Urban Prep Charter Academy succeeded Englewood High School, Englewood Technical Prep Academy and TEAM Englewood Academy High School in Chicago. Englewood was a public four-year high school located in the Englewood neighborhood on the South Side of Chicago, Illinois, United States. Opened in 1874, Englewood was owned and operated by the Chicago Public Schools (CPS) system. Englewood High School closed in 2008. The building is occupied by school in the Urban Prep Academy network. The school is a public charter high school for young men that opened in 2006.

Englewood is a neighborhood and community area located on the South Side of Chicago, Illinois, United States. It is also the 68th of the 77 community areas in the city. At its peak population in 1960, over 97,000 people lived in its approximately 3 square miles (7.8 km2), but the neighborhood's population has since dropped dramatically. In 2000, it had a population of approximately 40,000 inhabitants, and the 2010 census indicated that its population has further declined to approximately 30,000. Englewood to the north, 75th Street to the south, Racine Avenue to the west, and an irregular border that wends along the Metra Railroad Tracks to the east. On the southwest side of Chicago lies West Englewood, which is generally lumped in with Englewood by Chicagoans. Englewood, a low-income African-American community, has a high rate of foreclosed properties due to its population drop.