The teachers union has authorized a strike for as early as the second week of school.
Both sides are negotiating this holiday weekend and some activists are calling the situation a new fight for civil rights.
CPS says talks are expected to continue every day through at least the end of next week. This as the union plans a Labor Day rally to ratchet up pressure on school officials.
At Rainbow PUSH headquarters, the Chi-Lites sang in support of the teachers union, which Saturday tried to cast its labor battle in broader terms.
"Let me be clear, you all, that this fight is definitely the civil rights fight of our day," said CTU's Brandon Johnson.
Though the bargaining sessions continue, the rhetoric away from the table has gotten personal.
"We are tired of being bullied, belittled, and betrayed," said CTU President Karen Lewis. "We've done everything asked of us, and we continue to be vilified and treated with disrespect."
Labor relations professor Bob Bruno sees a series of missteps by Mayor Rahm Emanuel as contributing to the current impasse.
"We now have a situation where the teachers see Rahm and CPS as, quite frankly, the enemy," Bruno said.
It began last year, says Bruno, when the mayor canceled teacher raises, lobbied state lawmakers to raise the vote threshold for teachers to strike and made his pitch for a longer school day
"When one party does that even before the bargaining process starts, you're signaling that you don't trust the process, and in fact you're afraid of the process," Bruno said. Now, as talks are nearing the eleventh hour, the mayor is scheduled to speak Tuesday at the Democratic National Convention in Charlotte.
"We hope that the mayor, the board, and others will put their focus in town this week, and not so much on charlotte but Chicago," said Rev. Jesse Jackson, Sr.
"If he's going to go to Charlotte, he better go make a speech and get back here pronto because he looks like he's taking his eye off the ball," said ABC7 political analyst Laura Washington. "And right now, the most important issue facing his administration, and the biggest crisis of his administration, is this possible school strike."
The union Saturday announced it will stage a rally Monday in Daley Plaza, the day before the new school year starts. Also, next week we're expecting to learn more about the cps contingency plan.
A website and phone number will be made available to parents so they know exactly where their kids can go.