Chicago-area companies that earned lucrative contracts supporting President Donald Trump’s deportation push also benefited from deals with the city, the Sun-Times found.
A web of agreements shows Trump’s regime and the administration of Mayor Brandon Johnson have overlapping needs — even as they spar publicly and agree on next to nothing.
Ald. Rossana Rodriguez (33rd) is calling for a city review to determine whether Chicago taxpayer dollars should be going to firms working with the Department of Homeland Security and its on-the-ground agencies, Immigration and Customs Enforcement and Customs and Border Protection.
“We do have to take this seriously and make sure that we are not collaborating by hiring or benefiting companies that are acting against us,” says Rodriguez, who was born in Puerto Rico and represents one of the city’s most diverse wards.
The deals are among millions of dollars in contracts granted to Illinois firms supporting federal immigration enforcement agencies, including relocation services for agents and the sale of pepper balls that agents routinely use to fire on protesters.
The Chicago Sun-Times examined public procurement databases for city and federal contracts to find overlapping vendors who’ve served City Hall and the federal government.
The review found West Loop-based Motorola Solutions scored a $267,300 contract in late September to provide a radio network for Homeland Security Investigations agents stationed in Chicago — among $138 million in federal contracts the company has been awarded since 2007.
The company also has at least two ongoing contracts with Chicago for technology, including the city’s camera infrastructure and 911 call systems. Those deals are valued at nearly $87.9 million.
SP Plus, a Loop-based firm previously known as Standard Parking, has had a host of contracts with the city, including ongoing deals worth nearly $206 million to manage parking facilities and ground transportation at O’Hare and Midway airports. It has another contract to lease parking spots for ICE in Long Beach, California, for up to $895,000.
Also, Invisio Communications, a Danish company with Loop offices, got a $33,770 contract in June to supply communication equipment to HSI officials, part of the $4.3 million the company has been awarded by federal agencies since 2017. The company, which specializes in tactical headsets, got $31,000 from the city months earlier, but it’s unclear what the money was for.
The analysis of federal and city records shows at least four other companies that held contracts with immigration agencies are doing work for the city, including Vernon Hills-based CDW Government, which got a pair of contracts with ICE for forensic computers and software licenses. The contracts ended in 2023 and were valued at more than $45,000.
The company has had millions of dollars in similar contracts with the city for computers and technology, including a $10.5 million contract set to expire at the end of the year.
Brandon Lee of the Illinois Coalition for Immigrant and Refugee Rights says, “I do think that all levels of government, including the city, should take a look at who’s doing business with ICE and CBP and DHS at this moment.”
“I think we’re at a particular time where there are government agencies that are engaging in explicit harm and committing violence on our communities here in Chicago and here in Illinois, and in other cities across the country,” Lee says.
Motorola Solutions, SP Plus, Invisio Communications and CDW Government didn’t respond to questions. Neither did the mayor’s office.
Air launchers, pepper balls and bullets
The recent Trump-endorsed “Big Beautiful” spending bill is creating a windfall for companies profiting from his nationwide deportation blitz. The measure provides $170 billion more for border security and immigration enforcement. The funding began flowing July 4 when Trump signed the legislation.
Since he returned to the White House in January, his administration has reported that contracts worth at least $10.7 million were awarded to Illinois firms aiding ICE and Customs and Border Protection, including for weaponry.
United Tactical Systems, a Lake Forest-based company commonly known as Pepperball Solutions, was paid $47,500 in June to provide ICE with “non-lethal” weapons for crowd control during demonstrations at the ICE training center at Fort Benning, Georgia.
Customs and Border Protection has also entered into three contracts with the same company, worth $1.1 million since April 2025, for pepper balls used in the El Centro Sector, where Border Patrol Chief Gregory Bovino came from. The contracts also provided the agency with a “pressurized air launcher” sent to Tucson, Arizona. The Chicago Reader first reported on payments to the company.
Such weapons have increasingly been used by federal agents in the Chicago area, particularly at the Broadview ICE temporary detention center.
A spokesperson for PepperBall said the irritant-filled projectiles “can help reduce the risk of lethal force and deescalate situations” with “proper use and training.”
Under President Joe Biden, the Department of Homeland Security entered similar contracts with United Tactical Systems.
“For more than 20 years, PepperBall has been a committed member of the Chicagoland community — investing in the people and place we proudly call home,” the spokesperson says. “Our mission is to help law enforcement deescalate dangerous situations through non-lethal tools. With training and proper use, PepperBall is an effective way to reduce conflict and protect life.”
Winchester Ammunition, an offshoot of the company that developed a rifle used by actor John Wayne in dozens of Westerns, got five contracts valued at $180,739 to provide training ammo to ICE and Customs and Border Protection under Trump. Winchester, described in procurement records as Olin Winchester, has collected $10.5 million from federal agencies since 2019.
Winchester is headquartered in East Alton, about 20 miles north of St. Louis, and is a subsidiary of the Olin Corporation, a publicly traded firm based in Clayton, Missouri, that also makes industrial chemicals and has a history of environmental violations.
In 1978, the company was indicted for falsifying documents to send thousands of guns and millions of rounds of ammunition to South Africa, but the case ended with a settlement of $45,000. The company didn’t respond to inquiries.
Millions for moving
Trump’s immigration enforcement agenda hinges on a vast expansion of the number of federal immigration agents. His administration plans to hire 10,000 new ICE agents and 3,000 more Border Patrol agents, and is making costly buys for flashy recruitment commercials.
Loop-based Reliance Relocation Services, also known as RELO Direct, has been awarded nearly $7.8 million over five contracts between July 2024 and this past December, most of which were granted to relocate ICE employees.
Four of the contracts expired the same week the Trump administration began targeting Chicago in an aggressive immigration enforcement campaign in September. Block Club Chicago first reported on those contracts.
Among other things, Reliance Relocation Services assists with home sales and manages expenses and properties, says spokeswoman Caroline Underwood Burman. She wouldn’t answer most questions about the company’s contracts.
Noem ‘doing the job’
Democrats have slammed the Trump administration’s contracting and spending on immigration enforcement.
They seized on Homeland Security Secretary Kristi Noem’s purchase of two Gulfstream jets costing $172 million and the allegation that border czar Tom Homan was caught accepting $50,000 in cash from undercover FBI agents posing as business executives seeking government contracts.
During a congressional hearing in May, Noem pushed back on an assertion she had been spending “wastefully without authorization.”
“I’m doing the job that the secretary of homeland security is supposed to be doing, the one that the last secretary refused to do, that endangered the future of our country,” she said.
