January - February - March - April - May - June - July - August - September - October -November - December
| January 4, 1888 | The Chicago and South Side Rapid Transit Company is incorporated under the general railroad laws of the State of Illinois |
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| January 5, 1986 | The Chicago Bears beat the New York Giants 21-0 at Soldier Field to advance to the NFC Championship game |
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| January 6, 1958 | Chuck Berry records "Johnny B. Goode" at Chess Records studios |
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| January 12, 1986 | Chicago Bears defeat the Los Angeles Rams 24-0 before 63,522 at Soldier Field to advance to Superbowl XX |
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| January 16, 1967 | Fire destroys the first McCormick Place convention center, killing one worker |
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| January 18, 1909 | Theatrical manager William Morris opens The American Music Hall at 8th and Wabash to show independent vaudeville shows |
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| January 19, 2002 | Demolition begins on Soldier Field redevelopment following Bears playoff game |
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| January 22, 1893 | The South Side Elevated structure is completed to 63rd Street, allowing service from Congress to 61st Street station |
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| January 22, 1957 | Joffrey Ballet performs at the Eighth Street Theater, its first performance in a major city |
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| February 6, 1956 | The Chicago Defender begins daily publication |
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| February 27, 1926 | Louis Armstrong’s Hot Five demonstrates the musical recording process at “Okeh Race Record Artist’s Night” at the Chicago Coliseum |
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| February 29, 1940 | Robert S. Abbott, publisher of The Chicago Defender, dies of Bright's Disease |
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| March 5, 1972 | Last passenger train leaves Illinois Central Station |
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| March 8, 1971 | Closed circuit broadcast of Muhammad Ali-Joe Frazier championship fight fails in third round, patrons at the Chicago Coliseum initiate a brawl injuring a Chicago Fire Department captain |
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| March 12, 1971 | James Taylor and Carole King perform at the Chicago Coliseum, venue closed for multiple fire code violations the next day |
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| March 25, 1967 | Dr. Martin Luther King, Jr. says “we must combine the fervor of the Civil Rights movement with the peace movement” in a speech at the Chicago Coliseum |
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| March 27, 1939 | The Harlem Globetrotters and the New York Rens, two African-American basketball teams, play each other in front of 7,000 fans at the Chicago Coliseum; the Rens win 27-23 |
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| March 30, 2003 | Mayor Richard M. Daley orders closing and destruction of Meigs Field in the early morning hours |
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| April 16, 1956 | Chuck Berry records “Roll Over Beethoven” at Chess Records studios |
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| April 19, 1924 | First broadcast of the WLS Barn Dance; the show would later have a 25-year run at the Eighth Street Theater beginning in 1932 |
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| April 23, 1893 | South Side Elevated service extended to Dorchester and 63rd, accessible by a walkway to the World's Fair |
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| April 25, 1859 | Chicago’s first street car line, drawn by horses, opens on State Street between Madison and Roosevelt |
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| May 2, 1921 | The Field Museum opens as the first institution in what will become the Museum Campus |
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| May 2, 1927 | The Stevens Hotel (now the Chicago Hilton) opens as the World's Largest Hotel |
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| May 5, 1905 | Robert S. Abbott publishes the first edition of The Chicago Defender |
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| May 10, 1930 | The Adler Planetarium, the first institution of its kind in the United States, officially opens on the lakefront |
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| May 10, 1968 | Rock band The Doors perform at the Chicago Coliseum |
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| May 12, 1893 | South Side Elevated service extended to Jackson Park, site of the 1893 World's Columbian Exposition, almost two weeks after fair opening |
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| May 15, 1917 | The Chicago Defender proclaims this the date of the "Great Northern Drive," when African-American Southerners are urged to move North |
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| May 21, 1955 | Chuck Berry has his first recording session at Chess Records studios |
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| May 27, 1933 | Century of Progress World’s Fair opens on 427 acre lakefront site between 12th and 39th Streets |
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| May 30, 1930 | The John G. Shedd Aquarium officially opens on the lakefront at 12th Street |
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| June 3, 1965 | President Lyndon B. Johnson speaks at the Cook County Democratic Party Dinner at the first McCormick Place |
