I can always get a late check out at a HGI or HI. I've never been told no to a late check out at either-- sometimes as late as 4 or 5pm.

At Hilton properties, especially resort property, I have usually gotten a 12 or 1 check out. Only one time have I been told no to a 2pm. And they offered to give me internet and the exec lounge, so they did make up for it in some way.

Typically, it is up to the manager on duty to say yes. I have not found that VIP status has mattered too much-- they tend to do it if they can.