CPD said those hurt were near two others, who began shooting at each other before fleeing the scene just before 2 a.m. in the 6000-block of South Winchester Avenue in West Englewood.
Both mass shootings, in West Englewood and West Humboldt Park, seemed to start as large gatherings, celebrating over the Father's Day holiday weekend, with both ending in gunfire.
Mary Retta Beamon Robinson lives just steps away from the West Englewood scene. She said she heard dozens of gunshots.
"It was a whole lot of them, I know that," she said. "The chairs were still sitting on the sidewalk. Like, everybody just got up and ran away and just left everything."
The circumstances of the shooting were not immediately clear, and police said it's unclear if those firing the shots are among the wounded.
"Shut it down, go home!" Beamon Robinson said. "I don't care that people come. I don't have a problem with that. I have a problem with it ending like this."
She said police had already been at the scene before the shooting happened, but did not disperse the large crowds.
"This all could've been avoided," she said. "The police had been down the block already."
Just over an hour before the South Side shooting, six people were shot in the city's Humboldt Park neighborhood.
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"This isn't just an event that happened over here," said her husband Fred Robinson. "It's happening all over Chicago and there's nothing being done."
In West Englewood, a 20-year-old man was shot in the neck and taken to University of Chicago Medical Center, where he was listed in critical condition, CPD said.
A 33-year-old woman shot in the back was taken to Holy Cross Hospital in good condition; a 34-year-old woman shot in the hip was taken to Holy Cross in good condition; and a 24-year-old woman was shot in the leg and taken to Holy Cross in good condition.
A 31-year-old man was taken to U of C in good condition after his ankle was injured; officials earlier said he had been shot, but later clarified he had not.
A 32-year-old man was shot in the foot and taken to St. Bernard Hospital in good condition, CPD said.
A 31-year-old woman walked into St. Anthony Hospital, with a graze wound to the right thigh, and is in good condition.
No one was in custody later Monday morning, and Area One detectives are investigating.
The Robinsons have a health care advocacy initiative called Prayers on Winchester, and they said their prayers have changed.
"God really needs to work on this block and in this community, and for the people who do have people come to their house, control the people," Beamon Robinson said.
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