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Travel Rewards 101: Planning Your First Trip Using Travel Rewards

Travel Hacking Tool Kit

As I’ve mentioned in my New Year’s Resolution/intro to the Pillars of FI post, travel rewards were basically my gateway into the FI community. After I had made my first trip to London, I sat at the airport and got curious about optimizing travel spend.  Sure enough, a couple of web searches lead me down the travel rewards rabbit hole and then the FI rabbit hole.

So what am I talking about with travel rewards? Basically, the idea is earning and building up enough miles to fly and stay at hotels for a heavy discount. You maybe saying, “doesn’t it takes forever to earn flights and stays at hotels even if you are a frequent traveler?” and you are correct. However, we can boost our points balances in a big way using one simple method: credit card sign up bonuses. You simply get the credit cards you need, earn the bonus by meeting the spend requirements, and that trip is yours.

(Important: Pay your credit cards on time and in full. Do not go into debt and spend more than you normally would to meet the minimum spend requirements. Everybody who advocates this method of earning points recommends this as debt avoidance is paramount to hitting FI.  The interest payments will immediately wipe out any gains you made from the bonuses.)

How can we do this? I’m going to demonstrate how I use four travel tools to plan a trip with flight and hotel paid for. In this example, I’ll pretend I’m going to fly from Seattle, Washington to Honolulu, Hawaii for a 3 night stay. Then I will show you a tool find a credit card for this trip and finally a way to track your points progress.

Awardhacker for Flights

First, we want to see how many points it will cost us for the flight portion of the trip. For that, we’ll use Awardhacker. Simply type in where you are flying to and from and it’ll show the amount of points you will need for each flight. In addition to the airlines frequent flier program, it will show the credit card travel points that can be transferred to the airline like Chase Ultimate Rewards or American Express Membership Rewards. In our simple example, we see that it costs us 24000 points on Singapore Airlines to fly from Seattle to Honolulu. We also see that any of the credit cards out there can be used to transfer points for extra miles, so we have a number of options for how to get the points for this flight.

AwardHacker shows us how many miles we need for a flight.

Awardomatic for Hotels

Now we need a place to stay, so we’re also going to look at hotels next.  For this, we’re going to type our destination into Awardomatic and it will scan the area for hotels in the major chains. Clicking on each one will show how many points you’ll need for one night’s stay. As Hawaii is a popular tourist destination, it can be a bit pricey both with dollars or just with points.  We are imagining a three night stay (like anyone can just stay in Hawaii for three days, but I digress), and look at that there is a Hyatt for 12000 points a night, meaning we’ll need 36000 points.

When searching for hotels, use Awardomatic to find out how many points you will need.

Credit Cards

Quickly to recap what we need:

  • 24000 points for the flight to Hawaii
  • 36000 points for the flight for the hotel.
  • 60000 points total

Let’s figure out which card you will need.  We’ll need to figure out which reward program we want to use.
Awardhacker tells us which credit cards we can use for flights. Sadly, for hotels, this part requires a bit of sleuthing (I’ll probably talk about that in another blog post). We’re using Singapore Krisflyer and Hyatt, but both of those work with Chase so I’m going to focus on getting a Chase card. We can use the Mad Fientist’s card finder tool and look for cards that we need.

Mad Fientist’s credit card finder can help you find the right card for your trip.

Unless you own a business (which can be as simple as a side hustle), you can’t sign up for one Chase card and get all the points you need from one card. If you do, though, you see that one of the Chase Ink Cards with the 80000 points can be used to fund the trip and still have 20000 points left over. For personal customers, you’ll have to get two cards, like the Sapphire Reserve and the Chase Freedom and earn the bonuses on them, it’s 65000 points, enough for the trip and a little extra. (Note: Those are referral links for the chase cards above.)

Awardwallet for Points Tracking

Now we need a way to track all the miles we may have and continue to accumulate over time. For this, I use Awardwallet. Think of it as a Mint or Personal Capital for your points. You simply input in your travel information and it’ll aggregate your points in one interface.

Use Awardwallet to track all your points you’ve gathered.


As you can see, it can be fairly simple to get a free trip with a little research.  You are however subject to award availability, though, meaning that point slots from the hotel or airline maybe taken.  Also, I did not cover hitting minimum spends as I felt that was best for another post, but that can be tricky as well and might require some planning as well.  That said, if you do get your slots and earn your bonuses, there is a great feeling of satisfaction when your travel plans come together like that.

If you want some more travel hacked trips, search online and you may find a few ideas people have already posted. One person who plans a few of these is Sebastian Fung, who goes by Ask Sebby on his website and YouTube channel.  You can see how he planned for a Maldives hotel stay here. Feel free to also share them with us in the comments and we’ll likely highlight them in the future.

There are also a wealth of tools out there or travel that will likely cover at another time. If you want to learn about them now, though, I recommend the list over at Upon Arriving, one my of favorite travel hacking blogs of late.

Got some favorite travel hacks? Let us know in the comments below.

Posted in Travel


    • Allen

      Mr. Robot,

      This particular travel plan only applies to US Residents from a credit card stand point and the credit cards give more points in the bonuses in the States as well (also Chase only has credit cards in the US), but the basic ideas can be done in other countries as well and the tools all work everywhere minus the credit card finder. Singapore Airlines is an airline any one can use and has partners everywhere (basically anywhere you can get American Express or SPG points), so if you fly to Seattle, you use this plan. There are a few Dutch blogs as well that are part of Boarding Area that talk about it as well: Hope it helps.

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