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A teacher strike could have students closing up their books and putting down the pencils in less than one week.
The Chicago Teachers Union says its members may walk picket lines instead of entering classrooms next Monday if a new contract is not reached.
The two sides continue to negotiate as thousands of students face the possibility of placing learning on hold.
Both sides say progress is being made but won't mention specifics.
Though sticking points include traditional areas of pay and job security, the union says much of what they are grappling with goes beyond employment issues.
Tuesday morning at Clemente High School, as a false start to the school year looms, the Chicago Public Schools' chief executive officer Jean-Claude Brizard rang in this first day of classes with the help of Bears offensive lineman J'Marcus Webb.
"It's going to mess it up completely, because if they strike, I can't play football anymore, and that's my ticket out," said student athlete Corey Brown. "You know, I need this."
"Academically, it would mean a lot to me because all last year I made honor roll, and I want to keep that pace going. I don't want to stop that," said CPS student Demetrius Harris.
Both sides say progress is being made, though at Monday's Daley Plaza rally, the head of the teachers union called Mayor Rahm Emanuel a "liar and a bully."
"I don't think anyone should have thin skin around here," said teachers union president Karen Lewis. "If you're going to play in these games and be in this area, if your feelings get hurt by name calling, I mean, I've been called names too."
"The one good thing is, that when you look at negotiations, that kind of acrimony does not make its way to the table," said Brizard.
St. Xavier University labor relations professor Cheryl Luczak sees both sides doing more campaigning than negotiating.
"They need to respect each other and how they're talking and find that common ground," Luczak said. "Rally around the students, what they have in common. Why are they there?"
Key sticking points include pay, a new teacher evaluation system and a policy to rehire recently laid off teachers.
But also at stake, says the union, are philosophical issues about how kids should be educated, a "battle over the soul of public education" being waged by outside groups.
"The billionaires who have an agenda, which is actually to privatize education," Lewis said.
"This might not be the time for that overarching discussion," said Luczak. "Let's make sure to keep the kids in school. The overarching discussion is something that's going to take a lot of time."
Both sides met again Tuesday and plan to negotiate at least through the end of this week.
The union's House of Delegates meanwhile is scheduled to meet Wednesday, and if there is progress, they could vote to extend that strike deadline. So far, there is no indication that will happen, so everyone still has their eyes on Monday.