Most of the suspects were riding on Divvy rental bikes, police said one of the men opened the door and tried to pull the 82-year-old driver out at around 10 a.m.
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The victim initially resisted, but eventually, he got out of the car.
The incident was caught on video by a nearby police pod camera.
A woman who worked down the street witnesses the group of young men by the car. The security cameras from her business captured images of several of the suspects, but the carjacking itself happened just out of range of their cameras.
"I saw the old man.. picked up his bag...looked at them and walked away," a witness said.
The 82-year-old man was not injured, police said.
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The men who stole the car were seen throwing his items outside on the street.
Police said four men got into the car and took off westbound on Grand Avenue. The others in the group followed on their bikes.
"I just saw they ran away with the car...I was so scared," the witness said.
Police said no one is in custody.
Anyone with information is being asked to contact the Chicago Police Department.