‘They are people. Chicago forgot.’

How urban life taught Chicagoans not to see its own—and how one homeless outreach group fights to make the invisible visible.

BY BELLA VRY
November 10, 2025 

Angel doesn’t own a closet, but she talks about clothes like old friends. On a mild Saturday in the Fulton River District, as volunteers haul bags of shoes and sweaters from SUVs, she requests women’s size eight shoes—“maybe heels, if you’ve got them,” she mumbles, as if she knows how rare that request is in a donation drive. When they hand her a pair of red velvet pumps, she clasps them to her chest and laughs with her eyes bright. Around her, the city hums indifferently. Cars pass. People pass. But Angel, for a moment, feels seen.

In a city where it’s become routine to step over sleeping bags on sidewalks, volunteers like real estate advisor Leticia Andrade are working to challenge that reflex. Her group, Chicago Homeless Outreach, gathers each month to bring clothing, food, and conversation to unhoused residents—our ”friends on the street” as Andrade addresses them. Many of these friends are facing the twin pressures of poverty and immigration enforcement.

As U.S. Immigration and Customs Enforcement (ICE) intensifies detentions across the city, the Chicago Coalition to End Homelessness (CCH) warns that some of Chicago’s most vulnerable—including asylum seekers and longtime unhoused residents—are at risk. Since September, the homeless once visible along the Northern Chicago River or under the viaducts of Logan Square were cleared without warning by ICE. Homeless shelters, schools, churches, and hospitals, once considered protected locations from ICE, are no longer protected under the new federal administration.

Ten years ago, CCH released its first annual estimate of Chicago’s homeless population using census data. In 2015, 14,639 people experienced street or shelter homelessness. Seven years later, it doubled to 31,333. Since then, the City of Chicago has welcomed over 51,000 new arrivals from the southern border, whose housing data is not represented in the estimates.

Andrade maintains that homeownership among migrant families works to “change family legacy so that each generation to come is better than the last.” “Whatever it is,” Andrade insists, “there is no reason why we should have a growing number of tent cities.” Even so, for every one person reported as homeless, ten more people access city homeless services. So, Andrade approaches her real estate work as selfless, unlearning the ways the city has taught residents not to see its own.

One student who commutes past homeless encampments daily, Kyla, 19, praises the efforts of Chicago Homeless Outreach. “Otherwise, you keep your eyes up and pay no mind,” she comments. Kyla, who moved to Chicago from the sleepy coasts of Australia in 2021, was horrified by the “dehumanizing solution” practiced in the city. “At home, you’d stop. You’d at least say hello.” “Here, it’s like everyone’s learned to pretend. I started pretending too.” For her local community, Kyla hopes that the outreach can better replicate Australia’s safety nets.

Mary, 80, window shopping the day of October’s Chicago Homeless Outreach, perched around the gathering volunteers in curiosity. Squinting at their matching merch, she nodded. “This volunteer work should be a given,” she said. For her, she still rolls down her car window to pass a few bills to the friends on the street. “How can you not?” she asked. Mary, who immigrated from Belgium after World War II and once faced homelessness herself, condemns Chicagoans’ “unthinkable habits” toward the homeless. “They are people. Chicago forgot.” She nudges one volunteer on the shoulder to push on, clicks her tongue, and shuffles into her KIA en route to the suburbs.

In 2013, Illinois passed one of the strongest laws in the country when it comes to protecting the rights of homeless people, the Illinois Bill of Rights for the Homeless Act. “It affirms that Illinois residents may not be treated any differently simply because they don’t have a home,” CCH says.

However, the 2024 U.S. Supreme Court Grants Pass v. Johnson decision now allows municipalities to criminalize camping on public grounds. Illinois ranks second in the nation after California in the number of municipalities adopting these ordinances, in some cases “before homelessness has even become an issue in their community,” CCH explains in their 2025 agenda.

In the new year, the shelter beds capacity was reduced from 18,000 to 6,800.

Through years of volunteering, Andrade’s husband, Javier, realized the humanity omitted from the journeys of the friends on the street. “We’re not trying to support them living on the street,” he clarified. “We have testimonies of people who are no longer homeless.” 

During the October 2025 outreach day, Steven, a long-term volunteer, emphasized the grace volunteers must give each friend on the street, regardless of circumstances: “We have no idea what these people have been doing or going through. Somebody could be left with no possessions, no hope, no home. They fall into depression. Bam, here comes a dose of life.”

John, another long-term volunteer, shared his motivations during the meeting: “I do it because it keeps you grounded about what you have.” Yet, when volunteers arrived at Fulton River District, a homeless man took just a single can of Pringles at the offer of dinner—an entire crate for protein and carb-rich snacks, yet he insisted the can was enough. Somehow, whether it be gratitude or shame, the man’s dignity guided his restraint.

Andrade sees five to even twenty volunteers participate in her outreach month after month. She plans to formalize her project as a nonprofit, turning volunteer momentum and support from onlookers into infrastructure.

Mary can roll up her window and head toward the quiet of Cook County’s southwest suburbs. Kyla can board the Blue Line back to a rented apartment where the heat always works. Their departures mark the divide between the housed and unhoused. For the unhoused, their exile happens in place, beneath the same skyline. Some get to go home; others keep dreaming for one.

Angel slips on her new heels and stands a little taller. Around her, the city keeps moving—a rhythm of trains, tires, and indifference. But for one heartbeat, on a cracked stretch of pavement in Fulton River District, dignity has form: velvet red, size eight and a half.