Citadel Center

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.

The Singer Building is a skyscraper located at 120 S. State St. in the Loop community area of Chicago, Illinois. The ten-story building was designed by Mundie & Jensen and built from 1925 to 1926. The building's Gothic Revival design features terra cotta decorations, piers at the corners, and sets of three double-hung windows on each story separated by two thin piers. The Singer Corporation initially used the building as office space; the building has had many owners since the Singer Corporation left the building, and was nearly demolished in the 1970s. It is currently owned by FDN Network.The Singer Building was added to the National Register of Historic Places on February 10, 1983.

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 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 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.

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.

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 Everett McKinley Dirksen United States Courthouse, commonly referred to as the Dirksen Federal Building, is a skyscraper in the Chicago Loop at 219 South Dearborn Street. It was designed by Ludwig Mies van der Rohe and completed in 1964. The building is 384 feet (117 m) tall with 30 floors; it was named for U.S. Congressman Everett Dirksen. The building houses the United States Court of Appeals for the Seventh Circuit, the United States District Court for the Northern District of Illinois, the United States Bankruptcy Court, the United States Marshal for the Northern District of Illinois, United States Attorney for the Northern District of Illinois, and local offices for various court-related federal agencies, such as the Federal Public Defender, United States Probation Service, United States Trustee, and National Labor Relations Board. It is one of three buildings making up the modernist Chicago Federal Center complex designed by van der Rohe, along with Federal Plaza, the U.S. Post Office (Loop Station) and the Kluczynski Federal Building. Separate from the Federal Plaza, but opposite the Kluczynski Building across Jackson Boulevard, is the Metcalfe Federal Building.

Great Northern Hotel was a historic hotel in Chicago's Loop area. It was located at the northeast corner of Jackson Boulevard and Dearborn Street in Chicago, Illinois. The building was designed by Burnham and Root. They created a new design, with an urban office block floor plan that was free of historical or European influences. The site is now occupied by the Dirksen Federal Building.

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.

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