Lightfoot was elected just a few months ago. In her first State of the City address, she unveiled a plan for how the city could address an $838 million budget deficit. The city budget is separate from the school district budget, but the shortfall does indicate that the city doesn't have extra revenue beyond what it has already offered. The city has already agreed to one of the teachers union's key demands, a 16 percent pay increase.

The city Board of Education canceled its monthly meeting and will not meet until the city and the union reach an agreement. The strike reached its fifth day, with no sign of an agreement. The current union contract ended June 30. Teachers went on strike a week ago.

The union had held fast with a series of 13 demands, including smaller sizes, more support staff such as nurses and teacher's assistants, and an increase in salary for all school employees. The Chicago Board of Education had responded with a number of proposals, and the two sides had agreed on several issues. However, it was not enough to convince the union to call off the strike. For example, the union wanted a salary increase to be phased in during three years; the city had countered with a five-year plan.

For a fifth day, many parents struggled to find child care for the nearly 300,000 students who would normally report for learning in the U.S.'s third-largest school district. Schools remained open to provide three meals a day. Teachers were not at work, but administrative staff were. School buses were not running. Some students reported to school, and at least one teacher had crossed the picket line and was instructing students; the vast majority of those students who were at school during the schoolday were not in teacher-led sessions.

As well, because school was not in session, student athletes were missing out on competition, including state playoffs. Students on soccer and tennis teams have already missed out on playoffs tournaments, and the football playoffs start November 2.

It was the first strike in Chicago school since 2012, when teachers stayed away for seven days. The union had sanctioned a one-day walkout in 2016. Not affected were the hundreds of teachers and nearly 62,000 students at the city's charter and private schools.