Thousands of protesters packed the streets near downtown Chicago on Monday, singing, chanting and waving signs protesting US President Donald Trump’s threats to flood the city with National Guard troops and federal immigration agents.
The march was one of roughly 1,000 “Workers over Billionaires” protests across the country on the US Labor Day holiday. But Chicago’s demonstration had a decidedly more pointed tone as residents bristled against Trump’s promise to target Chicago next in a deployment similar to those under way in Los Angeles and Washington DC, two other Democrat-run cities.
Mayor Brandon Johnson, speaking to the crowd, vowed that Chicago would resist federal encroachment.
“This is the city that will defend the country,” he said, receiving loud cheers from protesters waving blue-striped Chicago flags.
As the crowd wove through the city, some walking dogs and carrying children on their shoulders, diners sitting outside at local restaurants and cafes pumped their fists and cars honked in support. Organisers estimated 5,000 to 10,000 people were in attendance, though Reuters was not immediately able to verify the size with city officials.
Protesters said they were concerned by Trump’s threat to send out the National Guard and additional ICE agents.
Filiberto Ramirez, 72, feared violence if additional ICE agents come to the city. “Do we feel there’s gonna be trouble? Yes,” Ramirez said. “I hope nobody gets hurt.”
Trump has singled out Chicago in recent weeks over violent crime, calling the city “a mess,” “a hellhole” and a “killing field.” But on Monday, Chicagoans at the protest said they did not feel the National Guard was a solution to crime in the city.
“There is a crime problem,” said Yvonne Spears, 67, “but the National Guard is supposed to fight for us, not against us.”
Homicide rates in the nation’s third-largest city have plunged in recent years, according to city crime data. And though a 2025 University of Chicago survey reported roughly half of Chicagoans feel unsafe in their neighbourhoods at night, many protesters said on Monday that they felt largely safe in the city.
City and state leaders have already readied measures to shield Chicago from federal troops and would likely launch a slew of lawsuits challenging a deployment, which legal experts said would violate the US Constitution and a 19th-century law prohibiting the military from enforcing domestic laws.
Mayor Johnson signed an executive order on Saturday saying that Chicago police will not collaborate with federal agents or National Guard troops and directing all police officers to wear official uniforms and not to wear masks. Meanwhile, immigrant rights groups have worked to fortify their defences amid threats of stepped-up immigration enforcement by working to hire more attorneys, staffing immigration hotlines and launching more “know your rights” training.
“The people here are proud that we’re a sanctuary city,” said Andrea Reyes, 42, referencing city policies prohibiting its government from involvement with federal immigration enforcement.
“I don’t think it’ll go well if the National Guard comes here.”
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