By Richard T. Herman, Esq., Immigration Lawyer (Herman Legal Group)
Introduction: Chicago at the Frontline of ICE Resistance
Need to Know:
Since early 2025, Immigration and Customs Enforcement (ICE) has intensified raids and detentions across the Midwest — and Chicago has emerged as the national epicenter of resistance.
Fast Fact:
Chicago now leads the country in community-based counter-enforcement networks, rapid-response legal teams, and political defiance against federal deportation forces.
As federal agents escalated Operation Midway Blitz — a multi-state deportation campaign launched in September 2025 — the city mobilized a broad coalition of politicians, businesses, and residents to shield immigrant communities. From city-hall directives and “ICE-free zones” to plastic whistles and legal injunctions, this multi-layered resistance has transformed Chicago into the symbolic heart of the American ICE push-back. The “ICE-free zones” initiative aims to designate city-owned property, such as schools and libraries, as off-limits to ICE without a warrant.
Why Chicago? Geography + History + Legal Context
Key Insight: Chicago’s sanctuary identity, immigrant density, and progressive leadership make it the perfect collision point for immigration enforcement and resistance. The city and state have enacted laws such as the Welcoming City Ordinance and the Illinois Trust Act, which limit the extent to which local police officers and police officers can cooperate with federal authorities during immigration enforcement actions. Federal agencies and the federal government, including ICE and DHS, continue to conduct operations in Chicago and the surrounding Chicago suburbs, prompting local leaders to implement policies that resist or regulate federal intervention. This ongoing tension between local and federal authorities shapes the unique legal and social landscape of immigration enforcement in the region.
Immigrant demographics & sanctuary identity
Home to hundreds of thousands of immigrants from Mexico, Poland, India, the Philippines, Nigeria, and beyond, Chicago has long prided itself on being a “welcoming city.” Its Welcoming City Ordinance restricts local police from cooperating with ICE — a principle reaffirmed by Mayor Brandon Johnson in 2025. Mayor Brandon Johnson also signed an executive order to prevent federal agents from using city-owned land for staging areas and reaffirmed the city’s “Welcoming City Ordinance.”
This legal foundation gives organizers a strong footing to resist federal incursions while empowering city agencies to refuse collaboration on detainers or raids.
Legal & municipal context
Illinois law further reinforces Chicago’s stance. The Illinois Trust Act prohibits state and local police from detaining anyone based solely on ICE requests. The Illinois Trust Act and Illinois Ways Forward Act prohibit local law enforcement from participating in federal immigration enforcement and from detaining individuals based on immigration status. It is important to understand your legal status when interacting with immigration enforcement, as this can affect your rights and protections. Additionally, federal agents are required to have a warrant signed by a federal judge to legally enter private property; ICE warrants are often not signed by a judge and do not grant legal entry rights. Together, city and state laws have created a firewall between federal agents and local governance.
Important Note:
Federal officers can still act under warrant — but Chicago’s layered protections complicate their operations and public perception.
2025 escalation: Operation Midway Blitz by federal agents
In September 2025, the Department of Homeland Security launched Operation Midway Blitz, targeting immigrant-dense Chicago neighbourhoods. ICE’s presence in the Windy City intensified, with a marked increase in immigration raids across apartment buildings and public spaces. The campaign relied on vehicle checkpoints, surveillance drones, and courthouse arrests — prompting what The Washington Post described as “the largest urban ICE mobilization in recent memory.”
ICE arrests were carried out by ICE officers, ICE agents, federal immigration agents, and other agents, often in coordinated sweeps. There were incidents where agents shot civilians during confrontations, and in one case, individuals allegedly rammed a federal vehicle. To disperse crowds during protests, law enforcement deployed smoke grenades and tear gas canisters, with masked agents and national guard troops present on the ground. Border patrol agents also participated in these operations, with the Broadview ICE facility and other ICE facilities becoming focal points for both enforcement and protest activity.
