The Palmer House Hilton

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.

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.

The Silversmith Hotel is a boutique hotel located in downtown Chicago, Illinois. It occupies the historic Silversmith Building, designed in 1896 by Peter J. Weber of the architectural firm of D.H. Burnham and Company, who also designed the Fisher Building. The building's architecture reflects the transition from Romanesque Revival architecture to Chicago school architecture. The Silversmith Building was listed on the National Register of Historic Places in 1997.It became a member of the National Registry of the Historic Hotels of America in 2016.

Adams/Wabash is an 'L' station serving the CTA's Brown, Green, Orange, Pink, and Purple Lines. Until 1963, it also served interurban trains of the Chicago North Shore and Milwaukee Railroad. It is the closest CTA station to Symphony Center, home of the Chicago Symphony Orchestra, and the Art Institute of Chicago.

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 Haskell-Barker-Atwater Buildings are a trio of buildings located in the Loop community area of Chicago that were together declared a Chicago Landmark in 1996. The buildings, constructed between 1875 and 1877, represent some of the last remaining pre-skyscraper architecture in the East Loop. The bottom two floors of the Haskell building's facade were completely remodeled and spanned with decorative ironwork in 1896 by Louis Sullivan.

Mid-Continental Plaza is a 583 ft (178m) tall skyscraper in Chicago, Illinois. It was completed in 1972 and has 49 floors. Shaw and Associates designed the building, which is the 62nd tallest building in Chicago. It was originally planned as two 40-story black glass towers. The top 10 floors have been converted to condominiums called The Park Monroe.

MacCormac College is a private two-year college in Chicago, Illinois. The college is accredited by the Higher Learning Commission and approved by the National Court Reporters Association and American Bar Association. MacCormac offers associate degree programs in court reporting, criminal justice, paralegal studies, business administration, and entrepreneurship. The school is located in downtown Chicago, at 29 East Madison Street, on the second floor of the Historic Heyworth building.

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 Jewelers Building at 15–17 Wabash Avenue between East Monroe and East Madison Streets in the Loop community area of Chicago in Cook County, Illinois, United States was built in 1881/82 and was designed by Dankmar Adler and Louis Sullivan. It is the only example of the early work of Adler & Sullivan that survives in the Loop. It is also known as the Iwan Ries Building, and the "Little" Jewelers Building to distinguish from the larger structure at 35 East Wacker Drive, which was built in 1925–27. The building is a common loft building in construction and plan, but its facade departs dramatically from others of its type. An open exterior, using cast iron mullions rather than masonry piers in the central bay, and Sullivan's stylized floral ornament provide distinction.The building was listed on the National Register of Historic Places on August 7, 1974, and was designated a Chicago Landmark on December 18, 1981. It is located in Chicago's Jewelers Row District.

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 Sullivan Center, formerly known as the Carson, Pirie, Scott and Company Building or Carson, Pirie, Scott and Company Store, is a commercial building at 1 South State Street at the corner of East Madison Street in Chicago, Illinois. Louis Sullivan designed it for the retail firm Schlesinger & Mayer in 1899 and later expanded it before H.G. Selfridge & Co. purchased the structure in 1904. That firm occupied the structure for only a matter of weeks before it sold the building (the land under it was owned at the time by Marshall Field) to Otto Young, who then leased it to Carson Pirie Scott for $7,000 per month, which occupied the building for more than a century until 2006. Subsequent additions were completed by Daniel Burnham in 1906 and Holabird & Root in 1961.The building has been used for retail purposes since 1899, and has been a Chicago Landmark since 1975. It is part of the Loop Retail Historic District.