true I've not been to Calgary, but there are some pretty good steakhouses here in Toronto, and my experience has been that the best ones are in chicago - the US meat grading system leads a fattier, more flavourful cut.
I haven't eaten at Hy's whistler but it's a chain and I've eaten at other locations. Personally I liked Gibson's in chicago more, also liked Morton's and Harbor 60 in toronto more. It's a good steakhouse but there are better. It will be better than Milestones which I recommended as there was a bit of talk of price, but much more expensive.
If the OP's got the budget and is craving steak I'd say he'd be happy but not amazed at Hy's.
The Rimrock is same price range and has more interesting food IMO - more of a signature whistler place as opposed to steakhouse - in a 2.5 day tour if I was going to do one big dinner Rimrock would be it in Whistler.