One of the victims was a Chicago blues musician. Police say a 74-year-old church deacon man was shot to death inside a car in the 7000-block of South East End. Soon after, a 41-year old man was also shot and killed in a car just three blocks away.
It's still unclear if these two attacks are related, but police are looking into the possibility that the gunmen ambushed one of the victims after trying to carjack the other.
Relatives say Willie Cooper was one of two men shot to death within blocks of one another early Thursday morning.
"You couldn't find a better person, he was just a sweetheart. Always a smile on his face, always a nice word to say," said Vivian Vest, victim's sister-in-law.
Witnesses say the 74-year-old retired CTA bus driver and church deacon was killed during an ambush attack.
"Bam, bam, bam, bam. And then you heard a loud crash," said Michelle Smiter, neighborhood resident.
It happened Thursday morning around 4:45 a.m. near the intersection of 70th and East End Avenue.
Steve Herron says he and Cooper had been carpooling for over a year and that his best friend had come to the neighborhood to pick up him up to go to work at a charter bus company.
"I was walking out to the door and heard gunshots. He had just pulled up in my driveway and they just shot him," said Herron.
Cooper was active in his community and ordained by the Catholic Church in 2002 and served as a deacon for nearly 20 years at St. Phillip Neri Church.
The attack happened just minutes after 41-year-old Eric "Guitar" Davis was targeted. The blues guitarist was found shot to death inside a car several blocks away in the 6700-block of East End.
"It don't make sense. Dealing with something, it just kind of comes at you. You know, you don't have no time to catch your breath, you're kinda back on your heals, and you're still dealing with this," said Qwelian Raoduss, victim's brother.
It's still unclear why Davis, a south suburban resident who is the son of noted blues drummer Bobby "Top Hat" Davis, was in the South Shore neighborhood.
Investigators have not said if the killings are connected in some way, but the slayings have devastated a community.
"My main concern is the kids. My grandson was asking me, 'Grandma, is he dead?' We just had a funeral, so trying to explain to them, yes. So really, I'm worried about them," said Deborah Henderson, South Shore resident.
Police have not said what type of weapon was used in either attack, and so far, no one is in custody.
The Chicago Police Department is asking people who have information about these crimes to call detectives at (312) 747-8380 or text the tip hotline 274637. The text must begin with the letters CPD.