One week ago, he completed his mission after 680 days. Along the way, he experienced the kindness of everyday Chicagoans.
He visited neighborhoods that some people said were dangerous, and built a devoted following on social media.
So much so, that hundreds of people joined him for his final run.
Barbosa says he wasn't always a runner. Instead, he played soccer.
Barbosa took up running after an accident on Mt. Washington in New Hampshire. He suffered hypothermia and frostbite.
Doctors urged him to run to help improve his circulation.
Part 1 - Our Chicago: Man Completes Mission To Run Every Street In Chicago
Now, Barbosa lives in the Loop.
"I just thought I just want to get out of my comfort zone. Because a lot of people were telling me when when I started this like 'oh, you shouldn't go to certain neighborhoods in Chicago. You certainly shouldn't go to certain neighborhoods at night.' And so, it was like of like me being stubborn," he said.
Despite the warnings, he ran and discovered something very different: "everywhere I've gone, people have been so, so nice to me. I've been treated so, so well by everyone."
Barbosa says people offered him water, invited him to their homes and even fed him.
"My perspective on Chicago has definitely changed. And one thing that I told myself after all the interactions I've had, you can hear a thousand stories, but just one experience can change everything," he said.
One of his best experiences happened in Englewood. He met a man named Jerome while running at night.
Part 2 - Our Chicago: Man Completes Mission To Run Every Street In Chicago
He gave Barbosa his phone number and called at the end of the run to make sure he was okay.
The two have kept in touch.
Another memorable experience was an encounter with a 7-year-old boy named Bryce whose dream was to go viral. A video of the two of them attracted a lot of views.
Now that he's done, Barbosa says "I was sad I finished. But happy I finished."