As Chicago, Illinois, slowly inches through late February—away from the frigid temperatures of winter—and toward the warmth of spring, many homelessness services outreach workers expect to find that their jobs get just a bit easier. This may be especially true for the network of outreach workers employed by the city, nonprofits, and faith institutions to connect unhoused community members with essential services by meeting them in a particular outdoor public space where they can frequently be found throughout the long winter: Chicago Transit Authority (CTA) trains and stations.
Every Wednesday night, outreach workers from a homelessness services nonprofit called The Night Ministry gather at the CTA Red Line’s terminal on Howard Street on the city’s North Side. On Thursday nights, they do the same at the Blue Line’s terminal stop in the west Chicago suburb Forest Park, Illinois, near where in 2024, a mass shooter killed four people reportedly experiencing homelessness who were sleeping while riding the train. They typically engage with roughly 200 people, according to David Wywialowski, the director of outreach and health, but the numbers fluctuate based on the weather.
“On the really, really cold nights . . . we were seeing 200 to 300 people,” Wywialowski tells The Progressive. During the summer months, he says, outreach workers typically see fewer unhoused riders, who instead find shelter in encampments or other local hotspots for the unhoused. But during the winter, those solutions become untenable. “They’re riding the trains for warmth, for safety,” he says.
A 2024 report by the Chicago Coalition to End Homelessness (CCH), using data from 2015 to 2022, estimates that roughly 76,000 Chicagoans experienced homelessness in 2022—a 30 percent increase from the year prior. More than 58,000 people were still unhoused through 2024—a decrease that CCH says may be attributed to the effectiveness of increased resources.
Though the CTA typically prohibits riders loitering on buses and trains, or remaining for more than two hours without exiting and paying an additional fare, it regularly works with local outreach groups to connect unhoused riders with support services and track their numbers. From January 2023 to September 2024, the CTA estimated that trained outreach teams from the Haymarket Center and Thresholds, both partially funded by a partnership with city offices, interacted with nearly 18,000 unhoused riders on Red and Blue Line trains, where trains operate a twenty-four-hour service and unhoused riders tend to be found most often. Following a pilot that began in early 2023, the CTA pledged up to $2 million annually in 2024 for a two-year program with the Chicago Department of Family and Support Services to expand outreach and support for unhoused riders.
With the city continuing to lag behind on providing new affordable housing amid a cost-of-living crisis including skyrocketing rents, a web of interrelated social failures has left more of the most vulnerable community members sheltering on the train. People who struggle with mental health challenges or substance use conditions find it particularly difficult to access safe and affordable housing. While some have found shelter and community in encampments in public areas, these have been targeted by city-led sweeps and closures, with local officials citing fire hazards and other safety concerns. Shelters are far from a catchall solution: They may not be accessible for many people experiencing homelessness based on their relationship or marital status, family makeup, or history with substance use, and issues with cleanliness, theft, and safety in common and sleep areas can also serve as deterrents.
Since 2013, the Illinois Bill of Rights for the Homeless Act has established that homeless individuals cannot be legally deprived of shelter or prohibited from sheltering in public spaces—including public sidewalks, public parks, public buildings, and public transportation—because they lack housing or employment. But despite the total number of crimes committed on public transit having fallen in the past few years, violent crimes like assault and battery committed on the CTA have spiked more than 33 percent since last year. The city has responded with a new “security surge plan” to increase the number of law enforcement officers patrolling CTA buses and trains, as well as banning unhoused individuals on the sex offender registry from sheltering on public buses and trains entirely.
“That’s why [outreach workers are] riding the CTA,” says Sam Guardino, area director of clinical operations at Thresholds, a nonprofit services provider. “Their job is to ride the trains or be around the trains and meet people on platforms, on trains, in areas right around the stations and try to build rapport. Part of building rapport is meeting basic needs—something to eat or something warm to wear, but also [trying] to engage people into services, which sometimes takes a long time.”
Thresholds, which is Illinois’s largest provider of supported housing programs for people with severe mental health challenges or substance use conditions, formed its first CTA outreach team in the late 1980s. For the past fifteen years, the organization has been providing outreach to unhoused people on Red and Blue Line trains. Thresholds launched a second outreach team nearly three years ago. The key to this type of outreach, Guardino says, is long-term consistency and persistence.
“We’ll keep showing up at a location for a person as long as it takes to engage them in services,” he says.
In Chicago, which has experienced devastating funding cuts for social services and mental health care for almost the past twenty years as a result of a long-standing state budgetary crisis, transit outreach is a collaborative effort. On Thursday nights, Night Ministry partners with groups like Loyola Street Medicine and a West Suburban Cook County organization called Housing Forward to form a one-stop hub at the Forest Park Blue Line terminal. At the hub, those experiencing homelessness can receive help accessing shelter or more long-term housing, as well as health care services, food, water, clothing, and other resources.
