Inserting footnote references in Word with EndNote is a two step process. You need to use both the Reference and EndNote ribbon in Word, and the EndNote program.
1. In Word, place your cursor in the document where you want to add a footnote (for Chicago, the footnote superscript number in your text should be inserted after a punctuation mark in most cases). Follow instructions below to insert the number:
For Windows devices, in the References ribbon, click on Insert Footnote
For Mac, see Insert in the Word toolbar, choose Footnote
2. Once you have inserted the footnote, you will see that the cursor is now located at the foot of your page beside the relevant footnote number. You can now add your EndNote citation.
With your cursor in the relevant footnote area, go to the EndNote ribbon and choose Insert Citation.