Most of Chicago was sleeping overnight when weary negotiators from Chicago Public Schools and the city’s teachers union emerged around 2 a.m. and reported progress — but not enough to get a deal over the finish line.

Could Tuesday be the day?

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

8:40 p.m. It’s official: No school

Teachers came out of the House of Delegates meeting reporting that there would not be school Wednesday, and Chicago Public Schools confirmed the news in a tweet moments later. Wednesday will be the 10th day of the teacher strike.

Here’s how one local elementary school’s Twitter account responded to the news:

7:23 p.m. Betsy DeVos weighs in

The nation’s top education official, U.S. Education Secretary Betsy DeVos, has just commented on Chicago’s teacher strike for the first time, posting a column by a Chicago Tribune editorial board member that disparages teacher protests as “team-building exercises for teacher unions that are trying to stay relevant.”

MUST READ: After 12 days of a @CTULocal1 strike... “why are they still striking? It’s rhetorical. You know why. The union was never not going to strike.” - @McQuearyKristenhttps://t.co/Pp1s77PaPe — Secretary Betsy DeVos (@BetsyDeVosED) October 30, 2019

6:30 p.m. A closer look at the numbers

Just as the House of Delegates meeting is getting going, Chicago Public Schools posts its latest offer to teachers on its website, offering some of the most insight so far into its side of recent proposals. All in all, the city’s offer totals more than $1.5 billion more across five years than the union’s current contract. Here are the highlights:

Teacher pay

Increases to pay for paraprofessionals, with immediate jumps of 5% or 9%, depending on their certification level.

An additional $5 million toward pay for veteran teachers.

Context: The district’s offer of 16% cost-of-living raises for teachers across five years actually consumes the bulk of the proposals. Nearly two-thirds of the city’s proposed spending would go toward individual teachers’ compensation. Besides pay, that includes the district’s offer to pick up most of the increasing costs of health care premiums.

Class size

The city ups its offer from $25 million to $35 million to be used to reduce oversized K-12 classrooms across the district. Priority would go to schools serving the most vulnerable students. A joint CTU/CPS council would have enforcement authority on how the money is spent.

Sports

In recent days, the city has added to its proposal a sports committee that would have an annual $5 million budget to spend on increases to coaching stipends and new equipment. The union surfaced inequity in athletic facilities and equipment as one of its issues, outside of its five core demands of reducing class size, increasing support staffing, pay for paraprofessionals and veteran teachers, prep time, and the length of the contract.

Staffing

By 2023, the city’s latest offer would fund 209 more social worker positions, 250 additional nurses, and 180 additional case manager positions for children with disabilities. The social workers and nurses would be enough to staff every school, it says.

Schools with the highest needs could choose from additional counselors, restorative justice coordinators, or librarians — up to a total of 120 positions across schools — by 2022-23.

The offer also puts money toward growing the pipeline of qualified nurses, social workers, bilingual teachers, and special education teachers with money for recruitment, training, and licensure programs, and, in some cases, partial tuition reimbursements.

5:30 p.m. Heated rhetoric as delegates meeting nears

If there’s a deal to end the strike, neither the union nor Mayor Lori Lightfoot is saying so. Speaking late this afternoon, Lightfoot said she and Chicago Public Schools CEO Janice Jackson met for hours today with union leaders.

“We moved our position even further to where CTU said it was most critical to getting a deal done,” Lightfoot said. “And what we heard is it’s still not good enough.”

The city increased its offer for class size reduction efforts from $25 million to $35 million a year, Lightfoot said, and also promised to spend an additional $5 million a year on pay increases for veteran teachers.

Just minutes earlier, the union had sent out a press release with the title “Shame on the mayor and CPS for their disinformation campaign.” The message said the city had mischaracterized tonight’s House of Delegates meeting in its communication to families by saying that the union could be voting to accept a deal.

“In fact,” the release said, “the more than 700 elected leaders of the union are meeting to review the current status of bargaining – what’s been landed and what continues to remain unsettled at the table – and to discuss next steps to push Mayor Lori Lightfoot and the CPS bargaining team to reach a just settlement of this strike.”

4:30 p.m. No, it’s really not clear what’s going to happen tonight

Here’s another update from the Chicago Teachers Union second-in-command, which suggests that if union’ delegates review an offer tonight, it will be the last one that city officials laid out.

