The PDF, above, is a guide developed from the Chicago Manual of Style.
For general information about Chicago -- such as formatting and notes -- refer to Purdue's Online Writing Lab. It even has a sample paper that shows you how the paper should be formatted.
If you would like me to help you get set up with Zotero, a free Citation Reference manager, make an appointment to see me and bring your laptop.
You can insert Endnotes using Microsoft Word. Refer to this Lynda.com video to learn how.