Washington Park National Bank Building

Cottage Grove (formerly East 63rd-Cottage Grove) is an 'L' station and the current terminus of the CTA Green Line's East 63rd branch, located in the Woodlawn neighborhood. The station, situated at 800 E. 63rd Street, opened on April 23, 1893. This station is the current terminal of the East 63rd branch of the Green Line, and the easternmost station on the 'L' system.

The Strand Hotel is a historic apartment hotel at 6315-6323 S. Cottage Grove Avenue in the Woodlawn neighborhood of Chicago, Illinois. Opened in 1915, the hotel offered both traditional guest rooms and long-term residences for customers who sought luxury amenities in apartment-style housing. Architects Davis & Davis designed the Classical Revival building, which has a red brick exterior with a terra cotta clad first floor, piers outlined in terra cotta, and an entablature and cornice at its roof. The hotel included a restaurant and banquet hall, the latter of which was used as a live music venue for many years. Once part of a major commercial district in Woodlawn, the hotel is now one of its few remnants and the only surviving apartment hotel building in the neighborhood. The hotel was added to the National Register of Historic Places on January 29, 2013.

The Tivoli Theatre was a movie palace at 6323 South Cottage Grove Avenue, at East 63rd Street, in the Woodlawn neighborhood of Chicago's South Side. It was the first of the "big three" movie palaces built by the Balaban & Katz theatre chain run by brothers A. J. Balaban, Barney Balaban and their partner Sam Katz, who were also owners of the Rivera Theater (North Side) and the Central Park Theater (West Side), that opened on 16 February 1921.

The Sonia Shankman Orthogenic School, also known simply as the Orthogenic School or informally as the O-School, is a therapeutic day school for children and adolescents typically classified as emotionally challenged. The O-School specializes in the treatment of youth and help them with their behavioral and emotional problems. The school is located adjacent to the campus of the University of Chicago (UC). The school works with many schools and universities, and has affiliation with several Chicago area schools including the Family Institute at Northwestern University, the School of Social Service Administration of the UC, and the Jane Addams School of Social Work of the University of Illinois at Chicago.

Cosmopolitan Church of Prayer is a Chicago church founded by gospel singer and pastor Charles G. Hayes.

Washington Park Race Track was a popular horse racing venue in the Chicago metropolitan area from 1884 until 1977. It had two locations during its existence. It was first situated in what is the current location of the Washington Park Subdivision of the Woodlawn community area of Chicago in Cook County, Illinois, United States. This is located immediately south of both the current Washington Park community area and Washington Park. The track was later relocated to Homewood, Illinois, which is also in Cook County. The original track and its accompanying Jockey Club were social draws in the late 19th century, but modern developments and changes in the law led to the decline of both. In its prime, the track was an especially important social gathering place on opening day and the day of the American Derby, which ranked as one of Horse racing's highest purses. The Jockey club, designed by Solon Spencer Beman, hosted a social gathering led by General Philip Sheridan who was an early leader of the track and club. The track was closed and reopened according to the contemporary state and local laws on gambling and eventually waned in popularity and social importance. Over the years, numerous famous horses and jockeys appeared at the track. In the 19th century, notable horses of the time, such as Emperor of Norfolk and Domino raced. In the 20th century, some of the most notable Thoroughbreds to race at Washington Park included Triple Crown winners Citation and Whirlaway. Other notable horses included Native Dancer and Swaps, who each won legs of the Triple Crown. Jockey Eddie Arcaro won both the 1948 and 1953 American Derby races at the track. In addition to the American Derby, several other notable graded stakes races were run at the track such as the Stars and Stripes Turf Handicap and the Washington Park Handicap. In addition, notable match races were held at the track.

Midway Gardens (opened in 1914, demolished in 1929) was a 360,000 square feet indoor/outdoor entertainment facility in the Hyde Park neighborhood on the South Side of Chicago. It was designed by architect Frank Lloyd Wright, who also collaborated with sculptors Richard Bock and Alfonso Iannelli on the famous "sprite" sculptures decorating the facility. Designed to be a European–style concert garden with space for year-round dining, drinking, and performances, Midway Gardens hosted notable performers and entertainers but struggled financially and the structure was torn down in October 1929.

The Lorado Taft Midway Studios are a historic artist studio complex at South Ingleside Avenue and East 60th Street, on the campus of the University of Chicago on the South Side of Chicago. The architecturally haphazard structure, originating as two converted barns and a Victorian house, was used from 1906 to 1929 as the studio of Lorado Taft (1860-1936), one of the most influential sculptors of the period. A National Historic Landmark, it now houses the university's visual arts department.

Woodlawn, on the South Side of Chicago, Illinois, is one of Chicago's 77 community areas. It is bounded by Lake Michigan to the east, 60th Street to the north, Martin Luther King Drive to the west, and 67th Street to the south. Both Hyde Park Career Academy and the all-boys Catholic Mount Carmel High School are in this neighborhood; much of its eastern portion is occupied by Jackson Park. The Woodlawn section of the park includes the site of the planned Obama Presidential Center, an estimated $500 million investment. The northern edge of Woodlawn contains a portion of the campus of the University of Chicago.

Fountain of Time, or simply Time, is a sculpture by Lorado Taft, measuring 126 feet 10 inches (38.66 m) in length, situated at the western edge of the Midway Plaisance within Washington Park in Chicago, Illinois, in the United States. The sculpture is inspired by Henry Austin Dobson's poem "Paradox of Time". Its 100 figures passing before Father Time were created as a monument to the 100 years of peace between the United States and the United Kingdom following the Treaty of Ghent in 1814. Father Time faces the 100 from across a water basin. The fountain's water was turned on in 1920, and the sculpture was dedicated in 1922. It is a contributing structure to the Washington Park United States Registered Historic District, which is a National Register of Historic Places listing. Part of a larger beautification plan for the Midway Plaisance, Time was constructed from a new type of molded, steel-reinforced concrete that was claimed to be more durable and cheaper than alternatives. It was said to be the first of any kind of finished work of art made of concrete. Before the completion of Millennium Park in 2004, it was considered the most important installation in the Chicago Park District. Time is one of several Chicago works of art funded by Benjamin Ferguson's trust fund. Time has undergone several restorations because of deterioration and decline caused by natural and urban elements. During the late 1990s and the first few years of the 21st century it underwent repairs that corrected many of the problems caused by these earlier restorations. Although extensive renovation of the sculpture was completed as recently as 2005, the supporters of Time continue to seek resources for additional lighting, and the National Trust for Historic Preservation has nominated it for further funding.

The Washington Park Subdivision is the name of the historic 3-city block by 4-city block subdivision in the northwest corner of the Woodlawn community area, on the South Side of Chicago in Illinois that stands in the place of the original Washington Park Race Track. The area evolved as a redevelopment of the land previously occupied by the racetrack. It was originally an exclusively white neighborhood that included residential housing, amusement parks, and beer gardens. During the late 1920s and 1930s, the area became the subject of discriminatory twenty-year covenants (private real-estate agreements), which at first had been upheld by the United States Supreme Court but were later determined to be unenforceable by the court, beginning with a challenge in a seminal case brought by Carl Hansberry. The case is a vital part of legal studies and considered an important part of a broad class of histories. The play Raisin in the Sun is based on Lorraine Hansberry's struggles in this neighborhood.

The Crown Family School of Social Work, Policy and Practice, formerly called the School of Social Service Administration (SSA), is the school of social work at the University of Chicago.