Completely different reasons why both hotels in large cities and hotels in WDW are expensive, though. In Chicago, there is literally no land. The only way you can build is up. Most hotels don't even own their own parking, the garages are owned and managed by separate companies. When space is so scarce, of course it will be expensive. WDW, on the other hand, literally owns ALL the empty land around their parks. With the exception of the Swan/Dolphin (not sure of the history on why they were able to be built so close to parks) it is impossible to stay close to parks without staying in a WDW hotel because they own everything and won't let anyone else build on it. So it's actually opposite reasons why a big city is expensive and why WDW is expensive. Big cities have no land, WDW has ALL the land. And WDW can, and does, mark their hotels way way up because of this. I'm pretty sure they got the land their resorts are built on for dirt cheap. That's why Walt chose it.