Singer Building (Chicago)

The Waterman Building is a historic building on State Street in Chicago's Loop. Designed by Holabird and Roche, construction began in 1919 was completed in 1920. The first floor originally housed the Waterman Pen Company's Chicago store, while Waterman's offices were located on upper floors.

The Citadel Center is a 580 ft (177m) tall skyscraper in the Chicago Loop. It is located at 131 S. Dearborn St., Chicago, Illinois 60603, and was designed by Spanish architect Ricardo Bofill and his firm, Taller de Arquitectura. As of 2020, Citadel Center is the 65th tallest building in Chicago. It was completed in 2003 and has 37 above ground floors and 3 below (40 total) covering 1,536,548 sq. ft. It was certified as LEED Gold in 2017. A limited-edition cast of the Winged Victory of Samothrace, one of the world's most famous sculptures, was displayed in the lobby, and removed in late 2018. The original is on display at the Louvre Museum. The lobby previously featured a curved wall of Padauk red wood.The Citadel Center was the first building in Chicago to use a raised-floor pressurized plenum system, allowing for more individual control of climate by the use of adjustable floor diffusers.

The Century Building is a high rise office building in Chicago's Loop. It was designed by Holabird & Roche, and was built in 1915. It is a contributing property to the Loop Retail Historic District. The building is representative of the transition of Chicago high rise design from the Chicago School to Art Deco, and its north and east facades feature Neo-Manueline ornamentation. It is owned by the General Services Administration and currently sits vacant.

The Berghoff restaurant, at 17 West Adams Street, near the center of the Chicago Loop, was opened in 1898 by Herman Joseph Berghoff and has become a Chicago landmark.

Monroe (also Monroe/State) is an "L" station on the CTA's Red Line. The station opened on October 17, 1943, as part of the State Street subway. The station is located in the Chicago Loop, and is open 24/7.

CIBC Theatre is a theater located at 18 West Monroe Street in the Loop area of downtown Chicago. It is operated by Broadway In Chicago, part of the Nederlander Organization. Opened in 1906 as the Majestic Theatre, it currently seats 1,800 and for many years has presented Broadway shows. In its early years, the theater presented vaudeville celebrity acts. In the 1940s, the theater became part of the Shubert Organization and was known as the Sam Shubert Theatre. Since the 1990s, it has been owned by Nederlander, which refurbished and restored the building and sells naming rights; it has been named for LaSalle Bank, then Bank of America. The PrivateBank acquired the naming rights in December 2015, later becoming CIBC Bank USA, and in 2017, the theatre's name changed to reflect the new bank ownership.

214 South State Street is a building in Chicago's Loop, which was designed by C. M. Palmer and was built in 1887. The building is owned by the General Services Administration and currently sits vacant.

The Consumers Building is a Chicago school high rise office building in Chicago's Loop. It was designed by Jenney, Mundie & Jensen, and was built by Jacob L. Kesner in 1913. The building is owned by the General Services Administration and currently sits vacant.

The Palmer House – A Hilton Hotel is a historic hotel in Chicago's Loop area. It is a member of the Historic Hotels of America program of the National Trust for Historic Preservation. The Palmer House was the city's first hotel with elevators, and the first hotel with electric light bulbs and telephones in the guest rooms. Although the hotel has been dubbed the longest continuously operating hotel in North America, it closed in March 2020 due to the COVID-19 pandemic and reopened on June 17, 2021.

The Chicago Federal Building in Chicago, Illinois was constructed between 1898 and 1905 for the purpose of housing the Midwest's federal courts, main post office, and other government bureaus. It stood in The Loop neighborhood on a block bounded by Dearborn, Adams and Clark Streets and Jackson Boulevard. The site held an 1880 post office, courthouse and customhouse which was cleared to make way for the new building. The 1905 building was itself demolished in 1965 and replaced with the Kluczynski Federal Building. The push for a new building was spearheaded by postmaster Washington Hesing with backing by civic leaders and Illinois's members of Congress. The explosion of Chicago's population, especially after the World's Columbian Exposition of 1893, strained the earlier facility beyond capacity. When the Exposition began, the Post Office Department in Chicago employed 998 clerks and 935 carriers. By the time Congress approved funding for a new building, the post office had expanded to 1,319 clerks and 1,096 carriers. Other agencies housed in the building complained of poor planning and shoddy construction which resulted in crumbling plaster, broken plumbing and flooding.The new building was designed in the Beaux-Arts style by architect Henry Ives Cobb. The floorplan was a six-story Greek cross atop a two-story base with a raised basement. The building was capped by a dome at the crossing that held an additional eight floors of office space in its drum for a total of 16 floors. The gilt dome extended 100 ft (30 m) above the drum.

The Benson & Rixon Building is a Streamline Moderne building in Chicago's Loop. It was designed by Alfred S. Alschuler, and was built in 1937.

The Chicago Tunnel Company was the builder and operator of a 2 ft (610 mm) narrow-gauge railway freight tunnel network under downtown Chicago, Illinois. This was regulated by the Interstate Commerce Commission as an interurban even though it operated entirely under central Chicago, did not carry passengers, and was entirely underground. It inspired the construction of the London Post Office Railway.