On a street in the South Shore neighborhood of Chicago, Reverend Ciera Bates-Chamberlain stood in front of a five-story apartment complex praying with other city faith leaders and residents. Windows across the facade of the building were broken. Inside, occupants told Chamberlain, doors had been torn from their hinges and the apartments they belonged to had been ransacked.
“You could tell that something happened that destroyed that building,” Chamberlain, the executive director of Live Free Illinois, which mobilizes Black churches to improve public safety and enact criminal justice reform, recalls to TIME. “Once you walk up, it looks like it’s an abandoned building.”
A couple nights earlier, around 1 a.m., federal agents arrived in unmarked trucks and a helicopter to carry out a raid on the building using what Illinois Gov. JB Pritzker called “military-style tactics.” As the agents kicked down doors and detained people with zip ties, including children, residents told Chamberlain that they had been left outside past 3 a.m. with their kids, that their apartments had been pillaged, and that guns had been pointed at them by federal law enforcement.
The early October raid marked a flashpoint in President Donald Trump’s targeting of Chicago, which has become a proving ground for his Administration’s aggressive crackdown on immigration and the sanctuary cities that have made noncooperation with federal immigration enforcement their official policy. Since early September, a campaign dubbed “Operation Midway Blitz” has drastically increased the presence of federal immigration agents in the nation’s third-largest city and brought on a wave of raids and, according to the Department of Homeland Security (DHS), nearly 2,000 detentions. Weeks into the operation, with local officials and residents pushing back against the federal crackdown, Trump deployed hundreds of National Guard troops into the greater Chicago area to quell what White House spokesperson Abigail Jackson described as “ongoing violent riots and lawlessness.”
Pritzker and Chicago Mayor Brandon Johnson have been active in their opposition to what the governor has repeatedly described as a federal “invasion,” challenging the Guard deployment in court and barring city personnel and spaces from being used in the Administration crackdown. Speaking with TIME, Johnson described his office as “beating back tyranny at the federal level” even as he works to govern Chicago in more typical ways.
The escalating struggle in the city is one piece of a larger battle unfolding around the U.S. as the President seeks to carry out mass deportations and deploy troops in American cities. But what happens in Chicago and around Illinois over the next few months—in the streets, in the courts, in the fight for public opinion—could help determine the direction of the country for the remainder of Trump’s second term.
The fight from the inside
Trump has long painted Chicago as a hotbed of crime, calling it “the most dangerous city in the world” last month and accusing Pritzker last week of “letting people be killed in his city because he doesn’t want to deal with Chicago.”
DHS similarly pointed to crime, and city and state leadership, when announcing Operation Midway Blitz. “This ICE operation will target the criminal illegal aliens who flocked to Chicago and Illinois because they knew Governor Pritzker and his sanctuary policies would protect them and allow them to roam free on American streets,” the agency said in a statement at the time.
Earlier this month, Trump further escalated his attacks by calling for Pritzker and Chicago Mayor Brandon Johnson to be jailed over their opposition to the federal deployment.
“The fact that President Trump describes people who disagree with him as ‘enemies from within’—it’s a real evil precedent that he has created,” Mayor Johnson tells TIME.
Data indicate that Chicago is not the most dangerous city in the world and that crime in the city—like many others in the U.S.—has been declining after rising during the pandemic. “Sending in the National Guard is the wrong solution to a real problem,” Johnson wrote in a New York Times op-ed in early September. “If President Trump had listened to the city’s leaders, he would recognize that Chicago just experienced record-low homicide numbers, making this the safest summer since the 1960s, a result of effective collaboration between communities and law enforcement.”
Read more: Here Are the Facts About Crime in Chicago
Prior to the beginning of Trump’s enforcement campaign, with the President threatening to deploy troops in the city, Johnson signed an Executive Order at the end of August that instructed city law enforcement not to cooperate with federal agents or members of the Guard. After the operation began, he signed another to establish ICE-free zones, restricting the areas where federal agents could operate.
