Chicago/Turabian has a two-step process for creating references:
The second step can be initiated from Word or EndNote.
The Find & Insert My References dialog box will open
EndNote returns you to Word. The footnote will now contain citation details for the reference and a bibliography will appear at the end of the document with this citation as the first entry.
Select the reference/s to insert. To select multiple references:
Both references should be highlighted.
EndNote returns you to Word. The footnote will now contain citation details for both references and a bibliography will appear at the end of the document listing the citations in alphabetical order.
In Chicago/Turabian Style, you can also include sources in your bibliography which you have consulted in your research, but which you have not cited in the footnotes to your text.