Wood, along with volunteers for his Wood Family Foundation handed out school supply kits to thousands of youngsters at Humboldt Park's Hopefest.
There were games, including the always popular dunk tank, and kids got free haircuts along with dental and eye exams.
And a celebration on the South Side gave families a chance to get ready for school as well.
The Summer of Abundance and Hope community health fair offered free health screenings and school backpacks.
The gospel-themed celebration took place at the Salvation Army's Kroc Community Center and included pony rides, and games for kids and adults alike.