Friends and family of Terrell Bosley unveiled a billboard Saturday advertising the reward.
The billboard sits at the corner of 117th and S. Halsted, not far from where Bosley was killed in April 2006.
A gunman shot him outside of a church as Bosley was getting his drums for choir rehearsal.
Chicago Police Superintendent Jody Weis and Father Michael Pfleger joined Bosley's family in urging anyone with information to come forward.
"The silence is killing the community, and when I just look at his face, it's almost like 'Dad, you're still out here fighting for me,'" said Tommie Bosley, Terrell's father. "That's what we're doing. I'm fighting for my son and all of the other parents who have lost their kids to gun violence."
Bosley's mother warned that the shooter probably thinks they got away with her son's murder, and that the shooter will likely strike again.
"Please turn in the person who murdered my son because if they did it to him, they would continue to it. They'd shoot another child because they got away with it," Pam Bosley said.
Pfleger said Saturday the key to ending the violence is the community deciding enough is enough.