[Jake’s Tips] – Finding Cheap Vacation Flights

Want Cheap Vacation Flights

Hola my fellow Flight Searchers,

Vacation airfares suck…….

I remember flying to my favorite Margarita destination for $279.

Now $279 is just the tax.

But – don’t despair, mi amigos – there are still ways to find some very cheap vacation flights.

In this episode of Ramblin’ Jake,

I will share insider secrets my teammates use to get me to the sand – without taking out a loan.

But first,

for you ADHD mofo’s who open a book and head for the last chapter, let me answer your question about how to find the cheapest vacation flights.

There are 2 ways…..

  1.  Find a Travel Wholesaler that is liquidating ‘Charter’ or ‘Risk Air’ seats at a huge discount.
  2. Do a MetaSearch for prices given to companies outside the US.  (its called Geo-Pricing and these deals find their way back to the US via the MetaSearch engines  

There you have it…….you don’t need to go any further.


you dare follow me down this page to the ‘Dark Side’.

If you do, you will know more than 99% of the so-called ‘Travel Experts’ out there.


a checklist of the methods we use to uncover cheap flights – we’ll cover each below:

  • 1. ITA Matrix – The ‘Magic Tool’ that savvy Frequent Fliers use
  • 2. Google Flight Search
  • 3. Discount Airlines
  • 4. Online Travel Agencies (OTA’s)
  • 5. MetaSearch Engines
  • 6. Charter Airfare & Risk Air Seats (the cheapest)
  • 7. Finding ‘Airfare’ or ‘Instant’ Credits
  • 8. Using Airline Credit Card Mileage
  • 666. The ‘Dark Side’  – use at your own risk.
    • Sleep with a Travel Agent
    • Frequent Flyer mileage brokers
    • Discount Coupon Books
    • Become a Travel Writer
    • Mistake Fares –  aka ‘load’ errors

Here goes:

#1. ITA Matrix


The ‘Magic Tool’ hard-core Frequent Fliers use.

The backstory….

In July of 2010, Google spent $700M and bought ITA, the grandmother of all airfare search engines.

ITA Matrix Homepage

That sent a HUGE shiver down the spine of the travel industry.

And for good reason.

ITA is ‘THE database’ that airlines use to distribute their flight info to most websites like – Google Flight Search, Expedia, Kayak, Cheaptickets etc.

Let’s look under the hood:

What sucks about ITA Matrix?

  1. ITA’s interface is old school and can be complex
  2. It is sometimes very hard to find ITA flights on the airlines’ own websites
  3. Sometimes a search will ‘stall’ after 90 seconds (this is a bug they are fixing)
  4. You cannot book your flights thru ITA once you find great prices

What’s great?

  1. It is the only site that does not restrict you to what ‘they’ want you to see
  2. It is fast once you get used to it
  3. You can check other currencies if that works out cheaper for you
  4. It’s a magic secret that very few people aside (from the Pros) know about

Tips on how to milk ITA for great insights once you have done a Standard Search:

  1. Check other airports around you (click on ‘Nearby’) or currency if you’ve got a bag of Pesos.
  2. Use the Calendar Option to check cheaper dates (click on ‘see calendar of lowest fares’)
  3. Check the advisory filter for warnings (like “it’s always freakin’ late”)
  4. You can book the ITA results using www.bookwithmatrix.com website

Start by doing the Standard Search from the Homepage

1.   Check other airports around you  (click on ‘Nearby’) or currency if you’ve got a bag of Pesos.

ITA - Standard Search

2.   Use the Calendar Option to check cheaper dates (click on ‘see calendar of lowest fares’)

ITA - Calendar Search

This is the ITA – Calendar

ITA - Calendar with Stops & Airlines

3.   Here you can have fun with the Filters.

ITA - Flight Display

4.  Click through to the Flight Display for details.

ITA www.bookwithmatrix.com

5.  After you have found the perfect combination of flights – you can’t buy it – (unless you use www.bookwithmatrix.com)

Start here, you will be glad you did

Now on to #2, Google Flight Search…

#2. Google Flight Search


Google Flight Search Homepage

Google Flights stomped onto the scene like a giant gorilla and crushed Kayak’s grip on the best way to find cheap flights – in less than a year.

For 1 reason……

Google dominates the search process.


now Google has forced airlines to compete with themselves (and each other) on providing Google Flights with their cheapest prices.

It was brilliant.

Spirit Air was the first airline to realize they could use Google Flights to upend their competition.

The last time I checked, if you wanted to fly from Phoenix to Cancun you paid:

– American = $600+

– Spirit Air = $241

Guess who was #1 in the search results?

People did not care if they had to leave at midnight, spend hours in another airport and arrive in Cancun the next night…….Hell, they were saving money!

