Original Date Announced

CNN reports that the Trump administration is preparing to conduct a “major immigration operation” in Chicago. The operation will include personnel from ICE, CBP, and possibly other agencies. Officials are also preparing the National Guard to help if a "peacekeeping" presence is needed. Preparations, already underway, include sending armored vehicles to the city and surging federal agents. The blueprint for the operation is the administration's actions in Los Angeles.

Trump 2.0 [ID #1946].

Subsequent Trump and Court Action

2025.08.30 Chicago - Executive Order Denouncing Any Attempts to Deploy the US Armed Forces in Chicago and to Establish the protecting Chicago Initiative

Mayor Brandon Johnson issued an executive order outlining how the city will work to resist the anticipated immigration-enforcement operation. The executive order "demands" that President Trump "stand down from any attempts to deploy the U.S. Armed Forces . . . in Chicago." It further provides that "no [Chicago Police Department] personnel shall be assigned joint law enforcement patrols, arrest operations, or other law enforcement duties alongside federal law enforcement, or military personnel, or National Guard units engaging in civil immigration enforcement." It also establishes the Protecting Chicago Initiative to coordinate the City's work "to promote the well-being and safeguard the rights of all Chicagoans in response to threats arising from the actions and inactions of the federal government."

Subsequent Trump and Court Action

2025.09.08 DHS - ICE Launches Operation Midway Blitz

ICE and DHS announced the launch of "Operation Midway Blitz," an immigration-enforcement operation in Chicago. The operation will target immigrants who have committed crimes, with an allegation that they "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."

Subsequent Trump and Court Action

2025.09.19 Reported: ICE arrests nearly 550 in Chicago area as part of ‘Midway Blitz’ - AP News

The Associated Press (AP) reports that ICE officials have arrested almost 550 people in the Chicago area as part of its "Midway Blitz" operation. This DHS-provided figure includes arrests by ICE and other assisting federal agencies. Marcos Charles, the acting head of ICE’s Enforcement and Removal Operations, said that roughly 50 to 60% of the arrests were targeted, while the rest were collateral arrests.

Subsequent Trump and Court Action

2025.10.02 WBEZ Chicago - Massive immigration raid on Chicago apartment building

WBEZ Chicago reports that federal agents from the Border Patrol, FBI, and Bureau of Alcohol, Tobacco, Firearms and Explosives (ATF) arrested 37 people in a Chicago raid on an apartment building. DHS claims that it targeted the South Shore neighborhood since it is "known to be frequented by Tren de Aragua members and their associates.” Federal agents used flashbang grenades to burst through the building and forcibly entered and searched residents' apartments overnight. They "pull[ed] men, women and children from their apartments, some of them naked, residents and witnesses said. Agents approached or entered nearly every apartment in the five-story building, and U.S. citizens were among those detained for hours."

Subsequent Trump and Court Action

2025.10.06 Complaint - State of Illinois v. Trump

The State of Illinois and the City of Chicago filed a lawsuit against the Trump administration to challenge the Illinois National Guard's federalization and deployment to perform federal law-enforcement functions in Chicago. On October 4, 2025, DOD Secretary Pete Hegseth invoked 10 U.S.C. § 12406 to federalize 300 members of the Illinois National Guard and sent 400 Texas Guard troops into Chicago.

The complaint states that the federal government has infringed Illinois' sovereignty and right to self-governance: The federalization and deployment of the Illinois Guard will cause harm to the State's interests by preventing those members from engaging in other critical work and will redirect valuable social and health-care services away from their proper use. It alleges that the administration's actions violate federal statutes (Posse Comitatus Act, Administrative Procedure Act), as well as the Constitution's Tenth Amendment, Take Care Clause, Militia Clause, and separation of powers and equal sovereignty principles. State of Illinois v. Trump, No. 1:25-cv-12174 (D. Ill.).

**Link to case here.**

Subsequent Trump and Court Action

2025.10.06 Complaint - Chicago Headline Club v. Noem

The ACLU filed a lawsuit against the federal government, representing members of the press, clergy and ordinary citizens to protect free speech under the First Amendment. The lawsuit responds to federal agents interfering with protestors' right to peacefully protest at the Broadview ICE facility and general Chicagoland area. The complaint also alleges violations of the Religious Freedom Restoration Act, the Fourth Amendment's limitations on the use of excessive force and unreasonable seizures, and the Administrative Procedure Act (APA). The Plaintiffs seek a TRO for immediate relief against the suppression of free speech. Chicago Headline Club v. Noem, No. 1:25-cv-12173 (D. Ill.).

**Link to case here.**

Subsequent Trump and Court Action

2025.10.09 TRO - State of Illinois v. Trump

U.S. District Judge April M. Perry granted the State of Illinois' and the City of Chicago's motion for a Temporary Restraining Order (TRO). The TRO enjoins the administration from "ordering the federalization and deployment of the National Guard" in Illinois. It will expire on October 23, 2025. A hearing is scheduled for October 22, 2025 to address whether the TRO should be extended for 14 days.

State of Illinois v. Trump, No. 1:25-cv-12174 (D. Ill.).

**Link to case here.**

Subsequent Trump and Court Action

2025.10.11 Order - State of Illinois v. Trump

The U.S. Court of Appeals for the Seventh Circuit granted a partial administrative stay of the district court’s October 9 order enjoining the National Guard's federalization in Illinois. The court denied a stay of the prohibition on deployment. As a result, federalized National Guard troops may remain under federal control within Illinois but may not be deployed pending further proceedings. The court clarified that Guard members are not required to return to their home states unless so ordered by a subsequent court ruling.

State of Illinois v. Trump, No. 1:25-cv-12174 (D. Ill.).

**Link to case here.**