Many who've crossed are trying to make it 1,400 miles north to Chicago, but Chicago leaders visiting the border are trying to inform them that their life in Chicago may not be as easy as they think it will be.
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Late into the night border patrol keeps guard at an unofficial crossing site near Brownsville. Agents say migrants often arrive en masse in the pitch dark.
When they finally make it through to the first step of immigration processing at the border many have declared Chicago as their desired city.
"Even though we might say Chicago is cold or it's going to be hard to find, that's not going to stop someone who now has the hope that there's possible work," said Deputy Mayor of Immigrant and Refugee Rights Beatriz Ponce de Leon. "It's been helpful to hear that from the folks who are on the ground."
Every one of them has legal papers that they visibly hold close, but this is just the beginning of a complicated legal process, that even seasoned immigration lawyers in Chicago are still learning to try and help navigate.
READ MORE: Chicago delegation warns migrants at Texas border of city's lack of shelter space, oncoming cold
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"Immigration can issue them a notice to appear in Chicago. That doesn't necessarily mean that it's been filed with the court order that he's gotten to the court in Chicago or that the court system in Chicago recognizes them. So they're given this address, and there's lots of different addresses in Chicago that people are given. And they're coming to Chicago with hopes of entering the system, however the system is quite backed up," said Ellen Miller, pro bono manager for National Immigrant Justice Center.
Brownsville is just a way-station, and the border city has honed a quick plan to get migrants connected to legally declared sponsors.
"It's a process that we do to make sure that they are not going to your shelters, they are not going to your police stations, anywhere that you have designated as a shelter in your area," said Rene Tabarez, emergency management administrator. "We're not passing our issues, our city to our receiving city. That's the last thing we want."
Chicago city leaders said it's become clear through multiple stops in multiple cities that Texas is a temporary stop for migrants after crossing the border. They're also not part of the state's efforts to send buses of migrants to Chicago.
"The main kind of theme is everything is federally funded here and their operations are very tight in terms of the timeline," said Deputy Chief of Staff Cristina Pacione-Zayas.
With a migrant population of more than 18,000 and counting, and a small fraction of the federal funds these border cities have access to, Chicago's challenge is more permanent.