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The city of Chicago ignored concerns raised by an advocate about immigration raids at O’Hare’s rideshare parking lots for weeks before federal agents swept up more than 70 people there, emails obtained by the Tribune show.

An advocate for rideshare drivers first emailed the city on Sept. 19, saying she was concerned federal agents might target a parking lot near O’Hare International Airport where rideshare drivers wait for ride assignments. But the city did not appear to take any action in response to her warning until U.S. Border Patrol agents first conducted a raid at the parking lot three weeks later, on Oct. 10. 

Lori Simmons, lead organizer for the Chicago Gig Alliance, wrote an email outlining her concerns to Tom Stastny, general manager of landside airport operations for the Chicago Department of Aviation.

“I hope this email finds you well. I am reaching out about the (Transportation Network Provider) lot- specifically our organization is concerned that the lot may become a target for ICE raids,” Simmons wrote. “We are curious what airport policy is around this and if it might be possible to be notified of ICE activity so we can reach out to advocates to respond on behalf of the workers.” 

On Oct. 9 — the day before federal agents first raided the lot — Simmons followed up. 

“I am writing to bump this question,” she wrote. “What is airport policy around ICE raids, and is it possible to be notified of ICE activity so we can reach out to advocates to respond on behalf of the workers?”

The next day, federal agents descended on one of the rideshare lots for the first time, arresting 18 people in two separate raids. 

“Good afternoon,” Simmons wrote to Stastny. “We are getting reports that there is an ICE raid currently happening at the TNP lot. Are you aware of this?”

Stastny replied about 25 minutes later: “Thank you for the information.” Email records, which the Tribune obtained via a Freedom of Information Act request, show he then passed Simmons’ message along to other Aviation Department staffers. 

“You are welcome, but we really would like to know what airport policy is around ICE Raids,” Simmons wrote back after the weekend. “Could you share that information?”

Over the following weeks, federal immigration agents arrested dozens more people in raids near O’Hare. 

Border Patrol agents repeatedly targeted Uber and Lyft drivers while they waited for ride assignments in the designated parking lots. A witness to one of the first raids told the Tribune she saw agents “ripping” drivers from their cars; on another day, agents tased a man whom they accused of ramming their vehicle while he tried to flee. All in all, federal agents arrested at least 76 people during the O’Hare raids, according to the Department of Homeland Security. 

In an interview, Simmons said she had not received any communications from Stastny or other Aviation Department officials between the time of her first email and the day of the first raid on Oct. 10. 

Simmons said she had been worried the feds would target rideshare drivers because she knew many of them were immigrants.  “And sure enough they did,” she said. 

The city, Simmons said, “did nothing” with her warning, “and then acted surprised when it happened.” 

The Tribune asked the Department of Aviation whether it had taken any concrete steps to prepare for possible immigration raids at the rideshare lot following Simmons’ warning, as well as whether Stastny had elevated Simmons’ email to other relevant officials. 

The department declined to answer those questions. 

“Throughout the period of federal immigration enforcement at Chicago’s airports, the CDA closely monitored activity in the TNP lots as part of its regular patrols, with security and operations staff providing ongoing updates to senior officials,” a statement provided by the department said. 

The Tribune also reached out directly to Stastny, who did not respond. 

Rideshare drivers stand amid half a dozen or so abandoned vehicles whose drivers were detained by federal agents in the Alpha Lot just outside Chicago O'Hare International Airport on Oct. 25, 2025. (Stacey Wescott/baiduhai)
Rideshare drivers stand amid half a dozen or so abandoned vehicles whose drivers were detained by federal agents in the TNP Alpha Lot just outside Chicago O'Hare International Airport on Oct. 25, 2025. (Stacey Wescott/baiduhai)

Ultimately, the city — in conjunction with the Illinois Drivers Alliance – took several steps to attempt to prevent further raids at the airport. Those efforts proved to be more or less futile as federal agents repeatedly descended on the lots to arrest people throughout October. 

Days before the O’Hare raids began, Chicago Mayor Brandon Johnson signed an executive order barring federal agents from conducting immigration enforcement actions on city-owned land. 

The Friday of the first O’Hare raid, Aviation Department staffers appeared to be working to confirm that the parking lot was owned by the city, emails show. 

“In case it’s helpful, I’m attaching a map depicting the Alpha TNP Lot and the location of the City boundaries,” Chief Commercial Officer Amber Ritter wrote in an email to department staff. “The lot is circled in red. The orange boundary represents the boundaries of the City — the lot is within Chicago, not Rosemont.”

But the mayor’s executive order proved impossible for city officials to enforce at O’Hare.

“While CDA security personnel and signage were present in the lots, federal immigration agents chose to disregard CDA’s anti-trespassing efforts,” the Aviation Department said. 

Shortly after the first set of rideshare lot raids, Cassio Mendoza, a spokesperson for the mayor, said the city planned to post signs at the lots that said they were city-owned property and that immigration enforcement activities were prohibited there. The city also ended up posting security personnel in the rideshare parking lots.  

Mendoza said the city believed that once the signs were posted, it would have standing to take legal action against the feds if they violated them. 

But in the days between when the signage plan was announced and when they appeared to have actually been installed, the feds once again descended at the rideshare parking lot, arresting close to a dozen people. 

“It takes time to manufacture and install the signage,” Mendoza said. 

Then, once the signs were posted, Border Patrol agents repeatedly bulldozed through them, arresting dozens more people.

“The signs and security put the federal government on notice and created some potential options for legal enforcement,” Mendoza said. 

When asked if the city was considering taking legal action against the feds for ignoring the signs, Mendoza said the city did not discuss potential or pending legal actions. 

“Unfortunately, federal immigration agents decided to disregard the law and refused to comply. As we prepare for future rounds of militarized immigration enforcement in Chicago, the City is considering what further legal and operational strategies we can deploy to respond to federal use of City property for civil immigration enforcement,” he said. 

Mendoza also said the mayor’s office had not been notified of Simmons’ initial September warning. 

The Illinois Drivers Alliance — which is made up of the Gig Alliance along with locals of the Service Employees International Union and the International Association of Machinists — also said in a statement that the feds “were not abiding by the law or rules put in place.”

The Drivers Alliance, which is working to unionize gig drivers statewide, “worked closely” with the city to post signage and security in the lots and to deploy rapid response teams during raids, spokesperson Bailey Koch said. 

The Department of Homeland Security and U.S. Customs and Border Protection did not respond to a request for comment. In October, DHS sometimes alleged the people arrested in the O’Hare raids were guilty of various crimes but typically did not provide the names of those arrested when asked, making it impossible to verify whether or not detainees had criminal records. 

Throughout the saga, neither Uber nor Lyft provided comment to the Tribune on the raids.

But emails obtained by the Tribune appear to indicate the rideshare companies were in touch with the city about the raids.  

In late October, Simmons wrote to Stastny about the process of getting security posted in the lot. He appeared to forward her request onward, saying the department “had the same question from Uber and Lyft.” 

Uber declined to comment, and Lyft did not respond to a request for comment.