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| June 6, 1892 | First Chicago Elevated line opens to the public from State and Congress to 39th and State |
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| June 7, 1916 | 1916 Republican National Convention opens at Chicago Coliseum, nominates Charles Evans Hughes of New York |
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| June 10, 1964 | The Rolling Stones begin their first recording session at Chess Records studios, 2120 S. Michigan Avenue |
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| June 12, 1920 | Republican Party leaders meet in a “smoke-filled room” at the Blackstone Hotel to nominate Warren G. Harding as their compromise candidate at the convention held at the Chicago Coliseum |
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| June 12, 1926 | Ten jazz bands perform at the Chicago Coliseum at the “Okeh Cabaret and Style Show” to benefit African-American Musician’s Local 208; Louis Armstrong’s Hot Five headlines the show |
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| June 17, 1994 | Opening ceremonies for 1994 World Cup held at Soldier Field, Oprah Winfrey is the emcee and Diana Ross performs |
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| June 18, 1912 | Republican National Convention of 1912 opens at Chicago Coliseum, re-nominates William Howard Taft over former President Theodore Roosevelt |
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| June 21, 1904 | 1904 Republican National Convention opens at Chicago Coliseum, nominates President Theodore Roosevelt |
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| June 22, 1908 | Chicago street numbering system revised to count blocks from the corner of State and Madison, with 800 address units per mile |
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| June 26, 1902 | Volunteers of America hold free picnic for thousands of Chicago newsboys at the Gettysburg Cyclorama at Wabash and 7th Street (Balbo) |
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| June 28, 1932 | After suffering a loss of $1.5 million in 1931 and further losses in the first five months of 1932, creditors file suit against Chicago Rapid Transit to place it in receivership |
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| July 4, 1909 | Daniel Burnham issues his 164-page illustrated “Plan of Chicago,” calling for lakefront landfill, the widening of Congress Parkway, the straightening of the Chicago River, and many other changes to the South Loop |
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| July 4, 1940 | The American Negro Exposition, celebrating 75 years since American slaves were freed, opens at the Chicago Coliseum and will run through September 2 |
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| July 5, 1896 | Hopkins Theater at 531 S. State Street shows films of New York's Herald Square, a boxing match, and "Picture of a Kiss," first confirmed commercial exhibition of films in Chicago |
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| July 15, 1933 | Fascist Italian aviator Italo Balbo and a squadron of flying boats arrive in Chicago from Rome for the Century of Progress World’s Fair; 7th Street renamed in his honor |
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| July 15, 1943 | U.S. Army announces relinquishment of The Stevens Hotel and The Congress Hotel |
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| July 16, 1908 | 1908 Republican National Convention opens at Chicago Coliseum, nominates William Howard Taft |
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| August 1, 1942 | U.S. Army takes over Stevens Hotel, using the 3,000-room hotel for barracks, offices, and training |
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| August 5, 1912 | 1912 Progressive ("Bull Moose") Party convention begins at the Chicago Coliseum |
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| August 6, 1912 | Theodore Roosevelt addresses the 1912 Progressive Party convention at the Chicago Coliseum and accepts the new party's presidential nomination |
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| August 9, 1922 | Louis Armstrong arrives in Chicago for the first time at Illinois Central Station |
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| August 12, 1833 | The Town of Chicago was incorporated with a population of 350 |
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| August 12, 1933 | “Negro Day” at the Century of Progress World’s Fair is boycotted by civil rights leaders and receives only 1/6 of expected visitors |
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| August 13, 1927 | Dinner held in honor of Charles Lindburgh at The Stevens Hotel |
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| August 13, 1935 | First roller derby held at Chicago Coliseum |
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| August 25, 1925 | Ground is broken for The Stevens Hotel, which would hold the title of the Largest Hotel in the World for several decades |
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| August 26, 1900 | President William McKinley formally dedicates the new Chicago Coliseum at 1513 S. Wabash Avenue |
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| August 26, 1968 | 1968 Democratic National Convention officially opens at the International Amphitheater; most delegates stay at the Conrad Hilton Hotel |
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| August 27, 1968 | Yippies hold “Unbirthday Party for LBJ” at Chicago Coliseum, half of the 4000 in attendance march to Grant Park |
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| August 28, 1968 | Violence breaks out between police and demonstrators on national television at Michigan and Balbo during the 1968 Democratic National Convention as protesters chant, “The Whole World is Watching” |
