Travelling from Winnipeg to YVR to Haneda to Sydney, multiple airlines -- Can I through-check baggage?

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Air Canada and ANA are partner airlines (see the list on ANA's website) and you're travelling on one ticket, so your bags will be checked all the way through in both directions. As far as I can see, you don't need to pick up your bags in Japan to take them through customs, like you would in the US. You can confirm this with the check-in agent when you drop off your bags.

On your return trip, your bags will be checked through to Winnipeg but the Canada Border Services Agency guidance on Arriving by Air rather unhelpfully says "You may [their emphasis] not be required to retrieve your baggage until your final destination." In Vancouver, you might have to pick up your bags, take them through customs and then give them back to the airline for Winnipeg (like in the US, if you're familiar with that), or the airline might transfer them without you needing to touch them. CBSA says you should ask your airline which applies. Ask when you check your bags in, in Australia.

You should check your booking for the rules about carry-on (and checked-in) luggage. It's not necessarily the case that you'll be restricted to the rules of the carrier for that particular flight: you might get the allowance of whatever airline you bought the ticket from, for the whole trip.

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