(CNN) — Immigration enforcement operations are ramping up in Chicago and Boston, marking the latest escalation between the Trump administration and Democratic-led cities that limit cooperation with federal immigration authorities.
The Department of Homeland Security on Monday announced “Operation Midway Blitz” aimed at targeting “criminal illegal aliens who flocked to Chicago and Illinois because they knew Governor (JB) Pritzker and his sanctuary policies would protect them and allow them to roam free on American streets.”
The heightened rhetoric from President Donald Trump and his top officials aligns with how the White House plans to push forward its aggressive agenda aimed at undocumented immigrants. Ongoing arrests in Chicago are expected to expand as a federal presence builds up in a weeks-long, phased approach, according to officials familiar with the plans who stressed it’s still in flux.
Operations in Boston and Chicago are modeled after the June immigration sweeps in Los Angeles that the Supreme Court ruled Monday can continue under certain circumstances. The Homeland Security official charged with immigration operations in Los Angeles, Gregory Bovino, was deployed to Chicago to do the same there, officials told CNN, with one describing Chicago as “Los Angeles on the road.”
The escalating actions also follow a massive raid last week at a Hyundai plant in Georgia that, while not in a sanctuary city, previews forthcoming worksite operations, border czar Tom Homan told CNN’s Jake Tapper on Sunday.
“You can expect action in most sanctuary cities across the country,” Homan said, decrying as “problem areas” the next targets of the sweeping nationwide immigration enforcement agenda that helped propel Trump to a second term but Americans largely oppose.
In tandem with those moves, more Democratic-led cities also are bracing for the Trump administration to decide — “over the next day or two,” the president said Sunday — where to further deploy National Guard troops to crack down on violent crime, a purported problem the White House sometimes has linked with immigration.
The Department of Homeland Security on Sunday blamed Boston Mayor Michelle Wu for sanctuary polices that “not only attract and harbor criminals but also place these public safety threats above the interests of law-abiding American citizens.” Crossing the border or overstaying a visa and being undocumented in the United States generally is a civil infraction, not a criminal one.
Calling up the National Guard is “always on the table” for Chicago, Homan told CNN, even after a federal judge last week ruled Trump broke federal law by using the US military to help with law enforcement activities in and around Los Angeles — while use of the guard in Washington, DC, is unlike anywhere else.
“We used them in Los Angeles, and we use them in Washington, DC,” Homan said. “They’re a force multiplier.”
Sen. Dick Durbin, the Senate’s No. 2 Democrat, said in a statement Monday that such enforcement won’t make people feel safer.
“They are a waste of money, stoke fear, and represent another failed attempt at a distraction,” he said.
Cities push back against Trump threats
In Washington, DC, where more than 2,200 armed National Guard troops have roamed for weeks, officials are suing the Trump administration, accusing the president of violating the Constitution and federal law by sending soldiers into the city without consent from local leaders.
The lawsuit, filed Thursday by DC’s attorney general, claims the troops — many from out of state — have been deputized by the US Marshals office and are patrolling neighborhoods, conducting searches and making arrests, despite federal laws that generally bar the military from acting as local police.
The Trump administration has touted its efforts in the capital city, pointing to a sharp drop in violent crime since ramping up federal law enforcement last month. But critics argue the National Guard deployment is unnecessary and costly, with taxpayers footing an estimated $1 million a day, while troops take photos with tourists, pick up trash and lay mulch.
Trump has also repeatedly slammed nearby Baltimore for its crime, calling the city a “hellhole” and suggesting the National Guard could be deployed there next.
“We don’t need an occupation,” Baltimore Mayor Brandon Scott told CNN’s Manu Raju on Sunday. Scott said he’d explore all options when asked whether he would sign an order like Chicago’s that tells local police not to cooperate with federal law enforcement should they be deployed.
On Sunday evening, Trump told reporters Chicago is a “very dangerous place,” adding to anticipation of troops there. The president said he could “solve Chicago very quickly,” but stopped short of committing to deploy the guard.
The next morning, he lashed out at Illinois Gov. JB Pritzker, questioning the Democrat’s supposed aversion to federal intervention: “WHY??? … Only the Criminals will be hurt” by any federal efforts, Trump wrote on his social media platform, adding crime is “ONLY GOING TO GET WORSE!!!”
Pritzker denounced DHS operations in the state Monday, saying in a post on X that the operation “isn’t about fighting crime.”
“That requires support and coordination — yet we’ve experienced nothing like that over the past several weeks,” he said, adding that the administration has chosen to focus “on scaring Illinoisians.”
The governor’s office has still not recieved any “formal communication or information” from the Trump administration and that they are often learning of operations through social media, said Matt Hill, spokesperson for Pritzker.
Seven people were killed in Chicago from Friday evening through Sunday, preliminary police figures show. At least six victims were men, ages 21 to 42.
Still, fatal shootings in the city are down 34.2% this year through September 6 compared with the same period in 2024, with 237 killed in 2025, mayor’s office data shows.
The Windy City has prepared for more than a week for looming National Guard deployments and Immigration and Customs Enforcement raids, from the governor bracing for a court fight to parade planners postponing.
Fears gripped Chicago over the weekend
On the Lower West Side of Chicago, the start of Mexican Independence Day celebrations typically marks a raucous weekend of parties and parades drawing hundreds of thousands of attendees. While some crowds did gather Saturday waving green, white and red flags in the predominantly Latino Pilsen neighborhood, an undercurrent of caution persisted.
As costumed performers and children with baskets of treats paraded through the community, bright orange whistles swung from their necks, each one ready to cut through the music should federal immigration agents appear.
Elsewhere, celebrations were muted.
In Wauconda, a village northwest of Chicago, the annual Latino Heritage Festival was canceled due in part to “immigration concerns in our area,” the Wauconda Police Department said in a Friday social media post.
One of the largest events of the Fiestas Patrias, the parade for the Mexican Independence Day in Waukegan, has been postponed for the first time in its 30-year history to November 1 from September 14. The festival is celebrated every year in the suburb along Lake Michigan just north of the Great Lakes naval base, the facility Gov. JB Pritzker said Trump is set to use as a command center for incoming immigration agents.
Communities throughout the nation’s third-largest city are preparing for ICE presence by handing out flyers reminding families they have the right in the face of immigration enforcement to remain silent and don’t have to consent to be searched or share their birthplace or citizenship status, among other rights.
In Pilsen, neighbors gathered this weekend to celebrate Latino culture, choosing joy despite fear: “I think now more than ever is when we need to demonstrate that we are united and we are a community,” longtime resident Araceli Lucio said.
CNN’s Kit Maher, Alison Main, Samantha Waldenberg, Lily Hautau, Chris Boyette and Gabe Cohen contributed to this report.