I am a volunteer teacher of computers and software for hundreds of seniors at large senior centers here in Colorado.
Does it have a built-in camera? They use Skype quite a bit, and love seeing their grandchildren.
While it does have a camera, I do not think there is a Skype web app. Remember, this is a Chrome-everything laptop. If it doesn't happen inside Chrome,then it doesn't happen on a Chromebook.
Because Microsoft just bought Skype. I highly doubt that Skype will ever work. Fear not though! Google voice allows video chat and free as well.