Dozens of federal immigration agents were seen patrolling downtown Chicago Sunday afternoon.
Social media livestreams showed agents in front of Tribune Tower on North Michigan Avenue and in front of Millennium Park, detaining individuals. They also showed several U.S. Customs and Border Protection boats on the Chicago River.
The video of the agents walking in clusters downtown was recorded by lawyer Berto Aguayo, advising undocumented individuals to stay away and to be aware of their rights.
After sightings near Millennium Park and the Riverwalk downtown, the dozens of federal immigration agents — most of them wearing camouflage uniforms with U.S. Border Patrol patches — made their way up to the Gold Coast — a primarily white, affluent neighborhood — in the early afternoon, flanking the sidewalks of Clark Street.
Roughly 20 bystanders and passersby started following the officers, chanting “ICE, go home!” The agents stopped at the intersection with Oak Street. Several got in vans that drove away. For another 15 minutes, the crowd of protesters around them grew bigger, yelling “shame.”
A shrill whistle cut through the noise repeatedly.
Some of the civilians present confronted Gregory Bovino, the chief U.S. Border Patrol agent, who joined on the patrol.
When asked by the Tribune how many agents had been patrolling downtown Sunday, Bovino said, “a lot.”
Bovino declined to answer any additional questions from the Tribune. When he and the last of the agents drove away, protesters celebrated with applause and cheers.“The people, united, will never be defeated!” they intoned.
Present on Sunday was Enrique Espinoza, an attorney and member of the Hispanic Lawyers Association of Illinois, who said the agents’ presence downtown was performative.
Espinoza is an immigrant himself, hailing from Veracruz, Mexico.“Let’s be clear: This was a show. They wanted to get attention, and they got it,” he gestured toward the last remaining protesters as the crowd dispersed.
The Department of Homeland Security, which oversees the federal Immigration and Customs Enforcement agency, could not immediately be reached for comment.
‘A major escalation,’ immigration advocates say
The move comes in the midst of what President Donald Trump’s ICE is calling its “Operation Midway Blitz,” which has sown fear throughout immigrant communities in Chicago and its suburbs. Officials escalated a promised surge in immigration enforcement in the area over the last two weeks, with arrests reported and federal agents sighted near local schools, courthouses and workplaces. ICE claimed last week it had made 550 arrests during the first two weeks of the mission.
Chicago Mayor Brandon Johnson said he was closely monitoring the situation in a post on X. “While Chicagoans and visitors are enjoying another gorgeous Sunday, they are being intimidated and threatened by masked federal agents flaunting automatic weapons for no apparent reason. This is another brazen provocation from the Trump administration that does nothing to make our city safer,” Johnson said.
Illinois Gov. JB Pritzker also posted on X Sunday afternoon, “This is not making anybody safer — it’s a show of intimidation, instilling fear in our communities and hurting our businesses,” he said. “We cannot normalize militarizing American cities and suburbs.”
By mid-afternoon Sunday, the intersection was cleared, traffic was flowing and things went back to normal — much like in the Loop, where after earlier sightings and reports of a couple of arrests, tourists strolled under the sun and took photos of the city, most of them none the wiser.
After the downtown display, immigrant rights advocates held a news conference alongside local and state officials, including U.S. Reps. Jesús “Chuy” García and Delia Ramírez, Lt. Gov. Juliana Stratton and several aldermen. They did not have an exact number of arrests made.
Sunday’s downtown operation in broad daylight represented a “major escalation by the Trump administration,” said Veronica Castro, deputy director at the Illinois Coalition for Immigrant and Refugee Rights.
Hers was a sentiment echoed by other speakers.
“Today, we witnessed the further militarization of ICE tactics in Chicago, as they showed up downtown to indiscriminately continue to profile against people just because of what they look like, their appearance,” García said. “This … is part of a nationwide effort by Trump and his administration to instill fear in people.” But, he said, “We want Trump and his aides to be clear: We will not take this lying down. You claim that you’re out to get the worst of the worst,” García said. “But we see time and time again that the people that you are apprehending and kidnapping and interrogating and terrorizing are hardworking people that make Chicago and Illinois a better place for everyone.”
Illinois state Sen. Graciela Guzmán said the administration is seeking to intimidate immigrants “by air, by water, by force, by any means possible” — alluding to the federal immigration agents, including Bovino, out in boats on the Chicago River on Sunday and Thursday, when they were first spotted.
“I want to remind folks at home that (at) every single level of government, here you have folks that deeply care about you,” Guzmán said. “We are doing everything in our power because you are our constituents. We love you, we will protect you.”
Chicago journalist arrested during Broadview protest released
Early Sunday morning, a journalist for the Unraveled Press, who was detained by federal agents, was released after being detained at a Broadview protest Saturday night.
A social media post late Saturday showed Steve Held, being detained by federal agents.
After he was released early Sunday morning, Held described his experience of being detained on the social media app, Blue Sky.
His first words were “I’m out, I’m sore.”
Held saw four holding rooms while being detailed, he said, two small rooms being used to hold protesters and two larger rooms to hold ICE, Customs, and Border Protection captives. He also said he saw a man sitting in a room with gauze wrapped around his head, appearing to have a serious head wound.
The room he was held in “stank of sweat & pepper ball powder after just a few hours,” the post said. Another room, he said, “appeared dirty, filled with men dressed for labor, trying to get comfortable to sleep in chairs or on the cold floor in the cinder block room.”
When getting processed, he said he saw the faces of men that looked “heartbreaking.”
“We have never witnessed anything like what ICE has unleashed on our communities this week,” Unraveled Press posted on social media Sunday morning.
Originally Published: September 28, 2025 at 4:12 PM CDT