Oakland, located on the South Side of Chicago, Illinois, USA, is one of 77 officially designated Chicago community areas. Bordered by 35th and 43rd Streets, Cottage Grove Avenue and Lake Shore Drive, The Oakland area was constructed between 1872 and 1905. Some of Chicago's great old homes may be seen on Drexel Boulevard. The late 19th-century Mon…Oakland, located on the South Side of Chicago, Illinois, USA, is one of 77 officially designated Chicago community areas. Bordered by 35th and 43rd Streets, Cottage Grove Avenue and Lake Shore Drive, The Oakland area was constructed between 1872 and 1905. Some of Chicago's great old homes may be seen on Drexel Boulevard. The late 19th-century Monument Baptist Church on Oakwood Blvd. is modeled after Boston's Trinity Church. Oakwood/41st Street Beach in Burnham Park is at 4100 S. Lake Shore Drive. With an area of only 0.6 sq mi Oakland is the smallest community area by area in Chicago.