Tuesday, February 18, 2014

How to Find the Best Deals on Airline Flights

Flights: Thriftiness is a Points Game

But if you put in some work, the payback is awesome!

Traveling with Kids Series via

Welcome to the third installment of Take-a-Trip-Tuesday, our February special series about affordable ways to travel with families. Over the last two weeks we've talked about why we are devoted to traveling with our kids, how to save money on high-end lodging, and negotiating the airport with young kids. Today Ben is guest posting again, and this time he's sharing how he nabs us some amazing deals on airline tickets.

Just a heads-up, this is definitely another info-heavy post, so if you're new to the Frequent Flyer Miles and Credit Cards Points systems (and you're anything like me) you may want to read this post during some quiet time so you can concentrate. Also, since not everyone is familiar with "points-speak," I asked Ben to put together a glossary at the end of the post, and those terms are marked with an asterisk the first time you see them in the post.

So, with that introduction, here's Ben!

There’s a great line in Home Alone 2, when the father says, “The only flying that I ever did as a kid was in the family station wagon.” For me, that was almost always true when I traveled as a kid, with the exception of one vacation to Florida (the rest of the time we drove) and two visits to California to visit my grandparents; otherwise, we never flew on family vacations. I spent most of my time in the "way back" of the family truckster, a mid-1980’s Chevy Celebrity station wagon. Now, I know why.

Besides airline travel being a daunting experience (which Kristen helps alleviate with this post), flying can be expensive. Really. Expensive. Yet, driving with three small children poses its own challenges and limits you to a radius that makes it difficult (and sometimes impossible) to take trips to far-off places. In my last post on renting timeshares, I talked about our visit to St. John, somewhere that would be impossible to go without a flight. Yet, we paid almost nothing for our flights, except a small amount for taxes and fees. That’s right, free, non-stop direct tickets on American Airlines to the Caribbean during summer vacation.
While that trip is certainly the exception, we rarely pay full price to fly as a family. In fact, the only reason we even took the trip to St. John is because we were able to get those free tickets. Likewise, we are able to take a mid-winter trip to Florida because we are getting two free tickets for that trip, too. In fact, for the five of us to fly to Florida this winter (because baby still flies for free), we’re paying a net total cost of $520 for direct flights on Delta from New York City.

How to Save Money on Flights By "Using Miles" and "Points"

OK, sounds great, but how can you do this? We are able to accomplish most of our free or reduced-flight tickets through managing credit card offers and frequent flier miles. Here’s a primer:

(1) First, figure out which airlines are the best for your location. Perhaps there aren’t many choices, or perhaps, like us, the choices are nearly limitless. There are three airlines we fly the most, in this order: Delta, American, and Jet Blue. I used to have a weekly New York to Palm Beach commute for work (yes, weekly), and I fell in love with Jet Blue, and also that every 4th or 5th ticket was free (they’ve changed their award scheme since then). Jet Blue is a great airline, but they don’t always have flights where we want to go, and I’ve found that their frequent flier system is not as robust as Delta or American.
  • Once you find your airline, check the awards charts*. For example, here’s Delta’s. It’s important to understand how much an award ticket will cost you based on where you might want to go and when. For example, a round-trip domestic ticket on Delta may only cost you 25,000 miles; on the other hand, it could cost as much as 60,000 miles. I like to have miles banked with multiple airlines, partly because they may or may not fly where I want to go, and also because they may have different award tickets available. For example, this summer we chose to fly American to St. John because their award ticket was several thousand miles less than Delta's.

(2) Second, start looking at credit cards that offer rewards.
There are a host of offers out there, including bonuses for as much as 100,000 miles, enough for four free off-peak round-trip domestic tickets. Sign-up bonuses are a great way to start building a pool of miles, but don’t go crazy here. Think about what the bonuses offer, what the fees are like (some airline credit cards have fees in excess of $400), and how you will use the miles.
  • Capital One offers several popular miles credit cards, but because their miles are set at a 1¢ per point and are indirect rewards* via statement credits* (e.g., 25,000 miles gets you a $250 credit statement off your airline ticket), you may not be getting the full advantage you can from an actual award ticket. 
  • For example, using miles earned on a credit card for an actual Delta domestic Sky Miles Award Saver ticket for 25,000 miles might actually “buy” your ticket that otherwise would have cost $400, $500, $600 or more. Assuming the ticket cost more than $250, using miles from a credit card that can provide an actual award ticket is a better reward as compared to a statement credit from Capital One
  • On the other hand, since the Capital One approach is a credit (and the Disney Rewards Visa can work the same way), there are no blackout dates or restrictions, things that are fairly common in the awards world.


