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- 2006: May 1, the 2006 U.S. immigration reform protests draw over 400,000
- 2005: The Chicago White Sox win their first World Series in 88 years
- 2004: Millennium Park opens.
- 2003: Meigs Field closed.
- 1998: The Chicago Bulls win their sixth NBA championship in eight years
- 1995: The Chicago Heat Wave of 1995.
- 1992: April 13, the Chicago Flood.
- 1988: Lights are installed in Wrigley Field
- 1986: The Chicago Bears win Super Bowl XX
- 1984: The Chicago Cubs reach the postseason for the first time since 1945
- 1983: Harold Washington became the first African-American Mayor.
- 1979: May 25, the American Airlines Flight 191 crashes.
- 1979: Chicago's first female mayor, Jane M. Byrne, takes office.
- 1978: Heavy snowstorm and city's perceived slow response lead to upset of incumbent mayor.
- 1978: First BBS goes online on February 16.
- 1973: Sears Tower, the tallest building in the world for next 30 years, was completed.
- 1969: The Chicago 8 trial opens.
- 1969: The 100-floor John Hancock Center was built.
- 1968: August 26–August 29, 1968 Democratic National Convention.
- 1967: January 26–January 27, Major snowstorm deposits 23 inches of snow, closing the city for several days. [1]
- 1960: The 1st of the Playboy Clubs, featuring bunnies, opened in Chicago.
- 1958: Our Lady of the Angels School Fire.
- 1958: The last streetcar ran in the city. At one time, Chicago had the largest streetcar system in the world.
- 1955: The first McDonald's franchise restaurant, owned by Ray Kroc, opened in the suburb of Des Plaines.
- 1935: Jay Berwanger of the University of Chicago is awarded the very first Heisman Trophy
- 1935: January 19, Coopers Inc. sells the world's first briefs.
- 1934: John Dillinger was shot by the FBI in the alley next to the Biograph Theater.
- 1933: Mayor Anton Cermak was killed while riding in a car with President-elect Roosevelt. The assassin was thought to have been aiming for Roosevelt.
- 1933: Century of Progress World's Fair.
- 1930: Shedd Aquarium opens.
- 1930: Adler Planetarium opened, through a gift from local merchant Max Adler. It was the first planetarium in the Western Hemisphere.
- 1930: The Merchandise Mart was built for Marshall Field & Co. The $32 million, 4.2 million square foot (390,000 m²) building was the world's largest commercial building. It was sold it to Joseph P. Kennedy in 1945.
- 1929: February 14, the St. Valentine's Day Massacre.
- 1927: Originally called the Chicago Municipal Airport, Chicago Midway International Airport opened. It was renamed in 1949 to honor the Battle of Midway in World War II. Midway was the world's busiest airport until 1959.
- 1925: The Tribune Tower was completed on Michigan Avenue. The building's large Gothic entrance contains pieces of stone from other famous buildings: Westminster Abbey, Cologne Cathedral, the Alamo, the Taj Mahal, the Great Pyramid, and the Arc de Triomphe.
- 1919: July 27, the Chicago Race Riot of 1919.
- 1919: Real estate broker Archibald Teller opened the first Fannie May candy store.
- 1915: July 24, the Eastland Disaster.
- 1913: Great Lakes Storm of 1913
- 1906: The Chicago White Sox defeat the Chicago Cubs in the only all-Chicago World Series
- 1905: The Industrial Workers of the World was founded in June
- 1900: The Chicago River is completely reversed.
- 1894: May 11–August 2, the Pullman Strike.
- 1893: First Ferris Wheel built by George Washington Gale Ferris, Jr..
- 1893: The World's Columbian Exposition (World's Fair)
- 1892: Masonic Temple is, for two years, the tallest building in the world, using highest occupied floor criteria.
- 1891: Chicago's first elevated railway "The El," went into operation to begin the "Loop" that would circle the city's downtown area.
- 1890: The University of Chicago is founded by John D. Rockefeller.
- 1886: May 4, the Haymarket Riot.
- 1885: Home Insurance Building is world's first skyscraper.
- 1871: October 8–October 10, the Great Chicago Fire.
- 1868: Rand McNally is formed as a railway guide company.
- 1867: Construction began on the Water Tower designed by architect W. W. Boyington.
- 1863: Mercy Hospital becomes the first hospital in Illinois.
- 1860: September 8, the Lady Elgin Disaster.
- 1855: Lager Beer Riot.
- 1854: A cholera epidemic took the lives of 5.5% of the population of Chicago.
- 1851: Chicago's first institution of higher education, Northwestern University, is founded.
- 1848: Chicago Board of Trade opens on April 3 by 82 local businessmen.
- 1848: Illinois and Michigan Canal opens and traffic begins moving through the city at a much higher rate.
- 1847: The first issue of the Chicago Tribune is printed on June 10.
- 1840: Chicago's first legally executed criminal, John Stone was hanged on Friday, July 10, for the rape and murder of Lucretia Thompson, a farmer's wife.
- 1837: C. D. Peacock jewelers was founded. It is the oldest Chicago business still operating today.
- 1837: Chicago receives its first charter.
- 1818: Illinois joins the union.
- 1816: The Treaty of St. Louis is signed in St. Louis, Missouri. Ft. Dearborn is rebuilt.
- 1812: August 15, the Fort Dearborn Massacre.
- 1803: The U.S. Army constructs Ft. Dearborn near the mouth of the Chicago River.
- 1796: The Potawatomi Indian wife of du Sable delivers Eulalia Pointe du Sable, Chicago's first recorded birth.
- 1795: Six square miles (16 km²) of land at the mouth of the Chicago River are reserved by the Treaty of Greenville for use by the United States.
- 1779: Haitian immigrant Jean Baptiste Pointe du Sable establishes Chicago's first permanent settlement near the mouth of the Chicago River.
- 1705: Conflicts develop between French traders and the Fox tribe of native Americans. Fort de Chicago is abandoned.
- 1696: Jesuit missionary Francois Pinet founds the Mission of the Guardian Angel. It is abandoned four years later.
- 1683: French Jesuits establish Fort de Chicago, the area's first true European settlement.
- 1682: French explorer René Robert Cavelier, Sieur de la Salle, passes through Chicago en route to the mouth of the Mississippi River.
- 1673: French-Canadian explorers Jacques Marquette and Louis Jolliet, on their way to Québec, pass through the area that will become Chicago.