Johnson revealed to TIME that his office is currently working on an Executive Order that would prevent the Administration from purchasing property in Chicago to create detention centers, saying that efforts to develop such facilities are ongoing.
“I think it’s absolutely abhorrent that we have a president who is looking to create facilities where there’s a concentration of only immigrants or black and brown people being detained,” Johnson says of the attempts to build on Chicago land.
When asked about the atmosphere among his staffers over the last couple of months, the mayor says there “is a great deal of energy and strong conviction in my office, people working countless hours, quite frankly, to find creative, innovative and powerful ways in which we can protect the people of the city as we deal with an authoritarian government right now.”
On the state level, Illinois Lieutenant Governor Juliana Stratton says the environment in her office has been “chaotic” since Trump began his second term in January.
Stratton characterized Trump’s crackdown on Chicago as a ploy in his “authoritarian playbook,” saying the Administration’s immigration efforts have not targeted dangerous criminals—despite what Trump and Administration officials have repeatedly said—and arguing that the President has used protests against federal agents as a “justification” for sending in National Guard troops.
“Trump is invading the state of Illinois … and he’s done so without our consent,” Stratton says. “People are frightened, but they’re also being courageous.”
The lieutenant governor expresses concern that what she called the “manufactured crisis that Donald Trump has really brought to the city of Chicago and the state of Illinois” is pulling government resources away from other issues arising from his presidency.
She references rising costs associated with Trump’s sweeping tariffs and cuts to health care and food assistance in the President’s “Big Beautiful Bill.”
These ongoing issues, Stratton says, have not been forgotten by her office, but its attention has been forced in a different direction.
“I can tell you that we continue to fight back, and we will do so until he takes his hands off our state and leaves,” she says. “Chicago is not a sandbox for Donald Trump to play dictator.”
Johnson similarly points to his office’s ongoing work on other issues amid the federal crackdown.
Last week, the mayor presented his 2026 “Protecting Chicago Budget” to the City Council, in which he proposes new taxes on large corporations and seeks to protect Chicago programs and services from federal cuts.
“It’s not just these Executive Orders, because keep in mind, I’m still running an entire city,” he says. “And so my budget ensures that we’re investing in youth employment, that we’re investing in our first responders, that we’re investing in mental and behavioral health, that we’re investing in building more affordable homes, ultimately, to keep our people safe.”
The battle in the courts
Chicago and Illinois have been engaged in legal battles with the Trump Administration for most of the year.
Illinois Attorney General Kwame Raoul, who has been serving in his position since 2019, tells TIME that his office has been working tirelessly on a series of “reactionary litigation” to the President’s executive actions since Trump’s second term began.
“This is just a different level of activity this time around, and a sort of different level of emotional intensity as well to the work,” Raoul says about the current Administration.
The state moved quickly to challenge Trump’s efforts to send federal troops into the Chicago area after the President deployed roughly 200 troops from the Texas National Guard and 300 from the Illinois National Guard at the beginning of the month.
So far, the state has succeeded in halting the mobilization. The federalization and deployment of the Guard members has been blocked since October 9th by a temporary order from U.S. District Court Judge April Perry. The Administration appealed the order to the 7th U.S. Circuit Court of Appeals and later asked the Supreme Court to lift it after the appeals court denied the request.
Raoul says he has been able to lean on the “AG community,” especially California Attorney General Rob Bonta and Oregon Attorney General Dan Rayfield, whose states have also been fighting Trump’s efforts to deploy troops in their cities.
Read more: ‘This Is Not a Third-World Country’: Oregon AG Slams Trump’s Effort to Send Troops Into Portland
“While not all of the deployments have been identical, and while the facts surrounding them have not been identical either, a lot of the same law is applicable,” Raoul says.
The state contended in its lawsuit that the Guard deployment to the Chicago area “infringes on Illinois’s sovereignty and right to self-governance” and “will only cause more unrest.” The Trump Administration argued that the protests in the area had manifested in hostility and violence against DHS and ICE personnel, necessitating the intervention of Guard troops to maintain civility and order.
