The man was taken to Northwestern Memorial Hospital, according to Chicago Police News Affairs Officer Hector Alfaro said.
About an hour earlier, a 33-year-old woman sitting in a car with her boyfriend was shot in the West Pullman neighborhood.
The couple was sitting in the 11900 block of South Lafayette Avenue when someone walked up and started shooting, hitting the woman in the right thigh.
The woman's boyfriend drove her to Roseland Hospital.
About 9 p.m. Wednesday, a 23-year-old man was shot as he drove in the 7900 block of South Ashland Avenue in the Gresham neighborhood. The man was wounded in the chest and leg, police said.
People in the area called police and responding officers found the man about two blocks east near 79th and Bishop, police said.
He was taken to Advocate Christ Medical Center, police said.