Police said the crash happened in the Gresham neighborhood's 600-block of West 79th Street just before 1 a.m.
A 40-year-old man was driving when he struck a viaduct and lost control, police said.
The man was transported to the University of Chicago Medical Center, where he was pronounced dead.
A 41-year-old woman, who was a passenger in the vehicle, was taken to the same hospital in critical condition.
No other injuries were reported. Police did not immediately provide further information.