The men, 22 and 23, were near a parking lot around 6:53 p.m. in the 8400 block of South Holland Street when two gunmen got out of the vehicle, flashed handguns and demanded their property, according to police.
The men complied and the gunmen at some point started shooting the victims, police said.
The 23-year-old man was struck in the armpit and was transported to Advocate Christ Medical Center where he was later pronounced dead, police said.
The 22-year-old man suffered a gunshot wound to the chest and was taken to the University of Chicago Medical Center where he was listed in critical condition, police said.
No one is in custody as area detectives investigate.