How I Book Flights

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There are three factors I consider when booking a flight.

  1. Price
  2. Destination
  3. Departure Time

Two factors: departure time and price, matter a lot to me. As a weekend traveler, I have to maximize my time and want fly out the night I leave work (usually a Friday night) and I try to return as late as possible on the day before going to back to work (usually a Sunday but sometimes Monday morning). Because, like most people, I have limited funds and a budget, I have to be smart when booking flights. So far, I have been able to find good flight deals and almost never use miles.

The third factor, destination, sometimes matters. My flight booking strategy changes depending on whether the destinion matters or not.

Situation 1: No Destination in Mind

This accounts for at least 80% of my flights. I really do not care where the plane is going as long as it is going somewhere.

Step 1: Figure out how much flights costs

The only way to know what a deal looks like is to first know how much a flight normally costs. Sometimes advertised flight “deals” are not deals at all.

Building up this knowledge base is not easy, and requires many hours of searching for random flights on Kayak and Google Flights. The time spent will eventually pay for itself.

Step 2: Find the cheap destination

Once again, there are many “right” ways to find travel deals. Here are some methods that I use.


I “like” travel-related Facebook pages that tell me when there are flight deals. The links will usually say how to book the flight. If the link takes me to a sketchy page, I will search the flight details on Kayak/Google Flights and book it through there.

Some pages I “like” are the airline pages (JetBlue, Southwest, Spirit and Alaska have more flash sales than the legacy carriers), travel magazines (Conde Nast Traveler is a favorite), Travel Deal sites (TheFlightDeal, Travel Pirates, and Hopper), and travel bloggers (Points Guy, One Mile At A Time)

Example of a flight deal Facebook post

Flight Deal Websites

  • Kayak’s Explore Tool– This pulls up a map of the world with destinations with associated pricing based on date parameters. Usually the fare listed is at an inconvenient time, but it gives information on where the cheaper destinations are.
So many choices!
  • The Flight Deal– lists flight deals that fall under their allowed price per mile metric. They tell you how to book. Many of the deals on the site are error fares and are only valid for hours to a day.
  • Google Flights– Google’s airfare booking site has a unique “regional search” feature. Rather than having to select a specific airport or city, Google Flights allows you to search broad regions and countries such as “Europe” or “Mexico”.

Picking random destinations on Kayak

Set your dates and home airport and play around with typing cities you want to visit in the destination panel. This is surprisingly effective and can lead to unexpected results.

Probably not going to book Charlotte right now

Home Airport Flight Board

Look at your home airport’s flight board and then figure out how much it costs to go on those flights by using Kayak or Google Flights.lax-departures

Step 3: Book the Flight

  1. Before booking, I will often check the weekend before and for better deals.
  2. The sweet spot for booking cheap non-promotional domestic tickets is usually 3-6 weeks before the flight.
  3. Fidget around on Kayak/Google Flights/Momondo to make sure that you found flight times that work for your schedule.
  4. Book the flight on Kayak, Expedia, or the airline’s website even if you found the deal elsewhere. They are reliable and will ensure you book the cheap fare.

WARNING: Make sure to select either Kayak or the airline’s webpage when booking a flight. Kayak will often allow you to save $10 or so by booking on a third party site such as JustFly or CheapOAir. Do not book on these sites- they can and often- cancel your ticket without warning and make it a nightmare to change/cancel a reservation.

5. Airline sales often last only for a day or two. If you see a sale and the dates work, book it immediately because the price could change overnight.


  1. Empty the cache on your browser or browse with private mode on. When determining prices, airlines use your internet data to determine your level of income and travel savviness. Searching for flights in private mode will eliminate data points used by the airlines to raise prices on you.
  2. If you have a flexible schedule, flights are usually cheapest on Tuesdays, Wednesdays, and Saturdays.
  3. Consider flying to destinations in the off-season: cold destinations in the winter and tropical destinations in the summer. Due to a lower demand, airlines will have lower prices and often sales to these destinations.
  4. Look for new routes. Airlines will often celebrate the opening of a new route by offering promotional fares for the first month of its opening.
  5. If the deal looks good enough, just book it and be happy you’re going on a vacation. You may not always find THE cheapest fare, but in this game, close is good enough because of the uncertainty of airline fares.
  6. There are some destinations that never seem to be cheap (Cabo San Lucas is only a 90 minute flight from LA, but I have never been).

Situation 2: Specific Destination in Mind

Sometimes an event such as a wedding or a family reunion comes up and you have to be there.

Here is how you get the cheapest flight to a destination.

Step 1: Determine the range of prices to a destination.

The website and app Hopper will tell you how much flights are between destinations over the next 6 months. The low end of this range is how much you will want to pay. Do this step 3-4 months before the flight.

Looks like weekdays during the last week in March, May, and August are good times to book Seattle flights.

Step 2: Wait for the right moment

Track the flight on Google Flights. Google will send you emails when the flight price changes. Watch the fluctuation and be patient over the next 2-3 months.

Missed the boat on El Salvador tickets.

Step 3: Book the Flight

When you get an email from Google saying that the flight price is close to the bottom of the Hopper flight price range, go to Kayak or Google Flights and book it. Flight prices can change overnight so be ready to pounce.


  1. Sometimes two one-way flights on different airlines are cheaper than a roundtrip fare. This is especially helpful when looking at routes served by Southwest, which does not list fares on Kayak.
  2. When booking international tickets on an airline’s website, change your Home location to a foreign country that is cheaper than the US. This will actually give you better deals- although you will have to navigate a foreign website and convert currencies. Kayak is US-centric and will not give you the foreign fares that may be much cheaper than the listed Kayak fare. I have used this trick to save $50.

That’s about it. There is no exact science to finding the cheapest flight, as the airlines have very complicated reasons for their ever-shifting prices. Happy Flying!


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