He's running a scam in Chicago's Craigslist for a tutor for his son. He claimed to be from the Chicago area who relocated to Italy.
He claimed that his son would be coming in for "holiday" in the States with his mother, then later on in his letter, wrote that a nanny would be caring for his kid. I grew up in the Chicago area, and to my knowledge the term we use is "vacation".
The kicker for me, he ended his letter with "Stay Blessed"... another non-Chicago thing, but maybe Nigerian?