Officers responded to a ShotSpotter alert around 7:30 p.m. and found a man suffering from a gunshot wound to the arm in the 5900 block of South Ashland Avenue, police said.
At the same, 24-year-old Antwon Harrison fired shots at officers from a vehicle that was fleeing the scene, according to CPD.
No officers were struck by the gunfire.
The vehicle later crashed in the 5900 block of South Wells Street and Harrison and four other occupants were taken into custody. Two of the suspects were suffering from gunshot wounds. One was shot in the chest and the other was shot in the arm. They were both taken to the University of Chicago Medical Center, where they were listed in critical and good condition, respectively, police said.
No shots were fired by officers during the incident, police said.
Harrison was charged with two counts of attempted first-degree murder.
He is scheduled to appear in bond court Wednesday.