From the World’s Fair to the Obama Center: The Evolution of Woodlawn

Background and History

Woodlawn’s story begins in the late 1800s, when it was a quiet stretch of prairie land just beyond the growing edge of the city. The neighborhood sits on Chicago’s South Side, bordered by Lake Michigan on the east, Cottage Grove Avenue on the west, 60th Street on the north, and 67th Street on the south. Its location—just south of Hyde Park and east of Washington Park—has long placed it at the crossroads of Chicago’s cultural and historical development. Locals sometimes divide it along Cottage Grove into East and West Woodlawn.

In the decades that followed, Woodlawn grew into a dense, middle-class community. But its story, like much of Chicago’s, is one of both beauty and struggle.

Trivia Question

Which world-famous event held in 1893 helped shape the development and identity of Chicago’s Woodlawn neighborhood?
(Answer at the end.)

Woodlawn by the Numbers

A Neighborhood in Transition: From Exclusion to Empowerment

In the early 20th century, Woodlawn was almost entirely white, home to middle-class European immigrants and their descendants who enjoyed its tree-lined streets and proximity to the University of Chicago. Black families, migrating north during the Great Migration, were systematically excluded through racial covenants and discriminatory housing practices that kept many neighborhoods segregated.

That began to change after 1948, when the Supreme Court ruled restrictive covenants unenforceable. As African American families sought better housing and access to opportunity, they began moving into Woodlawn—often facing harassment, intimidation, and inflated rents. Many white residents responded by leaving the city altogether, moving to the suburbs in what became known as white flight.

Though the transition brought tension, it also marked the rise of a powerful movement for justice and community control. By the 1960s, Woodlawn had become a center of activism, faith, and self-determination. The Woodlawn Organization (TWO)—founded in 1961 by Rev. Arthur Brazier, Rev. Leon Finney Jr., and community organizer Saul Alinsky—emerged as a leading force in the national fight for fair housing, urban renewal, and political representation. TWO’s success inspired movements across the country, proving that organized residents could reclaim power and shape their own neighborhoods.

By the 1970s, Woodlawn had transformed into a proudly African American community—a neighborhood that turned exclusion into empowerment. Churches, block clubs, and local businesses became the anchors of stability and pride that defined its next generation.

Cultural Legacy and Landmarks

Shrine of Christ the King – 6401 S. Woodlawn Avenue
Originally St. Clara Church, this Renaissance-style structure was completed in 1923 and designed by architect Henry J. Schlacks. After a major fire in 2015, it was painstakingly restored and stands today as one of Woodlawn’s most striking architectural landmarks.

Hyde Park–Woodlawn YMCA – 6330 S. Stony Island Avenue
Built in the early 1900s, the YMCA has served generations of young people, offering recreation, education, and mentorship—an enduring part of the neighborhood’s social fabric.

Jackson Park – Portions within 6401 S. Stony Island Avenue
Much of Jackson Park lies within Woodlawn’s eastern boundary. Designed by Frederick Law Olmsted and Calvert Vaux, the park was the site of the 1893 World’s Columbian Exposition, a world event that helped define Chicago’s identity and placed Woodlawn on the map. Today, Jackson Park remains a central gathering space and is home to the future Obama Presidential Center, expected to bring renewed attention and investment to the area.

Notable Figures

Mahalia Jackson – The “Queen of Gospel” performed often in Woodlawn’s churches, her voice echoing through the South Side and shaping Chicago’s musical legacy.

Louis Farrakhan – The Nation of Islam leader’s ties to Woodlawn reflect its long history of religious and social activism.

Rev. Leon Finney Jr. – Pastor, activist, and community builder, Finney was instrumental in founding The Woodlawn Organization (TWO) and guiding decades of neighborhood development and advocacy. Also, the owner of Leon's Barbecue, once an iconic carryout restaurant on the south side of Chicago. 

Woodlawn Today

Woodlawn is once again at a turning point. The upcoming Obama Presidential Center, new housing developments, and strong resident-led initiatives are reshaping the community. Local schools, gardens, and small businesses reflect both progress and preservation—a balance between growth and honoring Woodlawn’s deep roots.

While issues of affordability, equity, and displacement remain front of mind, Woodlawn continues to lead with resilience and faith. Its history reminds us that community power can transform even the hardest challenges into opportunities for renewal.

Trivia Answer

Answer: The World’s Columbian Exposition of 1893, also known as the Chicago World’s Fair, helped define Woodlawn’s early development and set the stage for its rapid growth in the decades that followed.