On a late summer weekend in September 2025, downtown Chicago became the stage for a dramatic confrontation between federal power and local resistance. As thousands of demonstrators flooded the streets, their chants and signs sent a clear message: Chicago would not quietly accept the Trump administration’s plans to expand federal immigration enforcement in the city. The protests, which stretched from the heart of the Loop to the suburbs and even up to the gates of Naval Station Great Lakes, reflected not just anger, but a fierce sense of solidarity and determination among Chicagoans.
The spark for this latest round of protests came on September 6, when President Donald Trump posted a meme on Truth Social referencing the Vietnam War film “Apocalypse Now.” The post, which declared, “I love the smell of deportations in the morning,” was accompanied by an image of Trump in military garb, helicopters overhead, and the words “Chipocalypse Now” emblazoned across the sky. The message was unambiguous: the president was warning Chicago of an impending federal crackdown, promising that the city was about to “find out why it’s called the Department of War.” According to the Chicago Sun-Times, Trump had just signed an executive order authorizing “Department of War” as a secondary title for the Department of Defense, a move he said would “send a message of strength.”
The response from Illinois’ political leaders was swift and scathing. Governor JB Pritzker condemned Trump’s post as “not normal,” writing on X (formerly Twitter), “The President of the United States is threatening to go to war with an American city. This is not a joke. This is not normal.” Senator Dick Durbin echoed the outrage at the annual Mexican Independence Day Parade in Pilsen, calling Trump’s post “disgusting.” “To suggest that the troops are coming into Chicago is an embarrassment,” Durbin said, according to the Chicago Sun-Times.
Mayor Brandon Johnson also weighed in on X, urging Chicagoans to stand together: “The President’s threats are beneath the honor of our nation, but the reality is that he wants to occupy our city and break our Constitution. We must defend our democracy from this authoritarianism by protecting each other and protecting Chicago from Donald Trump.”
As the rhetoric heated up online and in the halls of government, the city’s streets filled with people determined to show their opposition. On September 6 and 7, at least a few thousand protesters marched peacefully through downtown Chicago and its suburbs. According to ABC7 Chicago, the demonstrators carried signs, chanted, and made it clear that they believed federal agents were not needed in their city. “We have to stand up together and say very loudly and proudly that this is not gonna happen,” said Cobi Guillory, co-chair of Coalition Against Trump. “We are not accepting this.”
Many of those protesting said they were motivated by concern for their neighbors and a belief that immigrants make Chicago—and America—stronger. “99% of the people that are here that come to America and Chicago are hardworking,” said a protester named Kevin. “They want a better life for their families.” Another demonstrator, Barbara, added, “I myself am an immigrant, and it’s very important for immigrants to be in this country. They make this country great.”
Protests were not limited to downtown. Demonstrators rallied outside Naval Station Great Lakes near North Chicago, where hundreds of federal agents were reportedly being sent to support Trump’s mission to curb crime and make immigration arrests. The New York Times reported that ICE officials had requisitioned thousands of handcuffs, belly chains, leg irons, gas masks, license plate readers, and buses in preparation for the operation. The city braced itself, with a fence remaining up at the federal building downtown to allow access in case operations escalated in the days to come.
Community organizations played a central role in organizing the resistance. The Coalition Against the Trump Agenda, which includes groups like the Illinois Coalition for Immigrant and Refugee Rights (ICIRR), the Chicago Alliance Against Racist and Political Repression, and Organized Communities Against Deportations, led the downtown protest. According to the Chicago Sun-Times, the purpose was to show the White House and the rest of the country that Chicago “will not be scared” of the president’s policies. “Trump talks hatefully about our neighbors on the South, West and Southwest Side of Chicago, but he doesn’t know our city,” said Nazek Sankari, a spokesperson for the U.S. Palestinian Community Network. “He doesn’t know and understand our city, he doesn’t realize that we have always produced some of the most powerful resistance in the U.S.”
The protests coincided with the city’s vibrant Mexican Independence Day parade in Pilsen, a celebration that stood in stark contrast to the fear and tension surrounding the federal enforcement plans. For many, the parade was a moment to reaffirm the importance of community and cultural pride even as uncertainty loomed. Priscilla Read, 76, explained her role as a legal observer: “We’re organizing to document detentions, report them, and do our best to defend people who are detained. In fact, that’s one of the main reasons we’re here today. Cameras at the ready. So far, there haven’t been any incidents, but [we are] prepared to document because that’s basically what we can do at this point. If you are defenders of democracy and human rights, you need to be in solidarity right now.”
For some, the president’s posts and federal plans only reinforced negative stereotypes about Chicago. Kenneth Morrison, watching the parade from a cafe in Pilsen, lamented, “It’s disturbing that [Trump] wants to pick a fight. People not living in Chicago believe the narrative that Chicago is a hellhole. They don’t see anything like what we just saw a moment ago. They just think we’re dodging bullets.”
Veterans and former military personnel also joined the protests, voicing their opposition to the use of federal troops for domestic law enforcement. Kevin Ryan, a U.S. Marine Corps veteran, carried a sign reading, “Veterans Demand No Troops on Our Streets.” He told the Chicago Sun-Times, “There’s no emergency that would warrant the National Guard or any kind of federal troops. And our military is meant to deter and defeat military threats, not to police our cities. It’s escalatory and dangerous. These people are not trained to handle crowds, to do police activity. They’re trained to conduct war.”
Ryan and others expressed skepticism about ICE’s stated goals, arguing that the agency’s actions go beyond targeting criminals. “They say that they’re targeting criminals, but we all know that’s not true,” Ryan said. “And they have these outrageous quotas that they’ve been trying to meet, and so they’re just taking our neighbors off the street without due process, detaining them indefinitely without due process and then trying to ship them off to third countries that they have no one there that they can contact to help them.”
As the weekend drew to a close, Chicago remained on edge. The protests had been peaceful, the city’s leaders had spoken out forcefully, and the community had shown its resolve. Whether the federal government’s plans would escalate remained uncertain, but one thing was clear: Chicagoans were ready to defend their city, their neighbors, and their democracy—together, and loudly.
