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Working mom Dequita Wade said that when the strike started, she sent her son 15 miles away to a cousin’s house so he wouldn’t be left unsupervised in a neighborhood known for violent crime and gangs. She was hoping the union and district would work things out quickly.

“You had a whole week. This is beginning to be ridiculous,” Ms. Wade said. “Are they going to keep prolonging things?”

Months of contract negotiations have come down to two main issues central to the debate over the future of education across the United States: teacher evaluations and job security.

Union delegates said they felt uncomfortable approving the contract because they had seen it only in bits. The union will meet again Tuesday, after the end of Rosh Hashana, the Jewish new year.

“There’s no trust for our members of the board,” Chicago Teachers Union President Karen Lewis told reporters Sunday night. “They’re not happy with the agreement. They’d like it to actually be a lot better.”

Mr. Emanuel showed his frustration at the striking teachers in a written statement Sunday night.

“This was a strike of choice and is now a delay of choice that is wrong for our children,” Mr. Emanuel said.

The strike has shone a spotlight on Mr. Emanuel’s leadership more than ever, and some experts have suggested the new contract — which features annual pay raises and other benefits — is a win for the union.

“I’m hard-pressed to imagine how they could have done much better,” said Robert Bruno, a professor of labor and employment relations at the University of Illinois at Chicago. “This is a very impressive outcome for the teachers.”

With an average salary of $76,000, Chicago teachers are among the highest paid in the nation, and the contract outline calls for annual raises. But some teachers are upset it did not restore a 4 percent raise Mr. Emanuel rescinded last year.

Mr. Emanuel pushed for a contract that includes ratcheting up the percentage of evaluations based on student performance to 35 percent within four years. The union contends that does not take into account outside factors that affect student performance such as poverty and violence.

The union pushed for a policy to give laid-off teachers first dibs on open jobs anywhere in the district, but the city said that would keep principals from hiring the teachers they think are most qualified.

The union has engaged in something of a publicity campaign, telling parents about problems that include a lack of important books and basic supplies.

Some parents said they remain sympathetic to teachers.

“I don’t think they’re wrong. The things they’re asking for are within reason,” said Pamela Edwards, who has sent her 16-year-old daughter to one of about 140 schools the district has kept open during the strike to provide meals and supervision.

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