Police said the driver of a Dodge Durango was heading westbound at around 2:10 a.m. on Lake near Kildare when he collided with a sedan.
Both of the vehicle slammed into CTA "L" train pillars, police said.
A man in the sedan was pronounced dead at the scene. Three others from that same car were taken to Mt. Sinai Hospital in critical condition.
The Major Accidents Unit is investigating a cause of the crash.