There are too many cards out there to spend time comparing them in this post. I encourage you to take a look to see what’s out there, from airline-specific cards to cards that can transfer to multiple airlines, to cards that offer miles in the form of statement credits. Be careful though - one thing most of these cards have in common is a higher APR than traditional credit cards, so if you plan to carry a balance, you’re better off finding a low APR card since the mileage benefits likely won't make up for what you’ll pay in interest.

I will talk briefly about several of our favorite cards, which include the American Express Platinum Card, the American Express Starwood Preferred Guest card, the American Express Delta Platinum Card, and the Citibank American Advantage Card. Here’s a quick breakdown of why we have so many different cards and how we use them.
  • My favorite is the American Express Platinum card; yes, it is expensive at $450 per year, but there are several reasons that this is a must-have for us. First, American Express customer service is excellent. From disputing charges to calling for help with travel or a reservation, Amex always seems to be available and helpful. There are many perks – in fact, too many to list. Some of the perks that interest us, and that really offset that $450 fee include: getting a $200 per year airline fee credit (which we use in its entirety), free entry into many major airline lounges (which has been a great place for us to decompress with the kids for free snacks, juice, and drinks before hoping onto a flight – and for mom and dad, too), free Global Entry (you must have an interview and pass a screening), which means no lines at customs when we get back home from abroad and expedited and less cumbersome security protocols at most major airport security checkpoints, and lots more – purchase protection insurance, car rental coverage, the list goes on and on. In addition, it has an excellent rewards system, where you can use Rewards for everything from statement credits to online merchandise to airline mile transfers. In addition, there are sometimes special offers, like a 40% bonus to transfer to a specific airline (e.g., Delta). You may also use points to pay directly for tickets through American Express’ travel site, and there are sometimes incentives to do this. On our last trip to St. John, the cheapest flights we could find were $500 per person, and we did not have enough miles banked with American to purchase all four of the tickets we needed. Instead, we were able to “buy” two of our tickets directly with Rewards points via the Amex travel site, and we got 20% back as part of their promotion at that time. So, a 50,000 reward ticket actually cost only 40,000 points. The added benefit of using your points that way is that you will likely still earn frequent flier miles for the ticket since it was “purchased” instead of being identified as a frequent flier award.
  • The American Express Starwood (SPG) Preferred card is also one of our favorites, and it’s the card we use for all of our daily expenses (things like groceries, gas, kids' activities). Those charges add up to more than one free domestic ticket per year. But, here’s the real reason why we love the Starwood card (besides loving the Starwood hotel brand, where we get upgrades almost every time we stay!). They have tons of airline partners you can transfer to, and you get a bonus of 5,000 miles for every 20,000 miles you transfer. A 25% transfer bonus is pretty sizable. Again, if you were to score a domestic Delta Saver Award* for 25,000 miles, it would really only cost you 20,000 miles. In addition to the airline flexibility, you can also use awards for vacation stays, like Cash and Points, where you can pay for part of your Starwood (e.g., W, Westin, Sheraton, etc.) hotel stay in rewards points and the rest in cash, which are usually a good deal. Further, Starwood offers their own direct booking of rewards flights (called SPG flights), which are sometimes cheaper than transferring miles and booking a frequent flier award through the airline (and like I pointed out above, these appear as “purchase” transactions to the airlines, so you will also earn frequent flier miles on your trip). They also offer something called Nights and Flights. This can be a GREAT DEAL because you receive 50,000 miles into your frequent flier account and 5 nights at a Starwood hotel. For example, for 60,000 rewards points, you can stay at the Four Points by Sheraton San Francisco Bay Bridge for 5 nights and get 50,000 miles deposited into your frequent flier account, which could net you two free round-trip tickets. You might think that earning 60,000 rewards points will be tough, but with a 25,000 or 30,000 sign-up bonus, you’re nearly halfway there. Add the points from charging monthly expenses, and by the end of your first year, you could take a free 5-night trip for two to San Francisco, hotel and flights included. Starwood has hotels everywhere, including places like Paris, Los Angeles, the Caribbean, and even Disney.
  • We also each carry the American Express Platinum Sky Miles Card. Although there is a yearly fee, we each get a free domestic coach companion ticket each year (which is how we scored our mid-winter Florida airfare for $520 for all of us). On top of that, you get a free checked bag (one per person) for everyone in your party (up to 9 people on your reservation). For us, that means we save somewhere between $100-$200 per flight, depending on the number of bags we check (since it’s $50 per checked bag…GRRRR). We also get priority boarding, which, although it has no monetary value, is certainly helpful for getting settled and finding space to stow your carry-ons in the overhead bins. This card more than pays for itself, and we earn double miles on fares we purchase with our cards for all Delta flights. Finally, if you are a card holder, you also have the option of paying for part of your flights with Delta Sky Miles (at the value of 1¢ per mile) – not a great value, but can be good in a jam.

