Faces of StreetWise: Get to Know Harry

If you’re downtown along the lakefront, you might run into Harry, one of our friendly StreetWise vendors. He got started with StreetWise thanks to his longtime friend and fellow vendor, Joe, and he’s been loving it ever since. For Harry, the best part of the job is meeting new people, hearing their stories, and gaining fresh perspectives.

He also loves the energy of Chicago—how easy it is to get around, how much is always happening, and how many people are out and about. When he’s not working, you’ll find him starting his day with Dennis the Menace and ending it with a good old-fashioned cowboy western.

Next time you see Harry, stop and say hi—he’s always up for a great conversation!

Faces of StreetWise: Meet Paula

Paula has been with StreetWise since 2020 and sells every Sunday at her favorite spot, St. Clements Church, in Lincoln Park, where she loves her customers. One of her best memories is working for the Census in 2020 while selling StreetWise, thanks to a job program connection. Another highlight was marrying fellow vendor Lee Holmes in 2022, with their wedding ceremony held at the StreetWise office.

For Paula, StreetWise is family, and she loves everyone there. A fun fact about her? She’s a big fan of purple and gold—and chili dogs (even though she’s not into regular hot dogs!).

PLEASE JOIN US

Don't miss our biggest event of the season! Join us for our annual spring fundraiser as we celebrate our mission in motion with an unforgettable evening of impact and inspiration.

This year, we're thrilled to honor our incredible friends at Giveashi*t for a decade-long partnership that has raised over $600,000 for StreetWise! 

📅 When: Thursday, May 1 

📍 Where: The Arbory, 2219 W. Grand Avenue, Chicago 

$100 Early Bird Tickets 

$150 Exclusive Tickets includes limited edition Giveashi*t t-shirt only available at the event

Be part of the celebration! Click here for tickets.

Click here to explore sponsorship opportunities and make a difference. 

Join these sponsors - The Kadens Family Foundation, Future Wanxiang Foundation, Inc., Marcel Digital, Cooper and Crane, CIBC, Revolution Brewing and Tito's Handmade Vodka - who are making a differenc!

StreetWise Takes Home Top Honors in Journalism Awards!

Congratulations are in order! StreetWise editor Suzanne Hanney, Creative Director Dave Hamilton, and journalist Sarah Luczko earned five first place honors in the 2025 Illinois Woman's Press Association (IWPA) contest! Additionally, we received four second place honors, two third place honors, and seven honorable mentions.

The first place winners were for:

Best Photographer-Writer "Facing Homelessness in Chicago's Harshest Elements";

Best Feature Story in a Magazine-style publication "Limited Run Play "Beyond the Door" Celebrates Hope and the Power to Change";

Podcast Where I Stay Season 2, Episode 4 "One Year Later";

Best Magazine-Style Writing and Design "Farmer's Markets 2024";

Best News Story in Print Publication "Facing Homelessness in Chicago: A Network of Support."

Next, these winners will go on to compete at the National Federation of Press Women (NFPW) 2025 contest!

Check out the 2025 collection here! Watch for our schedule of summer pop-up events starting in May. As always, 100% of the proceeds benefit StreetWise and StreetWise Vendors.

Friendly Reminder: Buy the Magazine,

Take the Magazine and Read the Magazine!