"The devastation was complete, total, comprehensive. It really was like the storm carpet bombed the island," said Cardinal Blase Cupich.
Cardinal Cupich was surprised to see how encompassing the damage on the island was, with critical needs in some areas for clean water and electric power. He expressed building frustration from those who need help. They say the recovery process is too long, and too slow.
Cupich will take that assessment back to Chicago and on to Pope Francis.
In the hillside communities around Galateo, about 25 miles southwest of San Juan, residents were not well-off before the hurricane but at least had homes. Now many of those houses are gone.
Iris Mareno Santo is battling colon cancer, but can't get the medical care she needs because she has no transportation. The only way she gets by, she said, is because she believes in god.
"I'd say for the most part people do not want a hand-out, they want a hand up," Cupich said.
In the island's mountainous region, people are frustrated by the pace of recovery.
Galateo's nursing home Hugar Dulce Sueno translates to "Home of Sweet Dreams," but not all is well there. Director Keyla Perez and her staff are doing the best they can to care for 28 seniors, but the private funding payments are only dribbling in while rain is dripping through the roof.
Where the rooftop should be is stringer board. The terrace is covered in tarps filled with water, the only things keeping the rain from pouring down on the senior citizens housed in the building.
Perez is moved to tears thinking of the people she's caring for.
"They're not worried because they're senior citizens that depend on me. I have to do whatever I can do so they can feel comfortable," she said through a translator. "And it's not easy."
A bit further up the mountains is the community of Villa Esperanza. If there's a community in need of hope on the island, it's that one. Jose Solano calls Villa Esperanza home. He said everyone there is just trying to survive.
Solano is a U.S. Army veteran who spent two years in Vietnam. He wears his tags around his neck with pride. Yet when he looks around his shattered home, he considers himself fortunate to have a place to live. A few doors down there is no door, no house; just a TV sitting on a dresser.
"There's a lot of people worse than I am," he said.
Salvador Oquendo has family in suburban Cicero. He's now in Puerto Rico, driving across the battered island looking for those in need of a helping hand.
Oquendo said there's a simple dream on the hearts of many on the island.
"To have everything go back to the same, or better," he said.
From Dorado to Punta Santiago, the island may be broken in circumstance but not in spirit. Chicagoans with big hearts are stepping in everywhere.
"This is America. I know American won't forget about us. That's the only hope we got," Solano said.