The hit-and-run happened at approximately 1 a.m. Monday in the Jefferson Park neighborhood in the 5200-block of North Loring, a quiet residential street.
After hitting the victim the first time, police say, the driver went around the block, then came back and hit the man a second time. Authorities are looking at the case as an intentional attack.
"I am shocked. I am shocked because this is a very quiet, lovely neighborhood, and I am really shocked what happened," said neighbor Marianna Pluta.
Many neighbors who live in the area never heard the hit-and-run. Longtime resident Sanjay Gupta heard a commotion that sounded to him like children.
"I remember being a little upset that there was noise, and then I just fell asleep thinking that whatever it was, was going to go away," Gupta said.
A short time later, paramedics found a 38-year-old man critically injured near an alley.
"Stuff like that does not happen in this neighborhood," Gupta said. "I've lived here all my life, and there's no gun violence here."
The victim was taken to Lutheran General Hospital in suburban Park Ridge. His name was not being made public Wednesday.
The scene was still visibly bloody later Monday morning as Chicago police circled blocks in the neighborhood looking for the hit-and-run car. A description of the car has not been released.
Some residents say they are worried about their own safety.
"[I'm] scared. I have three young children. So, to hear there's a hit and run, it can happen to any of us," Pisey Alvarez said.
"My reaction is, more than likely, he ran the stop sign on Lynch, but the fact that he came around again, that's uncalled for. I hope they catch the guy whoever did it," said Gale Birch.
Police say they hope surveillance video from nearby homes or businesses can help them identify the driver.