Travel Hacking Masters Share Their Secrets For Finding Airfare Deals

It’s travel hacking Thursday! So far, we’ve tapped travel experts and point hacking gurus for tips for earning and redeeming points, how to score last-minute deals, their favorite travel credit cards, and how to maximize points on everyday purchases.

One thing we haven’t yet touched on: is how to unlock incredible airfare deals. You can’t travel the world without getting yourself on a flight — so why not ensure that you’re practicing all the same strategies as travel experts to get the best deals?

If you want to get yourself to one of the coolest parties around the globe this winter and spring, head out on a gorilla trekking adventure in Rwanda, or make it to any of the month-long Mardi Gras parties in New Orleans this month, use these tips to unlock your greatest deals for airfare this year.

Thomas Lonergan (@travelliketommy): Use Positioning Flights & Sign Up For Award Alerts


First thing is first: be flexible!!! Base your travel on flight availability, not off of set dates. Also, positioning flights is key! Bigger airports have more flights and more business/first-class availability. You also should consider either booking way in advance or last minute.

It’s actually easier to book last minute when using points! You should also 100% sign up for award alerts like and Roame.

Michele Lowery (@fancytravelpointers): Do “Dummy” Award Searches Two Weeks Before Flights Are Released

Michele Lowery

There are two strategies for getting the best international award flight deals – book as soon as they are released. Or book within two weeks of the flight.

For many families, like ours, booking early is the best option as you need to work around school schedules and can’t realistically pull your child out of school/sports for a good deal you found last minute.

Many airlines release award flights at 330 days (11 months) out. It is in your best interest to start doing “dummy” award searches about two weeks before flights are actually released. This will give you a good idea of what airlines/routes may have award seats, how many seats they are releasing, and if you have enough points/miles for that booking.

Also very important, is to focus on earning transferable/flexible points (like Chase Ultimate Reward points, American Express Membership points, or Capital One miles) so that you have more options. If you only have “airline miles” with one airline, you’ll be stuck with whatever award flights that specific airline releases. But if you have transferable/flexible points, you can find the best award flight deal and then transfer points/miles for that award flight.

Spencer Howard (@straighttothepoints): Have Flexible Dates

Sign up for business and first-class flight alerts here.

spencer howard

Be flexible. Whether you’re looking for a cash ticket or an award ticket so you can use credit card points or airline miles, be flexible. The more flexible you are with your travel dates, your routing, and what airlines you’re willing to fly, the easier it will be to find something that works for you.

Adam Hill (@adamhillyeah): Flexibility Is Key


Adam Hill

First and foremost, flexibility. This is key. Airlines will release mistake fares, insane cash fares, and open coveted award availability for specific dates. When this happens, you either are an opportunist and jump on the deal or you miss out. Many people hold themselves back from this as they set a date first when they WANT to travel rather than having the mindset of when they CAN travel. People are bound by an allotment of vacation days or PTO available. I work as a fireman and am fortunate enough to have the ability to trade my 24-hour shifts with colleagues to have the flexibility to make travel dates possible. I still have to work the days my colleagues work, however.

For bragging purposes only: I managed to find a round-trip flight from LAX-CPH for $252. I was able to upgrade at the airport on the return leg to business class for $450. For those who rely on PTO or have to request vacation days, I recommend booking and securing a ticket first, then worrying about asking for PTO. With the DOT behind you, you have 24 hours to cancel an itinerary booked if it doesn’t work for you.

If you can try and incorporate your dates over a weekend or through the days you normally have off.

Finding good cash fares can be tricky. There are a ton of services like that alert paid subscribers of mistake fares or cheap cash fares, but that also require flexibility. Is there a theme arising here? Google Flights and is a superb way to search for flights. Using a VPN from another country can sometimes show lower fares, but we NEED to stop the myth of booking on a specific date or booking a specific number of days out and going incognito. Airlines typically publish fares based on demand and are dynamic. The cheaper fare class typically goes first and the price goes up from there, usually.

Using points for the lowest award rate can also be tricky as it requires the airline to release award space. You can make this easy on yourself by subscribing to a service like Straight To The Points or Thrifty Traveler. These sites alert you for award availability. If you are searching via airline award charts, I recommend starting early, or rolling the dice and booking close-in to the date you want to travel. I’ve found first-class award tickets two days before I wanted to travel.

