The Holy Family - Michelangelo Buonarroti

Flight Tips

People often ask me how do I find inexpensive flights? The answer is simple. Fly off-season and be flexible with your schedule.

The Holy Family: Michelangelo
Uffizi - Florence, Italy

Flight Tips


People often ask me how do I find inexpensive flights? The answer is simple. Fly off-season and be flexible with your schedule. I usually fly late fall or early spring. I look for the most economical flights within an extended range of possible dates and comfortable flight times for the outbound and inbound flight. Before purchasing the ticket I make sure I have reliable transportation to get me to the airport on time. I will never give up comfort to catch an out of the way flight to save a few dollars. The sheer anxiety and discomfort is exhausting. I am speaking from experience. Never again!


My rules when searching for a flight are as follows:

  1. Pick a month you want to travel.

  2. Pick how many days, weeks or months you want to travel.

  3. Pick what time of day is most convenient for you to leave according to your transportation arrangements.

  4. Pick a few airlines you want to fly.

NOTE: Don't always buy a ticket according to your frequent flyer program just to earn points. Sometimes it's best to get a cheaper more convenient flight instead of earning extra points.


On rare occasions it's cheaper to buy two one-way tickets on different airlines instead of a roundtrip ticket on one airline. Depending on your travels it's better to fly into one city or country and fly out another instead of purchasing a round trip ticket. This is called an open-jaw ticket (also known as multi-city ticket). This type of ticket is perfect for visiting several cities or countries. Why travel back to your arrival city if your hundreds of miles away? May cost a little more money but your time is very precious.


There are many websites that offer great deals on flights. I have listed below my favorite websites that I only use and why I use them. Each website offer something unique for finding flights. Get a feel for each website until you find the site that's most comfortable for you.

  1. Matrix Airfare Search - search flights using a calendar of lowest fares

  2. Kayak - search flights including nearest airports

  3. Skyscanner - search flights by the cheapest month to anywhere

  4. Orbitz - search flight and hotel package deals

NOTE: It's best to book the flights directly with the airlines or a travel agent. If anything goes wrong it's easier to deal with airline instead of a third party who sold you the airplane ticket. Make sure to write the flight numbers and time from your search in order to book the flights with your airline of choice.