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| August 31, 1957 | Final live performance of the WLS Barn Dance at the Eighth Street Theater |
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| September 1, 1940 | Paul Robeson sings on the second to last day of the American Negro Exhibition at the Chicago Coliseum |
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| September 2, 1940 | The American Negro Exposition at the Chicago Coliseum closes |
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| September 8, 1954 | An estimated 260,000 fill Soldier Field for Catholic Church Marian Year Tribute |
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| September 15, 1980 | East-West University begins classes at 816 S. Michigan Avenue |
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| September 19, 1971 | The Chicago Bears play their first game at Soldier Field, defeating the Pittsburgh Steelers 17-15 before capacity crowd of 55,701 |
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| September 22, 1927 | Jack Dempsey and Gene Tunney meet in controversial fight for the World’s heavyweight championship before 102,000 at Soldier Field |
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| October 1, 1947 | Chicago Transit Authority begins operation of the city's transit system |
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| October 3, 1897 | Official opening of the Chicago Loop elevated structure |
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| October 4, 1924 | First football game at Soldier Field (then known as Grant Park Municipal Stadium) between Louisville Male High School and Chicago Austin High |
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| October 8, 1871 | Great Chicago Fire destroys most of downtown and the Near North Side killing hundreds; South Loop is spared most of the damage |
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| October 9, 1871 | St. Mary's Church at 9th and Wabash is opened to shelter victims of the Great Chicago Fire |
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| October 17, 1931 | South Loop resident Al Capone is convicted of tax evasion and receives an 11-year sentence |
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| October 17, 1943 | State Street subway opens to the public |
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| October 22, 1883 | Gettysburg Cyclorama, a 42 foot high by 365 foot circumference painting in the round by artist Paul Dominique Philippoteaux, opens at 700 S. Wabash Avenue where it is shown for 20 years |
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| October 24, 2006 | The Wirt Dexter Building (1887) at 630 S. Wabash, one of the oldest surviving Adler and Sullivan designed buildings, is destroyed by fire |
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| October 26, 1933 | German airship Graf Zeppelin visits Century of Progress World’s Fair |
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| October 31, 1934 | Century of Progress World’s Fair closes; the fair attracts 48.8 million visitors over its two year run |
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| November 2, 1927 | Construction begins on the $3.25 million Shedd Aquarium on the lakefront at 12th Street |
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| November 4, 2008 | Minutes after being named the winner of the 2008 Presidential election, Barack Obama makes his victory speech on Hutchinson Field in Grant Park before an estimated crowd of 240,000 |
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| November 8, 1964 | The Rolling Stones record “Time is On My Side” at Chess Records studios |
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| November 8, 1969 | Last passenger train leaves Grand Central Station |
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| November 11, 1925 | Grant Park Municipal Stadium changes its name to Soldier Field |
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| November 16, 1929 | Notre Dame beats USC 13-12 before 112,912 fans at Soldier Field, setting the all-time college football attendance record |
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| November 18, 1960 | First McCormick Place Convention Center opens at the Lakefront and 23rd Street; it would burn in January 1967 in part because of a lack of nearby fire hydrants |
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| November 19, 1951 | The Stevens Hotel is re-named The Conrad Hilton |
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| December 1, 1968 | The Jimi Hendrix Experience performs at the Chicago Coliseum |
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| December 8, 1890 | Grand Central Station opens to passenger traffic |
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| December 13, 1908 | Chicago Coliseum bombed, believed in protest of First Ward Ball |
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| December 13, 1942 | The Stevens Hotel sold to the U.S. Army for $6 million; it was built in 1927 at a cost of $30 million |
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| December 15, 1955 | The Congress Expressway opens |
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| December 17, 1938 | Ground is broken on the State Street subway; it will not open until October 1943 |
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| December 19, 1889 | Fr. Augustus Tolton, first African-American Catholic priest, arrives in Chicago to begin his work at St. Mary's Catholic Church |
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| December 31, 1988 | Bears play Philadelphia Eagles in “Fog Bowl” NFC Championship game at Soldier Field |
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