I had to book two round-trip domestic flights recently. One was from New York to San Francisco, California to visit my friend Erin. Erin recently gave birth to her first baby (I'm an Auntie!). The other flight I booked is from New York to Nashville, Tennessee. I'm heading to the famous "Music City" in 2 weeks to celebrate the 30th birthday of my friend Dasha of Dancin' Down Them Dirty, Dusty Trails.

Both Erin and Dasha are my closest friends from the USA and we all love to travel and go on adventures. I jumped on the chance to book flights to spend quality time with each of them. Of course, I did not spend more money than I had to because I used a combination of miles/points to pay for them.

In this post, I give a brief overview of how I earn tons of miles and points to cover the cost of airfare. I also explain the exact process I went through to find available award flights and the best value for redeeming miles and points for these flights.

Contents of This Post

Earning Miles & Points With Credit Cards


Newark Airport Terminal on my way to California

I earn tons of frequent flyer miles mainly through credit card sign-up bonuses. Read on for a quick overview of how I do this, but you can also check out my detailed post on Travel Hacking: Earning Miles and Points With Credit Cards.

Lots of banks offer credit cards with tempting offers, such as "Spend $4,000 in the first 3 months after sign-up to earn 50,000 points!" Sounds great but kind of suspicious and intimidating, right?

For the suspicious, I am a living example of the real attainability of this offer. It's not a scam! But you should know the miles-earning "game" is not for every player—namely the financially irresponsible or unstable. With that in mind, I encourage you to check out my other post on How to Make Long-Term Travel Possible: Intro to Travel Hacking where I tell you exactly what you need to consider before beginning the miles-earning "game."

For the intimidated, you can listen to my story: When I was still a student, I rarely spent $4,000 in 3 months unless it included my apartment rent. I could not charge my rent to a credit card. As a new player to the miles-earning game, I had to get creative with my monthly purchases in order to meet the minimum spending limit and earn all those bonus points!

Manufactured Spending for Miles


Some of the miles-earning credit cards I've had in my wallet

The key was to make my spending higher on a credit card without going above my normal spending for the month.

Here are a few ways I, to this day, "manufacture spending" on my card without ever actually spending more than I normally would:

  • I pay for the entire bill at a bar or restaurant on my credit card, then collect the cash from my friends
  • I buy gifts for people in advance of their birthdays or the holidays
  • I wait to sign up for a credit card until I know I am going to need to make a lot of purchases (or expensive ones)

I earn additional points by using a credit card on purchases that will get me bonus points in specific categories (e.g., groceries, gas, restaurants, etc.).

For example, my Chase Ink Plus Business card gets me 2 points for every $1 spent at gas stations. This came in handy with all the road trips I took all over the world (e.g., road-tripping through Iceland). I was often sharing my ride with others, but I would offer to pay for the gas in full on my card and get half the price in cash from my travel companions.


Road block in Iceland

By manufacturing spending and focusing my purchases on bonus categories, I have been able to easily and quickly meet the minimal spending requirements necessary to earn tons of bonus miles for multiple credit cards.

Before long (about 1.5 years), I had earned nearly half a million miles and points spread across different programs. For example, I earned with Chase Bank's Ultimate Rewards Points program and United Airlines' Miles program.

Once I earned all those points, however, I had to figure out how to spend them in the most optimal ways.

Redeeming for the Best Value

What counts as "best value" is very personal in the world of miles and points. The value comes down to what you believe is the best way to use your miles.

Some people believe the best way to use miles and points is to redeem them for first class seats on flights. This means you will use more miles than you would for economy seats, but you get a much more luxurious experience in first class (ample legroom, higher quality meals, free booze, etc.).

Selfie in my perfectly fabulous economy seating on the way to San Francisco


Selfie in my perfectly fabulous economy seating on the way to San Francisco

Personally, I don't need to fly super fancy. I prefer to use the miles I work so hard to earn on as many flights as I possibly can obtain. This means redeeming the least number of miles possible on each flight. I want to fly more often to more places rather than less often in fancier seats.

I strategize my search for flights in a few different ways when I finally go to redeem or use the miles I've earned.

My main strategies center around two main questions:

1. What are the fewest number of miles I would need to take a flight in the time-frame I'd prefer to travel? I don't want to use 50,000 hard-earned miles on a round trip flight from New York to California if I could get the same flight for 25,000 miles.

