Police said the shooting happened in the South Austin neighborhood's 0-100-block of North Lockwood Avenue, near West Madison Street, just before 7:30 p.m.
A 15-year-old boy and three men, aged 32, 34, and 35, were on the sidewalk when an SUV pulled up, and someone inside fired shots, police said.
The 32-year-old, shot in the face, was taken to Mount Sinai Hospital, where he was pronounced dead.
The 34-year-old, shot in the leg, was transported to the same hospital in critical condition.
The 36-year-old, shot in the right flank, was taken to Stroger Hospital in critical condition.
The 15-year-old, shot in the leg, was transported to Mount Sinai Hospital in fair condition.
Neighbors and onlookers gathered in the neighborhood where several bullet markers now scatter the ground.
A violence interrupter was on the scene to support families in what he calls a quiet area.
"Keep in mind the families that may be suffering from a loved one being lost not only at this scene, but across the City of Chicago," said Hyson Harper with Anchor Inc. "Our biggest focus is, how can we reduce violence constantly in the City of Chicago?"
Area Four detectives are investigating. A heavy police presence, including officers with assault weapons, kept the crowds back from the crime scene.
"Right now, we are hitting our peak season where it is warm outside, and the biggest thing is to try and make sure children and our families are safe," Harper said.
Authorities did not immediately provide further information.
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