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Students in 243 Chicago public schools, roughly a third of the district, return to the classroom Monday at a time of transformation and uncertainty.

For many parents, teachers and administrators, the usual stress that accompanies the start of a new school year has escalated this summer after months of political discord and labor strife. Despite some progress between the district and the teachers union at the negotiating table, parents and students are still dealing with the possibility of a teachers strike in September that could close schools.

Teachers not only have to contend with thoughts of a strike, they’re busy preparing for a school year that will bring tougher new job evaluations and the more rigorous Common Core curriculum.

“It’s been such a nightmare,” said Claire Falk, a social studies teacher at Dunbar Vocational Career Academy, who has logged long hours over the past few weeks crafting lesson plans that meet the new requirements.

Principals at some schools say they have drafted numerous schedules for the fall, only to tear them up and start over every time CPS makes revisions to its plans to lengthen the school day. They’re also undergoing hours of online training so they meet the guidelines required under the state-mandated new teacher evaluation system.

A compromise reached by the district and teachers union to support the longer school day next year by rehiring CPS teachers who had been laid off has further complicated planning for principals. Many are cautious about which teachers they bring into their schools, worrying that if these tenured teachers have their seniority restored they’ll be able to bump less experienced teachers from their positions the next year.

The year will begin with new principals in 159 schools, the result of an exodus in the ranks at the end of last school year.

“When you’re on your third or fourth draft of the longer-school-day plan, and you have the Common Core and a new teacher evaluation system going in, it’s too much to absorb,” said Clarice Berry, president of the Chicago Principals and Administrators Association. “It’s too much, too soon, with too little resources.”

That has added layers of frustration to the start of a school year largely overshadowed by public battles over a teachers contract. Negotiators have scheduled talks through Labor Day weekend, an indication that a resolution still may be weeks away and that uncertainty will remain until most CPS students return Sept. 4.

Both sides are adamant that they want a contract resolved before Sept. 4.

“We recognize strikes are not popular,” union spokeswoman Stephanie Gadlin said in a statement Thursday. “However, they are the strongest tool public workers have in ensuring their rights are not trampled upon and working conditions are fair and equitable.”

Although the two sides have settled their differences over the longer day, they have yet to find common ground on teacher compensation, performance evaluations and other key issues. One dispute involves the recall policy for laid-off teachers. The union is fighting to make them eligible for all teacher vacancies, not just to supplement the longer day. That could include teachers whose “unsatisfactory” ratings contributed to their dismissals.

Another dispute centers on tying teacher pay to performance. Mayor Rahm Emanuel wants to eliminate automatic raises for working another year in the district. Those raises, in addition to salary bumps for pursuing graduate degrees, cost CPS about $40 million last school year, district spokeswoman Becky Carroll said.

Only days away from the official start of the school year, even the school calendar for 2012-13 is undecided as the union pushes to restore holidays such as Columbus Day that CPS had removed.

Talk of a strike has some parents on edge.

“I think it would be horrible and devastating for parents and kids throughout the city,” said Enrique Perez, whose twins will be starting preschool at Greeley Elementary School next month. “It’s like the entire city is on standby. … Both sides are arguing for things that are not necessarily doable.”

CPS parent Rebecca Labowitz, who writes a popular blog, “CPS Obsessed,” called the back-and-forth between the district and the union this summer “volatile” and said the longer school day will be a major adjustment.

“Things are changing for most parents because of the school day, and people have to figure things out,” Labowitz said. “On top of that there’s the possibility that school may not start on Sept. 4.”

Falk and others said the summer months have been a time of “uneasiness” for CPS teachers, whose annual worries about job security have been compounded by talk of a strike.

Veteran teachers, some of whom participated in strikes in the 1980s, said they have urged their younger colleagues to save money to protect themselves from a work stoppage. Many young teachers were caught off guard by the 19-day strike in 1987 and forced to take out small loans from the teachers union to cover their bills.

Some veteran teachers have told co-workers worried about rent or mortgage payments to alert their landlords and banks about the possibility of a strike and to see if they can make other arrangements.

CPS held firm on its initial 2 percent raise offer to teachers for months, building it into a proposed budget for next school year that also streamlines operations, raises taxes, cuts central office staff and drains its reserve fund to close a projected $665 million deficit.

Negotiators will tackle the contentious raise issue beginning next week. An administration official said the money the district had set aside for those 2 percent raises was used up when it agreed to rehire laid-off teachers. Each percentage point raise would cost the district about $20 million, officials said.

CPS officials said steep annual teacher raises are unsustainable for a district mired in a financial crisis and facing a $338 million spike in pension payments in 2014.

Carroll said large-scale reform is necessary in CPS.

“Change in a large urban district like CPS is never easy, but these changes can help transform the lives of our kids who deserve every opportunity at success in school and life,” Carroll said. “We can’t ask them to wait any longer for the kind of high-quality education they deserve.”

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