Police saw shots being fired from a vehicle around 9:45 p.m. Friday in the 2300 block of West Division Street.
Officers attempted to curb the vehicle, but the car took off and crashed into a pole near the intersection of Ashland and Grand avenues, police said.
A weapon was recovered from the scene.
The male driver, whose name and age were not immediately available, was pronounced dead at Northwestern Memorial Hospital following the crash.
Two women, ages 26 and 23, were taken to Stroger Hospital in serious condition.
A 9-month-old boy was taken to Children's Memorial Hospital for observation only. ABC 7 Eyewitness News has been told the baby is going to be okay.
Sun-Timed Media Wire contributed to this story.