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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.

Wintrust Arena at McCormick Square, previously referred to as DePaul Arena or McCormick Place Events Center, is a 10,387-seat sports venue in Chicago's Near South Side community area that opened in 2017. It is the current home court for the men's and women's basketball teams of DePaul University and serves as an events center for McCormick Place. It also is the home of the Chicago Sky of the Women's National Basketball Association (WNBA).The arena was announced in May 2013, with construction planned to begin in 2014, and use expected to begin with the 2016–17 season. The start of construction was delayed to November 2015, with completion delayed until the 2017–18 season. Although DePaul had been seeking a new home arena — it used Allstate Arena in suburban Rosemont starting 1980 — it rejected a November 2012 ten-year offer to play rent free at the United Center. Instead, DePaul planned to use Allstate Arena on a recurring one-year basis until it had a new home. On November 16, 2016, DePaul and the Metropolitan Pier and Exposition Authority (MPEA or "McPier") announced that the new event center at McCormick Square would be called Wintrust Arena. The announcement came after the signing of a letter of intent that contemplated a definitive 15-year sponsorship agreement between DePaul and Wintrust.

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 Vesta Battery Corporation (1897–1964), known until 1929 as the Vesta Accumulator Company, was an American manufacturer of automobile electrical gear. Based in Chicago, Illinois, the company was founded by a former garment worker in 1897. Originally intending to sell parts for electric bicycles, the company quickly diversified to manufacture electrical goods for the burgeoning automobile industry. At its peak, the company had branches in ten American cities. Vesta continued operations until it was purchased by Associated Battery Makers in 1964. Its 1913 factory in Chicago is listed on the National Register of Historic Places.

The R.R Donnelley Printing Plant, sometimes known as the Calumet Plant or the Lakeside Plant and now known as the Lakeside Technology Center, was built between 1912 and 1929 to house the operations of the RR Donnelley printing company. In 1993, the plant was closed after the discontinuation by Sears, Roebuck and Co. of its mail-order catalog, which had been the last major account printed there. In 1999 the building was retrofitted and is currently owned by Digital Realty Trust operating as a carrier hotel and data center. The newly outfitted building was the first and largest planned carrier hotel in the United States.The building was designed by Howard Van Doren Shaw to be a fireproof design of poured reinforced concrete columns and an open-shell concrete floor. Although considered to be expensive by the standards of that time, T.E. Donnelley agreed that the support would be needed for the many tons of paper they used and large presses they operated. Supported by 4,675 steel-reinforced concrete columns, this type of construction not only served the Donnelley well, it also provided the perfect infrastructure for future tenants. To further the building's support structure, reinforcing bars, normally laid perpendicular, were laid at various angles enabling the floors to bear loads of at least 250 pounds per square foot. Current major tenants of the building include the Chicago Mercantile Exchange, Telx, Equinix, Steadfast Networks and CenturyLink. Exterior ornaments depict symbols of printing history. Portions of the building, including the interior Memorial Library, were designed by architect Charles Klauder.

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 Lexington Hotel was a ten-story hotel in Chicago at 2135 S. Michigan Avenue that was built in 1892 (or 1891) for attendees of the Columbian Exposition. The hotel is notable for being Al Capone's primary residence from July 1928 until his arrest in 1931. After the Saint Valentine's Day Massacre, some commenters called the hotel "Capone's Castle." It was later renamed "The New Michigan Hotel" and functioned as a brothel with 400 rooms. The hotel closed in 1980. On April 21, 1986, locked vaults found in the hotel were the subject of a live television program called The Mystery of Al Capone's Vaults, which received 30 million viewers. The building was demolished in 1995, despite its presence on the list of Chicago landmarks and the National Register of Historic Places. The location where the hotel once stood is currently the site of a 296 unit residential high rise called "The Lex" that was completed in 2012.

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.

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.

The Motor Row District is a historic district in Chicago's Near South Side community area. Motor Row includes buildings on Michigan Avenue between 2200 and 2500 south, directly west of McCormick Place convention center, and 1444, 1454, 1737, 1925, 2000 S. Michigan Ave., as well as 2246-3453 S. Indiana Ave., and 2211-47 S. Wabash Ave. The district was built between 1905 and 1936 by a number of notable architects. Auto rows developed in numerous US cities shortly after 1900 as car companies sought to create districts where the sale and repair of cars could become an easy urban shopping experience. At its peak, as many as 116 different makes of automobiles were sold and repaired on Motor Row. Current-day marques that formerly had showrooms on Motor Row included Ford, Buick, Fiat, and Cadillac. Other marques with showrooms there that have since dissolved include Hudson, Locomobile, Marmon, and Pierce-Arrow. Currently, only one car dealer (Fiat/Alfa Romeo) still stands in Motor Row while the remaining buildings have been or are being redeveloped into condominiums, nightclubs, and retail storefronts.