Cityfront Plaza

Tribune East Tower is a 1,422 ft (433.4 m) mixed use supertall tower which could possibly start construction on the eastern edge of the Tribune Tower property, in the Streeterville area of Chicago. The building plans were approved on May 8, 2020 and construction has not yet began. When completed, the skyscraper will be the second-tallest building in Chicago after the Willis Tower.

The NBC Tower is an office tower on the Near North Side of Chicago, Illinois located at 454 North Columbus Drive (455 North Cityfront Plaza is also used as a vanity address for the building) in downtown Chicago's Magnificent Mile area. Completed in 1989, the 37-story building reaches a height of 627 feet (191 m). NBC's Chicago offices, studios, and owned-and-operated station WMAQ-TV are located here as of 1989 and on October 1, 1989, WMAQ-TV broadcast its first newscast at 10:00 that evening at its new home, NBC Tower, with the then-weeknight news team of Ron Magers, Carol Marin, John Coleman, and Mark Giangreco. Later, Telemundo O&O WSNS-TV has also occupied the building since its purchase by NBC in 2001. Formerly its former radio sister WMAQ/WSCR was located here. The studios of NBC's former Chicago FM property, WKQX, and its sister station WLUP are located in the NBC Tower.The design, by Adrian D. Smith of Skidmore, Owings & Merrill, is considered one of the finest reproductions of the Art Deco style. It was inspired by 30 Rockefeller Plaza in New York City, which is NBC's global headquarters. The tower is further enhanced by the use of limestone piers and recessed tinted glass with granite spandrels. The building takes additional cues from the nearby landmark Tribune Tower with the use of flying buttresses. A 130 ft (40 m) broadcast tower and spire tops the skyscraper. WMAQ and WSNS have STL and satellite facilities on the roof; the STLs link to WMAQ and WSNS's transmitter facilities atop the Willis Tower. WMAQ radio/WSCR studios and STL were located in the building until 2006 when they relocated to Two Prudential Plaza. Located in the Cityfront Plaza area, the building contains 850,000 sq ft (79,000 m2) of space and three floors of underground parking with 261 spaces. Connected to the main tower is a four-story radio and television broadcasting facility where popular shows such as Judge Mathis and WSNS's newscasts and WMAQ's newscasts are currently taped, and was the former recording facility for Jerry Springer and The Steve Wilkos Show before their tax credit-influenced move to Stamford, Connecticut in 2009. It was also home to the 1990s syndicated improv/sketch show Kwik Witz, The Jenny Jones Show until its cancellation in 2003, and Steve Harvey its move to Los Angeles in 2017.

Optima Signature (formerly Optima Chicago Center II) is a residential skyscraper in the Streeterville neighborhood of the Near North Side area in Chicago. The 57-story building is a joint venture between Optima Inc. and DeBartolo Development. It opened for occupancy in June 2017. The building has 490 units.

401 North Michigan is a 35-story skyscraper in the Streeterville area of Chicago, built in 1965 at 401 North Michigan Avenue, along the north bank of the Chicago River. It was designed by Bruce Graham and Natalie de Blois in the international style. Along with the Tribune Tower and Wrigley Building, it forms the southern gateway to Chicago's famous Magnificent Mile. The building was built atop the site of a cabin belonging to Chicago's first permanent resident, Jean Baptiste Pointe du Sable. In reference to du Sable, the large plaza adjacent to the building has been named Pioneer Court.

Chicago Rising from the Lake (1954) is a bronze sculpture by Milton Horn. The sculpture shows a woman, rising from waters of Lake Michigan, with flames, animals and wheat. It represents Chicago's rebirth after the Great Chicago Fire, and subsequent rise to become a leader in transportation, stockyards and commodities.

The Jean Baptiste Point Du Sable Homesite is the location where, around the 1780s, Jean Baptiste Point du Sable located his home and trading post. This home is generally considered to be the first permanent, non-native, residence in Chicago, Illinois. The site of Point du Sable's home is now partially occupied by and commemorated in Pioneer Court at 401 N. Michigan Avenue in the Near North Side community area of Chicago, Illinois.

