How to Use Miles to Buy Flights

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I’ve been saving up miles for more than half of my life but last year was the first time that I ever actually purchased a flight with them. And now that I’ve started, I just can’t stop. In the post below, I am going to tell you what I’ve learned along the way and give you the “how to” for actually booking a ticket with miles.

Fair warning, this is going to be a long post, so grab some snacks and settle in!


My Personal History with Earning Miles

Back when I first started collecting miles, I was only flying once, maybe twice, a year. The first flight that I distinctly remember collecting miles on was my first international trip with my high school to Europe. Everyone told me to get a frequent flyer number because you earn so many miles traveling internationally. While this is true in relation to other flights, it is going to take you a ridiculous number of trips to add up to enough miles to actually book an award flight if you are only earning miles by flying.

I went out of state for college and continued to collect miles on my trips home each year, hoping that by my senior year I’d magically have enough to go somewhere free. I was always flying with different airlines though and let’s be honest, I’d have to fly between Boston and Charlotte ~30 times to earn enough miles to take one free one-way ride.

Then I moved to Los Angeles and started working for an event company that required a little bit of domestic travel. My boss was obsessed with miles, exclusively flew with United and had their business credit card. She flew all the time and was actually earning enough miles to go places for free. I started really paying attention to miles and within a few weeks, I was hooked. Because the business used United, I extensively researched the United Mileage Plus program and started paying attention to the deals they offered.

Seven years later this really paid off when I got married at a venue that is part of the Mileage Plus Dining program. My husband and I earned 6 miles per dollar spent on our wedding because the venue was part of the program. We were paying a monthly payment with our United credit card (earning 1 mile per dollar) and because our venue was on the list of restaurants that participates in that program we earned 5 miles per dollar there as well. The dining program starts at 3 miles per dollar but once you’ve dined enough during the year, you start earning 5 miles per dollar. It caps out at $1000 per month at each place. Luckily our wedding venue split up our payments so we had a payment to them each month and got to capitalize on the points!

How to Earn Miles

The important thing that I’ve learned is that though you do earn miles by flying, you can earn way more by working with their partners. If the only way that you earn miles is by flying it will take you years to rack up enough to go anywhere and even more time if you want to fly far, book in first class, go international, etc.

The partner programs (like the dining program I talked about above) are a slightly better and faster way to earn your way to free flights. These partners range from car rentals, to mortgages, to shopping online. The airlines make deals with these outside companies so that when you purchase from them, the airline gets a kickback and you get miles. Do your research, be sure you are actually getting a deal, and don’t purchase anything that you wouldn’t already be spending your money on just to earn miles. Each airline outlines their mileage partners on their sites. These are the partner program pages for the airlines that I use and try to earn miles with: United, Southwest, Alaska, Delta, and Jet Blue.

The number one way to earn a large number of miles is to have a credit card with an airline or that is specific for travel rewards. My husband and I have decided to use the Chase Sapphire Reserve Card. This card has a big annual fee ($450) but we’ve decided it is worth it because of the perks that come with the card. We get a $300 travel credit that automatically applies to travel purchases on the card, we easily use that right away (uber/lyft rides, metro passes, flights, hotels, etc all count as travel purchases). They cover one Global Entry fee every 5 years and give us a Priority Pass membership with unlimited guest privileges. Those perks alone make the fee worth it to me, but on top of that you earn a ton of Chase Ultimate Rewards Points that transfer to a huge number of frequent flyer programs. We used those points to help us book business class flights to Africa! The flights we booked cost us 360,000 United miles. I had about 240,000 United miles and we transferred over the rest from our Chase Ultimate Rewards Points and converted them instantly to United miles. If we had booked the same flights and paid with dollars, it would have cost us around $25,000!!

How to Get the Most Value out of Miles

Getting the most value out of your miles depends a bit on the program that you use. These are the two I use the most and am the most familiar with, but you should be sure to research your particular program(s) for the best deals and ways to redeem.

United Mileage Plus

The United Mileage Plus program recently stopped publishing their award chart which listed a set amount of miles for specific flights. This means they have more leeway to change their dollar-to-mile redeemable ratios, and to change them more often. For this reason I definitely recommend booking early, and checking in often to see if the “mile price” fluctuates at all before you decide to spend those hard-earned miles!