So the BIG airlines had to play the game.  Here is what they said (and I paraphrase):

‘We hate f!@#ing Spirit Air!  Those b#$tards are nickle and diming us!  Don’t they know who WE are!

Actually, this is exactly what American Airlines said:

– 87 percent of American’s passengers fly once annually, but comprise half the airline’s revenue. “Given that 50 percent of our revenue is up for grabs in these markets, and these carriers (Spirit, Frontier) have had so much success when they weren’t matched, we know that we have to match their fares,”

(read the entire article here:  http://www.travelpulse.com/news/airlines/american-airlines-introducing-no-frills-fares.html)

So this is why Google Flights is the #2 stop on the yellow brick road to cheap flights.

Here are some tips on how to get the most out of Google Flights:

What sucks about Google Flights?

  1. They don’t have Southwest Airlines prices
  2. You need a Google Account to save Alerts and your fare searches
  3. Not much else

What’s great?

  1. How easy it is to use, especially the calendar pricing feature
  2. Airlines are offering prices on Google Flights that you can’t even find on their own websites.
  3. Once you do all your searching you go directly to the airline website to buy your ticket (no middleman)
  4. Their ‘TIP’ at the top of the flight display can save you lots of money
  5. You can save a search on your phone and buy it later on your laptop
  6. You can check hotel pricing at the same time you are searching for airfare

How do you get the most out of Google Flights?

  1. Search Tuesday at midnight to get the cheapest flights (per Google FAQ’s)
  2. Check 54 days before departure for the lowest possible price (per CheapAir )
  3. Search nearby airports with the ‘+’ button
  4. Set an Alert for price drops.  Pay attention when you get one. (but you have to have a Google account)


Set up Google Alerts for your airfare after you buy it……..if the price goes down you can’t do much…..but it will give you an idea of how badly you’re getting F’d by buying when you did. (It’s rare, but occasionally the price goes down by more than the change fee, in those cases, it’s worth calling the airline to take advantage of the price drop.)

Let me walk you through some tips and tricks:

[Tip]  1 – After entering your cities and dates you get a Flight Search results page – they usually have good tips.

Google Flight Search results page

[Tip] 2 – Check out the Search Tools Menu.  You can explore more options.

Google Flight Search Tools Menu

[Tip] 3 – Now check out the Explore Map to narrow down your interests (and get a price on your Hotel if needed).

Google Flight Search - Explore Map

[Tip] 4 – This is what the ‘Tracked Prices’ looks like.   It’s a handy tool that will keep you sane.

Google Flight Search - Track Price

[Tip] 5 – And finally……when you’re ready to buy your ticket…..Google sends you off to the airline to buy it directly.

Google Flight Search - Transfer Page

#3. Check Discount Airlines.

$1 flights

When you’re flying to the Caribbean and Mexico, check the airlines on this list:

#1 www.Southwest.com

They are one of the few big carriers that still does not play well with others. But, they bought AirTran and now are competing in Mexico and the Caribbean with the big boys.

[Tip] – If you go to www.SouthwestVacations.com you can occasionally find a scorching deal buying Airfare and Hotel as a package.

And Southwest does have occasional airfare-only sales that are incredible.

#2 www.Jetblue.com

Jetblue is not considered a ‘discount airline’ – but they occasionally offer specials to compete or to fill planes.

(IMHO Jetblue is the most comfortable airline to fly these days.)

#3 www.Spirit.com

Spirit Air offers a ‘Bare Fare’ that is pretty bare-bones….and it’s being copied now by Delta, United, AA, and others, typically called “basic economy”.

#4 www.FlyFrontier.com

Check these last 2 culprits for the lowest fares – Like these $1 flights – frontier-airlines-offers-1-flights-to-try-and-fill-seats/

Caveat Emptor – their customer service is legendary….not. And the cheapest airfares often mean NO pre-selected seats, NO use of overhead bins, and other NO’s.

[Tip]  Consider taking a discount airline to Miami, Dallas or Los Angeles – and then a major carrier like American/Delta/United for the short hop to the beach.

#4. Online Travel Agencies – (or OTA’s if you’re hip)


** Pay close attention.  OTA’s will sometimes price airfare and hotel together – lower than hotel only **

You know the OTA’s,

Expedia, which includes a bazillion other brands like Orbitz and Travelocity.

TripAdvisor, which was kicked out of Expedia’s nest and is currently trying to kick dad’s ass.

Priceline, with its big dogs – Kayak and Booking.com  (which get 2 thumbs up if you’re backpacking Europe)

Online Travel Agencies

and the little sisters:

CheapCaribbean and Bookit.

You can find the best price on OTA sites for 1 reason……volume buying power.

