Felton, 21, is a Morgan Park High School alumnus. The singer, whose best known for his hit song "Birthday Sex," has 75,000 followers on Twitter.
"He's agreeing to help twitter many of our students back to school," said Ron Huberman, Chicago Public Schools CEO.
Felton wants every cps student to read his tweets on Monday, September 7th, the day before classes begin.
"Make sure you all stay tuned on that date and definitely be looking forward to the message I'll be putting out," said Felton.
CPS officials hope his Labor Day messages are nothing like "Birthday Sex," which is racy and in some versions pornographic. The song has soared to Number 1 on the R&B charts.
"At the end of the day to me it's just a song. You know, I'm a writer, I'm a producer I'm an artist. I write a lot on the experiences or what I think other people would go through," said Felton.
Huberman said he's heard the song "Birthday Sex." While the song and video might not be appropriate for a CPS classroom, the CEO and local alderman would not second guess the choice of a pitchman for the back to school effort.
"We think he's a great role model. We think he's someone who can get the word about getting our kids back to school," said Huberman.
"It's on every radio station that plays urban contemporary music. So he is someone who can get their attention and when he gets their attention he has the opportunity to give them a positive message about coming back to school," said Ald. Fredrenna Lyle, 6th Ward.
Felton and Mayor Daley did not share the stage at Tuesday's event, but they did meet on the sidewalk where Felton gave Daley a signed CD.
"It's freedom speech. He's pursuing his career as well as making money on this. Why not, he's going to be a wonderful engineer or whatever you're going to do in life. He knows he can do something so let him do it," said Mayor Daley.
Schools Chief Huberman says the district will monitor and- if necessary- censor Felton's tweets on Labor Day.