We did Honolulu out of Brandon a little over a month ago.
Connected through Calgary (just over an hour) and Vancouver (just over 2 hours) to get there. The flight back was a nice simple Honolulu to Calgary to Brandon with about 2 hours to connect. On both ends we had the perfect amount of time to do customs, though imagine if one of those flights comes in a little behind one might have to sweat a little bit!
Havent checked to see if they're still booking those identical connections at decent rates, but I know that the options really differed depending on day of the week. In our case we flew out of Brandon on the afternoon flight on a Tuesday and came back home on a Wednesday (was Thursday afternoon by the time we were home so maybe still not the kind of long travel day you had in mind?).
As far as what to do in the Calgary airport. Stromboli. Lots and lots of stromboli if your heart can handle it
Edited by Adam, 2019-03-01 15:18:37