A dispatch from Chicago.
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OCTOBER 22, 2025

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It’s been nearly two months since ICE brought “Operation Midway Blitz” to Chicago. In that time, Chicagoans have seen a Blackhawk helicopter-assisted raid on an apartment building, children arrested, and tear gas canisters lobbed at protesters. Throughout it all, Chicagoans have been fighting back in small and large ways. Some are organizing rapid response groups that monitor ICE raids. Others buy groceries for their neighbors who are too afraid to leave the house. And 250,000 people marched in this weekend’s No Kings parade. As of now, there’s no clear end in sight. Here’s my overview of what the city has been through.

–Emma Janssen, writing fellow

Ashlee Rezin/Chicago Sun-Times via AP

Two Months of ICE Terror in Chicago

It’s been nearly two months since Chicago became the main target of President Trump’s Immigration and Customs Enforcement (ICE) regime in what the government calls Operation Midway Blitz. Since then, one person has died, agents have fired tear gas at peaceful protesters, and over 1,000 people have been arrested and, often, functionally disappeared from their communities and lawyers. We’ve seen apartment raids. Propaganda videos. Children in zip ties. Aggression, anger, and resistance.


Chicago is a notoriously segregated city, which means that some neighborhoods have been completely transformed by ICE’s presence, while in non-Latino neighborhoods, it’s mostly been business as usual.


But the response to the federal incursion knows no boundaries. Regardless of where in the city Chicagoans live, they have mobilized. Activists have started “migra watch” group chats on the secure messaging app Signal, where they monitor ICE sightings, share resources, and plan protest campaigns. Each chat has hundreds of participants, and my phone rarely goes more than five minutes without a buzzing notification.


The chats play an increasingly important role as the Department of Justice cracks down on other forms of organized resistance. This month, Meta succumbed to pressure and removed a Facebook group that Chicagoans used to monitor ICE. Two weeks earlier, Apple and Google removed ICEBlock, an app that allows users to report ICE activity, from their app stores.


The fear that ICE could be lurking in any car on any street has pushed many Chicagoans to avoid going out in public, where having brown skin makes you a target. Notorious U.S. Border Patrol chief Gregory Bovino said the quiet part out loud to a white WBEZ reporter, describing how ICE makes arrests based on “the particular characteristics of an individual, how they look. How do they look compared to, say, you?”

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