Mike-zed has a good point, and G Larry recommends Abp. Chaput’s book. From a book review, Chaput relies on John Courtney Murray, who was a liberal. The review doesn’t say whether Chaput condones redistribution of wealth, however. And that is the central issue.
Popes Pius IX, Leo XIII, and Pius XI unequivocally condemned socialism. In particular, they condemned taking money from one person to give it to another, i.e., redistribution of wealth. The USCCB has always come down firmly on the side of redistribution, and I don’t recall Chaput speaking out against that.
Abp. Chaput is quite liberal in his condemnation of the death penalty, and this makes me nervous about him. What else I’ve seen of him is good, however.
Folks need to understand that the USCCB has basically zero teaching authority. Canon law gives national bishops' conferences authority in certain very defined, narrow, areas of competence, mainly concerning things that need to be legislated on a national basis, like liturgical translations. Aside from that, they're basically a bureaucracy that generates words.
An individual bishop doesn't need to comment on every pronouncement or opinion of the USCCB for the simple reason that his authority is superior to that of the USCCB within the bounds of his diocese.