Jesse, that was probably mostly because it was your first time in Chicago and it's a pretty amazing city, right? I had been to Chicago several times before the Lolla I went to and it just wasn't anything special at all.
Tommyboy, I've wrote lots about what I think Phish is doing next year in other threads. Unfortunately, I can't remember which ones. I'll try to summarize. Instead of playing at any typical multi-band festivals, they just did their own festivals where it was just them playing like 8 sets for 3 days. Amazingly, 70 - 100,00 people showed up just to see Phish, so clearly Phish is bigger than Bonnaroo.
http://en.wikipedia.org/wiki/Phish_festivals
However, these US festivals didn't start becoming really, really popular until after Phish broke up. I'm very curious to see what they decide to do. I would absolutely love it if they played, but if I had to guess right now, I would say no. It's about a 30% chance in my mind. I'm a big Phishhead so I will see them multiple times next year regardless. The Dead however, I'm about 90% sure they'll be there. They're basically a lock, like MMJ, and I can't fucking wait!!! It's going to be so awesome to see Phil, Bob, Mickey and all the boys up there again. As old as they are they can still fucking rock!