Video captured the scene earlier on Saturday morning at Caldwell and Devon in the Norwood Park East neighborhood.
ABC7 was told that no students were on the bus at the time.
The man had to be extricated from his vehicle, and no one else was hurt.
Authorities did not immediately provide further information about the crash.
SEE ALSO | Chicago couple killed in 21-car Florida crash while celebrating years-delayed honeymoon, family says