Chicago Military Academy

The Eighth Regiment Armory, located in the Black Metropolis-Bronzeville District of Chicago, Illinois, was the first armory in the United States built for an African-American military regiment, known as the "Fighting 8th". The building later was used by a division of the Illinois National Guard, and during World War I was incorporated into the US Infantry. After closing the armory in the early 1960s, it became the South Central Gymnasium. In 1999, following an extensive renovation, it was reopened as a public high school military academy. The restoration and conversion into a school has been recognized by the National Trust for Historic Preservation.The nearby Victory Monument honors the regiment for service during World War I. The armory was listed on the National Register of Historic Places on April 30, 1986, and was designated as a Chicago Landmark on September 9, 1998. It is one of nine landmark structures in the Black Metropolis-Bronzeville District. In currently houses the Chicago Military Academy.

The Sunset Cafe, also known as The Grand Terrace Cafe, was a jazz club in Chicago, Illinois operating during the 1920s, 1930s and 1940s. It was one of the most important jazz clubs in America, especially during the period between 1917 and 1928 when Chicago became a creative capital of jazz innovation and again during the emergence of bebop in the early 1940s. From its inception, the club was a rarity as a haven from segregation, since the Sunset Cafe was an integrated or "Black and Tan" club where African Americans, along with other ethnicities, could mingle freely with white Americans without much fear of reprisal. Many important musicians developed their careers at the Sunset/Grand Terrace Cafe.

The Martin Roche–John Tait House is a historic house located at 3614 S. Martin Luther King Drive in the Douglas community area of Chicago, Illinois. The house was the home of architect Martin Roche, half of prominent Chicago architectural firm Holabird & Roche, from 1888 until 1917. Roche designed the house for his sister Bridget Louise and brother-in-law John Tait; as he was unmarried and consequently a key part of their family, Roche moved into a third-floor suite to live with the couple. He gave the house a Romanesque design; the design has similarities with his work at Fort Sheridan at the time, though the Fort Sheridan homes are less plain. The flat, rough-coursed sandstone front facade of the house is a sharp contrast to the surrounding homes, many of which are Queen Anne designs with extensive detail work.The house was added to the National Register of Historic Places on November 8, 2000.

The Ida B. Wells-Barnett House was the residence of civil rights advocate Ida B. Wells (1862–1931) and her husband Ferdinand Lee Barnett from 1919 to 1930. It is located at 3624 S. Dr. Martin Luther King Jr. Drive in the Douglas community area of Chicago, Illinois. It was designated a Chicago Landmark on October 2, 1995. It was listed on the National Register of Historic Places and as a National Historic Landmark on May 30, 1974.

Erected in 1927, the Victory Monument, created by sculptor Leonard Crunelle, was built to honor the Eighth Regiment of the Illinois National Guard, an African-American unit that served in France during World War I. It is located in the Black Metropolis-Bronzeville District in the Douglas community area of Chicago, Illinois. The structure was added to the National Register of Historic Places on April 30, 1986. It was designated a Chicago Landmark on September 9, 1998. An annual Memorial Day ceremony is held at the monument.

Engine Company 21, organized in 1872, was the first Black fire company in the Chicago Fire Department. The company was known for arriving at fires quickly. The fire pole was invented by members of the company.

The Supreme Life Building is a historic insurance building located at 3501 S. Dr. Martin Luther King Drive in the Douglas community area of Chicago, Illinois. Built in 1921, the building served as the headquarters of the Supreme Life Insurance Company, which was founded two years earlier by Frank L. Gillespie. The company, originally known as the Liberty Life Insurance Company, was the first African-American owned insurance company in the northern United States. Since white-owned insurance firms regularly denied black customers life insurance when the firm was founded, the firm played an important role in providing life insurance to Chicago's African-American community. The company ultimately became the largest African-American owned business in the northern states and became a symbol of the predominantly black Bronzeville neighborhood's economic success from the 1920s to the 1950s.In the 1990s, the building was nearly demolished before it was purchased by the Black Metropolis Convention and Tourism Council. The group rehabilitated the building in 2005, and it now serves as the Bronzeville Visitor Information Center.The building was designated as a Chicago Landmark on September 9, 1998. It is one of nine buildings designated as part of the Black Metropolis-Bronzeville District.

The Chicago Defender Building is the former Jewish synagogue that housed the Chicago Defender from 1920 until 1960. It was designated a Chicago Landmark on September 9, 1998. The building is in the Black Metropolis-Bronzeville District in the Douglas community area of Chicago, Illinois at 3435 S. Indiana Ave. It was designed by Henry L. Newhouse. You can read more about the nine designated landmarks, including the Chicago Defender Building and Robert S. Abbott, the newspaper's publisher, in this document from the City of Chicago Department of Planning and Development, The Black Metropolis - Bronzeville District.

The Hammer / Palmer Mansion is a historic mansion at 3654-3656 S. Dr. Martin Luther King Jr. Drive in the Bronzeville section of Chicago. It was designed by William Wilson Clay of the firm Wheelock and Clay (Otis Leonard Wheelock) in the Queen Anne style and built in 1885. It is considered endangered.It was built for and home to justice D. Harry Hammer. It was also home to Lu Palmer and her husband. Obsidian House proposed renovating it opening it as a home for its collection on Black journalists. The organization secured a $1.25 million loan to purchase the property in 2021.

The Calumet/Giles Prairie District is a historic district in the South Side, Chicago community area of Chicago, Illinois, United States. The district was built between 1870 and 1910 by various architects. It was designated a Chicago Landmark on July 13, 1988.

Douglas, on the South Side of Chicago, Illinois, is one of Chicago's 77 community areas. The neighborhood is named for Stephen A. Douglas, Illinois politician and Abraham Lincoln's political foe, whose estate included a tract of land given to the federal government. This tract later was developed for use as the Civil War Union training and prison camp, Camp Douglas, located in what is now the eastern portion of the Douglas neighborhood. Douglas gave that part of his estate at Cottage Grove and 35th to the Old University of Chicago. The Chicago 2016 Olympic bid planned for the Olympic Village to be constructed on a 37-acre (15 ha) truck parking lot, south of McCormick Place, that is mostly in the Douglas community area and partly in the Near South Side.The Douglas community area stretches from 26th Street, south to Pershing Road along the Lake Shore, including parts of the Green Line, along State Street and the Metra Electric and Amtrak passenger railroad tracks, which run parallel to Lake Shore Drive. Burnham Park runs along its shoreline, containing 31st Street Beach. The community area also contains part of the neighborhood of Bronzeville, the historic center of black culture in the city, since the early 20th century and the Great Migration.

Pilgrim Baptist Church is a historic church located on the south side of Chicago, Illinois, USA. The landmarked building was originally constructed for a synagogue, Kehilath Anshe Ma'arav. The church is notable both as an architectural landmark and for the cultural contributions by the congregation of the church. Located at 3301 S. Indiana Ave, the church is in the heart of Chicago's Bronzeville neighborhood.