My “Why Chicago” essay is around 630 words and my extended essay is about 1300 words (I picked the “design your own major” prompt and outlined all the required courses).
From U. of Chicago’s admission site: Is there a word limit or suggested word limit to your essay responses?
We suggest you note any word limits for Coalition or Common Application essays; however, there are no strict word limits on the UChicago supplement essays. For the extended essay (where you choose one of several prompts), we suggest that you aim for around 650 words. While we won’t, as a rule, stop reading after 650 words, we’re only human and cannot promise that an overly wordy essay will hold our attention indefinitely. For the “Why UChicago?” essay, we suggest about 250-500 words. The ideas in your writing matter more than the exact number of words you use!
IMO, you are doing yourself a disservice by not following the parameters. Edit both down, especially the extended essay which is double their suggested word count.
I doubt Chicago adcoms expect you to outline “all the required courses.” You’re a hs senior, haven’t gotten experience yet in college courses as an enrolled student. Imo, it would be more effective, for Chicago, to discuss the intellectual directions of the major, the sort of inquiry. And maybe the interdepartmental overlap.
Did you look at existing courses before doing this? They’re not asking you to reinvent the wheel.