They handle 95% of all online travel bookings,


Do you know how Amazon changed the way you buy a product? (Thank you Prime……..people now go to Amazon first –  before checking Google/Bing/Yahoo, etc.)

Well, Expedia is trying to accomplish the same goal – only in the travel industry (since Amazon quietly bailed out of travel).

Expedia is discounting heavily so you’ll start your search with Expedia, use their scratchpad, and come back to buy…… And it’s working.


We do approximately 200 price searches each day testing the market pricing……..searches done by real people, not robots.

And we almost always find OTA’s to be lower these days (especially Expedia).

**In Fact **

OTA’s are known for selling airfare and hotel – for less than you can buy the hotel room.

They don’t advertise this…..so set alerts or keep checking……..but we see it too often for you not to take the time to check.

#5. MetaSearch Engines (aka Meta)

Even websites that are driven by MetaSearch Engines don’t know how to explain themselves.

So I will steal from Wikipedia:

Travel MetaSearch Engines

The Travel MetaSearch engines convert this long list of places to find prices:

MetaSearch engines for the Cheapest Flights

And turn it into this list: (plus a few more) like www.otels.com and www.easyclicktravel.com.

Travel MetaSearch Engines

Travel MetaSearch engines make your life much easier……


these websites above pull pricing from outside the US  (from all over the world).

Which means your $600-$1200 savings may require you to hand off your credit card to a foreign country.

These engines are driving Hoteliers nuts.


Hotels charge different prices in different regions of the world to stimulate business (it’s called geo-pricing).

So if you search for “RIU Las Americas in Cancun”, a MetaSearch Engine will search a huge number of websites worldwide.

It might show that in the UK the package is $1200 cheaper than buying it here in the USA with airfare.

Of course, the company in the UK with the cheap price is not supposed to advertise in the USA, but the metasearch engines are robots, their job is just to find and return prices wherever they can be found.

Everyone in the travel industry is screaming at each other these days due to the explosion of MetaSearch.

And they are not going away……Trivago just went public (with Expedia’s help) and loaded up its marketing war chest with $287 Million – for a major push into the USA.

Your dilemma is – ‘Do I want to give my credit card to someone in Singapore to save $1200’.

Maybe not this year…..but the world is getting smaller.

#6. Charter Airfare and Risk Air – Offered by Travel Wholesalers & Travel Agents

Charter Airfare and Risk Seats are the #1 way to get the cheapest vacation airfare.

You have all heard about charter flights.

$200 round trip to Cancun,  $179 round trip to Punta Cana, $249 to Hawaii.

Yes, these are still around…..but not as many. When charters get too popular the airlines drop their prices to drive them out of business.


you may not have heard of Risk Air.

Risk Air seats are pre-purchased from the airlines (like Frontier and American etc) by travel wholesalers for a discount.

When these seats are not sold……Wholesalers will liquidate them to get some money back.


**You have to buy these through wholesalers, travel agents or SunCountry**

So be sure to check with an expert travel agent (the key word is ‘expert’) to see if wholesalers are liquidating charter or risk air seats

I am not here to judge your skill on finding the best vacation price, – but an expert travel agent who only sells vacations to your chosen destination is worth their weight in savings.

Charter & Risk Air Liquidating

How do you think Travel Wholesalers are pricing trips so low?

Liquidating Charter & Risk Air

Here are some companies who will sell you charter and risk air:




travimp.com (Note: Travel Impressions only sells through Travel Agents but has a big list of charter flights)

Be sure to read the fine print……

And here is a charter airline you can book yourselfhttps://www.suncountry.com/booking/search.html
Charter Airlines can offer cheap airfares

BTW…..Here is a list of places we monitor for news, deals and blog info.  ‘[Checklist] – Finding the Best Deals on All Inclusive Resorts’. It’s very comprehensive.

What to know: Airfare options that Travel Wholesalers and Travel Agents have at their disposal – Here they are:

  1. Published Air – this is the same airfare anyone can buy from the airlines.
  2. Bulk Air – this discounted airfare is given only to Tour Wholesalers.  It allows them to package Air & Hotel together at a lower price.  If you have a problem while flying most airlines, their Customer Service agents will tell you that you have to call your travel agent for help.   After you have stood in line for an hour……
  3. Charter Air – we covered above.
  4. Risk Air – also covered above.
[Tip] – Want to freak out a Travel Agent? Ask them which of these airfare options above they are using when they quote you a package price with hotel & airfare….

They will know you’re savvy if you understand this much about the types of airfare they offer.

The devil’s is always in the airfare……..

#7. Airfare Credits

There are 2 places which offer Airfare Credits

  1. Destinations (Islands or Countries)
  2. Resorts

Let’s start with Destination Airfare Credits.
Bahamas Air Credit

The Bahamas, the Caymans, and Curacao are a few of the destinations that regularly offer Airfare Credits to stimulate travel if their bookings are soft.

