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Destination weddings. Our features. Back to top. It's no coincidence that March 25th is the last day of school for Calgary, before their midwinter break. Plenty of people will be taking their families on holidays, which means increased demand, which means higher prices. Interestingly enough though, Easter is quite late this year, and doesn't seem to be subject to higher prices than usual.

Again we can see that about 5 weeks ahead offers the cheapest price, although it doesn't be appear to be significantly cheaper than 2 weeks ahead at the moment. What is noticeable however, is a large spike around the 2nd week of March. Just like with Calgary, it's no coincidence that this is when Ontario schools let out for midwinter break.

These are just two example cities, the situation will be similar from all cities. If you're ever looking to go on an all inclusive vacation, just ask yourself, are there a lot of other people with holidays at this time? If the answer is yes, expect prices to be higher, and the chance of an unusually good price to be quite low.

The problem is though, it's usually to just a few select resorts, while the specific resort you may have been hoping for stands a good chance of having a higher price than was available previously.

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That's a classic example of flexibility vs price in the world of travel. I'm sure there's plenty of people out there that wait for a 'last minute' deal to a specific resort, only to be disappointed. To lower their odds even further, most people also narrow it down to a specific date range. The chances of a truly great deal happening on the exact dates you want, to the exact resort you want are pretty remote. There are also overall price trends throughout the year.

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Christmas of course, is just ridiculously expensive, with the off-the-charts level of demand. I've found that the average Christmas all inclusive package is usually at least 1. Basically, anything that involves 'over' Christmas is going to be the worst of the pricing, but anything between Boxing Day and January 7th or so is going to be nearly as bad. Anoter bad time of the year to hope for a good deal is around the third week of February. Spring break, Reading week, Family Day, President's Day, and Christmas credit card bills being paid off all combine in a perfect storm to make sure there are impossibly few good deals to be found anywhere warm.

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  7. The shoulder seasons usually have some amazing deals, such as November up to mid December. Then the prices get ridiculous for Christmas, then they come back down to earth around second week of January, but still higher than the shoulder season, as winter sets in across Canada and people start looking to get away. During winter, there are still insane deals to be had for sure, but less frequently than in the shoulder season. Then comes April, and you're into the opposite shoulder season. There are still charter flights flying to warm destinations, but they're starting to wind down towards the end of April.

    As you get into late spring and summer, people might think, it's warm here, so there's probably always some amazing deals down south. And there's also a lot of people that take holidays during the summer.

    Then as you get into late fall end of November is approximately the end of hurricane season down south , and the charters ramp up the number of flights again and the cycle starts over. I know that sounds intimidating, 'everything else'. By everything else, I mean sites that aren't offering packages from the Canadian Tour Operator's mentioned above.

    This includes sites like Expedia, Travelocity, Orbitz, Bookit, etc, basically any of the big usually American owned travel sites out there.

    It sounds like an overwhelming task, with you wasting your precious time examining them all. I can tell you that They're basically just taking fares from the major airlines which are the same everywhere and mashing them together with whatever the latest hotel prices are which are virtually always the same everywhere. That way, you're comparing apples to apples with the CTO's above. One problem with World 2 is that these flight and hotel packages will be initially mashed together with the cheapest flight option, which can sometimes be a completely moronic flight, like a 20 hour flight with 2 or 3 stopovers.