The city's police department is grappling with gang violence that routinely spikes over the weekends.
In one of the shootings early Saturday, police found two men shot multiple times in a vehicle on the far southwest side. One of the men was killed and the other critically wounded.
Also on the South Side, a 19-year-old man was shot in the chest at his home. He was found dead at the scene.
Police on Saturday announced the arrests of 39 people and the seizure of weapons, drugs and vehicles over the last week in areas with heavy gang activity. The operation targeted drug markets, including one taking in more than $2.3 million a year.