2. How much is the normal cost of the flight I want, taking into account the additional fees (airport fees) which everyone has to pay, miles or no miles? I don't want to use miles when the flight is already extremely low-cost. I also do not want to use miles when I would still have to pay airport fees that cost the same amount (or more) if I simply paid for the ticket out of pocket.

The above usually translates into a formula for calculating the value of a mile for a specific flight:

**Warning! A tiny bit of math ahead!**

THE FORMULA is:
The cost of the flight – (minus) the fees / (divided by) the total miles needed * (multiplied by) 100 = (equals) the cents (¢) value of a mile

I'll demonstrate this formula below when calculating the value of my flights to California and Tennessee. But the main goal with this formula is to aim for a redemption value that is above 1 cent. The more cents you get out of a single mile, the better the value.

Flying United With Miles and Points

For my recent trip to see Erin and her new baby, I ended up flying round-trip on United after spending only 12,500 miles. I used a combination of Barclay Arrival points, Chase points, and United miles to purchase my flights.

Barclaycard Arrival World Plus MasterCard for Arrival Miles

This credit card gave me 40,000 miles for making my first purchase within one month of getting the card. So easy! Then I earned 2 miles for every $1 I spent on the card.

Uniquely, this card allowed me to redeem miles for travel purchases made on the card. According to the card benefits, a travel purchase counts as "airlines, hotels, motels, timeshares, campgrounds, car rental agencies, cruise lines, travel agencies, discount travel sites, trains, buses, taxis, limousines, and ferries."

I was able to redeem miles for the travel purchases I made on the card during my 15 months of travel—like hostel stays in New Zealand.

The card does come with an annual fee of $89, but it was waived the first year. So when my 1-year anniversary of owning the card approached, I closed my account to avoid paying the fee.

Before I close it, I needed to figure out what to do with 30,000 miles I had left in my account. I didn't want to lose the miles by closing the card, so I turned the miles into a $300 gift certificate on United Airlines.

Gift certificates purchased through United Airlines are counted as "travel purchases" so I was able to redeem the purchase with the miles I had leftover. I could use the certificate at any time in the future—like my return flight from California to New York!

Chase Credit Cards for Ultimate Rewards Points

Chase's points-earning program is called Ultimate Rewards (UR). I have used a combination of Chase credit cards to earn UR points over the years. The ones I have now are the Chase Freedom card (a no-fee card), the Chase Ink Plus (a business card with a $95 fee), and the Chase Sapphire Preferred card (a personal card with a $95 fee).

I always try to keep at least one of the two fee cards—the Ink Plus or Sapphire Preferred card—because I cannot transfer or redeem points earned with only the Freedom card.

The UR points program allows transfers to several different airlines. United is one of these. In my experience, United tends to have the best bang for your points. In other words, United will require you to use less miles for more expensive flights in comparison to other miles programs out there.

For example, I only needed to transfer 11,000 UR points to my United Airlines account to cover the cost of my flight from New York to California.

United Explorer Plus Card for United Airlines Miles

United Airlines has its own miles-earning program and a credit card to earn miles directly with their program.

The United Explorer Plus card is offered by Chase bank and I love it because I tend to transfer my Chase UR points to United the most often. I had 1,500 miles already built up through spending on my United Explorer card before I transferred the 11,000 UR points over.

Searching for Flights to San Francisco

You might remember my recent post about hiking Mission Peak in Fremont, California with Erin and her baby bump. Well, her bump became an actual living human being! On Sunday morning of March 20th, Erin and her husband, Brent, met baby Logan. On March 25th, I met him, too!


Erin, me, and baby Logan in front of their home in California

I had to find tickets at the very last minute to take me almost 3,000 miles across the country. On such short notice, I anticipated these flights being costly.

Round-trip flights on the dates I wanted were going to be nearly $800! That's the cost of a flight to Hawaii from New York! There was no way I was going to spend that amount, but there was also no way I was going to miss out on meeting little Logan in his first week of life.

So I got searching as soon as I got word that Erin and the baby were healthy and ready for visitors.

In addition to my main concerns for finding the best value in a flight (number of miles and actual cost of the flight), I had a few other key stipulations for my search.

My goals:

  1. I wanted to find non-stop flights
  2. I wanted to maximize my length of stay with the least number of weekdays missed (because I recently started working full-time!)
  3. I wanted to fly on a new carrier so I would have the option to connect to Wi-Fi and charge my Surface while I worked.

I searched many different options but finally settled on United Airlines because I was able to find award seats available meeting all of my desired criteria. I'm a big fan of United's flight search engine because it has tons of filters that help me find the perfect flights super easily.

