Monday afternoon, dozens of protesters marched in the city's West Side to the western suburbs, which is about a 10 mile trek from Chicago's Pilsen neighborhood to a prayer vigil in Berwyn.
Chicago joined 40-plus cities across the country urging President Obama to put a stop to deportations and create some relief.
Individuals and families who have been affected by deportations lead the march in Chicago, urging the White House to put a stop to deportations.
Four years ago, Gaby Benitez's father was on his way to work when he was arrested and sent to a detention center. He is now back home, waiting to be deported.
"It broke my heart," she said. "I didn't know what to do. Four years now, we are still fighting my dad's case."
Organizers claim 1,100 people are deported daily and that by mid-April, President Obama will have carried out two million deportations, more than any other president in US history.
"We're creating orphans with parents," said Lawrence Benito, Coalition For Immigrant and Refugee Rights. "This needs to stop."
The protesters left ICE headquarters and walked for miles until they reached St. Pious Church in Pilsen, where they prayed and had lunch.
Fifteen-year-old Saul Arellano was forced to go to Mexico to live with his mother when she was deported seven years ago. She recently returned to Chicago legally and is asking to be able live with her son, a U.S. citizen, without the fear of being deported.
"I had to move with my mom to Mexico," Saul Arellano said. "It's really difficult because I didn't know no one over there."
"Now it lies on President Barack Obama, it's in his hands," said community activist Emma Lozano. "He wants to go down in history as the "Deporter in Chief" of the Latino families that he separated, well then he'll go down this road."
"The only that they've done is created a nightmare," Benitez said. "It's a nightmare that's never-ending that we've had for every day of our lives, and we want this to stop."
Following Monday night's vigil, the marchers will then go on to Maywood, where they will spend overnight in a church.
In the morning, they will go to the Broadview Detention Center, where they will meet up with at least 500 protesters in an attempt to stop a bus from taking detainees to the airport.