I've noticed four things when writing my current essay:
LaTeX will automatically cause your title to be moved to the next page to avoid having the title and paragraph on separate pages
This on occasion leaves a really annoying amount of whitespace on a page, which is doubling annoying when you have a page limit.
biblatex-chicago will occasionally flow a citation from one page to the next automatically, but not very often.
Reading about Germany between 1933 and 1939 is really depressing.
Now 1 and 3 seem to suggest a solution to me: Is it possible to get biblatex to reflow the citations more aggressively to reduce the amount of whitespace at the bottom of pages? Even if I wasn't fighting a page count, it always annoys me when I look at the two page spread and there is a massively different amount of whitespace at the bottom of the page.