In Chicago, thousands of demonstrators poured into the streets near the downtown area on Monday, September 1, 2025, voicing their anger and defiance against U.S. President Donald Trump’s recent threats to deploy National Guard troops and additional federal immigration agents to the city. The rally, filled with chants, songs, and protest signs, coincided with the nationwide “Workers Over Billionaires” campaign, which staged roughly 1,000 events across the country to mark the U.S. Labor Day holiday.
Although part of a broader national movement, Chicago’s protest carried its own urgency and unique message. The city has been directly targeted in Trump’s recent remarks, where he vowed to expand federal deployments similar to those already under way in Los Angeles and Washington, D.C.—both governed by Democrats. Many participants expressed a deep sense of frustration at what they described as an attempt to undermine their city’s autonomy and character.
Mayor Brandon Johnson joined the demonstrators, delivering a defiant message that resonated strongly with the crowd. “This is the city that will defend the country,” Johnson declared, drawing thunderous applause as protesters waved blue-striped Chicago flags in solidarity. His comments reinforced the city’s commitment to resisting what leaders framed as federal overreach into local governance.
The demonstration itself was a mix of passion and community spirit. Families with children on their shoulders marched alongside activists, while others walked dogs or carried handmade banners. Restaurants and cafés lining the protest route saw patrons rise from their seats to clap, cheer, and pump their fists in support. Passing vehicles honked horns in solidarity. Organizers estimated that between 5,000 and 10,000 people joined the march, though city officials had not confirmed those numbers by press time.
The prospect of an increased federal presence struck fear among some longtime residents. Filiberto Ramirez, a 72-year-old Chicagoan, worried that an influx of ICE agents could spark violence. “Do we feel there’s gonna be trouble? Yes,” Ramirez said. “I hope nobody gets hurt.” Others voiced concern that Trump’s characterization of the city as “a mess,” “a hellhole,” and “a killing field” unfairly overshadowed progress made in recent years.
Indeed, crime statistics paint a more nuanced picture. Chicago’s homicide rates, while once among the highest in the nation, have dropped significantly in recent years, according to city data. A 2025 survey conducted by the University of Chicago found that about half of residents still feel unsafe in their neighborhoods after dark, but protesters on Monday largely emphasized that they did not see the National Guard as the solution. “There is a crime problem,” said 67-year-old Yvonne Spears. “But the National Guard is supposed to fight for us, not against us.”
Legal experts have also raised alarms about the constitutionality of Trump’s proposal. They argue that deploying the National Guard to enforce local laws would violate both the U.S. Constitution and the Posse Comitatus Act, a 19th-century law designed to limit military involvement in civilian affairs. Anticipating such conflicts, city and state leaders have already begun preparing legal challenges to block any attempted federal intervention.
Over the weekend, Mayor Johnson signed an executive order reinforcing Chicago’s stance. The order prohibits city police from collaborating with federal immigration authorities or National Guard units, while also requiring officers to wear official uniforms and banning the use of masks during operations to ensure accountability.
Meanwhile, grassroots organizations, particularly immigrant rights groups, are ramping up their defensive efforts. These groups are expanding legal aid by hiring more attorneys, strengthening immigration hotlines, and conducting widespread “know your rights” workshops to prepare residents for possible escalations. “The people here are proud that we’re a sanctuary city,” said Andrea Reyes, 42, underscoring Chicago’s longstanding policies that bar city agencies from aiding federal immigration enforcement.
The Labor Day protest in Chicago ultimately represented more than a rejection of Trump’s threats; it was also a reaffirmation of the city’s identity as a diverse, resilient, and defiant community determined to uphold both its local values and constitutional protections.
