It happened on Saturday as officers were taking him to the Lake County, Illinois jail.
The man managed to get away, and went on to carjack two different drivers. He physically forced one victim out of their van on I-294, and did the same to a second victim in Northbrook.
The prisoner drove the stolen Camaro into Kenosha County, Wisconsin, where video shows police starting to chase him.
They used the OnStar security service to actually shut down the vehicle before he got any further.
"Hands up! Hands up! He's got handcuffs on!" One officer could be heard saying.
The escapee, who was initially wanted on a warrant, is now back in custody. There's no word yet on additional charges.