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No deal came out of the negotiations on the third day of the strike, however, and Chicago Public Schools canceled classes for a fourth day on Thursday.
"We feel like we're in a pretty good place," Chicago Teachers Union Presidend Karen Lewis said. "Both sides [are] making movements."
Lewis said she was "very happy" about that status of teacher evaluation, which has been a sticking point in the contract dispute. "It's a lot better than it was this morning," she said. The other stumbling block is layoff recall.
"Very productive evening, really good discussions and proposals on the most difficult issues that we face," said Chicago School Board President David Vitale.
Earlier in the evening, Lewis said the possible closing of schools had become a big issue which was tied into the other two major issues, teacher evaluations and rehiring.
While school and union officials acknowledged progress had been made, teachers will be back on the picket lines and Chicago Public Schools (CPS) confirmed students will not be back at school again Thursday. Negotiations will resume Thursday morning.
The day ended better than it began.
Both sides arrived around 11 a.m. Wednesday, but CPS officials said several hours passed before the union was ready to talk.
"We started at 7:15, so we spent a lot of the time kind of waiting," said Barbara Byrd-Bennett, CPS chief education advisor.
CTU disputed that claim, saying talks began hours earlier.
"We have smaller groups and bigger groups. Some people have been excluded from those groups, so they haven't been meeting. But we have been meeting," said CTU President Karen Lewis.
School officials say Wednesday night's talks centered around teacher evaluations and CPS's demand that 40-percent of the rating be tied to student test scores.
"It's partly to make that a much less subjective and more objective measurement," said Jesse Ruiz, Chicago School Board member.
The union calls the evaluation system unfair and says it could prevent teachers from being rehired if they're laid off.
The union is digging in, in part because it believes CPS plans to close 100 or more schools in coming years, a charge CPS denies.
"The board seems to be wedded to proposals that will lead to thousands of experienced and dedicated teachers being replaced," said Lewis.
The day began with a verbal jab at Lewis, who at a rally Tuesday said before returning to talks, "I'm going back to the silly part of the day."
"We take these negotiations incredibly serious. It's not silly that our athletes are sitting on the sidelines and about to forfeit opportunities for college," said Byrd-Bennett.
CPS made public a two-page handwritten response from the union last week and drew contrasts to its own lengthy proposal.
On Tuesday, the Reverend Jesse Jackson of Rainbow PUSH Coalition, who has publicly backed the union, offered to play mediator.
"They should be meeting around the clock. Each passing day the pain is compounded," said Rev. Jackson.
CPS CEO Jean-Claude Brizard is asking the teachers union to voluntarily not picket in front of schools being used in the district's Children First program. More than 140 have been designated as safe places for kids to have meals and participate in supervised activities during the strike.
Beginning on Thursday, the sites will be open from 8:30 a.m. until 2:30 in the afternoon, two hours later than during the first three days of the strike.