Some of Chicago’s newest residents apply entrepreneurial skills to survive in a new country.
By Abena Bediako
Daniel, a barber; David, who sells tizana; and Samuel, a tattoo artist, have used their skills to make a living. All recent migrants from Venezuela, the men are hoping to get work permits. (Gaby FeBland/City Bureau)
Standing outside a Pilsen shelter on a spring day, Samuel, 27, observes the other residents as they transform the sidewalk along South Halsted Street into something akin to a Venezuelan street market. Parents keep their children close by as they peruse various gas station snacks, drinks and traditional foods such as arepas for purchase.
Samuel, who asked to use a pseudonym out of fear he could be targeted by law enforcement, is reflecting on his journey as an immigrant entrepreneur.
He started tattooing at age 19 in the city of Cali, Colombia, where his family opened a barber shop and tattoo parlor after fleeing Venezuela’s economic crisis in 2017. But financial troubles found them again, and Samuel said he and his family had no choice but to leave Colombia and embark on a dangerous journey to the United States.
“You see dead people, people who were raped, poisonous animals that got into your tent, and you can get killed,” he said of the trip.
As Venezuela faces economic collapse and skyrocketing poverty, millions like Samuel have fled the country and have sought refuge in places such as Colombia or made the sometimes months- or year-long journey to the United States.
Samuel crossed the southern U.S. border and became one of the more than 50,000 migrants who have arrived in Chicago since August 2022, when Texas Gov. Greg Abbott began a campaign to bus migrants to Democrat-led sanctuary cities as part of a protest against federal immigration policies.
Limited avenues to work legally in the United States, low wages and hiring discrimination have made starting a new life in Chicago challenging for many Central and South American migrants.
Samuel has turned to tattooing, a trade he learned in Colombia. Without meeting city and state licensing requirements, he could face daily fines that could quickly total thousands of dollars. But with few options for legal work and the need to support his growing family, the risk is necessary, he said.
Like other immigrants before them, recent arrivals are turning to entrepreneurship — often in street vending or trades like barbering — to provide food for their families, save for future housing and start a new life in the city. But the work is far from stable. Frequently, it’s an act of survival.
City Bureau interviewed more than 20 recently arrived migrants living in city-run shelters who have struggled to find legal pathways to work in Chicago. Here are three of their stories.
Samuel learned tattooing in Colombia. After his wife met a local organizer, he secured a tattoo gun and some regular clients to start earning money. (Gaby FeBland/City Bureau)
A Rising Tattoo artist
Samuel uses his body to advertise his love for his art form. His creativity jumps off his skin — a beautifully detailed owl spans his neck, and his left arm is completely covered in designs forming intricate patterns, to the point where the eye can’t tell where one tattoo ends and another begins.
The promising tattoo artist came to Chicago in October 2023 with his pregnant wife and 6-year-old son, he said. His perilous journey to the United States included several other relatives, some with children as young as 15 days old.
The group attempted to cross the Rio Grande to make it to the United States, but they found that the current was too powerful, Samuel said. They got stuck in the water and pleaded with Mexican police officers or immigration officials passing by on boats to assist them until a U.S. official patrolling the other side of the border took mercy on the group and called for help, he said.
“I think we touched their hearts,” Samuel said in Spanish. “They helped us and let us get into the country.” The group was detained but later released and flown to Chicago, Samuel said.
His tattoo equipment was lost on the journey. When he landed in Chicago, he attempted to find day labor at one of the many Home Depot parking lots across the city. But having to fight for each job often left him feeling defeated, he said.
Samuel’s wife met Chicago activist Luciana Diaz of the organization Panas en Chicago, who frequents shelters around the city, checking in on recent arrivals to see how they are settling in. Diaz arrived in Chicago from Venezuela in 2015.
“My wife [told her], ‘My husband is a tattoo artist, and he needs a tattoo machine to work, because we need money,’” Samuel said.
Within two weeks, he had received a new tattoo gun and a string of clients.
“She helped me to promote my work,” he said. “I got most of my clients thanks to her.”
His work comes with risks; in Illinois, tattoo artists are supposed to work from licensed shops and be trained on bloodborne pathogens, infectious disease control and skin diseases and disorders. Fines can be up to $1,000 per day, according to state law. Without the cover of a legally operating shop and a city business license, Samuel could face a similar fate as other migrants who have been arrested for working illegally.
