Barbara Byrd-Bennett, 66, will plead guilty to 15 counts of mail fraud and five counts of wire fraud, said Zachary T. Fardon, U.S. attorney for the Northern District of Illinois.
Byrd-Bennett's attorney, Michael Scudder, said his client would do so "as part of accepting full responsibility for her conduct."
Scudder said Byrd-Bennett will continue to cooperate with prosecutors and will testify if needed.
Byrd-Bennett is accused of helping SUPES Entities win contracts to train school administrators or consult in the school system. She was promised a 10% kickback from each contract that would be paid on the first day after she left her job as CEO of the school system and rejoined SUPES, an indictment alleges.
"Graft and corruption is never a good thing, but it is particularly troubling when it impacts our schools, our kids," Fardon said.
Byrd-Bennett also received bribes such as an airplane ticket, meals and seats at basketball and baseball games, according to the indictment. Prosecutors said one co-conspirator also promised jobs for her friends in exchange for contracts.
Two former owners of the SUPES Entities' subsidiaries that prosecutors say were involved in the conspiracy were also indicted, Fardon announced. Byrd-Bennett worked briefly for the companies -- SUPES Academy and Synesi Associates -- before she was hired by the school system in May 2012. She became CEO later that year.
The conspiracy started shortly after she got the top job, prosecutors said.
An email from December 2012 informed Byrd-Bennett that her payment would come in the form of a signing bonus from SUPES.
"If you only join for the day, you will be the highest paid person on the planet for that day," she was told, according to the indictment.
The money was being held in two accounts set up in the names of two of her relatives, the SUPES executives told her. As a result of one contract, there was supposed to be $127,000 in each account.
Her arraignment has not been scheduled. The maximum penalty for one count of mail or wire fraud is 20 years in prison, restitution and a fine.
Byrd-Bennett resigned in May, a month after the school system acknowledged that officials had been served federal grand jury subpoenas, The Chicago Tribune reported.