Landlord and tenants’ rights have been thrust into debate as tensions flare between local and federal authorities over the handling of immigration enforcement in Chicago.
Legal recourse is another matter, and landlords have little in that vein as uncertainty swirls around how they can respond to intensifying federal policing across the city.
“The bottom line is, there is not much a landlord can do as it relates to police conduct within their building, whether in a common area or a tenant’s apartment,” said Monu Bedi, a DePaul University College of Law Professor who specializes in criminal procedure and military law. “If there is damage to the building, landlords are able to recover money for the property but that is different than their rights to prevent officers from entering.”
Local and state officials are calling into question the tactics used last week by hundreds of federal agents to raid a 130-unit South Shore apartment complex at 7500 South South Shore Drive, and whether they violated typical criminal procedure while arresting dozens and reportedly detaining many more tenants, including children, temporarily during the operation.

Illinois Governor J.B. Pritzker on Monday called on the state Department of Child and Family Services and the Department of Human Services to investigate if federal agents used excessive force against minors.
Meanwhile, Illinois Attorney General Kwame Raoul is seeking an emergency order to block President Donald Trump’s request to activate the National Guard in Chicago. The Oct. 6 filing refers to the South Shore raid as an example of federal authorities’ already extensive presence in Chicago and possible overreach of immigration officers’ duties.
“While it is not clear whether any part of that conduct was within any lawful federal authority, [federal officials] were not impeded in executing this large-scale planned operation,” the filing reads.
A judge declined to grant Raoul’s request on an immediate basis but set a hearing on the matter for Thursday, even as President Donald Trump hinted Tuesday he could invoke the Insurrection Act to deploy military troops to various cities, should a court order blocking such action arise.
Along with Raoul’s litigation, several law enforcement officials and business leaders filed declarations supporting the attorney’s general’s request. Among them was the former commissioner of Customs and Border Patrol, R. Gil Kerlikowske, and prominent business lobbyists whose groups touch on real estate matters, such as Jack Lavin, president of the Chicagoland Chamber of Commerce, and Sam Toia, president of the Illinois Restaurant Association.
Also on Monday, Mayor Brandon Johnson signed an executive order aimed at prohibiting ICE activity on city-owned properties.
And on Tuesday, a U.S. District Judge in Chicago ruled that federal immigration agents illegally arrested 26 people without warrants back in January, violating a 2023 consent decree that dictates how such arrests can be carried out.
At least one Chicago landlord has faced public pressure to push back against ICE. Organizers on the Southwest Side on Tuesday called on Michigan-based Friedman Real Estate to block ICE from using one of its parking lots at The Yards Plaza as a staging area for agents, Block Club Chicago reported. Friedman hasn’t made any public response as of yet, and didn’t return the outlet’s request for comment.
Groups like the National Apartment Association have put together guidance on how to respond to ICE actions like subpoenas and raids. Key points include:
- Property managers are not required to allow ICE agents to enter a building unless they have a criminal warrant signed by a judge.
- Property owners can consult with an attorney before responding to a subpoena for information about tenants.

There’s little precedent, however, for the way ICE has been operating in Chicago, said Hugh Mundy, a law professor at The University of Illinois Chicago who specializes in criminal procedure.
“This [South Shore] raid was really unlike anything that I have witnessed, either as a lawyer or as a law professor,” he said. He added that a warrant typically targets specific units rather than an entire building.
The operation resulted in 37 arrests. The U.S. Department of Homeland Security identified two people arrested as alleged members of the Venezuelan gang Tren De Aragua, and an unspecified number of suspects were “believed to be involved in drug trafficking and distribution and weapons crimes,” according to the agency. Other arrests were due to immigration violations.
Mundy said the scale of the raid — which involved multiple agencies and officers arriving in helicopters and trucks in the middle of the night — seemed more fitting for a racketeering investigation.
“You would normally expect that kind of force to result in more arrests for more serious crimes,” he said. “There’d have to be some general collective knowledge or a common goal and crimes that relate to that goal.”
Still, city officials, the property owner, lender and more real estate professionals were informed of problems the building was facing well before the raid took place.
Chicago code inspectors visited the property just two weeks before it was subject to the massive operation, according to a legal filing in a $27 million foreclosure lawsuit against the building’s owner, Wisconsin-based investor Trinity Flood. The building was found to be unsecured, leading to increased criminal activity and shootings, and its property manager lost control of the situation as conditions worsened, according to legal filings.
A spokesperson for the mayor’s office said the city was unaware the raid would take place ahead of time and that the city didn’t collaborate with federal immigration officials to conduct the operation.
