How To Find and Book Cheap Flights and Airline Tickets

If you want to get the cheapest flights possible, focus on getting the cheapest fares across the ocean, even if it’s not from your home airport or to your ultimate destination. Two itineraries are frequently cheaper than one. Plus you can stay and explore the city (in this case NYC or Brussels) as long or as short as you like.

Flexibility. This is the way most people approach getting a flight: (1) pick where they want to go; (2) pick their dates; and (3) see what prices are available. Typically this results in high prices.

Instead, if getting a cheap flight is your priority, flip that approach: (1) see what prices are available via Google Flights, Momondo, etc. to various places are around the world; (2) decide which of the cheap destinations appeal to you; and (3) select the dates you like that have the cheap fares available.

Plus, like I discussed above, once you get to Europe or Asia or wherever, it’s really easy to hop a budget flight to your final destination.

Be flexible with where and when to go. If you’ve picked out your destination, picked out your dates, and don’t have flexibility, 95% of what you can do to bring down the cost of airfare is already out the window. Flexibility is king.

Sidenote: Be sure to search more than one date. (Clicking the calendar in Google makes it easy and shows you cheap fares for two months at a time.) Often times shifting the dates by even a day can cut the price in half.

Southwest & Skiplagged. Be sure to search Southwest.com separately since Southwest flights don’t show up on any flight search engines. For domestic flights, check out Skiplagged.com for some possible cheap hidden fares, but be sure to read up there on the basis of “hidden city ticketing” so you know what you’ll be doing.

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When is the cheapest time to fly?

Cheapest time of year to fly:

  • January through mid-May
  • September through early December

Most expensive time to fly:

  • Peak summer (mid-June through mid-August)
  • Christmas/New Year’s

It will also vary a bit by the specific destination, especially around popular festivals. Fares to Dublin for St. Patrick’s day or to China for Chinese New Year ain’t cheap.

When should I book my flight?

In terms of how far in advance, I typically recommend booking when you see a great fare 1-3 months in advance for domestic flights and 2-8 months in advance for international flights. (If you’re booking for peak summer, I’d add a month or two onto these recommendations, and if you’re traveling during low season it’s more likely cheap fares will pop up closer to departure date.)

Prices tend to jump in the last month or two before departure, so you don’t want to cut it too close. On the other hand, if you book too early and settle for a not-great fare, you’re missing out on potential future sales. Of course, if you’re looking to travel around major holidays like Christmas or during peak summer, I’d add a month or two on those recommendations.

In general Tuesday, Wednesday, and Saturday are the cheapest days to travel. Friday and Sunday are usually the most expensive days.

It’s a recurring Internet myth that booking at a specific time each week (typically cited as Tuesday at 2 pm or so) is when the cheapest flights are available. This was the case a couple decades ago when airlines loaded their fares once a week but hasn’t been true for years.

I found a great fare. How long will it last?

Hard to say for sure! Unless it’s an advertised sale (which usually aren’t that great, to begin with), there’s no public end-date on any given fare. The rule of thumb is that the better the fare, the shorter it will last. In general, I wouldn’t expect most great fares to last longer than a few days.

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Why aren’t there more deals from my airport?

Check on cheap flights  

I have specific dates/destination. How can I track fares for that?

Both Google Flights and Kayak let you track a specific trip and get alerted when the price drops.

General “really good fares” from US

  • Africa – $800 or below
  • Asia – $500 or below
  • Australia – $800 or below
  • Caribbean – $300 or below
  • Central America – $300 or below
  • Europe – $500 or below
  • Hawaii – $400 or below
  • South America – $600 or below

I found a cheap flight that departs from City A, connects through City B, and arrives in City C. If I live in City B, can I just skip the A-B leg?

No. Once you miss a leg of an itinerary, the rest of your itinerary automatically gets cancelled out.

The only way skipping a leg can work is (a) if you buy two separate one-way tickets rather than a roundtrip, or (b) if you just skip the very last leg of a roundtrip itinerary, in this case from City B to City C. This is a practice called “hidden city ticketing,” which the airlines don’t like (so don’t advertise your plans!) but has a seal of approval from the New York Times Ethicist.

Should I clear my cookies before searching?

No. It doesn’t make a shred of difference.

Where should I search for flights?

My three favorite tools to search for flights are Google FlightsPriceline, and Momondo. There are also some more complex ones like the ITA MatrixSkyScanner, and various plugins, but for most folks Google Flights, Priceline, and Momondo are plenty. (Remember that Southwest doesn’t show up on search engines, so check directly on their website.)

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Should I try to get a standby fare? Or book unsold seats at the last minute?

Basically, no. Last minute deals can pop up, but it’s increasingly rare. In the last week or so before a flight, the price tends to skyrocket. This wasn’t true 20 years ago as airlines slashed prices to fill unsold seats, but nowadays airlines jack up prices on unsold seats knowing that business travelers are far more flexible on price but can’t make plans until the last minute.

How do I find cheap one-way tickets?

For most carriers, one-way flights are significantly more than half the cost of a roundtrip flight. If you want to fly into a different airport than you will depart from, usually better to book an open-jaw flight (flying A to B, then C to A) on one itinerary rather than two separate one-ways.

Airlines whose one-way flights are around half of a roundtrip include jetBlueWOWNorwegianCondor, and basically all intra-continental budget carriers like Ryanair and Air Asia.

How do I find last-minute flights?

Pray.

In all seriousness, it’s pretty rare to find cheap last-minute flights because airlines typically jack up the price to gouge business travelers who are last-minute planners and not very price-sensitive. Cheap last-minute flights are more likely on international routes than domestic routes because business travelers don’t fly international routes nearly as much.

But other than using the tips above and generally searching Google Flights, Momondo, Skiplagged, and Southwest.com separately, there’s not a separate strategy for finding cheap last-minute flights.

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