Police said a 26-year-old woman, a 30-year-old man, and a 31-year-old man were standing in the West Englewood neighborhood's 6500-block of South Hermitage Avenue just after 12:45 a.m.
That's when a white SUV pulled up, and a male suspect inside fired shots, police said.
The 30-year-old man was shot in the head, and the 31-year-old man was shot in the chest, police said. Both were taken to the University of Chicago Medical Center, where they were pronounced dead.
The woman, shot in the body, was taken to the same hospital in critical condition.
Police said the SUV's driver fled northbound on Hermitage Avenue.
Area One Detectives are investigating.
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