The preservation of key evidence during legal proceedings related to these raids became a critical concern. Many detained immigrants did not have criminal convictions, yet national security and border protection were frequently cited as justifications for the actions. There were also reports of agents arrested during clashes, with President Donald Trump and the Trump administration playing a central role in escalating enforcement measures.
Specific incidents in Hanover Park drew attention, as did the leadership of Broadview Mayor Katrina Thompson in managing community response. Protests saw residents waving Mexican flags in solidarity, while apartment buildings were repeatedly targeted during raids. The city was described as a war zone, with concerns raised about social media interference potentially hindering law enforcement activities. Executive directors of advocacy organizations emphasized the importance of protecting free speech during demonstrations. The Illinois Department was actively involved in efforts to protect vulnerable populations during these raids.
Chicago, as the Windy City, became a national symbol in the debate over immigration enforcement and civil liberties. These operations resulted in arrests and raids that have affected hundreds of undocumented immigrants and their families.
2025: The Turning Point in Immigration Enforcement
Fast Fact:
In the first three weeks of Operation Midway Blitz, more than 500 immigrants were detained in Cook County alone, according to Time Magazine.
The scale of the ICE arrests and raids
ICE staged early-morning sweeps in Pilsen, Albany Park, and Little Village — areas symbolic of Chicago’s immigrant heart. Agents deployed armored vehicles and pepper-ball projectiles during protests near the Loop. Federal agents have also been reported using flash-bang grenades during these raids in Chicago, and there have been multiple incidents of federal agents shooting during operations, including one fatality. Additionally, federal agents have been reported to break down doors during these raids, causing significant property damage and further distressing affected families.
Immediate impact
The heavy-handed approach galvanized neighbourhood networks. Within hours of each raid, residents used social media to coordinate protests and block ICE vans from leaving communities. Chicago’s resistance, as WBEZ Chicago reported, was “rapid, organized, and increasingly visible.” Community groups have trained volunteers for rapid response efforts to monitor ICE activity, ensuring that federal actions are documented and that residents are informed in real-time.
Grassroots & Individual Resistance
Expert Tip:
The most effective resistance often begins at the street level — not in city hall.
Plastic whistles and “neighbourhood alerts”
Residents distribute thousands of plastic whistles to warn others when ICE vehicles appear. Reuters called them “a sonic alarm for immigrant neighborhoods.” A single whistle blast now triggers community responses — store closures, family alerts, and livestream documentation. Community members have also adopted low-cost, high-visibility orange whistles to ensure neighbors are quickly alerted to an active ICE presence.
Gym, clergy, and driver networks
Community groups have enlisted unexpected allies — gym owners, clergy, and delivery drivers — to accompany immigrants to work, school, or court. The Washington Post documented volunteer “street-escort patrols” that shadow ICE convoys to ensure accountability. Volunteer rapid response teams also document ICE activity and can physically block ICE vehicles to prevent arrests, showcasing the community’s commitment to protecting its members.
Business solidarity & economic protest
Immigrant-owned restaurants and grocers now stage coordinated shutdowns — echoing the national Day Without Immigrants movement. Local businesses hand out “Know Your Rights” flyers and provide shelter for families afraid to leave home.
Call-Out:
Some stores in La Villita offer “raid discounts” — donating profits to legal defense funds when ICE raids occur nearby.
Digital tools and real-time coordination
Chicago’s Illinois Coalition for Immigrant and Refugee Rights (ICIRR) and The Resurrection Project operate encrypted chat networks that instantly relay ICE sightings. These digital alerts, combined with legal hotlines, allow community members to react within minutes. Community organizations also run a text alert system called “Eyes on ICE” to warn residents of ICE raids, further enhancing the rapid response capabilities.
Mass protest & visibility actions
Thousands have protested at Gary/Chicago International Airport — the departure hub for deportation flights — and at the Broadview Detention Center. These demonstrations, often met with tear gas, have drawn national attention to Chicago’s role as America’s “ICE protest capital.” During these operations, federal agents employed aggressive tactics that included the use of tear gas and rubber bullets against protesters.
