The boys — ages 15, 16 and 17 — confronted the man about 10:40 p.m. Tuesday in the 10600 block of South Leavitt Street and demanded his belongings, Chicago police said.
The 69-year-old took out his gun and shot one of them in the knee, police said.
The trio drove away but crashed shortly after, police said. Officers arrested them after a foot chase.
The teens, who were not named because they’re charged as juveniles, each face a count of attempted robbery.
The two older teens also face a count each of possession of a stolen vehicle, while the 16-year-old also faces a misdemeanor count of theft between $500 and $10,000.