How was packing skis and a board...plus two sets of boots? When I fly, I normally choose one or the other, but I'm intrigued to try one of each for a trip this winter. One ski/board bag? Or tag team with the hubs, based on what he's bringing?
My strategy is contrary to
@Jilly's advice above especially on Air Canada -- which is to say it's not without it's risks:
I use a soft-sided bag to save weight. The weight limit is 50 lbs or 23 kgs. My bag is the Dakine Fall Line Roller bag, which is meant for snowboards. The bag comes with a separate sack in which to put snowboard bindings or boots or whatever.
The snowboard with goes on the bottom, of course with bindings off. Then skis lie side by side on top of the snowboard with the brakes tied flat. The snowboard bindings, screwdriver and hardware go in the side sack, and the snowboard boots go on top of the skis/board. Poles go in the side as well. Then I stuff with my helmet and pad some of my soft goods -- extra balaclavas, insulated ski jacket, insulated pants, etc. As per Jilly's post above, this is technically against the rules. I haven't had an issue with it though. Maybe Jilly's DH was unlucky. I wear my uninsulated ski shell on to the plane.
As for my ski boots, I mostly get away with being able to fit them without a separate boot bag because I have little feetsies (size 23/23.5 shell). They fit perfectly in one half of my roll aboard with some padding in that compartment. That said, I know a number of airlines treat the ski and boot bag as a single checked bag if you want to take that route.
FWIW I saw a number of soft-sided ski bags at the oversized bag pickup spot. But it's definitely contrary to the express policy of Air Canada.
Here's a pic of my half-packed snowboard bag showing the arrangement of board, skis, boots and snowboard bindings:
