Bordered by 35th and 43rd Streets, Cottage Grove Avenue and Lake Shore Drive, the Oakland area was developed between 1872 and 1905.

City transportation was greatly improved in the area when the Illinois Central Railroad terminal was constructed at 39th Street and Cottage Grove Avenue in 1881.

Located at 700 E. Oakwood Boulevard,[6] the historic landmark designed by Frank Lloyd Wright now serves as the home of Northeastern Illinois University's Center for Inner City Studies.

[7] By the 1930s, The area experienced the greatest diversity, with a mixture of African-Americans, Germans, Jews, English, Irish, Canadians, and Japanese.

As tensions flared, White residents resorted to violence and restrictive covenants to prevent African-Americans from moving into the area.

[citation needed] Due to the increase of Irish immigrants in the area, numerous single-family houses and apartments were constructed to accommodate them.

The notorious Black P. Stone Nation (later renamed El Rukn) had the largest presence in the area.

By 1979, the city of Chicago had demolished dilapidated buildings, in return leaving vacant lots scattered throughout the area.

Beginning in 1994, the North Kenwood–Oakland Conservation Community Council, led by Shirley Newsome, cosponsored the Kenwood-Oakland Parade of Homes, which helped the further development of single-family houses, townhouses, and rehabbed buildings.

[13] The four of the original six Lake Michigan High-Rises were vacated in late 1985[14][15][16] and sat vacant for 13 years until being imploded by the housing authority in December 1998.

[20] The Oakland community area has supported the Democratic Party in the past two presidential elections by overwhelming margins.