Raoul contends that “almost everything that they alleged in terms of facts, were just blatantly false,” which he credited for the state’s securing the temporary restraining order from Perry. He points to the Administration’s claims that protests outside of an Immigration and Customs Enforcement (ICE) facility in Broadview, where many of those detained in the Chicago-area operation have been taken, had gotten so out of hand that they justified sending in federal troops.
Eric Hamilton, a lawyer for the Department of Justice, stated before Perry’s decision that there was “brazen hostility” and “tragic lawlessness” in the Chicago area, listing examples of “agitators” who had thrown rocks, bottles, and fireworks at federal agents, amounting in an “unprecedented” and “blatant disregard for law and order.” The attorney for Illinois countered that the situation on the ground, specifically at Broadview, had been quelled by state police after restrictions on protest hours were instituted.
“DHS’s perception of events are simply unreliable,” Perry said at a hearing.
Looking ahead, Raoul doesn’t see the legal fight ending any time soon. The state’s litigation against the Administration will likely continue even if the federal troops are withdrawn and the immigration crackdown subsides, he says.
“We anticipate a lot of these matters to work their way up to the Supreme Court at some point,” he says. “The country is watching, right? And this is pretty important s–. It’s pretty weighty stuff.”
Read more: Judge Rules Trump’s Deployment of Troops to Los Angeles Violated Federal Law
Beyond the courts, Raoul worries that Chicagoans’ growing ire toward the federal presence in the city could affect the way they view the authorities more broadly.
“How do we in the aftermath of this, whenever that is, return to a place of respect for our law enforcement and trust that they’re not the same people as the ICE officers that we’ve been seeing?”
On the ground
Since “Operation Midway Blitz” began in September, the tactics federal immigration agents have used in the campaign have raised alarms from local officials, organizations, and residents.
“The reality here in Chicago is this,” Pritzker said over the weekend, addressing the city’s “No Kings” rally, where more than 100,000 people protested against what they perceived to be Trump’s rising authoritarianism and corruption as part of a broader demonstration movement across the country. “Black and brown people are being rounded up because of the color of their skin. Children are being zip tied and separated from their parents. Worshippers coming from church are being questioned and detained. Workers are being harassed and detained at our shops and restaurants.”
Veronica Castro, the deputy director of the Illinois Coalition for Immigrant & Refugee Rights (ICIRR), tells TIME about the ways in which members of the immigrant community she has spoken with have been affected by ICE detentions in and outside of Chicago.
In some cases, she says, construction workers are choosing to sleep at the sites of the unfinished homes where they work, instead of returning to their houses each night, for fear that they will be pulled over and detained while commuting. “That means that they’re leaving on Monday and not coming back home until the weekend,” Castro says, which puts strain on families. She says another woman she spoke with, who works as an Uber driver, has been sleeping in her car outside of the city instead of returning to her neighborhood, where she says ICE’s presence has increased.
At the ICE facility in Broadview, Castro says the family of a plumber who was detained by ICE while he was at work told her conditions are “terrible.” The family didn’t know if the plumber would be released from the facility, she recalls, or if he was still there.
Rebecca Glenberg, the chief litigation counsel at the American Civil Liberties Union in Illinois who has been involved in a lawsuit against the Administration’s crackdown and spoken with a number of protesters, called the Broadview facility “a real locus of the immigration enforcement regime in Chicago” and an “unofficial detention center,” saying food and water are limited and there are no showers.
“It’s just not a fit place to be detaining people. And I say all that just to explain why it is that all of these people gathered at Broadview to protest,” Glenberg says.
Incidents between ICE, protesters, clergy, and journalists outside of the facility created the basis for the case against the Administration for alleged violations of First and Fourth Amendment rights, she says, which led to another temporary restraining order blocking federal agencies from using forceful tactics to stop protesters or journalists. Judge Sara L. Ellis issued the order in response to a First Amendment lawsuit on behalf of several news organizations, clergy members and protesters, who alleged federal agents had responded to protests at the Broadview facility with “a pattern of extreme brutality in a concerted and ongoing effort to silence the press and civilians.”
