How to redeem points and miles for free flights

Wing an airplane mid air

There’s nothing better than flying for free but we have to make sure that we are getting good value for those points and miles (hereafter “points”). The sweet spot is usually international travel, especially in business class but we’ll discuss all the possible options. For purposes of this course, we’ll assume you have Chase Ultimate Rewards points since this website focuses on Chase. However, the basics will apply to any points currency. The steps laid out here are very basic. As you get more experienced, some of these steps can be combined or even skipped if you have certain aspects committed to memory.

Step 1 – Determine the value you are looking for

We value UR’s at 2cpp while others may value them at 1.5, 1.7, 2.1, etc. There’s no set standard. Thus, you have to determine what makes sense to you. We highly suggest sticking with 2cpp unless and until you get experienced enough to make your own determination. This will depend on your own experience. If you have more points than you could even use, getting less than 2cpp might not be a big deal. If you routinely book business class tickets at around 3cpp, then maybe you’ll look to get at least 3cpp. In the end, what’s a good deal is up to you.

Step 2 – What are your transfer options?

With Chase UR’s, you have a number of different options. As a reminder, you’ll need a Sapphire Card or an Ink Business Preferred card to transfer your points. The airlines that you can transfer your points to are Aer Lingus, Air Canada, British Airways, Emirates, Air France, KLM, Iberia, JetBlue, Singapore Airlines, Southwest, United and Virgin Atlantic.

To transfer your points to these airlines, you’ll need to create an account with their frequent flyer program. This is free to do. All of these transfers are 1 to 1 so 10,000 points will equal 10,000 miles. While a lot of these transfers are close to instant, some are not. That’s beyond the topic of this course but be sure to look into that before you transfer any points. Reminder to never transfer points speculatively.

Also keep in mind that most of these airlines belong to an alliance. This allows you to, among other things, book some (but not all) flights through a frequent flyer program on another airline. For example, you can use United miles to book an Air Canada flight and vice versa. This is an advanced topic so for now, we’ll keep it simple.

Of course, if you already have miles built up with an airline that is not included in this list, you can consider that as another option. For example, I have miles with American Airlines so I consider them when searching for award space.

Step 3 – What are the cash options?

This might seem odd that we are checking cash prices first and others might check award space first but this makes the most sense to us. Since most award flights are booked as one-way flights, you should search for both one-way and round trip flights. This is important because two one-way flights are usually the same price as a round trip domestic flight. However, round trip international flights are usually cheaper than two one-ways. This is just a rule of thumb so that’s why were are going to search both.

Google flights is going to be your best bet. Find the best flights that work for you and then compare the prices between two one-ways and a round trip. That price is going to be the measuring stick that we use moving forward. While you are at it, put on a Google flight alert on that flight and any others that may work for you regardless of the price. More on this later.

You also want to take note of other airlines that would work if the price was lower. Unfortunately, you rarely have too many options but let’s assume you have two options, United and Southwest. Let’s assume that the United flight is $400 and the Southwest flight is $500. You’ll want to make note of all of that and put flight alerts on for both of them.

Step 4 – Checking award space

We have our dates, we have our airlines and we know how much the flights cost. $400 is the measuring stick and if we value UR’s at 2cpp, we need to find award space at 20,000 miles round trip or 10,000 miles each way. So the first thing we’ll do is go to United.com, login and just type in the flights you want to search for. However, you are going to click “one-way” and “book with miles”. Even if you are booking more than one person, just search for one for now.

You’ll then see all the results. You may or may not see the exact same flights you saw before. Unfortunately, the cheapest flights are usually the most annoying flights but not always. Even if you can’t find the exact same flight you saw for $400, you want to see if the cheapest flights work for you. Since you already did the math, you know that you are looking for 10,000 miles or less. If you don’t see anything, you’ll know right away that this isn’t going to work out unless you are flexible with your dates.

What’s nice about United is that at the top of the screen, you’ll see a weekly view to compare the lowest points on different days. It looks like this:

If you click on “30-day calendar” you’ll see a screen that looks like this:

Again, that makes is really easy to see other dates if you are flexible. If you decide to move dates to take advantage of that cheaper award space, you should go back to Step 3 to make sure that the case price isn’t cheaper as well.

Since you may be able to book this flight on Air Canada, you may want to check that as well. Some people have found good award space on AC but we haven’t. The website is really annoying to use as well. Your other option is South West since we know that they fly that route but their award space is fixed at under 2cpp so we won’t bother with that. Let’s assume AC doesn’t have any good award space so it’s just United.

Reminder – the fees are going to impact the cpp. So 10,000 miles with $5 in taxes is much better than 10,000 miles with $150 in taxes. These are NOT the same value.

Assume you found two one-ways at 10,000 miles each that work out for you. Transfer the points over and book the flight.

Step 5 – Keep an eye on the prices

Airfare prices can fluctuate everyday. That’s why we put on a Google Flight alert. Let’s assume that $400 flight went down to $300. Now that cpp is no longer 2. You have to determine what makes sense to you but we would cancel the award space and book the flights with cash. You’ll get a refund of the points and the taxes that you paid. While this is usually automatic, you’ll want to set a reminder about a week later to make sure that this actually happened. This actually happens to us often.

Another thing to check at least once a month is the price of the award space. While it does not fluctuate everyday, it does fluctuate. If your award space goes down, you could rebook to that lower rate. There is no real rhyme or reason as to when or why it fluctuates but it does. For example, we booked a business class to Australia but the way there had us stopping in Auckland. Not ideal. A month later, we found space that went directly to Australia. We canceled and rebooked for the same price.

Helpful tips:

1. The best way to find good award space is to start early and search often. While you can find award space last minute, you’ll increase the chances of getting the best award space if you search early and often.

2. There are quite a few tools, websites and services that will help you search for award space and they will be covered in another course. However, you really need to learn how to do this on your own as we haven’t found anything that is 100% accurate or comprehensive.

3. Some airlines withhold some of their best award space for their credit card holder and/or elite members. For example, United has Saver Awards that are open to anyone with MileagePlus Premier elite status holders or anyone with an eligible United credit card. The credit cards that are eligible at the moment are Explorer, Business, Quest, Business and and Infinite. So if you don’t have elite status, it may make sense to get the lowest priced credit card to unlock this cheaper space.