500 West Madison

The Richard B. Ogilvie Transportation Center (; formerly Chicago and North Western Terminal) is a commuter rail terminal in downtown Chicago, Illinois. It is the terminus for the three commuter rail lines of Metra's Union Pacific District to Chicago's northern and western suburbs, which approach the terminal elevated above street level. It occupies the lower floors of the 500 West Madison Street building. The building occupies two square city blocks, bounded by Randolph Street and Madison Street to the north and south and by Canal Street and Clinton Street to the east and west. It is the second busiest rail station in Chicago, after nearby Chicago Union Station, the sixth-busiest railway station in North America, and the third-busiest station that exclusively serves commuter traffic.

The 500 West Monroe Building is a skyscraper in Chicago, Illinois. The building rises 600 feet (183 m) in Chicago's Near West Side neighborhood. It contains 45 floors, and was completed in 1992. The 500 W Monroe Building currently stands as the 44th-tallest building in the city. The architectural firm who designed the building was Skidmore, Owings & Merrill, the same firm who designed Chicago's Sears Tower and John Hancock Center and the Burj Khalifa in Dubai. The 500 West Monroe Building currently stands as the tallest building in Chicago situated west of the Chicago River. One year after its completion, in 1993, the building won the "Best Structure Award" from the Structural Engineers Association of Illinois. The building's design incorporated a unique turret-like structure on the structure's southeastern corner. The turret stands as the building's highest architectural point, and is illuminated in white lights at night.

540 West Madison, formerly known as ABN AMRO Plaza, is an office building located in the West Loop area of Chicago, Illinois, United States. The building was built for ABN AMRO, parent company of Chicago financial institution LaSalle Bank. To the east sits Citicorp Center building and to the south, residential-complex of Presidential Towers. In the base of the building, there is a Starbucks Coffee and a restaurant bar, Slightly Toasted. The building is anchored by West Madison Street, West Washington Street, North Jefferson Street and North Clinton streets. It was completed in 2003. The building has a total of 29 floors that span 453 feet. Cost are estimated to have been near $387 million (US). It took approximately 3 years to erect. The goal was to bring together all office workers in Chicago who comprised the staff of the five buildings the company occupied previous to the construction of the Plaza. When the building was acquired by Bank of America as part of the company's acquisition of LaSalle Bank from ABN AMRO in the spring of 2008, the green and yellow shield icon was removed from the building's top. In December 2012, Bank of America sold the building to a group of New York investors for $350 million. It was the largest office transaction in Chicago that year, both in price and cost per square foot.

The Riverside Plaza is considered one of Chicago's finest Art Deco buildings. It was originally known as the Chicago Daily News Building. At the time of its completion in 1929, the Daily News was one of the dominant newspapers in Chicago. The 26-story building helped revitalize the Chicago River and made innovations in engineering and urban design. In the 1920s, the buildings along the river were industrial in nature and butted up against a waterway that was polluted and considered undesirable. This building was the first to develop the Chicago riverfront aesthetically as well as commercially. It was the first American skyscraper with an open-air plaza as part of its design.In 1925, Walter A. Strong acquired the Chicago Daily News from the estate of Victor F. Lawson. Once he became publisher, Strong took immediate steps to build a modern newspaper facility. Lawson had owned a parcel along the river, which is now the site of the Chicago Opera House. Strong thought it too small and instead acquired the air rights over railroad tracks that ran along west side of the river opposite the original site. A year and one-half of meetings were required to reach an agreement between all parties. Once that was settled, Strong sold Lawson’s parcel to the utility magnate Samuel Insull, with the understanding that he construct a building that would include a new home for the Opera. Strong commissioned Holabird & Root to design a modern structure that would house 2,000 Daily News employees and provide studio space for his radio station, WMAQ. The building’s bold design and Art Deco façade were widely regarded as shot fired at the Chicago Tribune, which operated out of the Tribune Tower, a large Neo Gothic building on North Michigan Avenue completed in 1925. Inside, the building featured a much-admired mural by John W. Norton. It was dominated by diagonal lines, and divided into three sections: Gathering the News, Printing the News, & Transporting the News. In the fall of 1993, it was removed and put into storage, where it has remained. Outside, it had bas-reliefs depicting Benjamin Franklin, Charles Anderson Dana, Horace Greeley, Joseph Pulitzer, Samuel Bowles III, James Gordon Bennett and Joseph Medill and a fountain honoring Victor Lawson. The Chicago Daily News Building was completed in June 1929 at a cost of $8 million. During the dedication ceremony, President Herbert Hoover pressed a button that started the presses. The Daily News ceased publication in 1978. Although the building has since been renamed Riverside Plaza, according to the Tribune’s architecture critic, the Daily News Building remains, “one of Chicago's finest examples of Art Deco architecture and a path-breaking work of engineering and urban design.”A ramped concourse through the south side of this building now serves as the main entryway to the Ogilvie Transportation Center in Citigroup Center. This concourse was originally the main lobby, with an even floor in place of the ramp up to the bridge at Canal Street.

