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I supposed that getting to Cuba by flying from neighboring countries will be much cheaper than the same from Europe, but I have realized that fly prices from Cancun or Miami are very expensive (about $500, that's a 20-30% less than from Europe). And even from other islands there is a high fee to pay. Now I'm looking for alternatives, other cities where I can fly cheaper or, even, ferries, cargo or cruisers which could me take to Cuba for less money. What's the cheapest (and legal) way to get to Cuba from other country?

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I don't know if it's still true, but in the cold war days, maybe even the 1990s, Cuba was where you'd transfer for the cheapest flights between Europe and Latin America. –  Gilles Dec 3 '13 at 21:02

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up vote 6 down vote accepted

Since you mention that you are open to getting to Cuba not necessarily directly from Europe but through a intermediate destination, my recommendation would be to consider one of two Canadian travel hubs: Montreal and Toronto.

I recommend these because destinations in and around where Cuba are the main tourist places for Canadians for a big chunk of the year.

You will occasionally find some ridiculously cheap fares through one or more of these methods:

  • Air Canada Vacations: they have regular deals as well as last minute deals. If you have the patience to look around their site, you are going to find some good packages. The caveat is that these tend to be vacation packages rather than just air fares but none the less, it is worth looking in to.
  • WestJet: Air Canada and WestJet prices tend to go hand in hand a lot of the time. If one drops prices, the other one usually does as well. However, both airlines have partnerships with different hotels, etc. which gives you some more variety.
  • SunWing: This is a budget airline where you will be able to find both cheap flights and vacation packages- in most cases, cheaper that both of the above airlines
  • YDeals Toronto and YDeals Montreal: This site has a great collection of great deals picked out by Chris Myden where by you can get deals from all Canadian airports to other destinations. For example, on October 1st he discovered this which is in turn a deal from Air Canada Vacations.

All of the above methods usually require patience to be able to find the cheapest fares but then again, it is something to get started with :)

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Just adding two more items to your list: Air-transat (cheap, but with extremely bad customer service), and "Cubana de Aviación", which is also very cheap. –  yms Dec 27 '13 at 21:49

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