The 37-year-old was walking outside around 2:17 a.m. in the 10700 block of South Wentworth Avenue when someone in a passing car started shooting, police said.
He suffered a gunshot wound to each leg and two shots to the groin, according to police.
The man was taken to Advocate Christ Medical Center where he was listed in fair condition, police said.
About 10 minutes later, a man, 36, was shot sitting on his porch about a mile south in the 300 block of West 114th Street, officials said.
He was taken to the same hospital with a gunshot wound to the back, police said. He was in fair condition.
No one from either shooting was in custody.