On a cold and blustery Sunday morning, hundreds of Chicagoans gathered in Humboldt Park on Feb. 9 for the inaugural Winter Walk, a powerful event dedicated to raising awareness and support for people experiencing homelessness.
Inspired by similar walks in Boston and New York, the heart of the Winter Walk was a two-mile walk through Humboldt Park, symbolizing the collective journey toward resources and solutions to homelessness. Chief Homelessness Officer of Chicago Sendy Sota and Chief Homelessness Officer of the State of Illinois Christine Haley joined walkers from around the city, including 26th Ward Alderperson Jessie Fuentes and student groups from Loyola University Chicago, Christ the King, St. Ignatius College Prep, and Chicago Jesuit Academy to brave the winter chill and stand in solidarity with neighbors in need.
The Growing Impact of Homelessness in Chicago
The United States saw an 18% increase in homelessness last year. According to the Chicago Coalition for the Homeless, more than 75,000 Chicagoans experience homelessness annually. Beyond the immediate need for shelter, individuals facing homelessness often experience social isolation, a lack of safety, and barriers to regaining stability.
Because of the prevalence of homelessness in Chicago, the Winter Walk was more than just a fundraiser—it sparked meaningful conversations about homelessness and strengthened community solidarity. Chicago’s Chief Homelessness Officer spoke about the growing need for resources in the city and how her team is working to meet those challenges. Then, the leaders from each co-organizing agency shared insight about the work they’re doing to fight homelessness and isolation. Participants, led by motivating tunes from the Humboldt Park Orchestra, then took off on their walk through the Park.
The event was made possible by collaboration between Winter Walk and local co-organizing agencies, including the Chicago Help Initiative, Franciscan Outreach, The Boulevard, and the Ignatian Spirituality Project. These agencies work toward the shared mission of supporting Chicago’s homeless population. By walking together, participants sent a powerful message: no one should face homelessness alone.
Thanks to the generosity of donors and participants, the initiative successfully raised nearly $40,000. This money will directly support these organizations and their programs, which aim to provide shelter, recovery support, and pathways to stability to local individuals and families in need.
How to Help
Want to make a difference? You can help fight homelessness by making a financial contribution to Winter Walk. You can also volunteer with partner organizations such as the Chicago Help Initiative, Franciscan Outreach, The Boulevard, and the Ignatian Spirituality Project.
Follow the Winter Walk on social media to get updates and save the date for the 2026 Walk.
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