My organization uses Office 365 with exchange; on our workstations we use Office 2016. My question is, I have a user who is leaving our organization and I need to export his calendar and import it into another users calendar. I need this to happen both locally and also in the cloud so all of the events are visible in both the cloud and on his local machine. (so a saved .pst from one PC to another will not work)
The easiest way is to use the Outlook File -> Open & Export -> Import/Export menu. On the old account, select the "Export to a file" -> "Comma Separated Values" -> select the required Calendar folder and export it to a CSV file. After that you can import the resulting CSV on a new account using the same menu but this time select "Import from another program or file" in the "Import and Export Wizard".
If the users are using O365 client(Office 2016), you can export Calendar from user A's mailbox as .PST, then import the /PST file to user B's Outlook 2016 client. It will sync the Calendar to user B's mailbox, and user B can find user A's calendar in his own OWA(it means the imported calendar is not just in local). It works in my environment.
You can have a simple test with different ways before the user left company, then select the method which is most convenient for you. :)