StreetWise commemorated the day with a party at their headquarters in the South Loop.
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The magazine started as an alternative to panhandling and is the nation's longest-running street publication.
StreetWise is a social enterprise with the mission of helping the city's homeless and at-risk community reach financial stability by selling the magazine, the publication said. They also provide daily meals, hygiene and medical supplies, access to government benefits, and even a stable address to get mail.
"It's a job. It wasn't a hand out, it was a hand up and although I'm thrilled it's still going. I kind of wish we were out of business because that mean we've settled homelessness," said Judd Lofchie, founder of StreetWise. "40% of our vendors get a job or a place to stay. It's been a great run."
The magazine is sold on the streets of Chicago by low-income or homeless vendors, who are considered micro-entrepreneurs. They purchase issues of the magazine for $1.15 each and sell them for $3.00, plus tips, according to the company.
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They use the proceeds to meet their basic needs and begin on a path toward economic mobility, StreetWise said.
The magazine first hit Chicago streets on August 24, 1992.
For more information on how you can support StreetWise, visit the YWCA Metropolitan Chicago website.