Chicago police said the crash happened in the West Lawn neighborhood's 6300 block of South Pulaski Road around 2 p.m.
A 56-year-old woman was driving a Honda SUV northbound on Pulaski Road when she struck a 76-year-old man and a 23-year-old woman, police said. The SUV ended up hitting a nearby building.
The Chicago Fire Department said the man was transported to Christ Hospital in grave condition. The woman was taken to the same hospital in serious to critical condition.
CFD said the driver, who police say was cited for failing to slow down, was transported to Christ Hospital in fair condition.
The crash happened in the same area has seen several crashes involving pedestrians recently.
Those crashes have led neighbors to plead with state and local officials for more safety measures to cut down on speeding.
Authorities did not immediately provide further information about the crash.