Chicago entered the eighth day of a teachers strike in a precarious stalemate between the two sides, as parents continued to fork out money for strike camps and weigh sending children to minimally staffed schools.

Things could get hectic downtown, but not directly because of teachers. Students planned a strike-related march to start at 9:30 a.m. on South State Street and head north to City Hall. President Donald Trump also is in town on unrelated business, speaking to the International Association of Chiefs of Police at McCormick Place and then hosting a roundtable at his Michigan Avenue hotel. Several activist groups are planning Trump-related rallies.

The union told teachers that joining in would qualify as “productive,” even though the action is not on the list of official events for the group Monday.

Our team will be covering the latest today in negotiations, rallies, and more. Follow Yana Kunichoff (@yanazure) and Cassie Walker Burke (@cassiechicago) for the latest.

7:15 p.m. Big news?

The union is bringing its rank-and-file bargaining team into negotiations, saying it believes there is an additional $100 million in the city’s budget that could be used to meet its contract demands.

The full team’s arrival “signals that we intend to be here until we get [a tentative agreement],” said the union’s second in command, Stacy Davis Gates.

Earlier in the day, the Chicago Sun-Times published a story saying the mayor is taking $60 million from the school district. That’s reportedly to cover some of the city’s pension obligations for teaching assistants, clerks and other support staff. That money, Davis Gates said, could be used to close a contract deal.

The school district’s top lawyer has also joined the bargaining team for the first time, according to union officials.

7:06 p.m. An intense message

School district officials have been pretty even-handed in their daily updates to families — until now. Instead of just telling parents where they can send their children and what services schools will offer, tonight’s email comes directly from CEO Janice Jackson and makes the case that the teachers union is refusing to accept a compelling offer, at the expense of students.

“Today is the ninth time you have received a message from me that classes and after school programming are, again, not in session tomorrow,” Jackson writes. “This is the third week that students are not in school, and it’s unacceptable.”

6:44 p.m. The pressure’s on

Extended strikes introduce some complicated dynamics. When people at the bargaining table make concessions early on in contract talks, or even during strikes, it can be easy to paint that decision as peace-making. When the concessions come after days of apparent stalemate, they can look a lot like caving.

That means the pressure is on for the Chicago Teachers Union, which by all accounts has gotten lots of what it came to the table asking for — though absolutely not all of it.

Here’s one thread we just saw making this point:

6 p.m. Update from the bargaining table

As the eighth day of the Chicago teachers strike wound down, city officials said negotiations remain stalled over prep time and the cost of the contract. 

“We have a proposal on the table, of nearly half a million dollars, that addresses all of the key issues,” the district’s Chief Education Officer LaTanya McDade said. That includes $70 million in staffing and $25 million to reduce class sizes. 

“We put that in the contract in writing,” McDade said, nodding to the union’s demand that staffing and class size be included in the contract, which the city initially rebuffed before conceding. 

The city estimates that its offer to the teachers union would cost nearly $500 million more by the end of a proposed five-year contract than it is currently spending. It says the union’s remaining demands would cost another $100 million a year — and the city can’t afford that.

“We are a district that is still borrowing $1 billion dollars just to keep the lights on,” McDade said, addressing reporters Monday outside of Malcolm X College, where negotiations are expected to continue into the evening. 

Prep time remains a sticking point. The union wants elementary teachers to get an extra 30 minutes of prep time, which they lost when the city lengthened the school day. But the city says there is no way to increase that without students losing instructional time. One option, suggested by the union, could be for teachers to arrive to school 30 minutes early, but that would add costs to contract demands the city says are already too high. 

Still, even as negotiations remain stuck over the last few days, McDade said the city is committed to getting students back in school as soon as possible. “We are working really hard to get our students back into the classroom,” she said.

4:30 p.m. Yeah, about tomorrow

Classes are canceled again Tuesday, Chicago Public Schools just announced on its website. That makes nine straight school days without classes for more than 300,000 Chicago students.

Earlier this afternoon, the Chicago Teachers Union also announced plans for Tuesday.

3 p.m. More about the SEIU 73 deal

The union representing school support staff like bus aides and custodians has reached a tentative agreement with the city, but said Monday that its members would stay on picket lines until the teachers union has a deal. 

In a press conference on Monday, SEIU Local 73 president Dian Palmer said the contract will make real changes for members, but declined to give additional details. The union’s 7,500 members are voting on the agreement, which would run through 2023, on Monday and Tuesday. (The union’s last contract expired a year ago, and the new contract runs for five years.)

The agreement includes a minimum 16% raise over five years for all employees, and no changes to the health insurance plan for the length of the contract. 

According to a rank-and-file member, special education classroom aides have also won job protections that would keep them from being pulled to work as substitutes or other school duties. Read more here.

