"I think we've actually made a lot of progress and I think we're getting really close, even on thorny issues," David Vitale said. "I think absolutely a deal can be made."
The teachers' union and school district remain at odds over wages, benefits and job security, and teachers are prepared to strike if no agreement is reached by Monday.
Talks are expected to go through the weekend if necessary, the Chicago Tribune reported.
Chicago Teachers Union President Karen Lewis said she is also "very optimistic" an agreement can be reached before Monday. She said the union is working in the best interests of Chicago schoolchildren.
"This isn't about the money," Lewis says in a radio ad that aired Thursday. "We all know that teachers should be paid for the work we do, especially when it's longer and harder. We're fighting for art, music, physical education and world-language classes for the 400,000 plus schoolkids who depend on us."
Jessica Hawkins, a senior at Jones College Prep in Chicago, said she's worried a strike could affect her ability to gather teacher recommendations and transcripts for college applications.
"It's going to be hard," she told the Tribune. "They told us, 'Oh, the longest CTU strike hasn't been longer than two weeks.' But we're applying to colleges with deadlines. We can't just hope it doesn't last too long."