I think the difference is that rooms are a focus of HipChat, and an afterthought / hack in Skype. Similar to how individual, "not in a room" conversation is an

I think the difference is that rooms are a focus of HipChat, and an afterthought / hack in Skype. Similar to how individual, "not in a room" conversation is an afterthought in HipChat. In both cases you can technically do it, but the app doesn't go out of it's way to make it easy or well-supported. If you find you're using your favorited lists to chat more than one-on-one conversations, I'd really recommend trying out HipChat. For what it's worth, we regularly use Skype at our office as well as HipChat. They both excel at what they were designed to do, and we don't necessarily see a problem with using two tools if it means you don't have to shove a round peg into a square hole.