- 1882 - Chicago Police Chief William McGarigle , in the pay of Chicago crime lord Michael Cassius McDonald , is indicted for Graft later fleeing to Canada.
- 1907 - A group of leading Italian citizens, prominent businessmen, several ethnic organiztions, and the Italian Chamber of Commerce form the White Hand Society, a legal organization, to combat the Le Mano Nera ( The Black Hand ) in Chicago.
- 1907 - Chicago gambling racketeer Bud White 's gambling vessel the City of Traverse is closed down.
- 1908 - Kurt "The Man" Peterson is first arrested for burglary. It is this incident that, while caught robbing a perfume store, he is dubbed the "Perfume Burglar" by Chicago reporters.
- 1910 - Chicago police arrest over 200 known Italian gangsters and known Black Hand Members in a raid in Little Italy (Chicago) . However none are convicted as many of the notes of extortion threats cannot be traced to them.
- 1910 - Chicago racketeer Jim Colosimo brings his nephew Johnny Torrio , then with New York's Five Points Gang , to eliminate the Black Hand from the city in response to their extortion demands. Within a month ten Black Hand extortionists had been killed.
- 1910 - Jim Cosmano , a major Chicago Black Hand leader, is severly wounded in an ambush by Johnny Torrio on a South Side bridge. Cosmano had previously demanded $10,000 threatening to destroy Colosimo's Cafe.
- March 15 , 1910 - The Chicago Vice Commission , a civic organization to close the brothels and panel houses of the Levee District , is organized.
- January 1 - March 26 , 1911 - Thirty-eight Black Hand victims are killed by Black Hand assassins, many by the unidentified assassin known only as Shotgun Man, between Oak Street and Milton Street in Chicago's Little Italy .
- February 2 , 1920 - Chicago labor racketeer Maurice Enright is killed.
- May 11 , 1920 - Chicago gambling racketeer Jim Colosimo is killed, supposedly by Al Capone , outside his restaurant.
- February 2 , 1920 - Maurice Enright , Chicago labor racketeer
- 1923 - Al Capone establishes his headquarters in the Chicago suburb of Cicero, Illinois at the Lexington Hotel .
- September 17 , 1923 - George Meegan , a Chicago bootlegger allied with the Southside O'Donnell's, and Southside O'Donnell member George Bucher are killed by Frank McErlane .
- April 1 , 1924 - Frank Capone , brother of Al Capone , is killed by police during the fighting which broke out while leading around 200 gunmen into Cicero during the 1924 Chicago Elections in support of Mafia backed Republican politicians.
- November 10 , 1924 - North Side Gang leader Dion O'Banion is killed when three unidentified men enter his flower shop and shoot him several times. This begins a five year gang war between the North Side Gang , under Hymie Weiss , against Al Capone's Chicago Outfit that would end with the St. Valentine's Day Massacre in 1929.
- January 12 , 1925 - North Side Gang Hymie Weiss , with Bugs Moran and Vincent Drucci , attempt to kill Al Capone at a Chicago South Side restaurant and firing at Capone 's car injuring chauffeur Sylvester Barton although Capone in unharmed.
- January 24 , 1925 - North Side Gang leader Hymie Weiss , with George Moran , Vincent Drucci , and Frank Gusenberg ambush Chicago Outfit leader Johnny Torrio as he returns from shopping with his wife shooting him several times wounding him and his chauffeur Robert Barton. As George Moran is about to kill the wounded Torrio the gun misfires and is forced to flee as the police arrive on the scene. Soon after this attack Torrio retires to Italy giving leadership of Torrio's organization to his lieutenant Al Capone .
- February 9 , 1925 - Johnny Torrio is sentenced by Judge Adam Cliffe to 9 months in Waukeagan County Jail . The jail is chosen by Torrio's lawyers as a facility necessary for Torrio to receive proper medical treatment however it was actually chosen for Torrio's protection as the prison warden Sheriff Edwin Ahlstrom was in the pay of Torrio's organization. Torrio was later escorted by Capone out of the city after his release.
- June 13 , 1925 - Genna Brother Angelo Genna is killed, possibly by members of the North Side Gang or the Chicago Outfit .
- November 13 , 1925 - Samuzzo Amatuna is gunned down outside a Chicago West Side barber shop by the Hymie Weiss-Bugs Moran North Side Gang.
- 1927 - Al Capone's Chicago Outfit earns a yearly income of $108 million
- 1927 - Sam Valante, recently hired by Joe Aiello, is killed while arriving in Chicago.
- August 24 , 1927 - Green Ones members Anthony F. Russo and Vincent Spicuzza are killed in Chicago supposedly lured there by the rival Cuckoos Gang in an attempt to murder Al Capone. Hours later Green Ones member Benjamin Giamonco is killed in a gunfight attempting to avenge their deaths.
- April 21 , 1928 - Illinois gangster Charles Birger is executed for the ordered murder of West City, Illinois 's Mayor Joe Adams .
- July 25 , 1928 - Joe Aiello gang member Salvatore Canale is killed outside his home in Chicago.
- September 7 , 1928 - Capone's former '' Consigliere '' and '' Unione Siciliane '' president Antonio Lombardo is killed. This could have been a motivating factor for the St. Valentine's Day Massacre.
- 1929 - Al Capone serves a brief sentence on a concealed weapons charge.
- 1929 - Tony Accardo is made head enforcer for Al Capone 's " Chicago Outfit ".
- January 8 , 1929 - Unione Siciliane leader Pasquale Lolordo is killed in his apartment supposedly by Joe Aiello and members of the Bugs Moran 's North Side Gang .
- February 14 , 1929 - Four unidentified men, dressed as Chicago police officers, storm into a North Side Street garage and murder seven members of George Bugs Moran 's North Side Gang. Known as the St. Valentines Day Massacre , the attack effectively ends the five year gang war between Al Capone and George Bugs Moran .
- May 29 , 1929 - Thomas McElligot , a member of the Westside O'Donnell's , is killed in a Loop saloon in Chicago .
- December 30 , 1929 - Stephanie St. Clair is arrested by Chicago Police and sentenced to eight months in prison.
- March 19 , 1943 - Facing incarceration for the Extortion of Hollywood film studios, Outfit boss Frank Nitti commits suicide.
- The Latin Kings are formed. Their alleged motivation for forming this group was an attempt at overcoming the prejudices they faced.
- Tony Accardo decides to retire from the Chicago Outfit and appoints Sam Giancana to oversee day-to-day operations of the crime syndicate. However, Accardo remains a presense in the organization serving in an advisory capacity as '' Consigliere ''.
- January , 1986 - Joe Ferriola is appointed boss of the Outfit. With the approval of his top captains and consiglieri, Tony Accardo, he decides its time to kill Anthony Spilotro for causing problems in Las Vegas and the skim, as well as the Outfit.
- 1989 - James Basile , a bookmaker, agrees to become a government informant, later identifing a "Mafia graveyard" in the suburban neighborhood of Hillside .
- March 21 , 1990 - Outfit gambling boss of west suburban Elmhurst , Donald Angelini , who had operated a highly successful Sports Betting empire along with Dominic Cortina , is arrested and sentenced to prison.
- September 1997 - Harry Aleman is Retried for the murder of William Logan based on testimony by Robert Cooley and evidence showing the first trial was fixed. This is the first time in U.S. history someone has been retried for the same crime after being Acquitted .
- December 23 , 1999 - Ronald Jarrett, a mob lieutenant to John "Johnny Apes" Monteleone of the South Side Crew, is shot while going to a funeral. It is the first hit in seven years.
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