The meeting with the union comes a day after school board members set aside $25 million for a strike contingency plan, which reportedly would make libraries, park district buildings, and other places available for kids to go.
On Wednesday, the Chicago Teachers Union's House of Delegates gave their president, Karen Lewis, the authority to issue at 10-day strike notification as soon as she feels it is necessary.
On Thursday, teachers picketed at Doolittle Elementary on the Near South Side. The sticking points include pay, benefits, and how to implement the longer school day.
"They're trying to take advantage of the schools and not doing the hiring they're supposed to do, not providing the art and music teachers that the students need for a full education," said Jerry Skinner, CPS teacher.
As talks continue, students can only wait.
On Thursday, the head of the After School Matters Program said regular "fall programming will begin late September, but should there be a disruption to the start of the school year, we will explore ways to provide safe and meaningful opportunities for Chicago high school teens prior to that date."
"It's going to take a toll on most kids because they're going to be bored at home," said Milan Jackson, CPS student.
On the Far South Side, the Ray & Joan Kroc Corps Community Center, which is run by the Salvation Army, is preparing to beef up staffing.
"We're here to serve our members with recreation, any kind of education piece that we can put together," said Maj. David Harvey, Ray & Joan Kroc Corps Community Center.
Worried is the Reverend Phyllis Harrell who's helping to hire people for the CPS safe passage program, which helps kids to and from school.
A strike would mean fewer eyes and ears on the streets.
"You're like throwing the community up for grabs," said Rev. Harrell, Alliance For Community Peace. "You're going to have delinquents, gangs. You're going to have robberies. You're going to have theft."