Oakland is Chicago community area #36, a small lakefront community on the South Side between 35th and 43rd streets. At about 0.6 square miles it is the smallest community area by land area. CMAP estimates its population at 6,937 (2020–2024 ACS).
| Fact | Details |
|---|---|
| Community area number | 36 |
| Side of the city | South Side |
| Population (2020–2024 ACS estimate, CMAP) | 6,937 |
| Neighborhoods within | Oakland, North Kenwood–Oakland area, part of Bronzeville |
| Main L and Metra stations | None inside the area |
| Major parks | Burnham Park, including Oakwood/41st Street Beach |
Boundaries
Oakland lies between 35th and 43rd streets, from Cottage Grove Avenue east to Lake Shore Drive. Douglas is to the north and west, and Kenwood is to the south.
Neighborhoods within Oakland
Oakland is often paired with North Kenwood, and local groups have worked across both. The former Ida B. Wells and Darrow Homes site is also in Oakland.
History
Charles Cleaver bought 22 acres in 1851 and built a soap factory and a company town called Cleaverville. Developers renamed the area Oakland in 1871. An Illinois Central terminal opened at 39th and Cottage Grove in 1881, and the busy junction became known as the “Five Crossings.”
African Americans arrived in large numbers during 1916–1920, and by 1950 the area was 77 percent Black. Decline followed in the 1970s. In the 1990s, the Kenwood-Oakland Community Organization and a conservation council led rebuilding efforts, and the Lake Michigan High-Rises were imploded in 1998.
Landmarks and parks
- Abraham Lincoln Center, 700 E. Oakwood Boulevard, founded in 1905 and designed by Frank Lloyd Wright, now NEIU’s Center for Inner City Studies.
- Monument Baptist Church on Oakwood Boulevard.
- Historic homes on Drexel Boulevard; part of the area became a Chicago Landmark in 1992.
- Oakwood/41st Street Beach in Burnham Park.
Getting there
Oakland has no L or Metra station of its own. The nearest L stops are Green Line stations in neighboring Grand Boulevard, such as 43rd Street.
Frequently asked questions
What is the smallest community area in Chicago?
Oakland, at about 0.6 square miles, is the smallest by land area.
What was Oakland called before 1871?
It began as Cleaverville, a company town built by soap maker Charles Cleaver.
Is there a beach in Oakland?
Yes. Oakwood/41st Street Beach is in Burnham Park at 4100 S. Lake Shore Drive.
What were the “Five Crossings”?
The nickname for the busy junction at 39th Street and Cottage Grove that grew up around an 1881 Illinois Central terminal.
Related guides
- Best of Bronzeville
- Douglas (#35) community area guide
- Grand Boulevard (#38) community area guide
- Kenwood (#39) community area guide
- CTA buses guide
- All 77 Chicago community areas
Sources
- CMAP Community Data Snapshot: Oakland (June 2026 release)
- Encyclopedia of Chicago: Oakland
- Wikipedia: Oakland, Chicago
Last updated: October 31, 2026