Travel Tricks

Tools of the Trade: How to Book Award Travel


Booking 6 months of travel using primarily points took quite a bit of time. I’ve had to book 3 roundtrip flights, 5 one-way flights, 9 different hotel stays, and 3 Airbnb rentals. Plus, I decided to change my itinerary in February because of the severe water shortage in Cape Town which meant canceling and rebooking one month’s worth of travel. Needless to say, this process was quite time-consuming. However, with the right tools, making all of these reservations was actually quite manageable. Below, I’ll walk you through my process for booking award travel including the tools I use to do my research.

Before You Start

Get Organized

Before you start searching for award travel, it’s time to take inventory of the points you have at your disposal. Once you’ve been playing the credit card/loyalty points game for long enough, you find that your points are scattered across a wide variety of hotel, airline, and credit card companies. For the most part, this is a good thing as it will give you a wide array of options when it comes time to book; however, it can also be difficult to organize all this information.

Currently, I have points in 15 different accounts! To keep this all organized, I use AwardWallet, which is an app and a website which helps you keep track of each account, updates the balance in each account, and tells you if your points are in danger of expiring. When it updates your balance, it will also help you keep track of any reservations booked within that account. Once you have more than three or four different accounts, I highly recommend you use this or one of the other tools available for tracking your points across different loyalty programs.

Become an Expert

Once you know have a good handle on how many points you have at your disposal in the various loyalty programs, you absolutely must become an expert in how best to use them. For example, Chase, American Express, and Citi all have different ways that you can use your points. While each company allows you to exchange your points for cash, that typically isn’t the best way to maximize the value of these points.

I was able to spend 10 nights at the Hyatt Regency Amsterdam thanks to all the Chase points I had.

Instead, each of these companies has a different set of transfer partners. While there’s value across these transfer partners, some are generally seen as more valuable than others. Chase Ultimate Rewards points are generally considered more value than points given by Amex or Citi because their list of transfer partners includes Southwest, United Airlines, and Hyatt.

I won’t go into detail on the best way to use these points. That article exists in multiple forms all over the Internet. Just type “best ways to use _____ points” into your favorite search engine and you’ll find a bunch of great results. The Travel Sisters (Chase, Amex, and Citi) keep an updated list of all transfer partners and gives some basic recommendations.

It’s critically important that you remember that not all points are created equally. For example, one night in June in the Hyatt Regency Amsterdam costs US$350 or 15,000 points. However, to stay in the Hilton Amsterdam costs US$280 or 70,000 points. Again, there are a number of resources online to help you determine what the points are worth from each loyalty program. These valuations are fairly subjective but here’s one from Upgraded Points that I find useful.

Be Flexible

Booking with points can save you thousands of dollars but in order to maximize your value, you must be flexible in your travel plans. For example, I recently was able to stay for 9 nights in a Holiday Inn Express that was a bit outside of the city center in Amsterdam. Of course, I would’ve preferred to stay closer to the city center but nightly rates were well over US$200 and I was able to book this hotel for 20,000 points per night, which is a great value for IHG points!

Of course, flying during the peak summer months can also present a challenge. Again, as best as you can, be flexible with your travel dates and try to book as far in advance as possible. Most airlines let you book approximately one year in advance. Plus, booking with points typically offers you greater flexibility when it comes to changing your plans than booking a standard non-refundable rate.

Ready to Book!

Flight Booking Tools

Booking flights with frequent flyer miles is actually pretty straightforward because of two amazing websites. I begin every search by checking how much it would cost to just pay cash. That gives me a good baseline to work with and allows me to easily decide if it’s worth it to use my precious points. For this, Google Flights is hands down the best resource available after they purchased ITA Matrix Software several years ago. In fact, this site can even help you pick a destination if you aren’t totally sure where you want to go yet.

Tools flying
Last week, I flew from Amsterdam to Singapore (via London) on this beast! I actually paid cash because it was just a better deal than using points.

I usually keep this tab open and open another one and go to AwardHacker is so easy to use but is filled with great information. You simply enter in your desired route and the site tells you which airline requires the fewest points for that particular route. For each airline, it also tells you if you can transfer points from Chase, Amex, or Citi. Keep in mind, that while AwardHacker can tell you which airline requires the fewest points, it cannot tell you if your desired flight is available at that number of points. To determine award ticket availability, you have to go directly to the airline website or pay a small fee to use Expert Flyer.

Once you’ve made up your mind, I recommend booking your flight as soon as you can if you are using points (but remember that sometimes you’re better off just paying cash). Though you should always check the change and cancellation policies for each reservation, booking with points is generally easier to change later on provided you keep the route the same. If you are booking a popular route during peak travel season, the award availability is likely to change often. Almost everyone who regularly uses points for flights has a sob story about the great award redemption they missed out on because they waited too long.

Hotel Booking Tools

Unfortunately, booking hotels is slightly more complicated than booking flights. However, here’s where the homework you did earlier will really pay off. Since there’s no singular tool to tell you which hotels to book, your knowledge of your own points inventory will help you to streamline this process.

Just like with airlines, I also check the cash rates before I start looking to use my points., Priceline,, and other third-party booking sites will give you a great sense of what it will cost to stay in a hotel in your destination. I also recommend checking Airbnb as prices can vary dramatically from city to city between hotels and vacation rentals.

Now that you know roughly what it would cost to stay in a hotel, you can start searching for the best way to book using points. Again, look at your hotel points inventory and start searching. There aren’t any great tools available to do this for you so you have to visit each hotel chain website individually and search for award night availability.

If you don’t have points with any of the hotel chains, there are two solid options if you can’t find a cheap cash rate. First, Hyatt is a transfer partner to Chase Ultimate Rewards. Hilton and Marriott are also transfer partners of the various credit card programs; however, I generally think that the Chase – Hyatt partnership is the only one that presents a great value. Marriott and Starwood are currently merging and the unified program may be worthwhile once that happens but that remains to be seen.

Second, if you have the Citi Prestige card, you can use points to book hotels. The other card companies allow you to do the same at a rate of one cent per point (i.e., a very poor value); however, if you have the Citi Prestige card, you get the 4th night free on almost all hotel reservations. You can pay using cash or points but this option greatly enhances the value of Citi ThankYou points.

(Side note if you have the Citi Prestige card: If you book using Citi ThankYou points, you should book using the Citi ThankYou program website. You will not receive points for your stay and any loyalty status you have with the hotel will likely not be honored. If you book using cash, you should book by calling or emailing the Citi Prestige Concierge Center. In this case, you will receive points for your stay and any status you have will be honored as well. The downside here is that you have to pay for the hotel in full and wait for Citi to reimburse your account for the free 4th night a few weeks after you check out.)

Anyway, you will ultimately have to decide what kind of hotel you’d like to stay in and how much you’re willing to pay in cash or points to stay there. The search process can be a little time consuming but ultimately can save you hundreds, if not thousands, of dollars. Further, some travel bloggers have written points and miles guides for specific cities which can be valuable tools if they’re available and published recently. I recently posted something like this for Amsterdam.

Happy Traveling!

Some of you will find this process tedious and annoying while others will enjoy the challenge of getting the greatest value from your points. However, if you’ve used these tools and taken the time to do this right, the work you put in will absolutely pay off in the long run. For me, I spent countless hours planning my 6-month adventure but according to my calculations, this work saved me over $20,000!!

So good luck searching and happy traveling!

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