Be sure to check out the Star Alliance members, too, as there might be more options for business or first class at the same mileage redeem level with their partners.

Southwest Rapid Rewards

Southwest’s Rapid Rewards Points are redeemed based on how many dollars the flight is worth at the time of booking. They are also refundable, which is pretty much unheard of in the airline industry these days especially for the cheap seats.

My tactic when booking with Southwest is to book early and then cancel or change it closer to if I need to. That way if I get the best flight for the lowest point value but don’t have to be locked into the plans. I keep a calendar reminder and bookmark this page that says when flights are being released for the next range of dates.

One last great way to take advantage of the Southwest points is to also have the companion pass. This incredible pass allows you to book buy-one-get-one free flights with dollars or with points. It’s of course hard to get, you need to earn 110,000 miles in a calendar year to get it. These points can be earned by flying, through partners or by using their credit card (it also includes the one-time credit card signing bonus). My husband and I got the Southwest Credit Card at the end of last year when they were running a promotion to include a year of the companion pass as a signing bonus for getting the card. Needless to say, we are flying Southwest a lot this year!

Don’t forget that you have miles to use! I just booked a one way flight on Alaska with miles. I rarely use Alaska Airlines but have flown them a few times and had a decent number of miles rollover when they merged with Virgin America.

Make sure your miles don’t expire! If you fly with a lot of different airlines, be sure you know which ones have expiration dates and which ones offer lifetime miles. You certainly don’t want to spend time getting miles and then let them expire before you can use them! Delta and Jet Blue both let you hold onto miles forever, but with Spirit, the miles will expire after three months. This is a great chart for checking expiration dates or check directly with your favorite airlines.

My last time for how to get the most value out of miles is not dollar related. I always hold onto enough miles that will allow me to book a last minute ticket across the country to see my family, just in case. I like to call this my “Mileage Emergency Fund” just like I do with my Savings Account Emergency Fund for in case I loose your job or our financial circumstances dramatically change unexpectedly. My grandmother passed away at the beginning of this year and I was thrilled that I was able to book a flight days before her funeral with miles. It saved me about $800. Not only was the money savings incredible, but I don’t think I could have done the trip without having the miles. Spending time with family during loss is priceless. Save some of your miles, just in case.

How to Actually Book the Flight

Searching for award flights is relatively easy on most sites. These are a few key things to remember:

  • Go directly to the airline’s site to book. I love Google Flights for searching for flights that you pay for with dollars but unfortunately you have to go direct to search with points.
  • When you add in your flight details, select “points” or “miles” on the first page, you usually can’t switch it after you’ve searched, though it depends on the airline.
  • Try different dates and airports to see if that changes the point/mileage value that you’ll be spending on your flight. If your plans are flexible at all you might be able to save a lot of your points by changing your plans by a day and that could allow you to book another award trip in the future!
  • Be sure you are signed in. This will not only show you how many flights you are able to book with but if you are a credit card member, they may offer you more options than what they will offer to someone that is not a cardholder.

What’s Different When Flying on an Award Flight

The experience of flying on an award flight vs. one you purchased with money is almost identical. The one big thing you need to pay attention to is what kind of flight you are booking. If  you are booking an award flight it might be in a different class than you are used to or have different baggage restrictions. Just be sure to read the fine print for the type of flight you’ve booked. It very likely will be a positive change if any, but be sure you know how to maximize the perks. If you are usually an economy flyer but are finally cashing in to fly business class with miles, don’t forget that you get priority boarding and access to lounges at the airport! Do your research and you’ll be happy you did 🙂


That’s it, all of my silly facts and research about award flights summed up in one very long post. As you can probably tell by the length of this piece, I really love getting deals and cashing in on points/miles.

Looking for a movie recommendation to watch on those flights you just bought with miles? My favorite airline frequent flyer film is ‘Up in the Air‘ starring George Clooney. It’s an oldie but worth a second watch for sure!

If you have any of your own tips or tricks, please let me know in the comments, I can’t wait to learn more!

 

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