The Bahamas is most notable for their $250 Airfare Credit they’ve been running for years.

What is great? These are real discounts.

What sucks? Unless the destination allows travel wholesalers to give you an immediate up-front discount, you have to buy your tickets and it can take ages to get the money (credit) reimbursed.

Now on to Resort Airfare Credits.

Mexico Air Credit

We love these….because they are really just an immediate discount in sheep’s clothing.

The resort will typically give you a discount even if you don’t book airfare.

How do you get them? You have to keep your eyes open and ask the resorts you are considering if they offer any credits.

#8. Using Airline Credit Card Mileage

Airline Mileage Cards

This would normally be #1 for me.

But with the merger of USAirways and American,

and the improvements in Google Flights,

This dropped down on the list.

I have found it very difficult to use mileage these days.

The airline consolidation, the drop in the number of available flights and the increased miles you need to apply have taken this tool almost out of the quiver.

There are lots of sites that compare cards and mileage vs cashback.

Check out www.thepointsguy.com –  Brian has a great site.

and www.WebFlyer.com – Randy Peterson is an industry icon.

(and be sure to check out the old-school Amex Gold card’s “Membership Rewards” program for easy mileage accumulation and redemption. Same with Capital One’s “MilesOne” cards.)

Here is a post on how to determine if miles will work for you  http://lifehacker.com/5941339/use-frequent-flier-miles-or-buy-a-ticket-heres-how-to-figure-it-out

Ok….now we are on to the Dark Side…….

Use at your own risk!

#666. The ‘Dark Side’

Sleep with a travel agent – or an airline employee.

Airlines offer employees and friends of employees “Buddy Passes”. They can fly standby on any flight.

But, Standby has more levels than Chichen Itza.   Everyone from the company CEO on down is assigned a priority level.

With so few planes – and every airplane flying so full – this is not as much fun as it used to be.   Getting bumped sucks.

Airlines offer travel agencies ‘AD 75’s’ – Which is 75% off your airfare.   VERY big agencies get ‘AD100’s’ – yep, 100% off (aka “free”!).

But they are tougher than hen’s teeth to get.

Fortunately, these are guaranteed seats and your chances of getting bumped are low.

Hotels regularly offer free or heavily discounted rates for Travel Agents ($25 to $75 or so per night for a 5-star All Inclusive Resort)

But discounts are reserved for Travel Agents who sell a lot….so be sure you’re cuddling with a high producer.

Frequent Flyer mileage brokers:

These guys make bank. They are like ticket scalpers.

Unfortunately for them the airlines ‘frown’ on mileage brokers…… so they tend to come and go in the night.

Brian at ThePointsGuy has an interesting post – http://thepointsguy.com/2016/03/should-i-use-mileage-brokers/

And here is a website that has been around for a while – https://flipmymiles.com/

Discount Coupon Books:

In my past life, we made a fortune using airfare coupons from the Entertainment Book – remember those?

It is my understanding that now CheapoAir is providing Entertainment their discount coupons.

It’s worth checking out.

Become a travel writer:

A few years back we had some spare time and created a website to help Travel writers become Travel Bloggers.


We have been asked on tons of free trips if we pimp their property……but who wants to work on vacation?

Still….if you love writing and traveling with other writers…….it can mean free hotel, food and if you’re a great writer with loads of outlets and a strong social media following, airfare too. Once you’re famous you can avoid the typical ‘fam’ trips or press trips and arrange your own by working with local tourism boards.

Mistake Fares –  aka load errors

You have all heard the story of the airline that sold tickets for $7

Actually we catch mistakes all the time on the Resort sites.

But, seldom do the airlines screw up loading airfares.

When they do –  it really takes you by surprise….you think you’re seeing things.

You keep refreshing your browser to be sure it’s real.

However….if it keeps coming back as a round trip flight to Jamaica for $5, buy it immediately.

……..and hope the airline does not find wiggle-room to cancel it

And, you now have 24 hours to cancel any airline ticket you buy when you are SUI (aka drunk-surfing, it’s not good.)

Here is some more info to educate you:


http://www.huffingtonpost.com/grace-mcclure/how-to-catch-an-airline-p_b_4644139.html – good format


So there you have it…….Jake’s Tips on Cheap Vacation Flights.

If you agree, disagree or have to pee……..leave me a comment!

Keepin’ the sand warm for ya!

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About Jake Johnson 249 Articles
Jake Johnson is a full-time travel bum, who prefers warm climates where the women wear less clothing. We've tried to teach him things like manners and diplomacy, but we've given up and simply rely on our editors to remove the most offensive bits from his articles. We take no responsibility for his inane ramblings opinions - they are his own.
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