Keyes has become so gifted at landing super cheap tickets and getting the most out of his frequent flyer miles that he has booked an epic world trip that spans 13 countries, 20,000 miles, and 21 flights — all free.
He told Business Insider his process is a “labour of love,” and after spending five years dedicated to finding airline deals, Keyes now knows the best websites, tricks, and tips for getting tickets for dirt cheap prices.
Keep reading to see his 14 best travel hacks.
Set up a Tweet deck and email alerts
If you’re truly dedicated to finding cheap flights, it has to be a lifestyle. Keyes has alerts and a Tweet deck filled with airlines and websites that he follows to discover affordable tickets.
Your odds of scoring bargain tickets will also skyrocket if you set up newsletter alerts from travel websites like Airfarewatchdog and The Flight Deal. You can even sign up to get emails from Keyes himself when he stumbles across a deal.
Search for flights from all nearby airports
This one might seem obvious, but if you’re flying from a hub like New York City, make sure you’re not only searching flights leaving from JFK or LaGuardia and include the nearby Newark airport, too.
“If you live in an area or are flying somewhere where there are a lot of airports, search them all,” Keyes advised. This could save you hundreds of dollars, even if the airport is a little out of your way.
Do a ‘month search’ on your itinerary
“I flew to Costa Rica once a couple years ago and I did a month search on ITA Matrix,” Keyes told us. “Instead of going in the first week of April, I realised I could go in the second week of April and save over $US100.”
If it doesn’t make a difference when you get to your destination (even if it’s a matter of getting in Thursday instead of Friday), searching for an entire month can save you a significant chunk of cash.
Compare prices on Southwest separately
Affordable airline Southwest will not show up in aggregate search engines such as Kayak or Orbitz.
It’s annoying, but always worth it once you find a decent-priced domestic flight to see if Southwest has something even cheaper. This goes for all budget airlines that may not be showing up in search engines, too.
Always check for “throwaway tickets”
Throwaway tickets are flights you purchase to an unpopular destination. Let’s say you’re travelling from New York to Chicago — those tickets are going to be quite expensive. But New York to Milwaukee will be less expensive since fewer people will be travelling there.
A throwaway ticket would be if you found a flight from New York to Milwaukee with a layover in Chicago. Then instead of getting on the plane to go to Milwaukee, you would throw away that leg of the ticket and exit the Chicago airport.
“This one can be a huge money saver,” Keyes said of the hack. If you want to find throwaway tickets, check one of Keyes’s favourite websites Skiplagged that specifically searches for them (though due to a lawsuit, you currently can’t buy the tickets through Skiplagged, but through a third party site).
Book at the right time
“A big mistake that people make is buying either too early or too close to the departure,” Keyes told us. “Wait until between three months to a month out because that’s when you tend to get the best prices for domestic flights.”
That’s for off-peak flights. If you’re hoping to fly home during the holidays, book a trip to Europe, or fly during a time period where a lot of other people will be booking (like for spring break), Keyes suggests looking at flights about six months out.
Buy the cheapest ticket, no matter when it is
“The way most people approach airfare, they do it backwards: They decide where they want to go and then try to find the cheapest flight to get there,” Keyes told us. “But if your ultimate goal is to be able to find as cheap a flight as possible and go somewhere cool for not much money, then starting with an open, blank slate and going wherever there’s a cheap flight right now is going to be your best bet.”
That’s how Keyes wound up flying to Milan for $US130, going to Galapagos for $US45, and visiting Norway and Belgium for around $US350 instead of the typical $US1,000.
None of these destinations were necessarily on his ideal travel list, but because Keyes found deals on Twitter or through websites, he decided to buy them right away and ended up saving thousands for being flexible.
Fly on the cheapest possible days
Keyes told us the cheapest days to fly are Tuesday, Wednesday, and Saturday. If you’re going home to visit your parents over a long weekend and were planning to fly in Friday and leave on Sunday, search Thursday to Saturday or even Friday to Monday instead to see if there’s a cheaper alternative.
