The shooting occurred in the 200-block of West Garfield Avenue right next to the Dan Ryan Expressway.
Police said two men got out of a silver SUV and started shooting, wounding a 50-year-old man and a 27-year-old woman.
The man was transported to the University of Chicago Medical Center in critical condition with multiple gunshot wounds. The woman was transported to the University of Chicago Medical Center in serious condition with wounds to the abdomen and legs.
Area Central police are investigating. No one is in custody.