How to Find Cheap Flights to Anywhere

When it comes to finding and booking cheap flights, everyone has an opinion. People tend to say that in order to get the best deal you should be looking for flights from an incognito browser, or book them a certain amount of days before the flight or book on certain days. 

Sadly, these are all myths. There is NO evidence that searching incognito leads to cheaper deals. In fact, I have evidence that proves otherwise. If you don’t believe me – try it. It’s all based on algorithms that you cannot cheat these days.

Unless there’s a mistake fare available then you can cheat, but it doesn’t guarantee that the booking won’t get canceled. More on this further in the post.

How to Find Cheap Flights?

how to find cheap flights

1) Be Flexible

In this case, I recommend the good old Skyscanner. But there are several tricks to find the cheapest flight to anywhere. Here’s my guide to finding the cheapest flights.

STEP 1.

Let’s say you want to go from Chicago to Cuba. Great, but see whether they’re some better deals available from elsewhere.

Instead of searching for a flight from your home airport to your destination, put only countries in the search bar.

If you have some flexibility in terms of dates, set it up to ‘Cheapest month’ – just like I did in the screenshot below.

skyscanner


STEP 2.

As it turns out in the screenshot below, the cheapest city to fly from the US is actually Havana. But since it’s the most convenient place to fly into and the price difference isn’t crucial, I picked it as an example.

skyscanner travel hack


STEP 3.

Once I selected ‘Havana’ I got a number of option for departure cities within the US. Why?

For instance, if you need a flight from let’s say NYC, it’s often cheaper to get a flight from Orlando to Havana and buy a separate fly with a budget carrier to Orlando, rather than purchasing a flight from NYC, even with multiple stops. So let’s pick Orlando and see what happens…

skyscanner-3


STEP 4.

Once I picked Orlando it turned out that the cheapest month to go to Havana was February. Then you can experiment with dates and see what works for you. Voilà! Now head to Skyscanner to find your flight 🙂

direct flights to Cuba from USA


Don’t Forget About Travel Insurance

Don’t forget to arrange travel insurance before heading anywhere. In certain countries, visitors are often stopped at the border and checked if they have valid insurance.

Even if you’re not legally required to have travel insurance you want to have one. Not only because you’d be totally screwed if you got seriously injured abroad, but it can also give you money back if airlines delay your luggage, your flight gets canceled, etc.  The most reliable for most nationalities is World Nomads Travel Insurance.


Do you have any questions about how to book cheap flights?

10 thoughts on “How to Find Cheap Flights to Anywhere”

  1. I remember reading about Carnival cruise docking in Havana, but didn’t realize it has now been suspended. Any particular reason why?

    Reply
  2. Wow I never knew it was technically “illegal” to travel to Cuba as a tourist. As you explained, there are obvious ways around it. It is also crazy that they specifically have a message aimed at US citizens about traveling to Cuba.

    Reply
  3. Hey there! The things with travelling to Cuba are even more complicated. OFAC (US body setting new sanctions regulations), issued a new guidance in January – may be useful for some of you.

    certain specialty tours to Cuba that are offered by travel agencies in third countries are marketed to U.S travelers as being in compliance with the prohibitions of the U.S. embargo against Cuba. These trips are usually designed for individuals with an interest in outdoor activities, such as scuba diving, bicycling, hunting or fishing. The sales material often maintains that because the traveler prepays the third country travel agency for expenses that otherwise would be paid by the traveler while within Cuba, such as hotels, meals, ground transportation, equipment rental and services, etc., this type of trip is in compliance with the applicable U.S. regulations on travel-related transactions involving Cuba that apply to persons subject to the jurisdiction of the United States. This advisory is to alert U.S. travelers who participate in such trips that engaging in prepaid arrangements for travel expenditures otherwise prohibited by the Cuba Assets Control Regulations, 31 CFR Part 515 (the “Regulations”), will expose
    travelers to the possibility of civil monetary penalties from OFAC.

    A Cuban vacation package that is prepaid by U.S travelers through a travel agency located in a third country does not qualify as “fully-hosted” travel as described in the Regulations. This is true regardless of the type of currency that is used to purchase the package tour. This type of trip is simply an “all-inclusive” vacation package similar to ones available at most resort and vacation destinations anywhere in the world. The Regulations prohibit all transactions relating to travel-related tourist transactions in Cuba including prepayment in third countries for Cuba-related expenses.

    Reply
  4. I am Canadian and your site is useful to me, to find one-way flights from Cuba to USA. On one flight from Havana to Toronto I was surprised to find a large group of students from Michigan. They had duly obtained their “permissions” to travel to Cuba but were afraid Trump would suddenly prohibit travel, so they booked their flight from Toronto. US Citizens comtemplating a holiday in Toronto might add a side-trip to Cuba, but remember your name will be on the US flight lists, since the flights to Cuba fly over US territory. The only flights from Canada to Cuba that do not fly over US territory are the flights from Halifax, Nova Scotia. When you fly from Canada your Cuban tourist visa is normally included in the cost of the airfare and is issued to you onboard the plane. The only exception I know of is Air Cubana, when you buy an air-only (vs. vacation) ticket you need to pay extra from your visa, at the airport, before departing Canada.

    Reply
  5. Hi,
    Where did you stay in Vinales? I love the balcony you are standing on overlooking the valley. Was that your hotel or casa particulars? I am currently looking for lodging in Vinales so I would love it if you could pass along the information.

    muchas gracias,
    Shawna

    Reply
    • I stayed in one of the casas particulares. It was one of the no-name ones and we just showed up and in my opinion it’s the best way to do this in Cuba. many business owners don’t have any relatives abroad (it’s the only option to get listed on AirBnB, because of the lack of internet) so they aren’t listed but their casas are often better than these on AirBnB 🙂 The photo you’re referring to is actually at a restaurant/bar on the way to the hillside viewpoint overlooking the Viñales Valley (close to La Ermita Hotel).

      Reply
    • I stayed in one of the casas particulares. It was one of the no-name ones and we just showed up and in my opinion, it’s the best way to do this in Cuba. many business owners don’t have any relatives abroad (it’s the only option to get listed on AirBnB, because of the lack of internet) so they aren’t listed but their casas are often better than these on AirBnB 🙂 The photo you’re referring to is actually at a restaurant/bar on the way to the hillside viewpoint overlooking the Viñales Valley (close to La Ermita Hotel).

      Reply

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