First off there's a basic 15% off flights anytime this winter (blackout dates apply) with either Westjet or Air Canada. That takes your airfare down to about $500 per person, if you pick the right dates.
Secondly, Westjet is offering packages on sale right now which includes week in a beachside condo. For 2 adults, the cost is $2030, air, tax and accommodations from Winnipeg. OR, with 2 minor children I see it priced at $3244 for the same date package. That's a mere $811 per person, for a week in a condo in Maui. SWEEEEEEET deal!
Lastly, with this package deal in mind, I looked up what you could get for $1220 per person, which I would still consider a very good price for a package to Maui. Look what I found! The Waldorf Astoria in the highly coveted Wailea area for under $5K. This would be AMAZING!!! You'd be in the playground of the rich and famous, on a modest budget.
The only thing to keep in mind would be that in a condo, you would prepare your own meals and could realistically do so for a family at a cost of $500CDN total for a week. Whereas, staying at a hotel/resort and buying meals would be far more expensive.
Prices are in Canadian funds and can be found at Westjet Vacations or through your favourite travel agent. Prices subject to change.
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