Battle of Fort Dearborn

18th Street station is a commuter rail station on the Near South Side of Chicago, at 18th Street near Calumet Avenue. It serves the Metra Electric Line north to Millennium Station and south to University Park, Blue Island, and South Chicago. For many Metra Electric trains, this is a flag stop, and the train will only stop there if specifically requested by a passenger. As of 2018, 18th Street is the 226th busiest of Metra's 236 non-downtown stations, with an average of 23 weekday boardings.The station is also occasionally served by trains of the South Shore Line to Gary and South Bend, Indiana, on an exceptional basis for Chicago Bears home games during football season. As part of a non-compete agreement with Metra, eastbound South Shore trains will not discharge passengers, and westbound trains will not receive passengers. The station was originally built by the Illinois Central Railroad (ICRR). The railroad was first built in 1907.

The United States Soccer Federation (USSF), commonly referred to as U.S. Soccer, is a 501(c)(3) nonprofit organization and the official governing body of the sport of soccer in the United States. Headquartered in Chicago, the federation is a full member of FIFA and governs American soccer at the international, professional, and amateur levels, including: the men's and women's national teams, Major League Soccer, National Women's Soccer League, youth organizations, beach soccer, futsal, Paralympic and deaf national teams. U.S. Soccer sanctions referees and soccer tournaments for most soccer leagues in the United States. The U.S. Soccer Federation also administers and operates the U.S. Open Cup and the SheBelieves Cup.

The William W. Kimball House is a private residence located at 1801 Prairie Avenue in the Near South Side neighborhood of Chicago, Illinois. It was added to the National Register of Historic Places on December 9, 1971.

The John J. Glessner House, operated as the Glessner House, is an architecturally important 19th-century residence located at 1800 S. Prairie Avenue, Chicago, Illinois. It was designed in 1885–1886 by architect Henry Hobson Richardson and completed in late 1887. The property was designated a Chicago Landmark on October 14, 1970. The site was listed in the National Register of Historic Places on April 17, 1970, and as a National Historic Landmark on January 7, 1976, and is maintained as a house museum.

Chicago Women's Park and Gardens is a 3.23 acre public sculpture garden in South Loop that honors the contributions of women throughout the history of Chicago. Landscape architect Mimi McKay and architect Tannys Langdon designed the space. Its "Helping Hands" sculpture by Louise Bourgeois honors Jane Addams. Its fieldhouse was formerly the National Vietnam Veteran’s Art Museum before the museum was relocated to Portage Park.

The Reid House is a historic house located at 2013 S. Prairie Avenue in the Near South Side community area of Chicago, Illinois. Built in 1894, the house was designed by the firm Beers, Clay and Dutton in the Classical Revival style. The house's design features a narrow entry portico with Ionic columns and terra cotta decorations, a fanlight and sidelights on the front door, a cornice with a modillion, and Adamesque ornaments. In addition, the house was the first residence built with a steel frame. Chicago businessman William Henry Reid owned the house, which he built to replace his previous home at the same location.The house was added to the National Register of Historic Places on August 21, 2003.

The Wheeler–Kohn House is a Queen Anne and Second Empire Style house in the Near South Side neighborhood of Chicago, Illinois, United States. The house was built in 1870 by Otis L. Wheelock for Calvin Wheeler. It was designated a Chicago Landmark on February 5, 1998, and it was listed on the U.S. National Register of Historic Places in 1999. The house currently serves as one of Chicago's few intimate bed and breakfast hotels, operating as the Wheeler Mansion.

The Henry B. Clarke House is a Greek Revival style home, now serving as a house museum in Chicago, Illinois, United States. Built around 1836, it is considered the oldest existing house built in Chicago. Henry Brown Clarke was a native of New York State who had come to Chicago in 1833 with his wife, Caroline Palmer Clarke, and his family. He was in the hardware business with William Jones and Byram King, establishing King, Jones and Company, and provided building materials to the growing Chicago populace. The house was built by a local contractor, probably John Rye, who later married the Clarkes' housemaid, Betsy. Originally built on a large lot near Michigan Avenue and 17th Street, it has been moved twice, most recently in 1977 to Indiana Avenue and 18th Street, near to its original location. In the mid-20th century, it was cared for by a church and its leader Bishop Ford, who spurred its preservation as the city's oldest home. Its current location in a park and gardens is part of the Prairie Avenue Historic District in the Near South Side community area.

The Prairie Avenue District is a historic district in the Near South Side community area of Chicago, Illinois. It includes the 1800 and 1900 blocks of South Prairie Avenue and the 1800 block of South Indiana, and 211-217 East Cullerton. It was the site of the Battle of Fort Dearborn and became the city's most fashionable residential district after the Great Chicago Fire. It was designated a Chicago Landmark on December 27, 1979. The district was added to the National Register of Historic Places on November 15, 1972. The John J. Glessner House, designed and built by Henry Hobson Richardson in 1885–1886 at 1800 S. Prairie Avenue, has been restored as a historic house museum, and is open for public tours. In 2006, the Prairie District Neighborhood Alliance, a non-profit organization was formed to provide representation for thousands of South Loop residents, including the Prairie Avenue District, Central Station, Museum Park, Motor Row, and the South Michigan Avenue Corridor, as well as other areas of the Near South Side.

New Chicago Bears Stadium is a planned stadium to be constructed in Chicago, Illinois. It will be home to the Chicago Bears of the NFL. It will have a capacity of 77,000. Opening is planned for 2028. It will be publicly owned.

Marriott Marquis Chicago is a 39-story hotel near McCormick Place. The hotel has 63 meeting rooms totaling 89,407 square feet of space, and is considered by some as an expansion of McCormick Place, given that the hotel and convention center are connected via an enclosed footbridge.

The Harriet F. Rees House (1888) is a historic residence in Chicago, Illinois, United States. Located on the historically important South Prairie Avenue, the Rees house was built for the widow of a real estate developer. In 2014, the house and its coach house were moved a block north in the Prairie Avenue District to make way for expanded entertainment facilities near McCormick Place.