The hotel situation is much different than around a Disney park. I would be disappointed if my hotel was outside of walking distance too. There are already not enough hours in the day at celebration.
Wasting extra time traveling to and from (especially when I hear the traffic/people/crowds in Chicago are bad even when celebration is not going on) seems like it is costing a lot more than money. I expect this to be busier than Orlando considering how fast tickets have gone.