Chicago finds itself engulfed in turmoil as the city becomes a battleground amidst President Trump’s stringent immigration enforcement efforts. ICE agents are reportedly pulling individuals from the streets in a crackdown that has sparked both outrage and resistance, with some vigilante groups rising to challenge the federal forces. The President has notoriously labeled Chicago as “the most dangerous city in the world,” fueling the aggressive tactics.

Dubbed Operation Midway Blitz, this initiative began in early September with the goal of purging Chicago, the state of Illinois, and parts of neighboring Indiana of so-called “criminal illegal aliens.” The operation has been marked by a heavy-handed approach, drawing criticism from various quarters.

On his social media platform, Truth Social, President Trump provocatively declared, “I love the smell of deportations in the morning. Chicago is about to find out why it’s called the Department of WAR.” This rhetoric has only intensified the tension on the ground.

The U.S. Immigration and Customs Enforcement (ICE) agency has faced accusations of excessive force, with reports of agents using smoke grenades, tear gas, and pepper balls, transforming Chicago into what some describe as a “war zone.” Such actions have drawn widespread condemnation from local communities and advocacy groups.

Moreover, ICE has been criticized for allegedly targeting American citizens in their operations. One particularly disturbing incident involved a video capturing a masked ICE officer forcefully subduing a black teenager, despite the boy’s relative asserting his American citizenship. This incident highlights the fear and chaos permeating the city as federal actions continue to unfold.

In one clip, a masked ICE officer slammed a black teenager into the ground for running despite his relative telling them he is an American citizen. 

Video footage taken from near a Chicago Walgreens showed the immigration officer throwing the young man to the ground on October 14. 

The woman filming, claiming to be his sister in law, shouts at the officer: ‘He’s a citizen!’ 

The officer asks the teenager: ‘Why are you running?’ 

In a horrifying clip, a masked ICE officer slammed a black teenager into the ground for running despite his relative telling them he is an American citizen

Warren King (pictured, bottom) said he was held in an ICE truck for several hours

The young man, identified by local media as 19-year-old Warren King, said he began leaving the store on the city’s East 106th Street after the officer inside called for backup. 

He told ABC News: ‘When he called for backup, other people came in, and that’s when I start to leave’.

‘He was just saying, ‘Why are you running?” King said, adding: ‘I’m telling him, ‘I’m a U.S. citizen. I’m here. I’m legal. I’m born here.’ They didn’t try to hear none of that, though.’ 

He said he was held in an ICE truck for several hours: ‘I just graduated high school. So, they can come for, literally anybody. And that’s not right’.

Local media reported that ICE officers were in the area searching for people involved in a car crash. 

The US Department for Homeland Security said hat a red SUV had rammed an ICE truck, and alleged that the driver was an undocumented immigrant. 

Two individuals in the car reportedly ran off, with ICE agents chasing them into the Wallgreens. 

Trump described Chicago on Tuesday as  ‘the most dangerous city in the world’, adding: ‘I have an obligation. This isn’t a political thing. 

A U.S. Customs and Border Protection agent points a non-lethal weapon at protesters in East Side, Chicago, Tuesday, October 14, 2025

A government official throws a tear gas canister towards protesters in Chicago, Tuesday, October 14, 2025

Trump’s zeal in cracking down on immigration has been heavily criticised

‘I have an obligation when 20 people are killed over the last two and a half weeks and 75 are shot with bullets.’

But Trump’s zeal in cracking down on immigration has been heavily criticised. Illinois state governor JB Pritzker told CNN on Sunday: ‘They are the ones that are making it a war zone. 

‘They fire tear gas and smoke grenades, and they make it look like it’s a war zone.’

ICE’s alleged brutality has become such a problem in the city that many of its residents are starting to fight back, according to the New York Times. 

The newspaper reported that Chicagoans have begun forming volunteer groups to monitor ICE activity, posting their findings on Facebook and Signal group chats when agents are seen. 

If agents are spotted, motorists reportedly press their car’s horns to warn that they are in the area. 

Last month, Chicago city council member Andre Vasquez sponsored a ‘community defence workshop’ that aimed to inform residents of their rights and teach them how to politically organise. 

He told the New York Times: ‘Chicago’s been doing just fine, and then these guys showed up. 

A government official readies to throw a gas canister in Chicago, Tuesday, October 14, 2025

A detainee is taken back to official government vehicles during a protest in Chicago, Tuesday, October 14, 2025

ICE agents detain a protester as other protesters try to stop them in East Side, Chicago, Tuesday, October 14, 2025

‘There is big concern about what these unidentified, masked men are doing in this city without accountability. 

‘Chicagoans are just trying to live their life. We’re not going to tolerate unconstitutional authoritarianism.’

Local officials were initially told that the operation would only last for 45 days. 

But ICE’s field director has now said that there is now end date for Operation Midway. 

Last week, a Chicago pastor revealed he was praying as ICE agents shot him in the head with a pepper ball during a protest outside a federal detentions facility.  

Reverend David Black, a senior pastor at the First Presbyterian Church of Chicago, was participating in a demonstration outside the Broadview ICE facility in Chicago last month when he was struck by U.S. Immigration and Customs Enforcement (ICE) agents.

The incident, captured in a now-viral video, shows Black dressed in his clerical collar, standing among demonstrators before being hit in the head by a pepper ball fired from the roof. 

He quickly collapsed to the ground as fellow protesters rushed to his aid.

Black alleged that officers fired without warning, striking him multiple times before spraying him with the chemical irritants.

‘They shot me in my head and my face and multiple times in my torso, arms and legs,’ he said.

Government officials detain a protester and push back others in Chicago, Tuesday, October 14, 2025

Government officials push back protesters in Chicago, Tuesday, October 14, 2025

‘I was shielded by the bodies of others who were there who rushed in to support me and took many more hits that were intended for me. I was then guided away to where a street medic helped to wash out my eyes and tried to keep me safe. But I was completely disabled at that point.’ 

Following the incident, the Chicago-based pastor said he heard ICE agents ‘laughing’ as they were ‘shooting’ protestors from the facility’s roof.

‘We could hear them laughing as they were shooting us from the roof, and it was deeply disturbing,’ Black told CNN.

‘We got to witness a few things about these ICE agents operating in Broadview, and really it has shown us how disorganized they are and how poorly supervised and trained they are.’

Black explained that he had been standing to the side, praying for both the detained immigrants and the ICE officers themselves moments before he was ‘shot.’

‘There were no ICE vehicles attempting to leave the facility,’ he said. ‘I was standing to the side in a gesture of prayer and praying verbally for the ICE officers and those detained inside.’