Hi Gad!
I know just what you are talking about! There doesn't seem to be an exact science to finding this helpful chat session, so I will just share my experience with you. Every time that I visit the
Disney World website and select "Tickets and Packages" and then "Book your Vacation," I seem to have luck!
If you plug in your dates and resort and arrive at the page where you are given actual pricing options, the online chat session often pops up. I find that if you click around on the room options,the chat box always appears in the left hand corner. The box says, "Questions? Chat online with a Disney Vacation Specialist. Chat now." I've seen it appear in the upper left hand corner, as well as floating randomly in the left hand side of the page. I wish that I had a surefire solution for you, but I wish you the best of luck!
Of course, you can always talk to a Disney Cast Member LIVE by calling 1-407-WDISNEY - either way, you will find a friendly, helpful Disney travel specialist ready to answer your questions. Have fun planning that vacation!
Much pixie dust,
Jackie S.