More than 350,000 children in the nation's third largest school district have been affected by the strike, now in its second week.
The 29,000 teachers and support staff have been on strike since Sept. 10. The approximately 800 union delegates, who are representing them, met on Sunday but made no resolution as to when to end the walk-out. At that meeting, a majority of the delegates decided to continue with the strike, keeping children out of the classrooms.
Whether or not the strike will be called off could be known at 3 p.m. Tuesday when delegates meet. If the strike continues, a judge will decide on Wednesday whether to end it.
The court was brought into the mix after a frustrated Mayor Rahm Emanuel gave the go signal for the city's legal counsel and lawyers with the Chicago Public Schools to file an injunction in circuit court and force teachers to return to the classroom.
Emanuel, who said the strike - the first in 25 years - is one of choice, said the children are being "played as pawns" in the whole ordeal. He also called it illegal.
The union fired back, calling Emanuel's move to look to the court "vindictive."
"The Chicago Teachers Union is striking over mandatory subjects of bargaining such as compensation, evaluation procedures and the conditions within our classrooms," CTU spokeswoman Stephanie Gadlin said.
"If this was an illegal strike the Chicago Public Schools would have sought injunctive relief on day one," she added. "The law provides that if a strike is illegal only the labor board has jurisdiction to stop a strike. CPS has never filed any claim with the labor board that our strike is illegal."