Police said the crash happened just after 10:30 p.m. at North Ottawa and Touhy avenues in the Edison Park neighborhood.
A CPD helicopter was monitoring a 21-year-old man driving a stolen car, with three passengers inside, at a high rate of speed.
The 21-year-old lost control of the vehicle and struck another car, driver by a woman, before crashing into a building, police said.
Officers recovered a gun from the scene.
One witness said his car was first hit by the speeding car at North Milwaukee and North Elston avenues.
The stolen car's driver suffered a leg and spine injury and was transported to Lutheran Hospital in critical condition.
Three women and another man were taken to hospitals with minor injuries.
Area Five detectives are investigating. Charges are pending and traffic citations will be issued for the crash, police said.