Police said a vehicle was driving southbound in the wrong lane when it struck a vehicle and then hit a building at about 3:14 a.m. in the 9000-block of South Cottage Grove Avenue.
The driver of the vehicle in the wrong lane that struck the building was transported to the University of Chicago Medical Center in critical condition, police said.
The driver of the other vehicle was transported to Trinity Hospital in good condition.
The impact left a large hole in the side of the building.
"I was in my bed sleeping when I heard a 'boom' and I had no idea what it was," Verda Long said. "I jumped up and ran to the front of the apartment here and looked out and I saw the police cars."
No one inside the building was injured.