The incidents happened Saturday in the 4800- and 4900-blocks of Lawn Avenue in Western Springs.
Investigators say the suspects drove a late model, white Chevy suburban and drove up to young boys to ask if they wanted candy.
"In each instance the female asked the kids if they wanted candy, it was in back on the van," Western Springs Police Deputy Chief Brian Budds said.
Witnesses also told police the suspects appeared to be filming them with a smartphone. Police say the female driver asked the kids if they wanted to film some video. The boys did exactly what they should have done, police said, they told their parents and called police.
They made no physical contact with the children and drove off.
"We have no reason to believe this wasn't a criminal act and we are treating it as such," Budds said.
Police alerted every school in the area as well as nearby suburbs.
"It's freaky, we have a great community, very safe kids are safe," local parent Lisa Blaze said.
Parents who live on the street where the two incidents occurred have all had conversations with their kids about safety Monday.