They were walking about 2 p.m. in the 6300 block of South Oakley Avenue when two males got out of a vehicle and opened fire, Chicago police said.
A 23-year-old was struck in the abdomen and taken to the University of Chicago Medical Center in serious condition, police said.
The other man, 20, was shot in his arms and legs and taken to Christ Medical Center in Oak Lawn, police said. He was also in serious condition.
No arrests have been reported. Area One detectives are investigating.