Numbered styles such as Chicago Notes and Bibliography:

• In those styles, references are indicated by a number in the text, printed as a superscript. 
• Place the cursor after the punctuation..
• Create the footnotes using your word processor (in Word click on the References tab on the ribbon at the top of the screen, then select Insert Footnote).
• Then insert the citations into the footnote using the Chicago style.

• In the Chicago style, the number in the footnote is not superscript and you will need to change this manually.
• The first time a citation is used, it appears in the footnote as a complete reference,
• Depending on the Chicago version you are using, subsequent citations will be an abbreviated reference with just a short title (Chicago 17th), or appear as "ibid." in earlier versions.
• In order for the short title to display correctly, you will need to edit the reference in your EndNote Library and enter the short title in the appropriate field.

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The full reference will appear in the bibliography at the end of the paper.

• In EndNote, click on Tools on the top menu bar, then Output Styles > Open Style Manager
• Highlight the relevant output style and click on Edit
• When the edit window opens, go to Footnotes in the left-hand pane, and click on the subheading Templates. On the top left-hand side of the edit window, you will see a drop-down menu showing how EndNote formats citations in the footnotes.

• If the setting is Same as citations, EndNote will format the references like the citations in your text, e.g. (Smith, 1999).
• If the setting is Using footnote format, EndNote will format the references in a special footnote style, which is defined in the Templates pane below the drop-down menu.
• If the setting is Same as bibliography, EndNote will format the references in the footnotes in the same way as the references in the bibliography at the end of your document

Note: If you are using a prior version of EndNote, access to the Output Styles is under  Edit on the top menu bar.