At least for now, he’s willing to take the risk for the few hundred he can make here and there, thanks to some regular clients, he said. It’s also worth it for the independence, and it means he does not have to rely on day labor, he said.
Samuel relied on public transportation to get to his clients when he and his family were living in a shelter, he said.
“Transportation is the most challenging for me right now. I waste a lot of time going somewhere,” he said. “I calculate my time, but I cannot control the public transportation, and sometimes I’m late to my appointments. With a car, it would be easier.”
Samuel hopes to get an apartment, but eventually, he plans to return to Venezuela or travel to another country, he said.
“We don’t want to stay here [in Chicago] for a long time,” he said. “We just got here, and you do not know how your mentality changes. But time will tell.”
David works as a street vendor, selling his grandmother’s prized recipe for tizana, a sparkling Venezuelan punch. (Gaby FeBland/City Bureau)
A salesman on the move
Chicago has long had a reputation as the city that works. This Midwestern work ethic is something many Venezuelan migrants can relate to.
David* (City Bureau is using a pseudonym for him), 29, has worked to provide for himself since he arrived in Chicago in May 2023. While he quickly found work as a roofer and a butcher — getting paid under the table — neither of those roles spoke to his passions or his desire to work for himself, he said.
Sitting in a cozy restaurant at 63rd Street and Woodlawn Avenue on a gray, rainy day in March, David described in Spanish how he worked to earn money on his own terms.
His grandmother’s prized recipe for tizana brought him a sense of security in a new country, he said. David makes the sparkling Venezuelan punch with fresh-cut chunks of melon, grapes, strawberries, banana and watermelon, served with a drizzle of sweetened condensed milk. Vendors make the staple with the remnants of fruits leftover from street stands throughout Venezuela, David said.
David credits the drink with “saving his life” on his journey to Chicago. For 2½ years, he worked construction, fished and sold tizana in Lima, Peru to make made enough money to make his way north, he said.
The journey was dangerous, David said. He was kidnapped by a cartel in Colombia but later released. He also witnessed kidnappings and sexual assaults, saying some of the women taken were not released, eh said.
"If it was a pretty woman, then they made her stay with them,” he said. “I saw a lot of ugly things.
“After this experience, you see things differently. I felt very small.”
Last fall, David was selling tizana Downtown when five lawyers approached him for a drink. He immediately saw an opportunity to ask them for advice.
“I told them I needed a concrete answer because I wanted to work,” he said. The lawyers told him his best shot at obtaining Temporary Protected Status and work authorization would be to apply while staying at a shelter, he said.
He followed their advice, moving into a shelter in November 2023. Four months later, he received his work permit, which allows foreign nationals from certain countries to live and work legally in the United States.
While he has found customers throughout the city, David has had the most success in Little Village, the predominately Mexican neighborhood known for its storefront businesses and street vendors.
Despite being a newcomer, David immediately recognized the opportunities in the neighborhood and gained a consistent flow of clients.
His success there makes sense to Nilda Esparza, who worked at the Little Village Chamber of Commerce before joining the Logan Square Chamber of Commerce as executive producer.
Little Village is a neighborhood where immigrants and their descendants can come to “find those things that bring them closer to home, that bring that familiarity and that uniqueness that you can't find anywhere else,” Esparza said.
Organizations such as the Foundation of Little Village work with local leaders and community members to provide bilingual resources and education that help emerging entrepreneurs overcome the barriers they face, according to the group’s website.
“They can't move around the workforce very easily, either because of childcare, because they're living in multi-generational homes, or lack education,” said Kim Close, the foundation’s executive director. “I'm not just talking about higher education. They might also have come from a farm in Mexico and only have an eighth grade education. That's why they're pursuing entrepreneurism — to overcome all of these unique challenges that they face.”
“We understand their needs,” Close said, “but I do think our job is to inspire them to think bigger.”
Street vending and small-scale entrepreneurship have long been economic entry points for immigrants and others shut out of the formal economy — a significant chapter in Chicago’s history that has shaped the city into what it is today, said Beth Kregor, director of the Institute for Justice Clinic on Entrepreneurship at the University of Chicago Law School. The clinic provides free legal assistance, support and advocacy for low-income entrepreneurs in Chicago, who often struggle to obtain proper licenses.
