After its near destruction in the 1871 fire, Chicago rebounded to become America's "Second City". Many different groups have made it their home over the years.
- Mike Royko - Boss: Richard J. Daley of Chicago
- Studs Terkel - Division Street: America
- Karen Sawislak - Smoldering City: Chicagoans and the Great Fire, 1871-1874 (Historical Studies of Urban America)
- Arnold R. Hirsch - Making the Second Ghetto: Race and Housing in Chicago 1940-1960 (Historical Studies of Urban America)
- Nelson Algren - Chicago: City on the Make: Sixtieth Anniversary Edition
- Sandra Cisneros - The House on Mango Street
- Marty Weil - Jumping Off The Page: Essays Inspired by America's Cultural Flotsam
George Pullman tried to build the perfect company town, but a strike in 1894 destroyed his dream and led to Labor Day.
- 1673 - Jacques Marquette and Louis Jolliet explore the Midwest and Mississippi River. Most of the region becomes part of New France until 1763.
- c.1779 - John Baptiste DuSable builds a large house near what is now Chicago. The city is officially chartered in 1832.
- 1847 - Cyrus McCormick begins producing mechanical reapers in Chicago and sells them to Midwestern farmers.
- 1865 - Union Stockyards open in Chicago and slaughter millions of animals over the ensuing decades.
- 1871 - The Great Chicago Fire burns down a large part of the downtown, but the city is rapidly rebuilt.
- 1872 - Montgomery Ward produces its first mail order catalog and develops a business that serves millions of rural and small town consumers.
- c.1880 - Another great wave of immigration from Europe begins. Irish, Italians, Polish, Czechs, Slavs, and European Jews all diversify the nation's heritage.
- 1893 - The World's Columbian Exposition showcases Chicago's ascent as a world-class city. Millions visit from around the globe.
- 1916 - The Great Migration begins with the first large scale emigration of southern blacks to the south side's Black Belt.
- 1929 - The St. Valentines Day Massacre becomes the most notorious incident of Prohibition Era Chicago. Seven men are machine gunned at the behest of Al Capone.
- 1955 - Richard Daley is elected Mayor of Chicago. He holds the office until his death in 1976.
- 1968 - Two distinct riots break out in Chicago during 1968. One wave occurs after the assassination of Martin Luther King Jr., and a second during the Democratic National Convention.
- 1983 - Harold Washington becomes the first black mayor of Chicago after a close election. His first term was noted for his battles with City Council.
- 2000s - Mexican immigration to the United States reaches around 750,000 people per year at its peak, before declining after 2007.
- 2008 - Barack Obama becomes the first African-American to be elected President of the United States.