The crash involved a silver SUV and a black sedan in the 11900-block of South Ashland Avenue at about 11:52 p.m., police said.
A 45-year-old man in the black sedan was pronounced dead on the scene, police said. Authorities have not released his identity.
A 27-year-old woman who was in the black sedan was transported to Advocate Christ Hospital in critical condition, police said. A 40-year-old man in the SUV was transported to Advocate Christ Hospital in fair condition.
Area Two detectives are investigating and no citations are pending, police said.