I also really love United because I tend to get the best values for my points with them.

The flight I took from New York/New Jersey (EWR) to San Francisco (SFO) would have cost me $425. Instead, I redeemed 12,500 United Miles for the same flight and only spent $80.60 to cover the cost of airport fees and taxes.

Here's how the value per point worked out using the formula I outlined above:

$425 – 80.60 / 12,500 = 2.76¢ per point

That's an outstanding value considering the industry average is about 1.40 cents per mile/point.

My return flight cost $311. I ended up using the $300 gift certificate I redeemed with 30,000 Barclaycard Arrival points to cover the cost. The value for the return flight was significantly lower since 1 point was essentially worth 1 cent in this case. This is below the industry standard, but a year ago I was faced with either losing those points or paying an annual fee to keep them. So I consider this a great deal!

I searched for flights that were around $300 so I could use the gift certificate to cover it. Then I paid out of pocket for the rest plus the fees—which amounted to only $49.10 in total.

Spending this extra amount out of pocket means I actually got the flight for less than 1 cent per point. But the trip overall balances out to be a great value since I got such a good rate on my departure flight.

All up, I paid $129.60 (in fees) for a round-trip ticket to California worth $774.10. Pretty damn good!

Flying Southwest With Points


My Southwest flight to Portland, Oregon in summer 2014.

To make it to Dasha's birthday in Nashville next month, I redeemed flights with Southwest Rapid Rewards (RR) points earned through the Chase Southwest Airlines Rapid Rewards Premier Card.

I had spent the majority of my sign-up bonus points with Southwest's Rapid Rewards program on a trip to Portland, Oregon the summer before I left for my international travels. However, I had 16,000 RR points remaining to cover the cost of my Nashville flights.

If I had needed a few extra points, I could have transferred Chase UR points over to my Southwest account since they are partners. So a tip here is to try to have miles and points in multiple and complementary (partnering) accounts in case you need to top up one or another!

Searching for Flights to Nashville


Dasha and I eating some sweets to bring in the 2016 new year.

Southwest Airlines often has super low-cost economy class fares called "Wanna Get Away" seats. Seat prices vary depending on the dates and times you fly when you use Southwest's booking search engine, so flexibility is key.

I chose the "flexible dates" option on Southwest's search engine. This gave me a calendar view so I could identify the lowest typical rates for flights to Nashville in the next month. I learned that the lowest number of miles I could redeem for a one-way Southwest flight during April was in the 7,000s.

For me, flexibility is key for getting the best value out of my miles and points. I had to pick the weekend Dasha and the rest of her friends were planning to be in Nashville, too. But by being a little flexible about the exact day and time I departed and the day and time I returned, I was able to redeem for flights with a low number of Southwest RR points.

Southwest's "flexible dates" view for Nashville flights in April 2016

In the end, I redeemed 7,937 points for a flight from New York (LGA) to Nashville (BNA) that would normally cost $136. Then, I redeemed 7,285 RR points for a flight back from Nashville to New York that would normally cost $126. A wonderful benefit to flying on Southwest is that their domestic flight fees are very low at only $5.60 each way. So the value I was able to get out of the flights was excellent.

Here's how the value per point works out using the formula from above:

$136 – 5.60 / 7937 = 1.64¢ per point

Flying back I got a slightly better value:

$126 – 5.60 / 7285 = 1.65¢ per point

So, basically, I paid $11.20 for a $262 round-trip flight to Nashville.

Summary & Final Tips


Getting to my destination with miles and points makes flying that much more magical

It's completely possible to spend very little on domestic airfare when you learn how to play the miles and points game. Earn tons of miles and points to redeem on travel by strategically signing up for credit cards with big bonus point offers. Even if you have low income, manufactured spending in specific categories (e.g., 2pts / $1 spent on gas) that earn you even more bonus points will get you on your way to paying almost nothing for your flights.

Then it's all about balance when it comes time to redeem your hard-earned points and miles. Balance your travel needs with the current cost of flights to determine the best redemption value.

I always try to use the least number of points possible so that I will still have more points to use on travel later. For instance, I only used 27,722 points in total for these two trips across the country (not counting the gift certificate points). I still have over 150,000 miles and points to spend on travel in the future.

This post is a continuation of my travel hacking series. I will be making more posts like this one—about earning and redeeming miles—in the coming months. If you like what you've read, please provide some feedback below! Do you have questions about earning and redeeming miles? Ask below or contact me directly here.

Disclaimer: I offer all of the above information freely to my readers at no personal benefit to myself.