Police said the victim was walking in the 3400-block of North Cicero Avenue at about 2:08 a.m. when someone shot at him, near J & G Bar.
The man was not injured by gunfire and police said the shooter fled on foot. The victim was then hit by a gray 2016 to 2020 Jeep Grand Cherokee as he was trying to cross Cicero Avenue, police said.
The vehicle fled east on School Street toward Keating Avenue, and the victim was transported to Illinois Masonic Medical Center in critical condition.
The vehicle has front-end grill and driver-side headlight damage, Chicago police said.
No one is on custody and Area Five detectives are investigating.
Anyone with information is asked to call (312) 745-4521.