ICIRR, one of multiple organizations that are on the ground in the Chicago area documenting detentions and seeking to protect the immigrant community, has been coordinating a vast rapid response network across Illinois to respond to ICE detentions. The rapid response teams are scattered across the state and made up of local volunteers who document reports of ICE activity after receiving information through the organization’s Family Support Network hotline. In addition to that documentation work, they help provide legal resources to detainees and their families.
The hotline, which was used during Trump’s first term, has seen an exponential increase in the volume of calls this Administration, especially since the crackdown in Illinois began, according to Castro. In January, the month Trump returned to office, she says the hotline experienced a nearly 800% increase in calls compared to the same month last year.
According to internal ICIRR data, Castro tells TIME that in 2024 the hotline received a total of 11,000 unduplicated calls, marking individual instances of reported ICE activity. In September 2025 alone, there were 5,582 calls, putting the rate of reports on pace to surpass 2024’s number in just two months.
In the first week of October, ICIRR received 2,479 calls. October 10th marked the organization’s highest call volume in a single day, with 1,300 calls.
Chamberlain, the reverend from the South Side of Chicago, tells TIME many of her colleagues in different congregations have been providing physical refuge every day for members of the migrant community who fear prosecution from ICE. She recalls being on the ground at clashes with federal agents, where she says citizens and undocumented people alike have been profiled and detained by masked officers.
“The narrative that they’re putting out is not what we are actually seeing on the ground. What they’re doing is literally terrorizing communities, working class communities,” she says.
Read more: Trump Administration Accused of ‘Propaganda’ for Shifting Story in Shooting Amid ICE Protests
She says she has also witnessed U.S. citizens being detained, and that members of the Black community have been threatened and restrained by federal agents as a result of racial profiling tactics used by federal agents.
“They’re targeting citizens,” she says.
She also notes that although much of the attention has been given to ICE activity in Chicago and Broadview, she has been speaking with and supporting people in smaller cities outside of Chicago like Kankakee and Waukegan, where the agency has expanded its crackdown.
TIME has reached out to DHS for comment from ICE, Customs and Border Protection, and Border Patrol Chief Gregory Bovino, who has been leading the crackdown in Chicago. Judge Ellis has ordered depositions from Bovino, among others, on agents’ ongoing use of force despite her order providing protections to protesters and journalists. Federal officials have said agents used tear gas in response to threats to their safety.
In early October, Homeland Security Secretary Kristi Noem defended the tactics deployed by agents in the Chicago area operation, calling it “an extremely dangerous situation.” DHS said following the raid on the South Shore apartment building specifically that the building was targeted because it was “known to be frequented by Tren de Aragua members and their associates,” and a spokesperson for the agency told CNN that children were taken into custody during the raid “for their own safety.”
“The dehumanization that the immigrant community is facing right now should make everybody worried,” Castro tells TIME. “If they can get away with violating our basic rights within the immigrant community, that’s only a step away from taking away the rights of everybody.”
Pritzker similarly warned while speaking at the “No Kings” rally that “when we allow tyrannical policies against any group, we make tyranny possible against every group.” But, he said, tyranny fails “when ordinary people refuse to cooperate.”
“What Trump didn’t count on is Chicago coming together to stand up for freedom and individual rights, for American values, because we love America,” he said.
On the phone with TIME, Johnson recalled his work as a social studies teacher. He pointed out the “long history of resistance in Chicago,” citing the Rainbow Coalition, a political group formed in Chicago in 1969 by Fred Hampton of the Black Panther Party to bring together marginalized groups to fight against systemic oppression.
When asked how he would advise other cities to prepare for the circumstances Chicago is facing, the mayor encouraged partnerships across all aspects of the city and state communities, including faith congregations, elected leaders, and businesses. He urged other cities to “utilize government to its fullness,” passing ordinances, signing executive orders, and mounting challenges in court, as his city has.
“Black, brown, white, Asian, young, old, rich and poor. We have to come together to save our democracy,” he says. “To protect our humanity.”
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