60 minute meeting with Mayor Lightfoot. She reiterated the same things...this deal is already done and there’s nothing left to get except what’s left to get. @CTULocal1 see you at HoD. Time to unpack. — #CTUINC (@stacydavisgates) October 29, 2019

Davis Gates’s previous message laying out the meeting’s possible agendas has drawn divided reaction on Twitter. “#Takethedeal or Suspend strike.. We are done!” one person replied. “I choose number 2!” answered another.

One fact that could get lost in the noise tonight: The union did win concessions from the city since beginning the strike, though little has changed in days. One person who responded to Davis Gates made that point, and it’s one you can expect to hear again if the union’s delegates choose to end the strike.

I'm really proud of the gains we've made. I think it's time to claim our victory for a contract ***far better*** than what was on the table before the strike. Thank you to @SharkeyCTU1 , @stacydavisgates, and the Big Bargaining Team for your fantastic work. Much love and respect. — Andrew Johnson (@GburgAddress) October 29, 2019

4 p.m. An uncertain agenda

The agenda for tonight’s House of Delegates meeting isn’t set, according to Chicago Teachers Union Vice President Stacy Davis Gates, who just tweeted that two things are possible.

@CTULocal1 HoD Meeting hinges on Mayor Lightfoot. @CTULocal1 is holding an HoD to do one of two things: 1. Discuss a Tentative Agreement and decide to suspend strike OR 2. Fortify ourselves and press on. #PutItInWriting #10Months — #CTUINC (@stacydavisgates) October 29, 2019

It’s hard to imagine that there could be school on Wednesday. The meeting begins at 6 p.m., so even in the most optimistic scenario, a decision couldn’t be made about whether to hold school until several hours after the city has made its decision each day during the strike. And in 2012, teachers got a day to review a contract deal before it was approved and the strike ended.

But at the same time, families, educators, and city officials alike say they are eager to resume their regular lives, as soon as it makes sense to do so.

3:32 p.m. A different kind of message to families

For the first time in weeks, families have gotten a message from Chicago Public Schools that doesn’t say classes are canceled. Here’s what it says instead:

2 p.m. Protesters arrested at Sterling Bay

Several protesters inside the Sterling Bay headquarters were removed by Chicago police just before 2 p.m., about an hour after the red-clad educators arrived to deliver a letter to the developer. Police handcuffed those participating in the sit-in and detained them in squad cars, as their fellow Chicago Teachers Unon members who were outside chanted, “Shame, shame, shame.”

1:15 p.m. Taking the fight to Fulton Market

Ariel reports that a few dozen teachers have gathered at the Fulton Market headquarters of Sterling Bay, the real estate developer behind Lincoln Yards, to call attention to city tax subsidies that spur development. The union has tried to make the case that some of those dollars should go to schools, even as municipal finance experts and budget watchdogs have questioned that logic.

CTU members are parked outside Sterling Bay HQ and inside to deliver a letter asking the company to invest in students. #ctustrike #cpsstrike @chalkbeatCHI pic.twitter.com/NAoC9yJYrK — Ariel Cheung (@arielfab) October 29, 2019

12:34 p.m. House of Delegates meeting scheduled, but …

The union must have its 700-member House of Delegates vote on a contract deal before teachers can return to work. That has made meeting-watch an important indicator of how talks are going.

A member of the union’s bargaining team just tweeted that one is scheduled for tonight — and a union representative confirms the meeting for us — but that doesn’t indicate a deal.

Having a meeting on the calendar means that if the union and city are able to reach an agreement by later this afternoon — something that has seemed to grow less likely over the course of the morning — union delegates would be in place to act quickly on it.

If there’s no deal, the conversation would turn to the current state of negotiations.

11:30 a.m. About those new issues

Now we know more about those “new issues” that Chicago Public Schools’ No. 2 LaTanya McDade referred to earlier.

In a press briefing at City Hall, Mayor Lori Lightfoot, who was joined by CPS CEO Janice Jackson, said the teachers union is “moving the goalposts” and asking the mayor to now support a specific elected school board bill as well as a state bill that would broaden the list of grievances that the union can legally strike over.

Currently, the union can only strike over economic issues of pay and benefits. It has held off on a pay agreement while it raises what it calls “common good” issues, such as class sizes and staffing.

Lightfoot, who started the briefing by saying her team has made “significant compromises” in the deal, says such “11th hour” political requests have no place in a contract agreement.

