Police said the shooting happened in the Roseland neighborhood's 700 block of East 104th Street just before 11:45 a.m. Video from the scene shows several evidence markers on the ground.
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The men were standing on the sidewalk when someone approached them from an alley and opened fire, police said.
Police said a 64-year-old man, shot in his head, was pronounced dead on the scene.
Two other men, 35 and 53 years old, were shot multiple times in their upper bodies, police said. Both victims were transported to the University of Chicago Medical Center in critical condition.
The 35-year-old's cousin said the father and husband was with his 53-year-old uncle, visiting someone, when they were shot at. She said the two were innocent bystanders when the gunfire broke out.
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On Monday afternoon, the family is waiting to hear more information from doctors.
ABC7 spoke with victim advocate Pastor Donovan Price, who also talked with the family of the 35-year-old man. He shared the emotions this family is now going through.
"Shocked at what was happening. Said they didn't deserve this. A loving husband and father, people who were just out as I said, trying to live their life and do what we all do on an afternoon and it turned sadder than it needs to be," Price said. "People should kiss their loved ones and let them know they are appreciated because unfortunately, time may not always be on our side."
Officials have not yet identified the man who died, but neighbors told Price he was beloved.
"He was the person could fix stuff for you. We are all familiar with that person who can be your handyman, and just everybody knew him and everybody loved him," Price said.
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This shooting comes on the heels of a violent weekend in Chicago. And with the summer months ahead, a time when violence tends to increase in the city, Price hopes this is not a preview of tragedies to come.
"It's time for all hands on deck. You're either part of the problem or you're part of the solution, and now is the time to be part of the solution before it lands on your lap, before it lands on your front steps," Price said.
The shooter fled the scene in a black pickup truck. There is no one in custody and Area Two detectives are investigating.
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