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Woodlawn | Neighborhoods | Chicago by 'L'

Writer Lorraine Hansberry and her family moved into this Woodlawn home in 1937, despite restrictive housing covenants. The case that followed went to the Supreme Court. Photo: Alan Brunettin / WTTW

The Story of Woodlawn

With the Midway Plaisance and Washington Park to the north, Jackson Park to the east, and Oakwoods Cemetery to the south, the Woodlawn community area is practically bordered by green. Dutch farmers were the first to settle in the community in the mid-19th century, according to the Encyclopedia of Chicago.


Watch: Woodlawn

Woodlawn was a small community until it was announced that the World’s Columbian Exposition of 1893 was going to be held in Jackson Park. Businesses and residents flocked to Woodlawn. After the fair, however, the community suffered economically when visitors and businesses left.

In the 1920s, restrictive housing covenants kept people of color out of Woodlawn. One family, however, violated that covenant. When playwright Lorraine Hansberry was a child in 1937, her family moved into a home in Woodlawn. Their case fighting the covenants went all the way to the U.S. Supreme Court, and the Hansberrys won. The events inspired her play, A Raisin in the Sun––the first Broadway play by a black woman.

But white flight and redlining soon followed, and Woodlawn has since experienced the fallout from disinvestment. Once a population of over 80,000, Woodlawn now has 23,000 residents, according to 2019 data.

Currently, plans are in the works to build the Obama Presidential Center in Jackson Park. While some are hopeful that the center will encourage economic development, many residents in Woodlawn and other nearby communities are worried they won’t be included in that growth, and gentrification will displace longtime residents.

One branch of the Green Line ends in Woodlawn, with stops at King Drive and Cottage Grove.

Chicago's Oldest Restaurant

Watch: Chicago's Oldest Restaurant

Spotlight: Daley’s Restaurant

A Chicago staple, Daley’s Restaurant is a family-owned restaurant located on South Cottage Grove Avenue––and the oldest restaurant in the city. While some might connect the name of the restaurant with the two former mayors, the restaurant was actually founded by a young Irish ironworker named John Daley who wanted to provide food for construction workers building the University of Chicago, the World’s Columbian Exposition, and the rapid transit line.

In 1918, Daley sold the restaurant to two Greek immigrants, Tom Kyros and Paul Emmanuel. Today, the restaurant is still in the family and is a staple in the community. It recently moved to a new location––right across the street from the original––as part of a new affordable housing development.

Things to Do

Walk through Jackson Park to see what was once the site of the World’s Fair, including a replica the Statue of the Republic. In the summer months, relax on 63rd Street Beach and grab a drink at Reggie’s.