I've never done it online, but I've called in and made a reservation without having enough points. We went away in February, and after I made a reservation through Ritz Rewards, I called Chase and had the points transferred.

I don't believe you can transfer airline miles to hotel programs (unless you want to use points.com which does not offer an attractive rate). AA used to be able to transfer to Hilton, but I'm not sure if that's still the case.

Others may have other experiences of transferring, but I don't know of any outside of points.com.