William Velez, a sophomore, will start the semester in progress at Aspira Business and Finance High School in Chicago's Avondale on Tuesday. Velez and his mother are staying with relatives in the city while his father, older sister and other relatives remain on the island.
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"It was hard to leave my dad and family I really love," said Velez.
"Nobody wants to leave her husband but this Maria came and she divided us," said Mayra Casiano, Velez's mother.
The Puerto Rican Agenda is preparing for thousands of people to resettle in Chicago and preparing to help children continue their education.
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Fernando Grillo, head of the Puerto Rican Agenda's Education Committee, said the committee is ready to help those in need.
"We are ready, willing and able," he said.
At least four more students will enroll at Aspira later this month.