Starting Travel Hacking, Part 2: Redeeming Points for More Travel

By September 5, 2017 April 6th, 2020 No Comments
photo: @dzzdzz012

This is Part 2 of a series. In Part 1 we covered how to collect points for nearly free travel.  

Many — probably most — people who collect air miles and points never use them. Or they use them once, get disenchanted by its limitations and never do it again.

Too bad for them.

I’ve saved over $60,000 in the past 10 years thanks to travel hacking. But key to accomplishing that is understanding that collecting points and redeeming points are equal partners. In other words, being all strategic about collecting miles and points through credit card signups, spending on camera gear, learning about photo and video editing, etc. won’t do you any good if you can’t put them to good use.

To begin with, it’s important to understand two basic truisms of redeeming miles and points for travel:

1) Over time the value of your points will decrease. Since the beginning of these programs, airlines and credit card companies consistently devalued them or made them more difficult to use over time.

Key takeaway: Over-saving points works against you. Redeem them sooner rather than later to get the most value.


2) The chance that you can redeem miles and points for an “ideal” flight is slim. This means you’re going to have to settle for long-ish layovers, lots of stopovers on international flights, and less than perfect times departure and arrival times.

Key takeaway: Focus on being grateful for the opportunity, not upset that the opportunity doesn’t match your ideal itinerary. Be flexible on dates, location and timing to get the most out of your points and miles.

In other words, the most important tool to have success travel hacking is your mindset — have a flexible, adventure-seeking mindset and you’ll have a blast; have a fixed, “my way” mindset and you’ll be frustrated. Sometimes it’s OK if you can’t get the flight via points. I always search for better flights on services like Airfare Watchdog — just to be sure there isn’t a paid flight that won’t work better for me.

photo: - O‘ahu

photo: – O‘ahu

The Basics of Redeeming Air Miles and Points

While every system is slightly different, the basics are all the same. When you begin collecting miles and points in a given program — either airline programs like Delta SkyMiles or credit card/bank programs like Chase Ultimate Rewards — you’ll be given an account ID number. Use this number to setup an online account… you’ll need it to redeem your miles and points.

When you are ready to redeem your points, the easiest method is to go to the airline website or program portal to search for flights. Generally, you’ll find the best values for redemption come from redeeming your points directly through an airline versus a flexible points program portal like Chase Ultimate Rewards or American Express Membership Rewards. These are still great programs, but typically transferring them to an airline program partner will allow you to stretch their value.

If you are on an airline, like the United Airlines example below, search both by flexible date range and award points…

United rewards search image

Most airlines will then return a calendar showing availability…

United travel rewards image

In this United example, the dates with the blue stripe reflect “Saver Award Economy” availability. That’s what I’m looking for! Obviously if you are a big shot who demands first class or premium cabins, look for those. But my motto is travel cheap, travel frequently, and since Economy seats are a fraction of the cost of premium seats, I have always flown economy. That allows me to book 3-4x more flights at the same price.

If you see dates you like, select them and follow the normal booking process. On most programs the flights are free except for fees + taxes, which usually range from $15-$75 per ticket.

Tips for Finding Better Free Flights

This is where things get advanced. Because most airlines offer a limited number of award-qualifying seats, you have to shop smart to find the best flights. I’ll share some of the big concepts of how to do that here and then we’ll dive in deeper in later posts.

Collect miles and points for programs that go where you want to go. I love the Eastern Caribbean. Lots of airlines go there and lots of them don’t. Best to put my energy into programs like AAdvantage, which has great Eastern Caribbean coverage rather than Southwest Airlines, which doesn’t.

Start shopping early. Most airlines begin releasing seats, including award seats, about 335 days before the actual flights. When I have a target destination, I start searching that far in advance. Often the seats still won’t be available, but I’ve definitely booked some of the toughest-to-get seats 300+ days in advance. If you browse around on different programs and with different itineraries, you can start to get a feel for when/how they release them.

Travel off-peak. If you’re willing to go even just a few weeks outside of peak travel times for your destination, the number of “Save Awards” seats available grows exponentially.

If you’re stuck, use the phone booking agents. They will charge you, usually $25, but it can often be worth it because they are better at putting together complex itineraries. Be patient and extra nice to the booking agents for the best results. I once spent nearly an hour on the phone booking a trip for my family of four to St. Lucia. The major legs of the flight were easy, but the commuter flights to the larger airports didn’t have enough seats… so we had to get creative. The result was about $5,000 worth of airfare for $450.

Be flexible with your airports. Is there a nearby airport you can drive to or get a cheap flight to? Can you fly into Madrid and take a train instead of going direct to Barcelona? Last year, I was shocked to see I could rent a car to an airport four hours away for only $20. I planned to rent a car one-way, then return directly to my hometown airport, saving me $600 in airfare. After all that, the airline ended up moving my flight by 12+ hours, so I called and asked if they’d let me fly out of my hometown airport. They agreed and I had no need for the rental car after all!

Learn the sweet spots. Different programs have different sweet spots. For example, on United, awards to Mexico “cost” the same amount of points as to anywhere in the Caribbean — and for just a fraction more you can get to Peru. Since using cash to go to Mexico would normally cost you about ½ the cost of getting to much of the Caribbean, points offer a great value.

Look for flights on Award Partners. Airlines are part of associations and ownership groups that allow you to leverage your miles with one program on another airline. I’ll cover this in more depth later, but just be aware that such alliances exist and you might be able to use another airline’s website or find an option of flying on another airline to get you where you want to go.


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Like any hobby, to get good at travel hacking, education goes a long way. I rely on blogs like Million Mile Secrets to teach me the ins and outs. But I also just spend a lot of time planning trips. As I’ve searched for more flights on more programs, I’ve increased my skills and, as a result, my savings.

In the next post we’ll look at ways to use travel hacking to save on hotels and other accommodations.

Until then, happy travels!


Photo credit:; cover: @dzzdzz012


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