Res is a blast - I'd absolutely reccommend it. Just keep in mind the fact that (among other things) you're going to be doing a lot of drinking, and that will affect your wallet big-time, and maybe also your marks. IIRC, in my first semester, I probably spent about $2500 on alcohol/partying/etc. Not fun to pay off, especially on top of all of the other costs of school, but definitely worth it.
I'd also reccommend you consider going elsewhere. I didn't have the best experience at the U of C personally, especially as an Arts student. If you're taking engineering or business, go for it. But, usually, there didn't seem to be much going on at the U of C, it's a commuter school, and it's relatively small. They don't have much funding, and therefore focus really strongly on only a few particular areas. If you also live in Calgary, what are you doing? University is a great opportunity to get away from home for a bit.
I'd take a look at places like UBC, maybe UVic (if you want a smaller school), and U of A. There aren't a lot of positive things I can say about Edmonton, but the U of A is definitely one of them. It's an excellent school. Having been to U of C, U of A, and Mount Royal, I can tell you that in my opinion, the U of A is far and above the best. Great res, great atmosphere, excellent profs (not a million sessionals like at U of C), lots of great research going on, lots of student groups that people actually participate in, good location (right by whyte ave, one train stop from downtown), etc.
I'm sure there are a tonne of good schools east of Alberta as well, but I really don't know much about them.
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