Federal Raids Met with Community Resistance in Chicago
Tensions flared on the streets of Chicago in late October 2025, as residents and protesters confronted federal agents in the Little Village neighbourhood. The confrontations form part of a broader pattern of resistance emerging across the city in response to widespread immigration raids.
The Trump administration's 'Operation Midway Blitz', which commenced on 9 September 2025, has seen ICE and Customs and Border Protection agents conducting operations in almost every part of the city. According to estimates from the National Center for Immigrant Justice and the Illinois Coalition on Immigrant and Refugee Rights, approximately 1,300 people have been illegally detained since the operation began, with ongoing violations of a court order prohibiting warrantless arrests.
The situation grew so severe that Mayor Brandon Johnson called for the United Nations to investigate the force being used on city streets.
Grassroots Organising Takes Centre Stage
In the face of this federal action, Chicago's residents are mounting a formidable community-led response. The city, long defined by waves of immigration, has seen its vibrant streets, once filled with immigrant-owned businesses, turn into ghost towns. In response, countless hours and funds are being dedicated to keeping the community intact.
Diego Morales, a volunteer with PUÑO (Pilsen Unidos Por Nuestro Orgullo), reported that their MigraWatch trainings have consistently reached capacity. Since 2016, Morales has trained over 2,000 people on how to spot ICE and understand their rights. His goal is to achieve a critical mass of trained individuals across the city, ensuring everyone from bus drivers to students has the tools to respond and activate a network of support.
Meanwhile, the West Side group Belmont Cragin United has been hosting 'Whistlemania' events. Volunteers gather at local restaurants to pack whistles, community resource guides, and informational zines. These events, held across the city's West Side, have reportedly packed more than 17,000 kits, according to Block Club Chicago.
Businesses and Vendors Feel the Impact
The economic and personal toll of the raids is profound. Anaís Robles, co-owner of Colibrí Cafe on the city's East Side, experienced this firsthand in mid-October when she was teargassed half a block from her shop after going to investigate a commotion involving masked federal agents.
Local businesses have suffered significantly. Morgan Martinez, owner of the astrology-themed sober space Solar Intentions in Edgewater, helped organise a fundraiser for a neighbouring business, Edgewater Tacos, which was forced to close for an entire weekend due to the raids. The fundraiser raised thousands of pounds to compensate for lost revenue.
The Street Vendors Association of Chicago (SVAC) is also taking action. Maria Orozco, a development coordinator whose parents are street vendors, stated that the organisation has raised over $230,000 for vendors terrified of being detained. One of the first individuals detained under 'Operation Midway Blitz' was a flower vendor on the city's Southwest Side.
As Alonso Zaragoza told local media, these efforts demonstrate that 'the city of Chicago and our neighbours care about these individuals, even if the federal government doesn't.' Despite exhaustion and the administration's attempts to foster defeat, the community remains present and committed to standing up for one another.