Municipal & Political Countermeasures
Key Insight:
Chicago’s government has gone beyond symbolic gestures — implementing tangible legal shields against ICE operations.
Mayor Brandon Johnson’s executive order
In October 2025, Mayor Brandon Johnson signed an order barring any city department from aiding ICE or the federal National Guard in immigration enforcement. This came in direct response to federal troop deployments to Chicago.
Important Note:
The order declared city properties — libraries, schools, parks — as “ICE-free zones,” requiring warrants for any federal action.
Cook County courthouse protections
A Cook County judge issued a landmark ruling prohibiting civil immigration arrests at or near courthouses. The order ensures immigrants can attend hearings without fear of detention — a crucial safeguard for due process.
Legal challenges to federal overreach
The Illinois Attorney General and Governor Pritzker joined lawsuits accusing DHS and ICE of unconstitutional interference in local governance. These cases mirror those filed by California in prior administrations, underscoring growing state-federal friction.
Zoning “ICE-Free Zones” initiative
The city council is considering creating legally recognized “no-raid” areas in public facilities, echoing European sanctuary-zone models. These zones serve as moral and tactical barriers — even if federal law ultimately supersedes them.
Legal Defense: The Law-Firm Backbone
Fast Fact: As ICE escalates, Chicago’s immigration lawyers have become the strategic core of resistance.
Leading firms defending immigrants
| Firm | Specialization | Unique Strength | Website |
|---|---|---|---|
| Herman Legal Group | Deportation defense, humanitarian waivers, federal litigation | 30 + years’ experience in immigration law; multilingual team serving 10 + languages | Visit → Book Consultation |
| Minsky, McCormick & Hallagan P.C. | Employment- & family-based immigration, removal defense | Veteran Chicago firm with deep litigation portfolio | MMHPC → Website |
| Sverdloff Law Group | Deportation defense, bilingual advocacy | Focus on Latino and Eastern-European immigrant communities | Visit → Sverdloff Law |
| Aparicio Immigration Law | Removal defense near Chicago Immigration Court | Known for accessibility and rapid response | Visit → Aparicio Law |
Expert Tip:
Connect with an attorney before enforcement occurs. Pre-planning enables emergency filings (stays of removal, bond motions) and rapid-response representation during raids.
What This Means for Immigrants & Advocates
Need to Know:
Chicago’s resistance model is both practical and replicable.
Action steps for individuals & families
- Carry contact information for a trusted lawyer such as Herman Legal Group.
- Do not open the door to ICE without a signed judicial warrant.
- Document encounters when safe and call the ICIRR hotline: 855-435-7693.
- Participate in local “Know Your Rights” workshops through churches or nonprofits. These workshops provide residents with bilingual “Know Your Rights” toolkits, equipping them with essential information on how to interact with immigration authorities.
Business response strategies
- Post “Sanctuary Business” signs and educate employees on their rights.
- Join coalitions supporting workers targeted by ICE.
- Provide safe waiting areas during raids.
Challenges & risks
Important Note:
Resistance can provoke federal retaliation — including funding threats and intensified audits. Yet, Chicago’s example shows that unified legal and civic fronts can withstand that pressure.
Avoiding Scams and Staying Safe
Common scams targeting immigrants
In the heightened climate of immigration enforcement in the Chicago area, community members must be especially vigilant against scams. With federal agents and law enforcement officers conducting more frequent operations, scammers have seized the opportunity to impersonate immigration officers or federal agents. These individuals may call, text, or even show up in person, demanding payment or sensitive information in exchange for supposed immigration benefits, legal services, or to avoid deportation.
The Trump administration’s intensified immigration enforcement has unfortunately created fertile ground for these schemes, as fear and confusion make it easier for scammers to prey on vulnerable individuals. Always remember: legitimate law enforcement officers and immigration agents will never ask for money or personal details over the phone or through unofficial channels. If you are approached by anyone claiming to be a federal agent or involved in immigration enforcement, ask for official identification and do not provide any information until you have verified their credentials.
