Newspaper Article in Book -- Best way to include this information?

I’m working on a paper that involves citing a lot of newspaper articles that were later collected into a book and (in some cases) translated into English from the original German.  Ideally, my citations would include the original publication date and newspaper of origin.  I see that there’s an “original publication date” field in the reference window.

Would the best way to do this be to just put the original date of publication AND the newspaper into this field, or is there a better way for this that I haven’t figured out yet?

If it matters, I’ll be using Chicago style for my end product.

You should check your Chicago manual for guidelines citing secondary sources as there may be exceptions governing the use of them.  But one way would be to list the newspaper article (in the usual Chicago style format) followed by a phrase such as  “cited in”  then the book source (in the usual Chicago style format).