To migrate your MAC Outlook (OLM) files to Window Outlook (PST) files you need a converter tool to perform such action of conversion. Mail Passport Pro is such an OLM to PST Converter to convert your entire mails, calendars, contacts, attachments, etc and its other database to PST file for Outlook. More over it preserve your data and maintain a hierarchy structure of your mail database so you get your database exactly as it was. An easy to use tool with free trial version is available which help you in taking look how conversion is successful using this tool.

For more details: mailpassportpro.com/olm-to-pst-converter