The shooting happened around 9:19 p.m. in the 1000 block of North Lake Shore Drive, Chicago police said.
Two victims, a 19-year-old man and a 21-year-old woman, were shot while driving northbound on DLSD when they were shot.
A light-colored sedan had pulled up next to the victims' vehicle when an offender fired shots at them, police said.
The man was shot in the head was taken to Northwestern Hospital, and he was initially listed to be in critical condition. The woman was shot in the left calf and was taken to Northwestern Hospital as well, police said.
The offenders fled the scene in the sedan after the shooting, police said.
No one was in custody. Chicago police continue to investigate.
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