Someone walked up to a man standing outside a food mart and shot him in the head in Englewood about 8:20 p.m. Tuesday night.
Police said the shooter ran south and shot a 23-year-old man in the hip in the same block before fleeing south and firing at police who were stopped and talking to people on the street.
The 23-year-old was taken to St. Bernard Hospital and Healthcare Center and his condition had been stabilized.
The shootings happened on the 7100 block of South Vincennes Avenue at about 8:20 p.m.
The man was pronounced dead at the scene.