Plaza 440

Andy's Jazz Club, located several blocks north of the Chicago Loop, was founded as "Andy's 11 E. Lounge" in 1951 by Andy Rizzuto. A group of investors bought the property in 1975, changing its name to "Andy's". The club is one of the city's most popular jazz venues.In 1977 jazz promoters Penny Tyler and John Defauw began producing midday jazz sessions at Andy's, which was later expanded to include performances later in the day with sets at 5pm and 9pm. The 5pm performance - known as "Jazz at Five" - has since become a Chicago tradition.Performers at the club have included Larry Coryell, Franz Jackson, Von Freeman, and Joey DeFrancesco.

River Plaza is a 524 ft (160m) tall skyscraper in Chicago, Illinois. It was completed in 1977 and has 56 floors, of which 51 are residential with a total of 678 units. Gordon & Levin designed the building, which is the 74th tallest building in Chicago. River Plaza was converted from a rental building to condominiums in 1994 and is currently managed by Community Specialists.

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.

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.

Hubbard Street is a street in Chicago, Illinois named for early settler Gurdon Saltonstall Hubbard. Hubbard Street has three distinct sections. The first, east of the Chicago River, runs from Kingsbury Street to Michigan Avenue. The second, longer section runs from Des Plaines Street west to Campbell Avenue (2500 W) The third and shortest section is a three-block stretch from Kilpatrick Avenue (4700 W) to Lavergne Avenue (5000 W) where it ends at the Hubbard Playlot Park. Notable buildings on this street include Courthouse Place at 54 W. Hubbard.

Urban Prep Academies (also known as Urban Prep Charter Academy for Young Men or simply Urban Prep) is a nonprofit organization that operates a network of free open-enrollment public all-male college-preparatory high schools in Chicago. Founded in 2002, and receiving its first charter approval from Chicago Public Schools in 2005, it operates the first all-male public charter high school in the United States. The network opened a second campus in 2009 and a third in August 2010. From 2010–2019, 100% of the seniors in the school's graduating classes were admitted to four-year colleges or universities.

330 North Wabash (formerly IBM Plaza also known as IBM Building and now renamed AMA Plaza) is a skyscraper in downtown Chicago, Illinois, United States, at 330 N. Wabash Avenue, designed by famed architect Ludwig Mies van der Rohe (who died in 1969 before construction began). A small bust of the architect by sculptor Marino Marini is displayed in the lobby. The 52-story building is situated on a plaza overlooking the Chicago River. At 695 feet (211.8 meters), 330 North Wabash is the second-tallest building by Mies van der Rohe, the tallest being the Toronto-Dominion Bank Tower at Toronto-Dominion Centre. It was his last American building.The building's original corporate namesake no longer owns nor has offices in the building. IBM sold IBM Plaza to the Blackstone Group in 1996. IBM all but completed its move out of IBM Plaza as of early 2006, taking up space in the new Hyatt Center building closer to Union Station. Current major tenants are the American Medical Association, Langham Chicago managed by Langham Hotels International, WeWork and law firm Latham & Watkins.The former IBM Plaza has several design features that are rare in an office building but understandable given its original owner. The building's electrical system, environmental system, floor strength, and ceiling height (on certain floors) can support large raised floor computing centers. With even more need to contain possible electrical fires, fire safety was especially important, and asbestos was one of the most useful fire prevention materials of that era. As with most other buildings of that era, asbestos abatement is an ongoing aspect of building life, with air quality monitoring, asbestos "mapping," and opportunistic asbestos removal when feasible. Also, given IBM's traditional office hours, large number of workers, and commercial interest in marketing then emerging electronic building control systems (notably the IBM Series/1 and its predecessors), the "banked" intelligent passenger elevator system (with separate all-floor cargo elevators) is significantly over-provisioned for a building of its size and rarely keeps anyone waiting long for service. IBM Plaza stayed dry during the 1992 Chicago Flood. In 2007, plans were announced to convert floors two through thirteen of the 52-story building into a high-end hotel. The Langham, Chicago which opened in 2013, occupying floors two through thirteen. The Langham Hotel in the building was named the best hotel in the United States by US News in 2017. The building was declared a Chicago Landmark on February 6, 2008, and added to the National Register of Historic Places on March 26, 2010. It is the youngest building in Chicago on both lists. On December 9, 2011, the American Medical Association announced it would move its headquarters and entire workforce to 330 N. Wabash from its previous headquarters on State Street. The move occurred in September 2013 and the building was renamed AMA Plaza.

A full-length statue of Benito Juárez, who served as president of Mexico from 1858 to 1872, is installed in the Plaza of the Americas, along Michigan Avenue, just north of the Wrigley Building in Chicago, Illinois.The 16-foot statue was donated to the city by the counsel general of Mexico in February 1999, and replaces a bust given by the Mexican President in 1977.

The Wrigley Building is a skyscraper located at 400–410 North Michigan Avenue on Chicago's Near North Side. It is located on the Magnificent Mile directly across Michigan Avenue from the Tribune Tower. It was built to house the corporate headquarters of the Wrigley Company.

Plaza of the Americas is a public space in Chicago, in the U.S. state of Illinois. Located between the Realtor and Wrigley buildings, the plaza was dedicated by the Mexican consulate general in 1963.The plaza features a statue of Benito Juárez, a fountain, and flags of the nations in the Organization of American States. Jorge Marín's Wings of Mexico was installed in the plaza temporarily in 2022.

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.

Grand (Grand/State in station announcements) is an "L" station on the CTA's Red Line. It serves Navy Pier, which is accessible via bus on Illinois Street one block south.