Chicago schools will be shut for an eighth day on Monday as a weekend of bargaining between the city and Chicago Teachers Union has failed to yield any progress, even after schools chief Janice Jackson came to the table for the first time. 

On Monday, the current strike will become the longest in more than three decades

After several days of gridlock, the biggest sticking point continues to be how much the city is willing to spend on its teachers contract. 

“Last night we left with the same deal on the table that is here tonight,” union Vice President Stacy Davis Gates said. 

While both sides have estimated the costs of their proposed contracts, neither has provided a comprehensive financial breakdown of the proposals on the table. 

On Saturday, union officials estimated the gap between what the city has committed to spending and what the union is demanding at $38 million a year for three years. But the district’s Chief Operating Officer Arne Rivera on Sunday morning estimated the cost at closer to $100 million over five years. 

The city has underscored what it considers dire fiscal implications of agreeing to the union’s demands. The city estimates its offer to the teachers union at $500 million over a proposed five-year contract.

 “This is, by any estimation, an incredible offer,” Mayor Lori Lightfoot said at a press conference at City Hall on Sunday evening. She said her current offer, which includes placing a nurse and social worker in each school within five years, will transform education in Chicago. 

 “Despite all of this, the CTU has not accepted it. We are enormously disappointed,” Lightfoot said. The city does not have any more money beyond what it already has offered, she said.

After negotiations at Malcolm X College broke for the day, union officials took a combative tone as they lashed out at Lightfoot and the city. They mentioned part of a long list of demands, from smaller class size and more prep time to increased funding for athletics and more librarians and restorative justice counselors. Gates stood by the union demand for a three-year contract; Lightfoot has insisted on a five-year pact.

Over the seven days of the strike, the union has varied in the demands that it publicly stresses. It’s unclear where it would compromise. On Sunday, Gates hinted that it may be holding out to secure all of them. “Our members didn’t walk the picket line to go back to their communities with half measures,” she said. 

Teachers, meanwhile, risk losing their health insurance on Friday if the strike continues. In a Sunday evening call-in town hall with members, its second in two days, union leaders spoke about protest plans for Monday and Tuesday, meaning the strike may continue into a ninth day. At the end of last week, teachers said they were tired but still resolute

In separate negotiations, SEIU Local 73, the union representing school support staff, struck a tentative agreement with the district on Sunday. Its members still need to approve the agreement; in the meantime, they will be on picket lines Monday morning, union President Dian Palmer said.