- 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 Negra ( The Black Hand ) in Chicago.
- 1907 - Chicago gambling racketeer Bud White 's gambling vessel, ''City of Traverse'', is closed down.
- 1908 - Earl "Hymie" Weiss is first arrested for burglary. Weiss was caught robbing a perfume store and was immediately 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 . However, none are convicted as many of the notes of extortion threats cannot be traced to them.
- 1910 - Chicago racketeer James "Big Jim" Colosimo brings his nephew Johnny "The Fox" Torrio , then with New York's Five Points Gang , to Chicago to eliminate the Black Hand due to their extortion demands. Within a month, ten Black Hand extortionists had been killed.
- 1910 - Jim Cosmano , a major Chicago Black Hand leader, is severely 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 Mn, between Oak Street and Milton Street in Chicago's Little Italy .
- February 2 , 1920 - Chicago labor racketeer Maurice "Mossy" Enright is killed.
- May 11 , 1920 - Chicago gambling racketeer Jim Colosimo is killed outside his restaurant. The alleged killer was Al Capone .
- 1923 - Al Capone establishes his headquarters at the Lexington Hotel at 22nd and Michigan Avenues in Chicago. He also gained control of the Chicago suburb of Cicero, Illinois as a safe base of his illegal operations.
- 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 "Deanie" 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 George "Bugs" Moran and Vincent "The Schemer" Drucci , attempt to kill Al Capone at a Chicago South Side restaurant, firing at Capone 's car and injuring chauffeur Sylvester Barton , but leaving Capone unharmed.
- January 24 , 1925 - North Side Gang leader Hymie Weiss , with George Moran , Vincent Drucci , and Frank "Tight Lips" 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 - "Bloody" Angelo Genna is killed, possibly by members of the North Side Gang or the Chicago Outfit .
- November 13 , 1925 - Samuzzo "Samoots" Amatuna , an ally of the Genna Family, 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 "The Scourge" Lombardi 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 "Patsy" 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.
- 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 identifying 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.
- January 25 , 2000 - Ronald Jarrett dies from the gunshot wounds he sustained in late 1999.
- January 15 , 2001 - William Hanhardt, former chief of detectives is indicted by a federal grand jury on charges of masterminding a ring of Mafia related thieves who stole $4.85 million in jewels in heists across the nation. {Link without Title}
- November 20 , 2001 - Anthony "the Hatch" Chiaramonti is shot outside a Brown's Chicken & Pasta in south suburban Lyons . {Link without Title}
- Hired Truck Program scandal
- April 25 , 2005 - The U.S. Department Of Justice 's Operation Family Secrets Indicts 15 Outfit mobsters and associates under the RICO Act . Joseph "the Clown" Lombardo and Frank "the German" Schweihs evade the indictment and become fugitives.
- January 13 , 2006 - Joe Lombardo is apprehended in Elmwood Park . FBI agents find him while a " Person Of Interest " is under surveillance, most likely John "No Nose" DiFronzo , but this is yet to be confirmed.
- April 17 , 2006 - Former Governor Of Illinois George H. Ryan is found guilty of all 22 Racketeering and Bribery charges against him.
- June 14 , 2006 - Former City Clerk James Laski sentenced to 24 months in prison after admitting he pocketed tens of thousands of dollars in bribes as part of the Hired Trucking Scandal.
- June 15 , 2006 - A 26 year old member of the Vice Lords on the West Side is arrested. He may have information on where the supply of Fentanyl -laced Heroin is coming from which has already killed at least 60 people. {Link without Title}
- August 31 , 2006 - Mobster Anthony Zizzo disappears. His car was found in Melrose Park , and there was no sign of foul play.
- September 6 , 2006 - George Ryan is sentenced to six and a half years in prison. {Link without Title}
- June 18 , 2007 The trial for Operation Family Secrets begins.
- Al Capone , Chicago Mafia leader
- Mickey Cohen (Meyer Harris Cohen), Chicago Crime Syndicate member
- William Daddano, Sr. (William Russo), Chicago crime syndicate enforcer
- Sam Giancana (Salvatore Giancana), Chicago Crime Syndicate leader
- Johnny Torrio , Chicago Mafia Don and Chicago syndicate leader
- Paul Ricca (Felice DeLucia), Chicago Outfit leader
- Jake Guzik , "Chicago Outfit" member
- Frank Nitti (Francesco Nitto), Chicago Outfit enforcer
- Gus"Gussie"Alex High Ranking Member of the Chicago Outfit, main political "fixer"
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