Statue of Irv Kupcinet

The Wabash Avenue Bridge (officially, Irv Kupcinet Bridge) over the Chicago River was built in 1930. Standing west of the Michigan Avenue Bridge and east of Marina City, the bascule bridge connects the Near North Side with "The Loop" area. The single-deck, double-leaf bascule bridge was designed by Thomas Pihlfeldt and built by the Ketler and Elliot Company. The American Institute of Steel Construction awarded it the "Most Beautiful" bridge in 1930.The control houses for controlling bridge operations are on the northwest and southwest corners of the bridge. The control houses are identical in design. In 1961 the control houses were upgraded to allow single man operation. Electrical modernization also accompanied this upgrade. While the northern control house is no longer in use, it still stands.

Seventeenth Church of Christ, Scientist, built in 1968, is a modern style Christian Science church building located in The Loop at 55 East Wacker Drive, (at Wabash Avenue) in Chicago, Illinois in the United States. It was designed by noted Chicago-based architect Harry Weese, whose most famous work is the Washington Metro but who is remembered best as the architect who "shaped Chicago’s skyline and the way the city thought about everything from the lakefront to its treasure-trove of historical buildings."Built by Sumner Sollitt Construction Company of concrete in a circular design, the building has no windows in the interior amphitheater. Outside light comes through a skylight at the top of the oculus in the center of the conical roof. Pedestrian entrance to the building is via a bridge over a sunken garden, which Weese said "was for the benefit of the [subterranean] Sunday School, which didn't have any windows" but is lit through the garden by the light from the street level above. The semicircular auditorium which seats 764 is designed so that no seat is more than 54 feet from the Readers' Platform, which is the focal point of all Christian Science church auditoriums. An invisible sound reinforcement system with 350 hidden microphones allows those in attendance at the Wednesday evening testimonial meetings to give testimonies without having to leave their seats. Off street parking is provided by a subterranean parking garage. A feature of the lower lobby is an acrylic painting on canvas entitled "Millenium Garden: Psalm 23,” completed by Chicago artist Anne Farley Gaines in 2001. In 1996, Seventeenth Church received the 25 Year Award of the Chicago Chapter of the American Institute of Architects. In celebration of the 2018 Illinois Bicentennial, the Seventeenth Church of Christ, Scientist was selected as one of the Illinois 200 Great Places by the American Institute of Architects Illinois component (AIA Illinois).

The Heald Square Monument is a bronze sculpture group by Lorado Taft in Heald Square, Chicago, Illinois. It depicts General George Washington, and the two principal financiers of the American Revolution, Robert Morris and Haym Salomon. Following Taft's 1936 death, the sculpture was completed by his associates Leonard Crunelle, Nellie Walker and Fred Torrey.Heald Square is located in the Michigan–Wacker Historic District of Chicago's Loop community area. The square was named for Captain Nathan Heald, commander of Fort Dearborn from 1810 to 1812.The sculpture was designated a Chicago Landmark on September 15, 1971.

Mather Tower (later Lincoln Tower, as designated on the Michigan–Wacker Historic District roster; now identified primarily by its address) is a Neo-Gothic, terra cotta-clad high-rise structure in Chicago, Illinois, United States. It is located at 75 East Wacker Drive in the downtown "loop" area, adjacent to the Chicago River. The 521-foot (159 m)-high building is sometimes called "The Inverted Spyglass" by Chicagoans due to its highly unusual design, an 18-story octagonal tower atop a more conventional 24-story rectangular "box." Briefly the tallest building in Chicago at the time of its completion in 1928, it remains the city's most slender high-rise structure at only 100 by 65 feet (30 by 20 m) at its base. The interior space within the upper octagonal spire contains the least square footage per floor of any Chicago skyscraper.It was designed by Herbert Hugh Riddle (1875–1939), the architect of the Chicago Theological Seminary, as headquarters for the Mather Stock Car Company, a builder of rail cars for transporting livestock. Its design was greatly influenced by the pioneering Chicago Zoning Ordinance of 1923, which placed no limit on the height of new buildings as long as the surface area of the structure's uppermost floor did not exceed 25% of its footprint. This resulted in a multitude of tall, slender, "setback" towers, of which the Mather is an extreme and unusual example. The top floor of the octagonal spire has only 280 square feet (26 m2) of floor space.Mather Company's founder, Alonzo Mather (a descendant of Cotton Mather) is said to be responsible for a number of the building's distinctive design features, including the octagonal tower. Initial plans called for construction of a second, identical building on North Michigan Avenue, behind the Mather and connected to it by a ground-floor arcade, but onset of the Great Depression in 1929 forced its cancellation.By the 1990s the building had fallen into significant disrepair. In 2000 the 4-story "cupola" at the top of the building was demolished because of structural deterioration and safety concerns, after chunks of terra cotta began falling from the facade. Damage was sufficiently extensive that consideration was given to dismantling the remaining 17 stories of the octagonal spire as well.In 2000 Masterworks Development Corporation purchased the structure and undertook a complete restoration. In November 2002, the final phase of the project was initiated when a helicopter lifted the steel framework for a new cupola from a river barge to the top of the tower.The lower, rectangular portion of the building currently houses the River Hotel, while the octagonal upper stories are occupied by a branch of the Club Quarters chain of membership corporate accommodations. Mather Tower was designated a Chicago Historic Landmark in 2001, and in 2006 it received a National Preservation Honor Award from the National Trust for Historic Preservation.

The Vietnam Veterans Memorial is a war memorial in Chicago, in the U.S. state of Illinois, dedicated on November 11, 2005.