The outreach work “can be hectic,” says Romiesha Tucker, Housing Forward’s director of prevention, diversion, and street outreach, “but it’s also a smooth process, because of just how integrated [our] specific programs are.”
Many outreach workers say the effectiveness of their support is not just about the tangible assistance they offer, but also about their regular presence on public transit, allowing unhoused individuals to rely on them even if they’re not choosing to access housing services at this time.
“People are constantly moving, which makes sense,” says Jaclyn Story, a licensed clinical social worker and homeless outreach program director at Thresholds. “They have to for their own safety. If they’re experiencing homelessness, they could be a victim [of a crime] if they’re just in the same place all the time, right?” But, she says, “at the same time, it can then be hard to find some people sometimes . . . if they don’t have a phone, if it got stolen or it got broken.”
Outreach teams at Thresholds share a caseload of clients, and split their time between engaging with people they’ve built relationships with, and seeking out people they haven’t engaged with yet. While doing outreach, they wear highly visible, identifiable gear, and go from train car to train car or up and down CTA platforms looking for people who may be in need of help. They have food, water, and in the winter, hats, gloves, and hand warmers. And they tell people about the services they can access at Thresholds, which include case management, psychiatric care, and group and individual therapy.
“Some people may be more willing to engage with others,” Story says. “We are totally respectful of that, and we still are going to leave any supplies or snacks that they may need. Our items that we’re giving away are not conditional.”
Given the traumas that many unhoused individuals have endured, it is crucial that outreach workers present themselves as seeking to help in whatever way they can, without transaction or coercion.
“If you need [something], we’re going to give that to you, whether you want to talk to us or not,” Story says. “And sometimes they’ll recognize us, and they’ll be more willing to talk to us.”
As the need for these outreach programs grows, recent threats to federal funding have left transit outreach programs to face an uncertain future. In early January, following bipartisan backlash from states, provider programs, and advocacy groups, the federal government reversed its decision to cut $2 billion in funding for mental health and addiction grants less than twenty-four hours after announcing the cuts. Late last year, the Trump Administration announced policy changes for the Department of Housing and Urban Development (HUD) that would slash funding in half for its Continuum of Care program, which supports local organizations that provide housing and other resources to those experiencing homelessness. Funding cuts for the program would have also capped investments into permanent housing for the unhoused at 30 percent—a nearly 60 percent decrease that would put upward of 170,000 formerly unhoused people already receiving housing assistance at risk of returning to homelessness, as reported by Politico.
A federal judge halted HUD’s efforts at the end of December, citing conflict with a statutory deadline for the issuance of a notice of funding and requirements of the McKinney-Vento Homeless Assistance Act, which protects the rights of youth experiencing homelessness. Still, the recent attention from federal administrators has local outreach programs and organizations on edge, fearing that the Trump Administration will attempt to slash funding again.
Outreach workers say that the pervasive stigma against the unhoused can also have an adverse effect on their ability to build trust with potential clients. Tucker, who herself was previously unhoused, recalls an incident in which one of her clients was denied entry to a convenience store where she’d hoped to buy a bottle of water and use the restroom.
“This lady is very lucid,” Tucker explains, “and she is very much aware of her surroundings and the people that are in her space. She minds her business, and a lot of times, because people don’t like the ‘eyesore’ of an unhoused individual, they speak very negatively about her as if she is not there. So in turn, she responds to that negative feedback. When she responds to the negative feedback, and she gets loud, and maybe sometimes, she’ll say a cuss word, here or there—now, she’s a problem for the community. But the community started with her first.”
Guardino says he often sees a lack of appropriate services blamed for the precipitous rise in homelessness, but places the city’s lack of affordable housing at the center of the issue, noting that “the commodity-based real estate market in the city of Chicago and probably throughout the whole United States, is a train wreck.” He says he would like to see more funding for Housing First programs, which provide unhoused people with permanent housing regardless of employment status, substance use status, or treatment program participation.
“Housing First is an evidence-based practice that leads to people obtaining and maintaining permanent housing,” Guardino says. “Not everybody does it, but it is so much different than it used to be in terms of housing options and giving people a chance to be housed and maintain their housing.”
Wywialowski says that the public must take a step back and consider whether we are doing enough to care not just for ourselves, but for the “most vulnerable in our society.”
“I think it’s gonna take all of us working together, including individual citizens, to try to contribute in some way to help our fellow neighbors,” he says. “And I keep emphasizing that, because sometimes [you] see somebody who’s homeless, you walk right past them and ignore them, not thinking anything of them. But they are a member of our society, and a human being who’s living in our city.”