How to get the cheapest flights

I was in Italy when I booked a flight to Japan. It’s not because I’m rich (I’m a very sore Powerball loser, actually). It’s because I’m a smart traveler. I go to several countries each year and at a couple of domestic cities and I never spend more than a couple of grand on any one vacation. Usually much less. Often times, the key to cheap travel is getting the cheapest flights.

There are a few tricks I use to make sure I always get the best deal. It’s how I’m able to travel so often without being completely broke.

Be flexible about time

For one, I’m flexible. For many people, vacation planning starts with an exact set of dates and a destination. Those people usually pay through the nose for their vacations. Because everyone wants to be in New York over Christmas and the prices of flights (and hotels) rise with demand. Everyone wants to avoid taking extra days off if they can help it so the weekend flights are more expensive. Being flexible means giving yourself a little bit of leeway at the start or end of the trip so you can fully see the range of prices for your desired destination. You may not end up with the most desirable itinerary but a red-eye flight or a connection is often worth saving $200.

Be open to new places

But maybe even more important than dates is flexibility with regard to destination. Certain locations are simply less popular at certain times of the year. If your desire is to travel, being open about the where can save you hundreds and hundreds of dollars over time. So if you know you want to travel the second week of May, come up with a list of destinations that would interest you and start looking at flight prices around those dates. For an abundance of reasons from weather to major events to political or economic news, the flights to two different places will be extremely different for any given time period. If you don’t want to stay on top of fluctuating prices, create an email alert through Kayak or your favorite search engine (Protip: Use Kayak).

That’s precisely how I ended up booking a flight to Tokyo while still vacationing in Florence. I knew I wanted to take a trip to around Thanksgiving and I had a few alerts for different cities, Tokyo, Bangkok, Paris. Again, flexibility is key. I woke up one morning in Italy to an alert informing me that flights from the continental United States to Tokyo, Japan were a whopping $639.70 round trip. For those of you that fly with some regularity, you probably know that sometimes flights from Florida to California can be that expensive. Whereas flights to Japan are usually in the $1000-1400 range. I was not going to pass up this opportunity. I spent an entire train ride to Pisa trying to book it on my phone (and continuously getting rejected because my credit cards thought it was fraud), but I finally succeeded. And six months later, I would be on this ridiculously cheap flight to Japan.

Don’t wait on a good deal

This brings me to my other key tip: always strike while the iron is hot. Booking a flight – no matter how cheap – while on another vacation where you’re already spending a lot of money and may be taking unpaid time off may not be everyone’s cup of tea. That’s understandable. But I prefer to spend a little bit at an unexpected or imperfect time than to spend a lot more when I’m perfectly ready. At the end of the day, if you’re going to spend the money anyway, it’s better to do so when it will mean the most savings. As they say, sometimes you just have to jump and build your wings on the way down.

While all of this has helped me consistently fly the world on a budget, there’s nothing cheaper than free. That’s why I’m a huge proponent of using credit cards that give you airline reward miles. At least once a year, I take a flight that costs me all of $12 in fees. Sometimes to Las Vegas or Washington, but sometimes to Europe. If you don’t have such a credit card yet, you’re in luck. Most credit card companies offer sign up deals that give you anywhere from 20,000 to 40,000 for joining. By earning miles from travel and your regular spending, you’ll start to see your balance go up steadily. The more you can use the credit cards for the better – rent, car payments, groceries, gasoline. Even if you can pay for those things in cash, take an extra step and charge it to Visa before you pay it off. Take it from me and my gnome, when you’re on a free flight to Germany, you’ll be glad you did.


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