Chipper's reason for deciding to immigrate was the unfortunate death of both of his parents. Unfortunately, his father passed away in the early 1970s and his mother died suddenly from cancer around 1980. A year later, Chipper decided to not let the grief make him forget his dreams and go to America like his parents would've wanted. He also wanted to see what life was like outside of the small village of Cave in the County of Galway. 

Chipper emigrated from Ireland when he was about 21 years old. This was the summer of 1981. He was quite young and scared of what would happen. However, the excitement of all the new possibilities outweighed that fear.

Chipper went alone when he left and he wrote letters to his siblings (who were around the same age) and his brother, John, came and joined him.