Max Allender and his sister Coral were born three months premature back in the spring of 2012.
He spent more than a year at Lurie Children's Hospital.
On Friday, he got to go to the Bixler Playlot in the Hyde Park neighborhood with the whole family.
Max is dependent on a ventillator for breathing.
In May he moved to a transitional facility where his mom began training to care for him at home.
"I want him to know what normal things are like. We just signed him up for Sunday School and we're gonna go and have a good time and just be regular people," said Jessi Allender, mother.
Max now lives at home.
His family credits the waiver for medically-fragile children, which helps provide in-home nursing for helping Max enjoy a more normal life.