“If you have any flexibility in being able to fly on those days, that’s usually when you’re going to find the best fares,” Keyes said.
Don’t be afraid to complain (politely)
“One of the things I’ve been able to employ rather effectively is when things go wrong on your flight, you can get compensation for those errors,” Keyes said. “I’ve gotten miles for it and I’ve gotten money for it.”
If something goes wrong — say the TV in your seat isn’t working or there are mechanical issues with the plane — it will never hurt to send an email to the airline politely informing them of the problem. Keyes even created special email templates in his book “How To Fly For Free” that he’ll use if something happens.
The key is to be polite, give the airline all of your information (what seat you were in, the flight number, etc.), and inform them that usually you love flying with them, which is why you were so surprised by the inconvenience.
“As long as your grievance is somewhat legitimate (and not outside the airline’s control like the weather), most of the time you’ll actually get some sort of compensation,” Keyes said.
Be open to getting bumped
One of the most dreaded travel experiences is being bumped from a plane or having a delay. But Keyes insists that this is a fantastic way to earn free money or frequent flyer miles.
If a flight is full and you’re not under any tight timeline, take advantage of being bumped and ask the ticketing agent if you can get money or frequent flyer miles instead of flight vouchers for your inconvenience (they will usually honour your request).
“I was once given a $US500 voucher and a confirmed seat on the next flight — an hour and a half later,” Keyes wrote in his e-book “How To Fly For Free.” “In other words, I earned $US333/hour. Like me, if your goal is to fly for free, you probably don’t make $US333/hour. Plus, unlike flights you book using miles, you actually earn miles when you pay using a voucher.”
Open credit cards (smartly) to get lots of miles
“If you’re financially smart and responsible, there’s so much opportunity for you,” Keyes told us.
Keyes currently had 25 credit cards that he uses to get hundreds of thousands of miles and points, which ultimately helps him fly for free. He monitors his credit score, always pays off his credit cards in full each month, and keeps track of his miles and cards at websites like AwardWallet.
Though that sounds like a lot of work, it’s a lifestyle that Keyes has built up to.
“Over time, you start to ramp up your credit cards slowly but surely,” Keyes said. “Don’t go open six cards right off the bat, but go at your own comfort level and slowly work your way up.”
Choose credit cards that give you the best perks
“I enjoy flying because I can get into these lounges and that just makes the experience a whole lot more pleasurable,” Keyes said. “You can have free beer and free WiFi and get out of the hustle and bustle. They even have perks like showers in here and free spas.”
To access the luxurious world of airport lounges, Keyes uses his credit card perks.
“Every airport has different lounges and it just depends on the credit card whether it will give you access,” he told us. Do some research about what lounges are at your most frequented airports and see if there is a travel credit card you can sign up for to access them.
Get a free stopover trip with your frequent flyer miles
Airlines charge a set number of frequent flyer miles for certain places around the world, no matter where you go. For instance, an economy ticket from the US to Eastern Asia on United will cost you 65,000 miles, whether you’re travelling to Taipei or Tokyo.
But Keyes said that airlines will let you have a free stopover with your frequent flyer miles — something many people don’t realise. That means you can book a flight from the US to Tokyo, but fly back to the US from Taipei.
You’ll need to book separate travel accommodations to get from Tokyo to Taipei, but the ticket will likely be pretty affordable. “You can add a whole other destination to your trip for almost nothing extra,” Keyes said.
Make your miles go further with long layovers
Most frequent flyer users don’t realise that you can take a layover of less than 24 hours for an unlimited amount of flights.
If you’re willing to do the legwork and research, you could see a lot of different countries on your way to a destination with this hack.
“Say you’re flying in the South Pacific and you’re willing to spend less than a day in each place, you can fly from New Zealand to Cook Island to Guam to Singapore to Bangkok and basically do all this for the price of one awards flight,” Keyes said.
You may not be able to soak up the feel of each city for only a day, but it just goes to show that with a little planning, you can see the world.