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These are the sights and sounds of Trump’s immigration crackdown in Chicago

Nov 19, 2025, 9:04 PM

Jose Aguilar, who recorded cell phone video of federal agents chasing and tackling a Black teen in ...

Jose Aguilar, who recorded cell phone video of federal agents chasing and tackling a Black teen in the East Side neighborhood in October, stands outside his family's business Tuesday, Nov. 18, 2025, in Chicago. (AP Photo/Erin Hooley)
Credit: ASSOCIATED PRESS

(AP Photo/Erin Hooley)

For nearly two months, federal agents have been carrying out surprise raids in Chicago in pursuit of the Trump administration’s immigration agenda, emerging from unmarked vehicles in neighborhoods throughout the city to confront and detain stunned members of the public.

The arrests have been aggressive and even violent, with agents striking restrained people, deploying tear gas outside of schools, and pointing pepper spray at brazen onlookers who inevitably gather to decry what’s happening.

A culture of fear has taken hold, with some people too scared to leave home, especially in the city’s predominantly Latino communities. In social media posts and interviews, many have expressed shock at the agents’ use of force.

Since it began in early September, “Operation Midway Blitz” has resulted in more than 3,300 arrests, according to attorneys for detainees. In addition to people who were in the country illegally, many U.S. citizens have been swept up in the crackdown.

The operations have been dizzyingly random. Agents have targeted both high- and low-income neighborhoods. They’ve made stops at schools, workplaces and grocery stores. Even Millennium Park, the site of Cloud Gate — the sculpture lovingly known as “The Bean” — has seen arrests.

The crackdown has galvanized Chicagoans, who have banded together to protect their neighbors. They have borne witness the best way they could: by pulling out their phones to document what was happening.

The Associated Press has gathered some of these videos. For this story, some of the details of the people involved in the arrests, including their names, ages and immigration statuses, were gleaned from interviews, local news reports and court records.

The Department of Homeland Security, U.S. Customs and Border Protection and Immigration and Customs Enforcement didn’t respond to emails sent Friday seeking further information and comment about the actions taken by agents seen in the footage. But Trump administration officials have previously routinely defended agents’ actions.

A South Side arrest

On Oct. 14 in the East Side neighborhood on Chicago’s far South Side, Jose Aguilar had just heard from family that federal agents were in the area when he spotted four in uniform following two people into a nearby pharmacy.

“That guy just ran inside a Walgreens,” Aguilar said while shooting cellphone video from his car. “Here comes the other one.”

“God, please protect our people,” he said.

Seconds later, an agent chased a Black teen coming out of the store and tackled him to the ground as onlookers gathered and began yelling at the agents.

“What is wrong with you? He’s a citizen!” one girl yelled.

“You don’t know what’s going on, so get the f—- back!” the agent barked as he sat atop the teenager.

He was detained for hours before his eventual release, according to local news reports.

Shattered peace in Lakeview

On Oct. 24 in Lakeview, blocks from iconic Wrigley Field, where the Cubs play, federal agents deployed tear gas on a street lined with multimillion dollar homes.

Skip Yates was in his home office when he heard screams and the shrill whistles Chicagoans have been blowing to signal immigration agents are nearby. He peered from his veranda to see large vehicles and tear gas wafting down the street.

Yates shut the door as he began coughing, his eyes burning.

“Skip,” a woman’s voice said sternly from inside the house. “Do not go outside.”

Down the street, construction workers in red shirts were taking a break from replacing windows on a home when a white SUV pulled up. Before the agents even sprang from the car, the contractors knew what was coming and took off in every direction.

Within seconds, the peaceful street dissolved into chaos. One worker eating lunch on the stoop scrambled back from the scene, watching from the front porch as the agents chased the contractors amid yelling and popping sounds.

A woman emerged from inside the home to witness the scene unfolding.

“Excuse me, you don’t have a warrant,” she told the agents in her yard. They were not deterred.

A family member detained

The next morning in Old Irving Park, a neighborhood a few miles (kilometers) west, Uriel Villegas and his older brother were doing construction work on a home when federal agents pulled up in a car and asked if they had papers.

Villegas did, but his brother, Luis, didn’t. He didn’t want to get caught, so he ran. Four agents chased him.

“Chill! That’s my brother!” Villegas yelled as he ran after them. When he caught up to them, he saw the agents pinning his brother to the ground on someone’s lawn.

“Get off of me!” he said, his voice breaking as agents pushed him back from his brother.

In the background, a resident told agents to get off his private property as members of the public flocked to the scene and began recording the agents.

“Don’t get away, don’t get away,” Villegas pleaded, pushing past people to watch the agents put his brother into a white SUV.

The scene intensified as the crowd grew, the agents becoming more aggressive with onlookers. Villegas captured two more arrests on video showing agents restraining two people flat on the ground. One was a 70-year-old man who was out for a run and whose ribs were broken by agents kneeling on his chest, according to the man’s running club, which posted about the incident on social media.

Villegas’s brother is now in Michigan, awaiting a Dec. 6 immigration hearing.

Resistance in Evanston

On Oct. 31 in Evanston, the suburb just north of Chicago that’s home to Northwestern University, witnesses captured video of how a collision with a Border Patrol vehicle escalated. Agents began making arrests, and people screamed as an agent punched a man’s head even though he was restrained on the ground.

“You’re punching him! You’re punching him!” one woman repeatedly yelled.

As agents pushed onlookers back and pointed pepper spray at the crowd, dozens of people began chanting and encircling the agents’ vehicle.

“Shame! Shame! Shame!” they chanted over and over.

___

Associated Press video journalist Laura Bargfeld contributed to this report.

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These are the sights and sounds of Trump’s immigration crackdown in Chicago