The London Guarantee Building or London Guaranty & Accident Building is a historic 1923 commercial skyscraper whose primary occupant since 2016 is the LondonHouse Chicago Hotel. Formerly, for a time named the Stone Container Building, it is located near the Loop in Chicago, and is one of four 1920s skyscrapers that surround the Michigan Avenue Bridge (the others are the Wrigley Building, Tribune Tower and 333 North Michigan Avenue) and is a contributing property to the Michigan–Wacker Historic District. It stands on part of the former site of Fort Dearborn. The building was designated a Chicago Landmark on April 16, 1996.

The Trump International Hotel and Tower is a skyscraper condo-hotel in downtown Chicago, Illinois. The building, named for Donald Trump, was designed by architect Adrian Smith of Skidmore, Owings and Merrill. Bovis Lend Lease built the 98-story structure, which reaches a height of 1,388 feet (423.2 m) including its spire, its roof topping out at 1,171 feet (357 m). It is next to the main branch of the Chicago River, with a view of the entry to Lake Michigan beyond a series of bridges over the river. The building received publicity when the winner of the first season of The Apprentice reality television show, Bill Rancic, chose to manage the construction of the tower over managing a Rancho Palos Verdes based "Trump National Golf Course & Resort" in the Los Angeles metro area. Trump announced in 2001 that the skyscraper would become the tallest building in the world, but after the September 11 attacks that same year, the architects scaled back the building's plans, and its design underwent several revisions. When topped out in 2009, it became the seventh-tallest building in the U.S. It surpassed the city's John Hancock Center as the building with the highest residence (apartment or condo) in the world, and briefly held this title until the completion of the Burj Khalifa. The design of the building includes, from the ground up, retail space, a parking garage, a hotel and condominiums. The 339-room hotel opened for business with limited accommodations and services on January 30, 2009, then full accommodation and services on April 28. The building topped out in late 2008 and construction was completed in 2009. Sixteen was one of five restaurants in Chicago with at least a Michelin Guide two-star rating in 2016 and one of three five-star Forbes-rated restaurants in the city until it closed in 2018. The spa is one of six with at least a four-star Forbes rating in the Chicago area in 2015.

35 East Wacker, also known as the Jewelers' Building, is a 40-story 523 ft (159 m) historic building in the Loop community area of Chicago, Illinois, United States, located at the intersection of Wabash Avenue and E. Wacker Dr., facing the Chicago River. It was built from 1925 to 1927, and was co-designed by Joachim G. Giaver and Frederick P. Dinkelberg. At the time of its completion in 1927, it was the tallest building in the world outside New York City. Formerly the Pure Oil Building and North American Life Insurance Building, 35 East Wacker was listed in 1978 as a contributing property to the Michigan–Wacker Historic District on the National Register of Historic Places, and was designated a Chicago Landmark on February 9, 1994.For its first 14 years, the building had a car lift that served the first 23 floors and facilitated safe transfers for jewelry merchants. Currently, the French-American Chamber of Commerce in Chicago is a tenant, and the showroom of architect Helmut Jahn was atop the building inside the dome, which was also once a restaurant called the Stratosphere Club, often erroneously said to be run by Al Capone. (In reality, the Stratosphere Club opened in 1937, long after Capone was imprisoned and too late for the building to have been an illegal speakeasy). The building is currently being renovated, by Goettsch Partners, and the facade is being maintained, but the interiors converted into a more modern configuration. Both the Chicago chapter of the American Institute of Architects and the City of Chicago have recognized the renovation project with awards.

Sixteen was an American restaurant on the sixteenth floor of the Trump International Hotel and Tower in the Near North Side community area of Chicago. It was one of three food and dining options in the hotel's room service offering. Sixteen opened in early February 2008, and an adjoining outdoor patio terrace, named The Terrace at T, opened on June 25, 2009 following the completion of the hotel's construction.The restaurant and its terrace were known for their views of the city. The eastward view included Lake Michigan, Chicago River, and the Wrigley Building clock tower. During the summer, the view included the seasonal semi-weekly fireworks displays over the lake from Navy Pier. The restaurant held a five-star rating, according to the Forbes Travel Guide, one of only 3 restaurants in Chicago to attain such a rating in 2015. It earned a two-star rating in the Michelin Guide, and was one of only 5 restaurants in the city to achieve a two-star or greater Michelin rating. After more than a decade of operating, the restaurant closed at the end of April 2018. A few months later the space reopened with an American cuisine restaurant called, Terrace 16.

Wacker Drive is a major multilevel street in Chicago, Illinois, running along the south side of the main branch and the east side of the south branch of the Chicago River in the Loop. The vast majority of the street is double-decked; the upper level intended for local traffic, and the lower level for through-traffic and trucks serving buildings on the road (and originally a dock). It is sometimes cited as a precursor to the modern freeway, though when it was built the idea was that pleasure vehicles would use the upper level. It is the only street in the city that is prefixed with all four cardinal directions, albeit on different parts of its route. The drive is named for early 20th century Chicago businessman and city planner Charles H. Wacker. The upper level is normally known as Upper Wacker Drive and the lower level is Lower Wacker Drive. A short part has a third level, sometimes called Lower Lower Wacker Drive.

The Virgin Hotels Chicago (formerly Old Dearborn Bank Building or 203 North Wabash Avenue) is a historic building in the Loop community area of Chicago, Illinois, that has been converted from use as an office building to use as a hotel run via a mobile app-based business model. The 250-room hotel is the first of Richard Branson's Virgin Hotels brand boutique hotels geared toward the female business traveller.

Harold Washington College is a community college, part of the City Colleges of Chicago system of the City of Chicago, in Illinois, United States. It is located in the downtown "Loop" area of the City, near the series of parks along the lakefront of Lake Michigan, centered at 30 East Lake Street. Founded in 1962 as Loop College, the college was renamed for the first African American to be elected Mayor of Chicago, Harold Washington, (1922–1987), after his sudden death in office in November 1987.