Does WordPress support Plupload chunking when uploading asynchronously?

To the best of my knowledge, no, the async-upload process on the WordPress side does not support chunking from plupload. You can find this code in /wp-admin/async-upload.php.

To handle the uploaded file, it calls the wp_ajax_upload_attachment() function, in the ajax-actions.php file. This function refers directly to the PHP $_FILES array, meaning that the file would be completely uploaded and saved to a tmp file by PHP before WordPress is invoked. Therefore chunking is not directly supported.