“For hundreds of years, [immigration has been] part of what makes our neighborhoods have different character and different flavor, literally and figuratively,” Kregor said.
David’s time selling tizana in Little Village has inspired him to seek out a street food vending license.
“My dream is to have a cart, like other Mexican street vendors,” he said.
Daniel learned to cut hair in Venezuela. After making his way to Chicago, he struggled to find consistent work and had to look for day laborer jobs. (Gaby FeBland/City Bureau)
A barber in the making
Daniel, 22, learned to cut hair after his mother gave him a set of clippers as a birthday present in Venezuela. He asked to use a pseudonym out of fear he could be targeted by law enforcement.
“I started out practicing on my cousins’ and friends’ heads, and I was very bad,” he said in Spanish through a translator. “But as I did it more often, I got better. Eventually, I realized I was pretty good.”
Daniel charged $1 per cut in Venezuela. By age 20, he’d used his clippers so frequently they fell apart. But ultimately, there wasn’t enough work to make ends meet, he said.
“I would wake up in the morning, and sometimes there was food, but sometimes my mom didn’t have any food to give me,” he said. “I would sit some days and say, ‘I want to help my mom, and I want to achieve things, but I can’t do it here.’”
In 2023, he traveled to Cúcuta, a small Colombian city on the Venezuelan border. From there, he and his friends made their way to Ecuador by hitching a ride on the backs of trucks, because they’d heard it was easier to find work there, he said. The journey was difficult — the friends slept on the streets and arrived in Quito dirty and sunburned.
“But I had a purpose,” Daniel said. “I started asking around for a barber job.”
When he finally met with a salon owner, she eyed his dirty T-shirt and sneakers skeptically before asking him to prove his skills by shaving the head of a walk-in client, he said. Daniel’s talent landed him a job, but it wasn't sustainable. He owed the salon half of what he made every day— typically around $4 per cut — to use its supplies and space, he said.
He then decided to go to the United States, hoping to make enough money to buy a home for his mom in Venezuela, he said. He arrived in Chicago in September 2023, but he quickly realized there were different challenges to finding consistent work in his new country. He got shaving equipment secondhand and had about five customers, but the noisy aluminum blades quickly wore down, forcing him to work day labor jobs instead, he said.
He visited Home Depot sites, hoping to get jobs as a day laborer. The most consistent work he found was assisting a contractor, who paid him about $200 per day but eventually ran out of work to give him, he said.
Daniel, who was staying in a now-closed Loop hotel converted into a temporary shelter when City Bureau spoke with him in the spring, hopes for more consistent work to open up soon. Long term, he’d like to return to the fields he studied in Venezuela: engineering, computer science and mechanics — which he knows will be expensive.
Recent arrivals told City Bureau the process to obtain work authorization is confusing and cumbersome.
After months of advocacy, the federal government expanded eligibility for Temporary Protected Status in September 2023, opening the door for thousands of recently arrived Venezuelan migrants to apply for work permits throughout the United States.
City and state officials partnered with The Resurrection Project on workshops to screen thousands of people for eligibility for protected status or employment authorization through humanitarian parole.
For some employment authorization applications, the turnaround time was a few weeks, which “is the fastest [U.S. Citizenship and Immigration Services] has ever processed applications,” said Eréndira Rendón, vice president of immigrant justice with The Resurrection Project. After the first round of workshops in early 2024, about 40% of the people who applied received work permits, according to The Resurrection Project.
But that only applies to Venezuelans who came to the country before July 31, 2023. Only 30% of migrants staying in Chicago shelters as of late 2023 were eligible for TPS or Employment Authorization Documents, according to a spokesperson from the Illinois Department of Human Services.
Because of the federal restrictions, IDHS officials estimated only 5 to 10% of new shelter arrivals will be eligible for parole-based work permits and less than 2% would qualify for Temporary Protected Status, the spokesperson said.
Despite not having his barber equipment day, Daniel continues to look for steady work. He’ll take a job where he can get one, but countless other recent arrivals such as Daniel need more options.
Until then, many migrants like Samuel, David and Daniel will have to rely on these forms of entrepreneurship to get by.
Find more coverage on migrant labor by City Bureau’s Civic Reporting fellows here, including a Know Your Rights guide, published in collaboration with Latino Union of Chicago. Support City Bureau’s Civic Reporting fellowship by becoming a recurring donor.