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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.

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 Battle of Fort Dearborn (sometimes called the Fort Dearborn Massacre) was an engagement between United States troops and Potawatomi Native Americans that occurred on August 15, 1812, near Fort Dearborn in what is now Chicago, Illinois (at that time, wilderness in the Illinois Territory). The battle, which occurred during the War of 1812, followed the evacuation of the fort as ordered by the commander of the United States Army of the Northwest, William Hull. The battle lasted about 15 minutes and resulted in a complete victory for the Native Americans. After the battle, Fort Dearborn was burned down. Some of the soldiers and settlers who had been taken captive were later ransomed. Following the battle, the federal government became convinced that all Indians had to be removed from the territory and the vicinity of any settlements, as settlers continued to migrate to the area. The fort was rebuilt in 1816.

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.

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 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 B.F. Goodrich Company Showroom is a B.F. Goodrich Company showroom located at 1925 S. Michigan Ave. in Chicago's Motor Row District. The showroom was built in 1911 to sell B.F. Goodrich tires and distribute them to other Chicago retailers. Christian Albert Eckstorm, a Chicago architect who designed many of the Motor Row showrooms, designed the building. The Second Empire building features a mansard roof with a terra cotta balustrade, three dormers with terra cotta frames, a partial cornice, and large second-story windows with arched lintels. Like most Motor Row buildings, its architectural ornaments are primarily located near the top of the building. B.F. Goodrich used the showroom until 1929.The showroom was added to the National Register of Historic Places on May 28, 2009.

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 Maxwell-Briscoe Automobile Company Showroom is a historic automobile showroom located at 1737 S. Michigan Avenue in Chicago's Motor Row District. The showroom was built in 1909 for the Maxwell-Briscoe Motor Company, which was founded in 1904 by Jonathan D. Maxwell and Benjamin Briscoe. William Ernest Walker, a Chicago architect who specialized in large-scale commercial buildings, designed the showroom. The four-story building is divided by brick piers; the ground floor features large plate-glass windows designed to showcase the company's automobiles, while the upper floors feature banks of double-hung and triple-hung windows between the piers. The building uses terra cotta extensively for decoration; a terra cotta stringcourse encircles the building above the first floor, terra cotta pediments and sills frame the window banks, and a terra cotta frieze runs below the roof line. Maxwell and Briscoe used the building as a showroom until 1915; it is one of the oldest surviving auto showrooms on Motor Row.The showroom was added to the National Register of Historic Places on November 18, 2002.

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.