Not always and it really does depend on a lot of factors. We have found that paying regular rack rate and getting Free Dining has always come out cheaper for our family of 4 (2 adults/2 teens - Disney adults). While the savings isn't as high as it used to be, we would still save using FD. Here's an example: I priced out a 9 day trip for next August at the BC, GV room. Regular rack rate with 9 day PH passes, total with FD if it was offered: 5249.96. Now I price out the same room using a 35% room only discount and add the 9 day PH passes, total = $3953.42, now if I add the dining price (1778.88) my total = 5732.30... Free dining would save me $482.34 - not a huge savings, but a savings nonetheless. Now, some folks would argue that a family of 4 could eat for less than the price of the dining plan and while that may be true for some families, ours is not the case. Once I started looking at the places we wanted to eat and looking at the menu's, we realized real quick that we'd be spending a lot more $$ without the plan so it really does just depend.