If you plan to fly by the end of summer, or in September, I'd encourage you to take a few minutes today and check out the prices at Westjet and Air Canada. Both are having a sale right now and are offering pretty great prices.
My rule of thumb is any domestic flight under $400 is a good deal. Any flight to the USA under $500 and any overseas flight in the $750 range.
Right now, both AC & WJ are offering YWG to YYC under $300. So, if you need to go from Winnipeg to Calgary this fall, you should look at booking now. Under $300 is fabulous.
Since the Canadian dollar is weak, (6 year low) I would encourage you to book a package that includes your hotel whenever possible and pay in advance, with Canadian funds. For example, if you are going to Vegas, pay the Canadian package price with Westjet rather than using a US supplier or paying for each separately. The package prices certainly have not jumped drastically in price so in my humble opinion you can still travel to the USA. Anytime I can go to Vegas for $500, is good enough for me.
Of course, prices are subject to change at any time. Bargains won't last forever. Sadly, you can't ever expect a last minute airfare bargain. Booking 6-8 weeks before you intend to travel, will offer the best prices. Also, do look into your airline's policy on price drops or price matching. The industry has changed in this regard in the last year or so. Never hurts to look.
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