A 14-year-old boy and a man were shot while traveling in a car in Woodlawn Tuesday night.
They were heading west in the 6600 block of South Greenwood Avenue when someone fired shots from the sidewalk about 11 p.m., police said.
The driver, 31, suffered a gunshot wound to the head and lost control of the car, which struck a tree and crashed into a building, police said.
He was taken to University of Chicago Medical Center in critical condition, police said.
The 14-year-old was shot in the right arm and was taken to the same hospital, where he was listed in fair condition, police said.
No one was in custody.