In an exclusive interview with CBS 2 Investigator Pam Zekman, the boy and his outraged parents described what happened.
"He came home crying. So I asked him why he was crying," said the boy's father, Anthony Woodman. "And he was like hysterical. He tells me he's been strip-searched."
It allegedly happened at Taft High school last month.
His mother, Michelle Woodman said she contacted the CBS2 Investigators "so this doesn't happen to anyone else. No one should go through what our son went through."
The student said two security guards, a Chicago police officer and a female assistant principal took him from an room where he was serving an "in school suspension" to a nearby washroom on the second floor.
Asked if the officer or assistant principal said anything, the student said, "They told me they had an anonymous tip. They were looking for drugs."
He said, while the others watched, one of the security guards put him up against the wall of a bathroom stall so his back was to the guards.
"And then he searched me with my clothes on," the boy said. "Then he told me to remove my belt. As I undid my belt he pulled my pants and underwear down to my knees."
After that, "He started grabbing and searching my privates," the boy said.
He said they did not find any drugs.
Records the Woodmans provided said CPS staff diagnosed their son with an emotional disorder and learning disability. He requires special education services.
Misconduct reports detail behavioral problems leading to numerous suspensions, some contested by his parents.
As for the strip search, his father said "there needs to be consequences for what they did to him."
Now his parents are suing everyone allegedly involved, and Chicago Public Schools and City of Chicago.
"What we are claiming is that his civil rights were violated when he was strip searched without cause and unreasonably," said Julie Herrera, the Woodman's attorney.
"The way it was done was outrageous," Herrera said. "Having a 15-year-old boy have to have a woman - an older woman - watch him with his pants down, while he is touched by another man. I think is horribly humiliating and embarrassing."
His mother said it was humiliating for her son, and it has adversely affected him.
"He is very withdrawn. He sleeps with his clothes on. He's had nightmares," said Michelle Woodman. "He is very angry. He's depressed. He is just not the same person."
The assistant principal who allegedly watched the strip search declined to comment, referring questions to the Chicago Public School's law department.
A CPS spokeswoman said their policy is that "under no circumstances are strip searches of students allowed on CPS premises."
The CPS policy manual also prohibits "washroom searches."
Spokeswomen for both CPS and the Chicago Police Department said they cannot comment on this case until their investigation is complete