Wednesday's shooting, taking place just a few days after the Orlando, Florida massacre at a gay nightclub, was a stark depiction of the gun violence that has plagued the United States and fueled a rise in murders in one of its premier cities.
In the Facebook Live video, Antonio Perkins, 28, inadvertently captured his own murder.
He can be seen broadcasting selfie-style on his smartphone, when suddenly about a dozen gunshots ring out in quick succession.
Perkins immediately drops the phone, after which there is only audio as panicked voices can be heard trying to keep the man alive.
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"Oh my God!" a woman screams.
"Call the police! Hurry up!" a man says.
"Tony, you're good Tony," says another woman, talking to the victim.
Perkins died from gunshot wounds to the neck and head, according to police, who say they have made no arrests in the ongoing investigation.
Officials say Perkins was a documented gang member, but people who knew the man told Chicago TV station WGN that he was no longer in a gang and that he was likely not the intended target of the shooting.
At least 13 other people were wounded in shootings in the city on Wednesday, according to a tally by the Chicago Tribune.
There have been some 269 murders so far this year, a staggering 49 per cent increase from the same period a year ago, according to statistics released by Chicago police.
"We must end the killing fields," said civil rights leader Jesse Jackson.
Jackson was speaking to a room of journalists about an upcoming summit his Rainbow PUSH Coalition is holding on a range of issues -- from the presidential elections to alleviating poverty in African American neighborhoods.