The men, aged 22 and 23, were near a car park at around 6.53pm 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 one point started shooting at the victims, police said.
The 23-year-old man was shot 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 while area detectives investigate.