Masked ICE and Department of Homeland Security agents were seen in the area of Grace Street and Olcott Avenue in the Dunning neighborhood. It's a quiet residential area.
A witness said he saw unmarked cars chasing a red car before the car crashed into a tree.
"I saw them coming down Grace. I saw them chasing a red car that looked like it already had damage to the bumper, and then one of the black Ford Explorer unmarked cars hit the back of that red car," Edward said.
Neighbors said they heard the loud crash before a brief foot chase.
The witness said he saw an older man being detained.
"It looked like they had taken someone. I couldn't tell if they were from that car, but I assume. It looked like an older gentleman, darker complexion, shorter cut, gray hair. They had him in handcuffs. He didn't seem to be aggressive or resisting or anything like that," Edward said.
Another neighbor said he saw half a dozen unmarked cars.
"I'm seeing from the back of some of their plate carriers that say Customs Enforcement on it; so it's definitely ICE," Edward said.
The car involved was later towed.
Neighbors say some federal agents stayed on the scene for a short time, while others drove off.
Chicago police were also seen in the area after the crash.
Neither DHS nor ICE immediately responded to requests for more information on the incident.
Last week, a man was seen being detained on the Northwest Side, as well.