A judge ordered 30-year-old James Whiteside held without bail Tuesday, calling him a danger to himself and to society.
Last Thursday, around 11 p.m., police say Whiteside pushed a 23-year-old woman into her car outside a White Castle in the 3100 block of North Park.
He displayed a pair of scissors and threatened to kill the woman, prosecutors said Tuesday. He drove her car to a second location where he demanded she give him $400. The money she had was given to her for Christmas.
Whiteside continued to drive around with the victim and forced her to withdraw money from an ATM machine, officials said.
Finally he paid another man to take her to his godmother's house in the 1100 block of North Keeler Avenue, where she was held for a couple of hours.
Eventually the woman was allowed to call a taxi and went home, officials said.
A day later Whiteside was accused of doing the same thing, this time in the parking lot of the Chicago Transit Authority's Orange Line stop at Midway International Airport.
Police said he pushed a 69-year-old woman into a car, told her he had a gun, threatened her life and made her give him all of her money. He then sexually assaulted her repeatedly, according to authorities.
Whiteside then drove around the West Side of Chicago with the woman in the car and stopped to purchase drugs twice, prosecutors said. At some point they stopped and he gave another man the woman's ATM card and PIN number and told him to withdraw money while he waited in the car.
Eventually Whiteside stopped the car and walked away. The victim was then forced to find someone she could borrow a phone from to call 911, prosecutors said.
Whiteside was arrested by police when he returned to his godmother's apartment. He fled and was apprehended a short distance away.