“Are we really keeping our kids out of class unless I agree to support the CTU’s full political agenda, wholesale?” she asked.

Toward the end of the briefing, Jackson brought up another core issue that remains outstanding: the union’s demand for an additional 30 minutes of prep time a day for elementary school teachers. To accommodate the request, schools would have to potentially start later. “What’s holding this up now is a set of political issues, and an effort to try and cut instructional time, which we cannot agree to,” Jackson said.

10:40 a.m. No change yet

Despite a vow to get a deal Monday and 16 hours of negotiating that creeped into early morning hours Tuesday, a deal remains out of reach, CPS Chief Education Officer LaTanya McDade said this morning.

In addition to the sticking point of prep time for teachers, “we also have some new issues that have been put forward by the union as of late that are concerns for us,” McDade said. The new issues, which McDade would not identify, were brought up during Monday’s negotiations, she said.

The district has agreed to meet the staffing levels and class size demands, with a written promise to have a nurse and social worker in every school, a $25 million investment in lowering class size, and a $75 million investment in staffing, McDade said.

“We put it in writing and we put it in the contract,” she said as she prepared to head back into negotiations. “And yet our students are not in schools for the ninth day.”

10:17 a.m. Scene on the streets

9:54 a.m. Coming soon

We just got an announcement about a Chicago Public Schools press availability outside Malcolm X College, where negotiations are taking place, in about 20 minutes. Unlike most of the advisories we’ve gotten, the announcement came from the mayor’s office, not the school district.

9:30 a.m. Field trips

The Field Museum is opening its doors for free today to Chicago Public Schools students and their families.

Indeed, for families able to make use of the opportunities, the strike has offered some benefits. On Monday, the Museum of Science and Industry offered a free day to families affected by the strike. And pop-up strike camps have kept students occupied and engaged, for a cost.

Here’s a tweet from one parent who says she thinks her children have kept learning during the strike:

I also would love for my kids to re-take their MAP test. I’m not an unschooling fan, but they have had a good two weeks. Board games, science projects, transit trips. Foreign language and instrument practice done before 3. They done well. https://t.co/ATtWsy6Lnu — Boo-lou (@CarmintheB) October 29, 2019

Noting that her family was lucky to have no-cost child care from grandparents, she immediately added, “But it’s time to go back.”

8:30 a.m. Change in plans

Mayor Lori Lightfoot has canceled her visit to the South Side YMCA. City Hall didn’t announce what she’s doing instead. But last week she said she would step in at the negotiating table with the Chicago Teachers Union when she could “add value.”

8 a.m. Principals ‘like Switzerland’

Attending work everyday to watch children while their teachers picket outside, Chicago’s school principals are “like Switzerland,” two school leaders tell WTTW-Channel 11, caught between the needs of their teachers and their responsibility to students and district leadership.

The principals, Anna Pavichevich of Amundsen High School and David Belanger of Hanson Park Elementary School, said students are coming to their North Side schools each day and largely have recreation time, doing arts and crafts, and, at Amundsen, meeting with the Becoming A Man program.

But as far as math and reading instruction, “No, we’re not doing that at this time,” Belanger said.

How do they feel about teachers’ demands for prep time, one of the issues that appear to be holding up a deal? “It’s important that teachers are well-prepared for instruction,” said Belanger. “At the elementary level, when teachers lost morning preparation time (a few contracts ago), it did impact learning and instruction. As a former teacher, I was in a classroom for 29 years, I would like time in the morning to prepare.” Find the full clip below.

6:30 a.m. The day’s itinerary

Teachers will not march on picket lines Tuesday morning; instead, the union has asked them to gather at one of several meeting points at 8 a.m. and march to the site of the Lincoln Yards development on the city’s Near North Side. The $5 billion, 50-acre riverfront redevelopment plan has been controversial, and teachers want to call attention to the city’s use of tax incentives to spur large real-estate developments.

Mayor Lori Lightfoot plans to tour a South Side YMCA where children displaced by the strike are spending the day. The YMCA has reported steady increases in the number of children attending its strike camps as the strike drags on.

Negotiators will return to Malcolm X and pick up where they left off. Yana reports from a late night of negotiations that the two sides are near agreement on class size and staffing — two of the union’s core issues — but talks foundered over the issue of increasing teacher prep time, according to city officials. Here’s the issue, explained.