Both women were alone and young, around the age of 20. In one alleged incident, the man offering his help followed the woman for miles in his vehicle.
The incident, which started at a Target store, still has Alexa Colangelo, 20, feeling shaken.
"I was like -- someone tried to harm me -- and I was completely scared for a couple days," said Winthrop Harbor resident Alexa Colangelo.
It was Monday of last week when Colangelo says she got into her SUV after leaving the store in Waukegan.
She took the long way out of the parking lot and noticed a white pickup truck that had been parked next to her in the lot was now traveling behind her.
Three miles later, it was still on her tail. The male driver eventually pulling up next to her.
"He said, 'Miss, you have a flat tire. The air is coming out of the valve of your tire,' And then he kept insisting -- 'Can you please pull over, and I'll help you,'" said Colangelo. "The fifth time I told him no, he pulled off and drove away from me."
After discovering the tire was indeed losing air, Colangelo called her father, Ron, whose job as the public works director in Zion requires him to manage hundreds of vehicles.
He says the cap and needle in the tire's air stem had been tampered with.
"I've got mechanics at work that do tires and stuff like that and other things, and I've seen them do it, and I know you have to have a little special tool that fits in there to unscrew it to back it out," said Ron Colangelo.
Concerned, Ron wrote about the incident in an email warning friends, and it soon ended up on Facebook, prompting another father to call Waukegan police about a similar flat tire incident involving his daughter.
"His daughter agreed to have help. The gentleman changed it for her, and he went on his way, and the daughter went on her way," said Waukegan Police Sergeant Cory Kelly.
Police say that incident also happened at Target, the help coming from a man also parked in an adjacent spot in a white pickup, the tire's air stem also damaged.
However, no money was exchanged or asked for, and the vehicles never left the lot.
"We ask people that if something seems weird, it probably is. Call the police. Also, if you don't feel safe, don't leave the parking lot," said Kelly.
Ron Colangelo says he notified Target security officials who said that they would look at their parking lot surveillance video. In a statement, a Target spokesperson referred all questions to law enforcement but said that the company takes reports like these very seriously.