Bottom line, there are many different methods and ways to go about finding cheap ways to travel, the biggest takeaway is being flexible. Happy travels!

Vivian Tu (your.richbff): If You’re A Student, Use Student Discounts To Get Cheap Airfare

Order “RICH AF: The Winning Money Mindset That Will Change Your Life” here.

Vivian Tu

This one goes out to all of my youngins because I really wish I had known about this when I was in college. There are so many cool websites and brands that you can tap into that provide student discounts on flights. Student Universe is a top site where you can book your travel through them and it typically lends 10-15% off. That allows you to keep more money in your pocket and use that money for books, housing, food, and more.

You can also go to Kayak and search for your departing and returning dates on your flight, under the traveler section you can choose the option for “student.” Instead of putting adult, put your traveler search as a student. Kayak actually aggregates flights through Student Universe, Flyla, and Scholartrip to offer discounted flights for students across all major airlines so you can see all the discounts available. Most of these require you to be a student aged 18-24.

These can be especially useful for those flights home for holidays during school breaks

Allison Tackette (@luckytictac): Be Flexible & Search For Flights Out Of Neighboring Airports


Allison Tackette

If you come into trip planning saying “I want to fly United on Saturday at 6 PM” — you’re setting yourself up for failure. Flexibility is the biggest factor in finding incredible airfare deals. Have flexibility with dates (even if it’s a day or two) and routing. There may not be a flight from your home airport, but there is out of different airport.

Your flexibility can be the difference between a 500,000-point flight and a 60,000-point business-class flight. The more flexible you can be the more successful your award searches will be. You might even get a better in-flight experience out of it!

Angel Trinh (@pennywisetraveler): Either Book Very Early Or Very Last Minute


Angel Trinh

You need to either book very early or very last minute when award space opens up. Most airlines open up award space availability almost a year out, but sometimes award space is not released until two weeks before the date of travel.

I have booked flights within a few days because the business class seat opened up at the last minute. For example, sometimes I will book an economy ticket to get a seat to my destination and then I will cancel my flight (it’s free on American Airlines) and the miles will go straight back to my account. I will then use the miles to book my business class seat once American Airlines releases the seat for business.

Ryan Horn (@profitsandpoints): Join A Cheap Flight Newsletter


ryan horn

There are five different strategies that I always use to make sure that I find the cheapest flights possible:

1) Join a Cheap Flight Newsletter: There are a growing number of cheap flight newsletters out on the market. For the price of a subscription, most of these newsletters will send the lowest-priced flight deals they can find right to your inbox. The companies that run these newsletters typically employ people who spend hours each day searching for the cheapest flights meaning you won’t only save money, but you’ll also save time.

2) Set Price Alerts: Google Flights has an awesome feature that allows you to receive an email whenever the price of a flight you’re looking at goes up or down. These alerts can help you time when to commit to purchasing your flight.

3) Consider Flying Out Of/Into Alternate Airports: Probably the biggest factor in determining the price of a flight is where you’re flying from or where you’re flying to. By looking at other airports that may be a short drive from your first choice airport, you open up the potential to save a lot of money. Advanced travelers may want to also consider positioning flights. A positioning flight is a flight that you would take to get to an airport whose airfare is cheaper to your final destination. It’s basically like creating your own layover. Just be careful to leave enough time in case something goes wrong with your positioning flight.

4) Rebook Your Flight If The Price Drops: Many airlines will allow you to receive a credit/points/refund if the price of your flight drops. My favorite example is Southwest Airlines. If the price of your flight drops, you can rebook your flight through Southwest and receive a credit for future travel equal to the difference in the fare. If you paid with points, the difference in Rapid Rewards points will automatically go back into your account.

5) Flexibility, Flexibility, Flexibility: Finding cheap flights ultimately comes down to flexibility. Are you willing to fly on a different day? Are you willing to have a longer layover? Are you willing to travel somewhere slightly different than you had first planned? The more flexible you are, the more likely you are to save money on air travel.

Angelo Minella (@paidwithpoints): Subscribe To Award Booking Newsletters

angelo minella

There are lots of newsletters that you can subscribe to such as Straight To The Points Premium Newsletter which sends out award bookings. This is a great way to always stay on top of when award availability opens up and to book your trip before news spreads too fast.