How to verify legal help and resources
To avoid falling victim to immigration scams, it’s crucial to seek legal services only from trusted, qualified sources. Organizations dedicated to immigrant and refugee rights—such as the Illinois Coalition for Immigrant and Refugee Rights—offer reliable legal services and resources. When searching for legal help, confirm that the provider is a licensed attorney or a reputable nonprofit organization.
Be wary of notarios or immigration consultants who are not authorized to practice law, as they may give false promises or incorrect advice. The Department of Homeland Security and U.S. Citizenship and Immigration Services provide official guidance on how to avoid immigration scams and connect with legitimate legal services. If you’re unsure, reach out to established organizations or check with the Illinois Coalition before sharing any personal information or making payments. Protecting yourself and your family starts with verifying every resource.
Staying safe during enforcement actions
If you find yourself facing immigration enforcement actions by federal agents, ICE agents, or other law enforcement agencies, your safety and rights come first. Stay calm and remember that you have constitutional rights, regardless of your immigration status. You have the right to remain silent and to request an attorney before answering any questions. Do not attempt to run or physically resist, as this can escalate the situation and put you at greater risk.
If you are tear gassed or exposed to pepper balls during an enforcement operation, seek medical attention as soon as possible. Community members can help by documenting ICE activity and supporting those affected, but should always prioritize safety. Be aware that the National Guard and Illinois State Police may also be present during enforcement actions, so it’s important to know your rights when interacting with any law enforcement agencies. By staying informed, prepared, and connected to trusted resources, you can better protect yourself and your loved ones during these challenging times.
Lessons for Other Cities
Expert Tip:
Chicago’s blueprint demonstrates that real deterrence requires legal, political, and community synchronization.
- Policy Integration: Sanctuary ordinances + court orders + rapid-response networks.
- Community Tools: Low-tech (whistles) + high-tech (encrypted alerts).
- Business Solidarity: Economic pressure and moral support amplify visibility.
- Legal Infrastructure: Law firms provide the backbone — ensuring due process and challenging unlawful detentions.
- Public Narrative: Visibility deters abuses; secrecy enables them.
- Economic Impact: Welcoming policies and the presence of immigrants can revitalize cities, resulting in higher household incomes in sanctuary jurisdictions.
Comparison:
Unlike Los Angeles or New York, Chicago couples city-hall resistance with real-time grassroots coordination, creating a more complete “defense ecosystem.”
Conclusion
From plastic whistles in Pilsen to executive orders in City Hall, Chicago’s multi-layered campaign has redefined what local ICE resistance can look like. Politicians, businesses, clergy, activists, and lawyers have collectively transformed the city into the nerve center of immigrant defense in 2025. However, federal immigration policies have also increased psychological stress in local communities, with many residents reporting heightened anxiety and fear due to the presence of federal agents.
Expert Tip:
For immigrants nationwide — and for cities watching — Chicago offers a playbook: resist smartly, legally, collectively, and with preparation.
Key Takeaways
- Chicago’s immigrant communities, legal advocates, and politicians created an unprecedented coalition against ICE raids.
- Operation Midway Blitz (2025) made the city the front line of enforcement — and resistance.
- Tactics include whistles, escort networks, digital alerts, economic protests, and ICE-free zones.
- Mayor Johnson’s executive order and Cook County court injunctions set national precedents.
- Businesses and law firms — especially Herman Legal Group — form the backbone of organized defense.
- Chicago’s approach blends municipal autonomy, civic solidarity, and rapid-response lawyering.
- The model is being studied by cities nationwide seeking to counter new federal immigration initiatives.
Author Bio / Profile
Richard T. Herman, Esq. is an immigration lawyer with more than 30 years of experience representing immigrants, families, and employers across the United States. Founder of the Herman Legal Group — known as “The Law Firm for Immigrants” — he is co-author ofImmigrant, Inc.and a frequent commentator on national immigration policy.
