I created a citation style for Zotero called Chicago Manual of Style (figures & illustrations). Using this style with Zotero’s Word plug-in allows users to create fully automatic figure citations. Using the toolbar in the add-ins section of Word, users can search through the items in their Zotero library and insert them as an in-line figure number as seen below. The advantage is that moving the image order or inserting new images will automatically change figure numbers throughout the document. When finished inserting in-line citations, an accounting of all items used in the document can be generated as a figure list, which will format the image metadata into Chicago style.
To use this tool, you'll have to have Zotero installed, and you'll have to have your image metadata entered into Zotero (either as an artwork or section in a book). Zotero can automatically collect image metadata from some databases. You'll also have to download the citation style from the Zotero Style Repository.
Zotero Style Repository [scroll down to Chicago Manual of style (figures & illustrations)]