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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.

Moose (W-02-03) is a sculpture of a moose by John Kearney on the Magnificent Mile in front of 401 North Michigan and across Michigan Avenue from the Wrigley Building in the Near North Side community area of Chicago, Illinois. It is a welded steel (chrome bumpers) work of art created in between 2002 and 2003. Its dimensions are 8 ft 9 in (2.67 m) x 4 ft 2 in (1.27 m) x 9 ft 0 in (2.74 m)The sculpture was part of the Artists & Automobiles (June 16 – October 15, 2006) summer public art display at the Chicago Cultural Center of artwork from recycled automobiles. The display was co-hosted by the City of Chicago Department of Cultural Affairs' Public Art Program and Allstate in honor of the 75th anniversary of Allstate's founding in Chicago.

A bronze bust of Jean Baptiste Point du Sable by Erik Blome is installed in Chicago, in the U.S. state of Illinois.

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.

An outdoor sculpture of Jack Brickhouse is installed along Michigan Avenue, near the Chicago River bridge, in Chicago, Illinois. The bust was originally dedicated in 2000, and renovated in 2009.

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.

The DuSable Bridge (formerly the Michigan Avenue Bridge) is a bascule bridge that carries Michigan Avenue across the main stem of the Chicago River in downtown Chicago, Illinois, United States. The bridge was proposed in the early 20th century as part of a plan to link Chicago's south side and north side parks with a grand boulevard. Construction of the bridge started in 1918, it opened to traffic in 1920, and decorative work was completed in 1928. The bridge provides passage for vehicles and pedestrians on two levels. An example of a fixed trunnion bascule bridge (which is also known as a "Chicago style bascule bridge"), it may be raised to allow tall ships and boats to pass underneath. The bridge is included in the Michigan–Wacker Historic District and has been designated as a Chicago Landmark. The location is significant in the early history of Chicago, connecting on the north near the 1780s homestead site of Jean Baptiste Point du Sable and on the south the early 19th century site of Fort Dearborn. Events from the city's past are commemorated with sculptures and plaques on the bridge, and exhibits in the McCormick Bridgehouse & Chicago River Museum—housed in one of the bridge tender houses—detail the history of the Chicago River.

The Billy Goat Tavern is a chain of taverns located in Chicago, Illinois. Its restaurants are based on the original Billy Goat Tavern founded in 1934 by Billy Sianis, a Greek immigrant. It achieved fame primarily through newspaper columns by Mike Royko, a supposed curse on the Chicago Cubs, and the Olympia Cafe sketch on Saturday Night Live. The tavern has eight locations with seven in Chicago, including the oldest extant location on Lower Michigan Avenue, Navy Pier, the Merchandise Mart, O'Hare Airport, Midway Airport, on Lake Street (1⁄2 block west of Michigan Avenue), and in the West Loop on Madison Street (near the United Center); and one location in the suburban Yorktown Mall in Lombard, Illinois. They expanded to Washington, D.C. in 2005, the first location outside the Chicago metropolitan area; it is intended to appeal primarily to Chicago transplants, as well as students from the Georgetown University Law Center located across the street.

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 bronze statue of Nathan Hale that stands in front of the Tribune Tower in Chicago, Illinois, is a replica of the one originally installed at Yale University in 1899. It honors an American hero from the Revolutionary War who was executed for spying on the Kingdom of Great Britain. The original statue was sculpted by Bela Pratt and the replica in Chicago by Guido Gargani. The architect who designed the statue's granite base was Leo Weissenborn. The statue was located in the Nathan Hale Courtyard until the conversion of the Tribune Tower into residential units, when it was moved to face the building along Michigan Avenue. The idea to erect the statue was by Chicago Tribune founder, Robert R. McCormick, a World War I veteran who became a staunch isolationist during the lead up to World War II. He had been a longtime supporter of the Reserve Officers' Training Corps (ROTC) program, which prepares students to enter the military. He wanted to install a statue of an American patriot and dedicate it to younger generations, who he hoped would show the same courage. The statue was first displayed at WGN's radio studio during a special event. The dedication and unveiling took place a few months later on June 4, 1940. It was attended by tens of thousands of onlookers and the parade was composed of 10,000 ROTC cadets.

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.