In a statement, Mayor Lori Lightfoot applauded the deal. “I am very pleased we were able to work together to agree on a strong, fair deal that will provide substantial raises and real improvements to working environments, and I commend negotiators on both sides for their tireless effort,” she said. 

2:45 p.m. “We’re willing to do whatever it takes”

Or maybe there’s a new union message? After Chicago Public Schools CEO Janice Jackson spoke with members of the City Council’s Black Caucus about the city budget today, she rejected a union claim that she had walked away from contract talks, according to a Chicago Tribune reporter. In response, according to the reporter, the union’s second-in-command made a bold proclamation about the stakes of today’s negotiations.

2:34 p.m. A new union refrain

For the first week of the strike, the Chicago Teachers Union’s main message was that Mayor Lori Lightfoot needed to put her promises in writing. Now that she has done that, in the city’s formal contract offer, the union has shifted to emphasizing the spending gap that it says separates its vision for the school system and what Lightfoot is prepared to spend. (The city says the gap is larger.)

We first heard the message overnight on Saturday and since then we’ve gotten several press releases and seen dozens of social posts sounding the same note. And after city officials said today that the gap is larger, union chief Jesse Sharkey just sent out a statement recapping the idea. Here it is, in its totality: “Thirty eight million dollars — one half of one percent of CPS’ annual budget — is what is preventing the CTU and CPS from landing a tentative agreement. $38 million.”

1:45 p.m. Pension tensions

City Hall reporter Fran Spielman has some important new details about Mayor Lori Lightfoot’s budget — including that she is asking Chicago Public Schools to spending $60 million on pensions for retired teachers, a cost that has the city has always borne from its budget in the past. This development would seem to take the school district further from being able to meet the teachers union’s demands at a moment when every dollar on the table appears to count. The city is disputing Spielman’s account but did not offer specifics.

1 p.m. Seniors in a crunch

Chicago Public Schools seniors facing early decision deadlines this week are feeling the crunch of going without counselors, teachers, and clerks who can help with transcripts and recommendations — and colleges are responding.

A spokesperson for the University of Illinois at Urbana-Champaign said that, while not moving its early decision application deadline of Friday, it is offering Chicago students flexibility with one part — application fee waivers, the only portion of the admissions application that needs to be completed with a school staffer’s help. The university posted an entire FAQ for anxious Chicago students titled “Applying to Illinois during the CPS strike? Here’s what you need to know.”

Northwestern University is encouraging students who want to apply early to submit their online application by the Nov. 1 deadline, then work with teachers and school staffers to send additional materials once schools have reopened, a spokesperson said.

And a spokesperson from the University of Illinois at Chicago said its campus has not made deadline adjustments yet, but is “monitoring the situation.”

11:30 a.m. Tell us what you’re thinking

Cassie just posted a thread about her family’s experience with the strike at this point and asked for reactions.

Here’s one parent response that she’s already gotten. Respond on Twitter or email us with your own take.

11 a.m. “It’s gone on too long”

The governor has weighed in. Speaking on WBEZ this morning, Gov. J.B. Pritzker said something that many are beginning to think: “It’s gone on too long.”

10 a.m. Signs of frustration

There was lots of sniping about the strike last week on social media, but mostly between city and union allies who were extending the rhetoric unspooled in public statements and press briefings. Increasingly, though, parents are weighing in — often anonymously — to argue for a compromise that lets schools reopen. Here’s one representative tweet from a new account, @StopCPSStrike, that launched late last week:

6:30 a.m. Same drill

Monday dawned with teachers walking picket lines at 6:30 a.m. Lengthy telephone town halls over the weekend aimed to keep them focused on the mission, even as teachers expressed concern over missing pay and possibly losing out on health insurance if the strike extends to Nov. 1.

While members of SEIU73 landed a tentative deal late Sunday, the union said it planned to continue standing on picket lines in solidarity with teachers, which mean schools will go on being minimally staffed.

Over the weekend

Marathon weekend bargaining sessions produced tense rhetoric but no resolution. Here’s what you need to know:

  • Schools chief Janice Jackson visited bargaining on Sunday.
  • The teachers union, which had signaled earlier that it would be willing to compromise on some of its core issues if it got relief in class sizes and commitments to new staffing, stuck a more obstinate tone late Sunday, hinting that it may be holding out on a broader list of issues, such as prep time and contract length.
  • In weekend calls with members, union leaders underscored the demand for an additional 30 minutes of prep time daily in elementary schools. The school district contends that it would have to potentially start schools earlier to accommodate that demand, cutting in on instructional time. 
  • Chance the Rapper gave the teachers’ effort national airtime on Saturday Night Live.
  • One bright spot in the weekend: Service Employees International Union Local 73 struck a tentative deal Sunday night. Read more here.
  • The teachers union and Chicago Public Schools each offered different estimates of how much their proposals would cost the city. Late Sunday, Chicago Public Schools offered this breakdown of its offer.