As Chance the Rapper was wearing a red Chicago Teachers Union sweatshirt on “Saturday Night Live,” union officials were still hunkered down with city negotiators.

When both sides emerged later, city and union officials said they had made progress but still remained far from reaching a deal to end the city’s seven-day teacher strike.

“We’re not close to where we need to be on the big issues,” said Deputy Mayor Sybil Madison. “We will return tomorrow and work diligently to close the divide.”

Another late night with no deal dims the prospect of classes resuming on Monday. If teachers do not return to work then, the current strike will become the longest in more than three decades.

There is still a $38 million gap between what the city has committed to spending and what the union is demanding, union President Jesse Sharkey said early Sunday morning.

“We have made what we believe is a reasonable proposal that would bridge the final gap and get a contract done,” Sharkey said. He added that the spending would account for three of the union’s core issues: class size relief, support staffing, and pay raises for paraprofessionals as well as veteran teachers. “We’re still waiting for a response from them.”

Sharkey said a fourth major issue, teacher prep time, remains a sticking point. He also suggested that the union could give in on teachers’ demand for a three-year contract if the city meets its other demands. The city has said it is committed to a five-year contract length.

There were multiple indications Saturday that the city and union are not necessarily planning on an immediate resolution. Union leaders said there were no changes in the bargaining team sent by the school district, meaning that neither CEO Janice Jackson nor Mayor Lori Lightfoot attended Saturday’s talks. Lightfoot has said she will participate in bargaining when she can “add value.” 

And the union had not scheduled a meeting of its 800-member House of Delegates, which must vote to end the strike and sending teachers back to their classrooms. It would be difficult — but in theory possible — for a meeting to be held Sunday if a deal is reached early in the day.

Going into the weekend, both sides described Saturday as a pivotal day for negotiations.

In updates Friday, city and union officials said negotiators had settled many technical items, leaving weekend talks to focus on five core issues of class size, staffing, teacher prep time, contract length, and pay. 

But substantial differences remained at the start of the day. A bargaining table document obtained by the Sun-Times on Friday pointed to a $71 million gap between what the city so far had agreed to spend and what the teachers union wants. Talks Saturday closed more than half of that distance but still left a substantial divide.

Plus, Sharkey detailed several unresolved issues beyond those five concerns in a conversation with union members late Friday night. Those included whether teachers who retire should receive payments for unused sick days, and when teacher evaluations should take place.

Teachers continued to make their case publicly on Saturday. Parents and teachers of students with disabilities met with Board of Education President Miguel del Valle and asked him to sign a statement pledging his support. The statement, which he signed, called for dedicated case managers and reasonable workloads for teachers and case managers. 

The meeting came a day after parents and educators reported continuing concerns with special education at a state legislative committee hearing about state and local efforts to address longstanding problems. 

“We can’t deny we’ve been deficient as a system about it. We have to do something about it, and we have to do it now,” del Valle told the group Saturday. 

And striking teachers got a boost from Chance the Rapper during his late-night appearance hosting “Saturday Night Live.” During his last appearance on the late-night show, he donated $1 million to Chicago schools. On Saturday, he quipped, “It completely fixed everything,” before growing more serious.

“To the teachers in Chicago, I know you guys are on strike right now, I fully support you,” he said. “I just wish that when I was in school, my teachers had gone on a strike.”

The contract talks continue as teachers at one Chicago charter school ended their strike. Late Friday, educators at Passages Charter School in Edgewater announced they’d reached a contract deal with their manager, ending a four-day strike. Under the agreement, Passages’ 50 teachers will see their salaries brought in line with district teachers within three years. Teachers said they also gained increased paraprofessional pay and protections for the school’s largely immigrant school population. The school’s roughly 420 students will return to school Monday. 

On Sunday, the union plans a 3 p.m. solidarity rally on the city’s West Side featuring civil rights activist Rev. William Barber. If school isn’t in session Monday, several student groups say they plan to stage a rally in the Loop. 

Negotiators for Service Employees International Union Local 73, which represents 7,500 bus aides, custodians, and special education aides who are also on strike, also said they returned to the bargaining table Saturday. In a late-night update, SEIU leaders said they were still waiting on a counterproposal from the city.