Federal immigration enforcement in Chicago has reached a boiling point, drawing intense scrutiny from the judiciary, state officials, journalists, and community advocates. In a dramatic week marked by legal showdowns and public outcry, federal judges have stepped in to rebuke the Trump administration’s aggressive tactics, while the streets of Chicago remain a battleground for immigrant rights and civil liberties.
The controversy centers on the Trump administration’s “Operation Midway Blitz,” a sweeping immigration enforcement campaign that has roiled the city since September 2025. According to Peoples Dispatch, the deployment has sparked nearly nonstop protests, with Chicagoans organizing mass marches, noise demonstrations outside hotels housing federal agents, spontaneous street protests, and even student walkouts. The operation, which the Department of Homeland Security (DHS) has promoted with movie-style montages of ICE raids, has resulted in over 900 arrests, many targeting Chicago’s Black and Brown communities.
The federal government’s response to this resistance has been forceful and, critics argue, unlawful. On October 8, 2025, the U.S. Northern Command announced the arrival of around 200 Texas National Guard troops and 300 Illinois National Guard troops in the greater Chicago area. Their stated mission: to “protect” ICE agents and federal property. This deployment, ordered by President Donald Trump, came amid mounting legal challenges and widespread condemnation. President Trump, taking to his social media platform Truth Social, even called for the jailing of Chicago Mayor Brandon Johnson and Illinois Governor JB Pritzker for what he described as their “failure to protect ICE officers.” Mayor Johnson fired back on X, alluding to a pattern of targeting Black leaders.
But the most decisive interventions have come from the federal courts. On October 9, Judge Sara Ellis issued a Temporary Restraining Order lasting 14 days against federal agents—including ICE and Border Patrol—prohibiting the use of riot control weapons, tear gas canisters, and excessive force such as pulling or shoving individuals to the ground, tackling, body slamming, and striking anyone with a vehicle in Chicago. As reported by Block Club Chicago and The Chicago Headline Club, the order was prompted by a string of violent incidents: in September, an ICE agent fired a pepper ball into CBS News Chicago reporter Asal Rezaei’s car without provocation; Reverend David Black was shot in the head with a pepper ball while praying outside an ICE facility in Broadview; and a CBP agent shot a woman five times before arresting her, an incident caught on camera.
The complaint, brought by local media organizations and unions, paints a grim picture: “Federal agents have responded with a pattern of extreme brutality in a concerted and ongoing effort to silence the press and civilians. Dressed in full combat gear, often masked, carrying weapons, bearing flash grenades and tear gas canisters, and marching in formation, federal agents have repeatedly advanced upon those present at the scene who posed no imminent threat to law enforcement. Snipers with guns loaded with pepper balls, paintballs, and rubber bullets are stationed on the roof of the Broadview ICE facility with their weapons trained on the press and civilians.” Judge Ellis’s order also requires agents to display visible identification with unique alphanumeric identifiers on their uniforms or helmets, even when in riot gear.
Meanwhile, another federal judge, Jeffrey Cummings, ruled on October 7 that ICE violated a federal consent decree by making at least 22 warrantless arrests earlier in the year in Chicago and Missouri. As detailed by Capitol News Illinois, the judge extended the decree—which limits agents’ authority to make warrantless arrests—until February 2, 2026, and ordered ICE to re-issue rules on probable cause nationwide. The ruling specifically cited a chaotic raid on September 30, 2025, in Chicago’s South Shore neighborhood, where roughly 300 federal agents, including some arriving via Black Hawk helicopter, arrested more than three dozen people, including American citizens who were primarily Black. Armed agents broke down doors, handcuffed adults and children with zip ties, and detained them in unmarked vans. The Department of Homeland Security had initially agreed to the consent decree under the Biden administration in 2022, but ICE rescinded the policy restricting warrantless arrests in June 2025. Judge Cummings found ICE had been violating the decree since at least January.
The judge’s order requires ICE to report warrantless arrests monthly and to meet with plaintiffs to resolve alleged violations before a mid-November hearing. The ruling also noted that, despite the Trump administration’s insistence that ICE targets only undocumented immigrants with criminal backgrounds, reports have mounted of agents arresting those with no criminal history, detaining children with their parents, and even handcuffing U.S. citizens. Immigrant and civil rights groups allege that nearly 100 people have been improperly arrested since Operation Midway Blitz began, including a family driving to church and a grandmother who has lived in the U.S. for over two decades.
Judicial scrutiny has also extended to the government’s narratives surrounding violent encounters. In early October, Marimar Martinez survived a shooting by Border Patrol agents; body camera footage revealed an agent telling her, “Do something, b—-,” before opening fire. This footage appears to contradict government claims that Martinez drove toward officers in her car. U.S. Magistrate Judge Heather McShain released Martinez and another defendant, Anthony Ian Santos Ruiz, as they await trial on felony charges of assaulting a federal officer, citing their lack of criminal history and strong community ties.
Another high-profile case involved the fatal shooting of Silverio Villegas-Gonzalez, an immigrant worker and father, by ICE agents on September 12 in suburban Franklin Park. DHS initially claimed the agent was “seriously injured” after Gonzalez allegedly fled a traffic stop and struck an officer with his car. However, body camera footage obtained by the Chicago Sun-Times showed the agent and his partner telling local police their injuries were “nothing major.”
Amid these developments, the legal system has shown rare resistance to federal prosecutions of protestors. On October 8, a federal grand jury declined to indict two protestors, Ray Collins and Jocelyne Robledo, who were charged with resisting and assaulting officers during demonstrations at the Broadview ICE facility. As reported by Bloomberg Law, grand juries rarely refuse to indict in such cases, but these outcomes have become more common amid the Trump administration’s escalated enforcement tactics.
Illinois and Chicago’s lawsuit challenging the deployment of federal troops is scheduled for a hearing, with the courts increasingly serving as the main front in the city’s resistance to federal shows of force. As the Headline Club’s Board of Directors put it, “The targeting of reporters and photographers covering demonstrations outside the ICE facility is more than an assault on the press—it’s an assault on the public’s right to know. When journalists are silenced, the public loses access to the truth about government actions.”
As the legal battles continue and federal agents remain on Chicago’s streets, the city stands at the center of a national debate over the limits of federal power, the rights of immigrants, and the protection of civil liberties in times of political crisis.
