One inmate, who spoke on the condition of anonymity, told DailyMail.com the guards didn't seem to care that they might be breaking the law.
He said: 'I asked him [the guard], 'Did you ask people first if they're registered to vote?' And he said 'no'.
'I said but you should because if I'm registered to vote somewhere else like I am, you are asking me and enticing me to vote even though I'm registered somewhere else and that's a felony. I can't be voting in two different jurisdictions.'
He claims another guard told him that he was 'just doing what I'm told'.
An inmate being held on murder charges, also says 21 of the 48 inmates in his Division 11, have already voted but none were asked if they were registered or eligible to vote.
'They just say who wants to vote? Line up to vote,' he said.
An unnamed source familiar with Cook County Jail said it is the ideal environment for ballot harvesting.
'Cameras inside the Jail notoriously don't work. There aren't any election observers. If an inmate complains, who would believe them? So, if you wanted to manipulate a ballot, who would know?'