Chicago – August 28, 2025
The Trump administration is preparing to conduct a major immigration enforcement operation in Chicago as soon as next week, according to multiple sources familiar with the planning, marking the latest escalation between the president and a Democratic-led city.
President Donald Trump and his aides have repeatedly slammed Chicago over policies that limit cooperation between local authorities and federal immigration enforcement. Chicago grappled with an influx of migrants during the Biden administration following surges along the US southern border and Texas Gov. Greg Abbott’s decision to transport migrants to Democratic-led cities.
Chicago was among the first cities targeted in immigration enforcement operations when Trump took office in January. The administration also sued the city over its so-called sanctuary policies, though the case was dismissed when a judge ruled the federal government lacked the legal standing to bring the challenge, and threatened to withhold federal funding, which was also blocked by a judge.
Now, the anticipated operations in Chicago are expected to be at a larger scale, using personnel from Immigration and Customs Enforcement, Customs and Border Protection, and possibly other agencies. Officials are preparing the National Guard to help if a peacekeeping presence is needed, akin to what unfolded in Los Angeles following protests, the sources said.
Preparations for Chicago are already underway, including sending armored vehicles to the city in the coming days and surging federal agents by next Friday, Sept. 5, when, according to two sources, the operation is expected to kick off. Discussions, however, are still ongoing and planning is in flux.
