Charges have been brought against four boys aged 10-to-16 years old.
David Coxhead was riding his normal route home from the Illinois Institute of Technology Wednesday night when he was attacked.
Police said the boys hit the cyclist with a toy rifle and knocked him off his bike. Then they allegedly punched him in the head and demanded money.
Police say one youngster took the man's book bag and the group fled when they spotted a Chicago Police car nearby. Officers quickly caught up with them.
Coxhead suffered a mild concussion and received stitches above his eye.