the mass displacement that resulted from the Great Migration created a social environment that necessitated the presence of local activists. In 1959, local residents connected with Saul Alinsky's Industrial Areas Foundation to start organizing against the increasing injustices. This effort birthed Temporary Woodlawn Organization, which was later renamed The Woodlawn Organization (TWO). Since its inception and to this day, TWO has been a strong and influential presence in the neighborhood.

The economic decline, combined with the racially motivated and systemic oppression of the residents, shaped Woodlawn’s social conditions. While general overcrowding (in buildings and schools), disinvestment, and over-policing perpetuated and exacerbated poor social and economic circumstances, Woodlawn became--and remains to this day--a stronghold for activist organizations that enacted meaningful and lasting change in the neighborhood. While Woodlawn has experienced periods of decline since the twentieth century, recent developments--including the restoration of Jackson Park and the opening of the nearby Obama Presidential Center--have opened the door for growth and transformation. Regardless of these developments, it’s already home to a substantial wealth of historic parks, locally-owned businesses, cultural institutions, and organizations that merit thorough exploration.