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School Climate & Safety Q&A

Inside the Fear at Chicago Schools Amid Federal Immigration Raids

By Ileana Najarro — October 31, 2025 5 min read
Sylvelia Pittman stands for a portrait outside of Nash Elementary School in Chicago on Oct. 30, 2025.
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Since early September, masked and armed federal immigration agents in unmarked trucks have been patrolling Chicago neighborhoods in an immigration crackdown known as “Operation Midway Blitz.”

U.S. Department of Homeland Security officials have said the effort staying in the country illegally. But most recently, agents have been seen deploying tear gas canisters in neighborhoods, including near elementary schools and in areas where children were gathering for a Halloween parade, according to .

A group of U.S. Senate Democrats has urged U.S. Secretary of Education Linda McMahon to ensure that Immigration and Customs Enforcement, or ICE, officers don’t conduct operations near schools, according to . In January, the Trump administration rescinded a long-held policy that classified schools as “protected areas” from immigration enforcement. While DHS spokesperson Tricia McLaughlin , she added that “if a dangerous illegal alien felon were to flee into a school, or a child sex offender is working as an employee, there may be a situation where an arrest is made to protect public safety.”

Sylvelia Pittman, an interventionist and multi-tiered system of supports lead at Henry H. Nash School of Fine and Performing Arts in the Austin community on Chicago’s West Side, has worked in Chicago public schools for 24 years. In an interview with Education Week, she said she’s never experienced the fear and uncertainty she is currently grappling with as immigration enforcement ramps up in her neighborhood and directly disrupts the lives of students and coworkers.

Pittman shared what it’s been like to teach under such circumstances and what advice she has for fellow Ķvlog across the city and country. This interview has been edited for length and clarity.

What’s been happening near your school over the last two months regarding immigration enforcement?

We’ve seen activity near our school … in our neighborhood. It’s been [happening] a couple of blocks from our school. [ICE agents are] just in the vicinity.

We have had a couple of our families be impacted—not just the students, even my colleagues. One of my colleagues, her husband was actually questioned the other day. Another one, her cousin had been deported back to Mexico. So it’s hit home. It’s not just stories anymore.

It has impacted those that we work with, so we are checking in on each other, making sure you are asking, “Are you OK today?”

How is “Operation Midway Blitz” affecting your day-to-day work as a teacher?

It hits differently, because when you come to work, the first thing that comes to mind when you don’t see a certain student, you’re wondering if they’re OK, if their family is OK. It’s almost like you don’t want to be in fear, but it makes you feel some type of way. You have to stay calm in front of the students, because you don’t want them to be upset. You don’t want them to know that you are worried about them.

We are also taking more precautions. We have weekly meetings for our safety team. We go over what is going on in the neighborhood, and we are coming up with plans if our kids are outside at recess, if they’re starting to get on the bus, all of those different things we have to think about now. You feel like you’re watching over your back every time you go outside.

Sylvelia Pittman stands for a portrait outside of Nash Elementary School in Chicago on Oct. 30, 2025.

How is your school working to keep students and families safe and willing to come to school?

We always say school is the best place for them to be because this is their norm. This is their place where they feel the most normal. At this particular time, when they are not at home, it’s probably the safest place for them to be during the day, and their families know their children are being cared for, that they’re being watched, and [we’re] making sure that they have everything they need.

We check on our students. We’re having discussions about their feelings, what it is that they need, [and] how they feel in this moment.

We’re careful about what is being said around our students when we know their parents have been detained. We had two moms who were detained. I can’t imagine being 4 or 5 years old and not understanding why my mom is not at home with me, and I don’t know when I’ll get a chance to see her, or I don’t know if she’s coming back. That’s a little disturbing. So we try to make them feel as comfortable as we can at this time, and even ask the fathers what they need from us.

There’s a crew of people who are at each door, who are ushering the students into the building and ushering them out of the building.

We’re in the process now of trying to make sure that we have rapid response teams, just in case we need to contact one. [In the event of ICE presence at the school], they [as community organizations] would help us with making sure that all of our students are able to get out of the building—safely into the cars or just walking in the neighborhood.

Have you experienced anything like this in your teaching career?

I’ve never experienced this. I feel like I’m living during a time I’ve heard about that transpired in the 1960s for our civil rights, when my grandparents and great grandparents fought for me to be able to be free to have a public education, to be able to have a higher education.

The things that my forefathers, my ancestors have fought for and I learned about as a little girl growing up—now, I actually live in it, making sure that my grandchildren that come to school with me every day are safe. I feel like it’s history repeating itself.

Any advice for Ķvlog who may find themselves in similar scenarios?

Find the courage to be able to be there for yourself and for the families that you’re representing, because the only way that anybody is going to be safe is if we stick together, and we keep each other safe. We don’t need federal agencies to come in here and make our spaces safe. It’s up to us as the citizens of the city, the citizens of the state and our neighborhoods, to keep each other safe.

Find the courage to be able to stand with your colleagues and with your families, and to make sure you’re educated. Educate your parents and your community about their rights.

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