How to Book an Award Trip on Points and Miles

American Express, Beginner Help, Capital One, Chase, Flights, Hotel Tips, Hyatt, Southwest

December 15, 2024

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Earning points and miles is the easy part. You jump on the best offers, or you follow a planned strategy, or you refer friends and family to cards and boost your points stash. There are so many ways to earn points. The harder part? Actually using them to book an award trip. It feels scary to transfer your points when you’ve never done that before. Or maybe you’re nervous that you aren’t getting the best value.

The thing is, you just have to book the trip. You can read and research all you want (or even buy a comprehensive course like Rewards Roadmap!). These are great starting points, but you have to put all you’ve learned into practice for it to really sink in. So, on that note, here are the steps to follow to help you feel confident using your points and miles to book an award trip.

Pick a destination

For beginners, the easiest way to book an award trip is to start with a destination in mind. This helps you narrow down exactly what is needed for your trip. Some destinations are easier to use points and miles than others. A few common beginner destinations are:

Hawaii (this is probably the #1 option for most people!)
San Diego
New York
Disneyland/Disney World
Paris
London

These are all easy destinations to get to and have multiple flight and hotel options.

Figure out the points needed

Once you’ve decided where you want to go, you need to figure out what points are needed. If you’re going somewhere within the domestic U.S., my top recommendation for your first points and miles trip is to do my favorite combo of Southwest and Hyatt. They are both transfer partners of Chase, so the points are easy to earn and use.

The most important thing to learn is how to do dummy searches. This basically means that you’re running pretend searches as if you were booking a real trip on points. This helps you understand how many points are needed for each part of your trip.

Award searches work very similarly to cash searches, the only difference is that you need to select to search by points instead of cash. Sometimes, there is a toggle button on the main page that says “points,” “award search,” or something like that. Other times, it’s a separate tab that says “award flights” or “reward search”. Additionally, sometimes you will have to log in to search, and other times you will not. It varies by hotel and airline. This is why it’s important to practice! The more you do it, the easier it becomes.

Running a dummy search

Let’s use Hawaii as an example. I’m going to look at a few different airlines to see what the best prices are. Many airlines and hotels have calendars you can look at to see the best prices a month at a time. This is helpful for picking the lowest-priced dates.

Southwest Airlines

United Airlines

American Airlines

As you can see, Southwest has the lowest prices, so my goal will be to earn Southwest points.

Now, let’s look at hotels. Hyatt is always my first choice because, like I mentioned, they are Chase partners so the points are easy to earn and use. Plus, their hotels are typically clean and easy to book, and they have great customer service. Also, they’re the only hotel chain that still uses an award calendar, which means there is standard pricing for each property depending on the hotel’s category.

So, if I look at the Hyatt properties in Honolulu, I can see that there are three options.

This tells me that I need 15,000-20,000 points per night for the standard pricing. The price may be a little higher if you go during peak dates. So if I’m planning a five-night trip, I know I need approximately 75,000 – 100,000 points.

You can also check out the other major hotel brands – Hilton, Marriott, and IHG – to look for other hotel options. When traveling internationally, IHG tends to have more options for rooms that sleep more than two people. Another good option for international travel is Choice Hotels. They aren’t the best quality within the U.S., but they have much nicer properties in other locations.

So, now that I’ve looked at flights and hotels, I need to figure out how to earn those points.

Earn the points and miles

Flexible points are always the number one goal when trying to plan an award trip. These points can be transferred to travel partners, giving us the most options for using them. In this case, I want to focus on Chase Ultimate Rewards® since both Hyatt and Southwest are Chase transfer partners. There are many card options for earning Chase points.

These three cards earn fully flexible points:

These four cards earn “cash-back” but actually earn Chase points as long as you also have one of the three cards above:

Additionally, Chase has co-branded cards for Hyatt and Southwest, so this would be a way to boost your points specifically for either of those brands.

Here are your card options for co-branded cards:

*All information about Southwest® Rapid Rewards® Premier Business Credit Card has been collected independently by The Traveling Hansens. The card details on this page have not been reviewed or provided by the card issuer.

Chase is the only bank that has Hyatt and Southwest as partners, but other flexible points programs may be good options for different flights or hotels.

Learn more about American Express Membership Rewards.

Learn more about Capital One Miles.

Transfer your points and miles

Next up, you need to transfer your points from the bank to the airline or hotel that you want to book. This article goes over the steps for transferring from each major bank to hotels and airlines. There is one important thing to note; do not transfer your points until you’ve found availability for your exact dates, flights, number of nights, etc. Once points are moved, they cannot be moved back.

Since we’re using the Hawaii example with Chase points, let’s briefly go over the transfer steps.

First, log on to your Chase account and navigate to your Ultimate Rewards®. Next, click Travel, then Transfer points to partners.

After this, you’ll see all of the available partners. Select the partner you want to transfer to.

Next, enter your loyalty account information.

Then, enter how many points you want to transfer.

Finally, review the details then hit Submit.

Most transfers are instant. Once you’ve submitted the transfer, log out and log back in to your hotel or airline account, and you should see the points.

If you’ve earned points through a co-branded airline or hotel card, the points will already be in your loyalty account with that brand. There is no transferring involved.

Book the trip

And finally, you get to actually book your award trip! This works just like a cash booking, but you will search by points/miles, just like when you ran your dummy searches. Then when it’s time to pay, you will use the points/miles. You will still need to enter a credit card to cover any taxes and secure your reservation. Be sure to use a card with travel protections, like the Sapphire Preferred or Capital One Venture X Rewards Credit Card!

And congrats, you did it! You learned a new skill, and moving forward, it will be easier and easier to do again.