"Getting all this stuff is really great, I'm glad they have events like this for kinds in the city like this," said Jashawn McClendon, college-bound student.
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McClendon, 18, graduated from a Catholic high school with honors, ready to start his college career studying pre-med and animal science at the University of Illinois Champaign-Urbana.
"I have a goal called 10-20-50 where, basically, I'm gonna start a global company that produces environmentally-friendly produce and meat products that are environmentally sustainable and friendly for mankind," he said.
McClendon is one of 175 college-bound students that took part in the 9th annual Take Flight College Send Off.
"If there's any obstacle or barrier, or anything that threatens a kid's persistence in school, we're there to help," said Kristen Hamer, Chicago Housing Authority director of external and corporate partnerships.
The giant trunk party is welcome help for the families who call the CHA home.
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"It was really difficult," said parent Khalid Muhammad. "We struggled and a lot of times we were homeless. A lot of times we didn't have a house to go to at all, slept out of my car for many months."
The students are attending around 50 schools across the country. And beyond the blanket sand linens and lamps and other supplies they're given, the students also get great advice.
"You gain relationship sand network," said Zendricka Thomas, student.
They also gain the confidence to succeed. Mikayal Ezell, 18, from Englewood will be attending Paul Quinn College in Dallas, Texas, to study psychology. She wants to become a mental health professional, giving back to her community.
"Right now, we're just worried about helping and giving back in that way so people can get help, you know. I want to be that change," she said.