The crash occurred at about 3:03 a.m. in the 3300-block of West Irving Park Road.
Police said a 34-year-old woman driving a Kia sedan with two passengers attempted to overtake in the right lane when it struck a Volkswagen sedan driving in the same direction.
The Kia sedan then hit a tree and the Volkswagen hit a building, police said.
The driver of the Volkswagen fled in an unknown direction, police said.
The driver of the Kia was transported to Illinois Masonic Hospital in critical condition, police said.
A 38-year-old man who was a passenger was transported to Illinois Masonic Hospital and listed in good condition, police said. The other passenger declined medical treatment.