Chicago shooting or Chicago massacre may refer to:
- Haymarket affair
- Chicago race riot of 1919, a racial conflict between White-Americans and African-Americans, that killed 38 people (23 of whom were Black and 15 were White)
- Saint Valentine's Day Massacre, a gang shooting in February 1929 that killed seven people at Lincoln Park
- 1937 Memorial Day massacre
- Richard Speck (1941–1991), American mass murderer who killed eight student nurses either by stabbing, strangling, slashing, or a combination of the three between in July 1966
- Assassination of Fred Hampton, an African-American man who was killed on December 4, 1969
- Chicago Tylenol murders, a mass poisoning that killed seven people between September and October 1982
- 1999 Independence Day weekend shootings, a spree shooting in July 1999 that killed two people and injured ten others that targeted Jews, Asian-Americans and African-Americans
- 2003 Chicago warehouse shooting, a mass shooting on the South Side of Chicago that killed six people in August 2003
- Killing of Rekia Boyd, an African-American woman who was fatally shot by police in March 2012
- Murder of Laquan McDonald, an African-American man who was fatally shot by police in October 2014
- Gage Park murders, a mass stabbing that killed six people of the Martinez family (five of whom were stabbed and one was shot by gunfire) at Gage Park in February 2016
- Killing of Paul O'Neal, an African-American man who was fatally shot by police during a grand theft auto chase in July 2016
- Mercy Hospital shooting, a shooting at a hospital that killed three people in November 2018
- Killing of Adam Toledo, a Latino boy who was fatally shot by police in March 2021
- Killing of Anthony Alvarez, a Latino man who was fatally shot by police which occurred two days after the killing of Adam Toledo
- Killing of Zheng Shaoxiong, a Chinese immigrant who was fatally shot in November 2021
- Magnificent Mile shooting, a mass shooting that killed two people and injured eight others near a McDonald's in May 2022
- 2022 Chicago school shooting, a school shooting that killed two people and injured two others in December 2022