Oakland (Lake Park): Chicago’s Historic Lakeside Gem

Nestled along the shores of Lake Michigan, Oakland is one of Chicago’s most historic and architecturally rich neighborhoods. Bounded by 35th Street to the north, Pershing Road to the south, Cottage Grove Avenue to the west, and Lake Michigan to the east, Oakland boasts a deep cultural legacy and a strong sense of community. Once a retreat for Chicago’s elite, the neighborhood has evolved over the decades, witnessing waves of change, challenges, and revitalization efforts that continue today. Today, this area is also known as Lake Park.

Oakland by the Numbers

Origins and Early History

In the mid-19th century, Oakland (Lake Park) was developed as a fashionable residential area for Chicago’s upper class. With its proximity to the lake and grand mansions lining Drexel Boulevard, it was a sought-after address for wealthy businessmen and professionals. The neighborhood’s development was closely tied to the expansion of Chicago’s streetcar system, which allowed easy access to downtown. As the city grew, Oakland became a vibrant, diverse community, welcoming new residents and adapting to the changing social and economic landscape.

Aldine Square circa 1920

Transformation and Evolution

By the early 20th century, Oakland (Lake Park) had begun transitioning from an elite residential enclave into a more diverse urban neighborhood. Waves of migration brought new residents, including working-class families and African Americans seeking opportunities in Chicago. During World War I African Americans began taking up residence in this community and by the 1920s many black families moved into the neighborhood despite several objections from white residents that tried to enforce racial covenants.  The community experienced economic shifts throughout the decades, and by the mid-20th century, disinvestment and urban renewal efforts led to significant changes in the neighborhood’s landscape. However, Oakland (Lake Park) has seen renewed interest and revitalization in recent years, with restoration projects, new developments, and community-driven initiatives shaping its future. 

One of the major landmarks in the neighborhood was the Oakland Square Theater, located at 3947 S. Drexel Blvd (near Oakwood and Drexel). Opened in 1915, the theater was a hub for fine cinema and the arts, drawing residents from across the South Side for decades. However, by the late 1960s, increasing crime and social unrest contributed to its closure in March 1968. That same year, the building found new life as the Afro Arts Theater, a cultural space dedicated to African American theater and the arts. The Afro Arts Theater was a beacon of creativity and community engagement until it closed in 1971, after which the building remained abandoned for several years.

In 1978, the theater building was acquired by the El Rukns, a faction of the Black P. Stones, who converted it into their headquarters, known as “The Fort.” During this period, Oakland (Lake Park), like many South Side neighborhoods, struggled with gang influence and economic decline. The El Rukns maintained significant control over parts of the neighborhood, regulating the drug trade and imposing their own order on local groups, including factions of the Gangster Disciples. Despite this, they famously resisted the influx of crack cocaine into the community, enforcing strict rules against its sale. This dominance lasted through much of the 1980s, until federal raids in 1989 led to the dismantling of their operations. The Fort was demolished in 1990, marking a turning point in Oakland’s history and paving the way for future redevelopment efforts.

Historical Landmarks and Structures

Oakland (Lake Park) is home to several notable landmarks that reflect its historic and cultural significance:

• Stephen A. Douglas Tomb and Memorial – The final resting place of Stephen A. Douglas, the U.S. senator known for his debates with Abraham Lincoln, this historic site is located along 35th Street near Lake Michigan.
  
• Drexel Boulevard – Once a grand boulevard lined with opulent mansions, it remains a key feature of the neighborhood, showcasing historic architecture and scenic beauty.
• Oakland Shoreline – A section of Chicago’s lakefront that offers stunning views of the skyline and serves as a popular spot for recreation.
• Oakland Square Theater - The 1,525-seat Oakland Theatre was opened on March 4, 1916 with William S. Hart in “Hell’s Angels” & Mable Normand in “Bright Lights”. It was designed by Henry L. Newhouse for the Ascher Brothers circuit.
  
  

Historical Figures

Oakland (Lake Park) has been home to several influential figures who have left their mark on Chicago and beyond:

• John J. Egan – A Catholic priest and social activist who worked extensively on housing and civil rights issues in Chicago, advocating for community development and social justice.
  
  
• Samuel Ellis – The land that is now the Oakland (Lake Park) neighborhood was first settled by Samuel Ellis (Ellis Avenue is named after him) in the year 1831 as he purchased 135 acres of property along the lakefront.  Ellis also had a tavern where present day 35th and Lake Park Avenue are located.
  
  
• Richard B. Ogilvie – Former Illinois governor known for his work on modernizing state government and infrastructure projects.
  
  

Historical Events

Oakland (Lake Park) has played a role in several significant but lesser-known historical events:

• The South Park Commission's Boulevard System (Late 19th Century) – Oakland was a key part of Chicago’s early park and boulevard system, designed to create scenic green spaces throughout the South Side. The neighborhood’s location along Drexel Boulevard made it an integral piece of this urban planning effort.
  
  
• Civil Rights Housing Struggles (1960s-1970s) – Like many South Side communities, Oakland was a focal point in battles for fair housing, as activists worked to end discriminatory practices and improve living conditions for African American residents.
  
  
• Urban Renewal and Preservation Efforts (1980s-Present) – Oakland has undergone waves of redevelopment, with efforts to restore historic homes, revitalize the lakefront, and attract new investment while maintaining its historic character.
  
  

Current Trends and Redevelopment

Today,Oakland (Lake Park) is experiencing a period of transformation, blending its rich history with modern developments:

• Restoration of Historic Homes – Many of the neighborhood’s historic greystones and mansions are being restored, attracting new residents and preserving Oakland’s architectural heritage.
  
  
• Lakefront Development – Improvements to the Oakland shoreline and park spaces have enhanced recreational opportunities and increased interest in the area.
  
  
• Community Initiatives – Local organizations and residents are actively working on initiatives to support economic development, affordable housing, and cultural programming.
  
  

Conclusion

Oakland (Lake Park) is a neighborhood deeply rooted in Chicago’s history, with a past shaped by social change, architectural beauty, and civic activism. While it has faced challenges over the years, today it stands as a testament to resilience and renewal. Whether exploring its historic boulevards, enjoying its lakefront views, or engaging with its vibrant community, Oakland (Lake Park) remains a unique and essential part of Chicago’s ever-evolving story.