Chicago police said a group of people were standing outside in the 800-block of E. 79th St. around 8:46 p.m. when someone fired shots and fled the scene.
All five victims were rushed to University of Chicago Medical Center, police said.
One man, whose age wasn't known, is in critical condition after being shot once in the arm, investigators said.
A 50-year-old woman was shot in the arm, a 50-year-old man was shot in the ankle, and a 43-year-old man was shot in the shoulder, police said. A fifth female victim was shot in the thigh. All were said to be stable condition.
No one is in custody. Area Two detectives are investigating.