The Gogo Building, formerly known as the River Center, is an 840,000-square-foot (78,000 m2) commercial building located at 111 N. Canal Street in the West Loop community area of Chicago, Illinois. Originally constructed as a warehouse in the early 1900s, the vintage, loft-style building is now home to various commercial tenants, most notably Gogo Inflight Internet, which has its logo on the cube topping the building. Other tenants include Twitter, Uber, Vivid Seats, SAP Fieldglass, Potbelly Sandwich Works and Kin + Carta. The building is one of the best surviving examples in downtown Chicago of the once vibrant industrial district along the Chicago River.

Truth in Accounting (TIA), formerly known as the Institute for Truth in Accounting, is an American think tank that promotes fiscal conservatism. Its stated goal is "to educate and empower citizens with understandable, reliable, and transparent government financial information."

The Madison Street Bridge, also known as the Lyric Opera Bridge, is a 1922 bascule bridge that spans the South Branch of the Chicago River in downtown Chicago, Illinois, United States.

The Monroe Street Bridge is a bascule bridge that crosses the Chicago River in downtown Chicago, Illinois.

The Washington Boulevard Bridge is a bridge that spans the Chicago River in downtown Chicago, Illinois, United States.

Batcolumn (or Bat Column) is a 101-foot-tall (31 m) outdoor sculpture in Chicago. Designed by Claes Oldenburg, it takes the shape of a baseball bat standing on its knob. It consists of gray-painted Corten steel arranged into an open latticework structure. Batcolumn stands outside the Harold Washington Social Security Administration Building at 600 West Madison Street near downtown Chicago. The United States General Services Administration commissioned the sculpture, which was dedicated in 1977. Oldenburg originally designed the sculpture to be painted red, but he abandoned that idea to distinguish it from Chicago's Flamingo sculpture by Alexander Calder. Oldenburg instead had Batcolumn painted gray, which he also hoped would make the sculpture easier to see against the sky. A plaque on the sculpture reads, "Oldenburg selected the baseball bat as an emblem of Chicago's ambition and vigor. The sculpture's verticality echoes the city's dramatic skyline, while its form and scale cleverly allude to more traditional civic monuments, such as obelisks and memorial columns."The sculpture has been a source of controversy. On the day of its dedication, a number of people came to protest, holding signs saying "Tear it down" and "Expensive joke". However, Batcolumn has also had its defenders. A 2005 Chicago Tribune article named it one of the newspaper's favorite Chicago sculptures (along with Standing Lincoln and the lions outside the Art Institute of Chicago Building).

The Washington Street Tunnel was the first traffic tunnel under the Chicago River. J.L. Lake was awarded the contract to construct the tunnel in July 1867 and its construction was completed January 1, 1869. This tunnel was 1605 feet long, from Franklin Street west to Clinton Street, and cost $517,000.

The Boeing International Headquarters (colloquially known as the Boeing Building and formerly known as the Morton-Thiokol International Building) is a 36-floor skyscraper located in the Near West Side of Chicago. The building, at 100 North Riverside Plaza, is located on the west side of the Chicago River directly across from the downtown Loop. The building was designed with a structural system that uses steel trusses to support its suspended southwest corner in order to clear the Amtrak and Metra railroad tracks immediately beneath it. The building was originally constructed for the Morton Salt Company in 1990, but became largely vacant a decade later after the company was acquired and downsized. Boeing moved their corporate headquarters there in 2001 when they opted to leave Seattle for Chicago. Navteq moved their headquarters to the Boeing Building in 2007. It has also housed offices of Ameritech.. By 2021, with Boeing executives handling political and economical fallout from the Boeing 737 MAX groundings and the impact of the COVID-19 pandemic on aviation, Reuters reported that the shift in priorities rendered the building a "ghost town". Boeing ultimately announced the following year that it would move its corporate headquarters to Arlington, Virginia, where its defense division is located; the division relocated there from St. Louis in 2017.