According to witnesses, the driver was traveling northbound over the Torrence Avenue Bridge just before 7 p.m. when he went through a retention net and into the water as the bridge was going up, police said.
The teen was rescued by a passing boat, while the Chicago Police Marine unit located the driver in the water.
The 16-year-old boy and a 40-year-old man were transported to the hospital. The teen is said to be in critical condition at Comer Children's Hospital, and the man is in grave condition at U of C.
No further details have been released at this time.