Pioneer Court is a plaza located near the junction of the Chicago River and Upper Michigan Avenue in Chicago's Magnificent Mile. It is believed to be the site of Jean Baptiste Point du Sable's original residence and trading post. In 1965, the plaza was built on the former site of his homestead as part of the construction of the Equitable Life Assurance Society of America building. The Jean Baptiste Point Du Sable Homesite was designated as a National Historic Landmark on May 11, 1976. John Kinzie, a prominent early settler, bought and expanded Point du Sable's post in 1800. The Plaza is bounded on the north by the Tribune Tower, on the east by 401 N. Michigan Avenue, on the south by the Chicago River, and on the west by Michigan Avenue, adjacent to the DuSable Bridge. In 2017, a newly designed Apple Inc. store was opened on the south side of the court, which created new levels linking down to the river. From 2011–2012 the plaza was the display site for the Seward Johnson statue Forever Marilyn. The statue was later moved to Palm Springs, California. The plaza was used as a location in the film Divergent in 2013. A new temporary statue was installed on November 1, 2016 in Pioneer Court. Also created by Seward Johnson, the statue, titled Return Visit, is 25 feet tall and depicts Abraham Lincoln standing next to a modern common man dressed in beige corduroy pants, sneakers and a cream color cable-knit sweater. The modern man is holding a copy of the Gettysburg Address.

William Ogden Plaza Park is a 1.38-acre (0.56 ha) park in Streeterville, Chicago, in the U.S. state of Illinois. The park is named after William B. Ogden.

The Tribune Tower is a 463-foot-tall (141 m), 36-floor neo-Gothic skyscraper located at 435 North Michigan Avenue in Chicago, Illinois, United States. Built between 1923 and 1925, the international design competition for the tower became a historic event in 20th-century architecture.The tower was the home of the Chicago Tribune, Tribune Media, and Tribune Publishing. WGN Radio (720 kHz) originated broadcasts from the building until moving to 303 Wacker Drive in June 2018. The last WGN Radio broadcast left from the Tribune Tower on June 18, 2018. The ground level formerly housed the large restaurant Howells & Hood (named for the building's architects), now closed, whose patio overlooked nearby Pioneer Court and Michigan Avenue. CNN's Chicago bureau was also located in the building. It is listed as a Chicago Landmark and is a contributing property to the Michigan–Wacker Historic District. The original Tribune Tower was built in 1868, but was destroyed in the Great Chicago Fire in 1871.

Apple Michigan Avenue is a retail location of Apple Inc., in the Near North Side, Chicago, United States. It is in the luxury shopping district of Magnificent Mile, adjacent to Pioneer Plaza. The store is considered one of several Apple flagship locations and the preeminent store for Apple in Chicago and the Midwest. The store's first location was originally at 679 North Michigan Avenue. In 2017, it moved to its current location at 401 North Michigan Avenue.

The McCormick Freedom Museum was the first museum in the United States dedicated to the First Amendment by the McCormick Foundation. It was open from April 11, 2006, until March 1, 2009. The museum offered visitors an interactive experience focused on first amendment rights which include freedom of speech, freedom of religion, freedom of the press, assembly and petition. It was located on Michigan Avenue along the Magnificent Mile next to the historic Tribune Tower. A sculpture by artists Amy Larimer and Peter Bernheim, titled 12151791 was put into storage when the museum closed. Its title represents the date of December 15, 1791, when the United States Bill of Rights was ratified.One journalist has noted the irony of a Freedom Museum being named after the Robert R. McCormick, owner of the Chicago Tribune newspaper, saying the name "puts ego before freedom". A scaled-down 45 feet (14 m) mobile version of the museum, dubbed the Freedom Express, made its debut in Chicago's Pioneer Court on May 27, 2010.

The Chicago Riverwalk is a multi-use public space located on the south bank of the main branch of the Chicago River in Chicago, extending from Lake Michigan and Lake Shore Drive westward to Lake Street. The Chicago Riverwalk contains restaurants, bars, cafes, small parks, boat and kayak rentals, a Vietnam War memorial, and other amenities. Its final extent will be beyond Wolf Point Towers, northward to the planned Bally's casino near the intersection of Chicago Avenue and Halsted Street.