(3) Third, sign up everyone in you immediate family for frequent flyer accounts for the airlines you plan to fly. Adult sign-ups are easy, but for children, there can be paperwork involved since they’re minors, so don’t wait until the last minute to do this (although airlines usually allow you to get credit within 30 days of a flight). For example, Delta requires you to fax an authorization form to them for the child’s account to be approved. If they’re old enough to pay for a ticket, they should be earning miles. Remember, every mile counts, and you can usually transfer miles between members. 

(4) Finally, be on the lookout for fare deals. I get weekly e-mails with fare specials from American Airlines (and recently received a 15% off coupon for my next flight). Airlines need to fill seats on flights, and certain routes (e.g., seasonal, those that are more heavily traveled for business at certain times, vacation hot spots, etc.) will go on sale throughout the year. I also subscribe to ThePoints Guy, and I get a daily digest of what’s going on in the airline world. Recently, he posted a fare special for two round-trip tickets from New York to Milan for $440 each. Less than $500 to Europe, direct, is a huge bargain, especially over Valentine’s Day weekend. I was tempted to find someone to watch all three kiddos and whisk Thrifter away for a romantic weekend, but then reality set in :)

(5) A final caveat: sometimes it pays to pay (using your miles credit card) the full fare. As an example, this summer we are flying to St. John, and because we booked so early, we only paid $318 per ticket. That’s pretty good, and it was not worth using 35,000 miles per ticket for the same flight. In fact, as a family, we will earn 16,250 miles for that flight (since we paid instead of getting award tickets), and on top of that, the $1590 charge earns double miles on my Delta Platinum card, meaning we’ll earn an additional 3,180 miles for this flight, for a total of 19,430 miles: almost enough for a free Saver domestic round-trip ticket. A good rule of thumb is that you should never get less than 1¢ per mile for your points, because that’s basically what you’re “earning” from your rewards card. In reality, you should look to do much better than that. I usually look to net somewhere in the 2+¢ per mile range, which means a domestic Saver Award* flight really needs to come in around the $500 mark for me to use miles. That can be tough, domestically, sometimes (many times an overseas ticket is a better bargain), but with a flexible card like the SPG Amex, instead of using my points for miles, I might decide to pay for the flight and instead use those points to book accommodations. Like I said, thriftiness is a points game when it comes to airline travel!

Does all of this sound confusing? Well, it certainly can be, but if you take the time to learn the ropes, it can pay off BIG TIME. To give you a little real-time context, here's my most current flight situation: I need to book an upcoming solo round-trip flight from New York to Los Angeles. I have several options: purchase the ticket directly and earn double miles using a credit card, use mileage redemption directly with miles already in one of my frequent flyer accounts, transfer miles from my SPG Amex card, purchase directly via one of my points-based options via Amex Platinum or SPG Amex, etc. It sounds overwhelming, but once you get the hang of checking the different options, it’s pretty easy – and clear. In this case, the Delta and AA fares are reasonable ($300 range), so it doesn't make sense to use miles to purchase an award ticket. Instead, my best option is to pay with my Delta Platinum Amex card and earn double miles, on top of the 5,000 or so frequent flyer miles I’ll earn for the flight, so I’ll net nearly 6,000 miles toward the next trip we take as a family. Even at 1¢ per point, 6,000 points is a $60 value, so the net cost of these tickets is about $240.

The Glossary {that Kristen strongly urged me to put together}:

  • Awards Chart:  Each airline has their own chart of the number of frequent flier miles it costs to obtain an award through them or a partner airline.  The number of miles depends on the time of year flown and the destination (e.g., Hawaii costs more than somewhere in the 48 states).  Below are two examples of awards charts.

    Source: American Airlines

    Source: Delta Airlines

  • Indirect Awards:  Some credit cards offer “indirect awards,” which are basically awards in the form of statement credits.  You buy any ticket from any airline, and you use the “miles” you’ve earned to offset the cost.  This means that the value of their award is set.  For example, if the Capital One card offers 1¢ per mile earned with their card, for cashing in 25,000 miles, you will receive a statement credit of $250 for the cost of the ticket.  With traditional awards, the amount of the underlying ticket does not matter; instead, the number of miles required depends on destination and season. 
  • Statement Credits:  Some cards allow you to use the points or miles you earn with them in the form of statement credits.  For example, the American Express Platinum card allows you to use their Reward points to offset regular purchases in the form of statement credits at the value of 1¢ per point.  For example, if you have 50,000 Rewards points, you could use them to receive a credit on your statement for $500 (this is typically not a good use of points). 
  • Saver Domestic Tickets:  Delta SkyMiles recently updated their Awards Chart and has three categories of tickets, depending on time of year and demand.  The seasons are Saver, Standard, and Peak. Saver tickets are the cheapest at 25,000 miles round-trip for domestic tickets.
Most of the information in this post has been amassed over time via websites like The Points Guy and Boarding Area, two sites I frequent. There are also forums, like flyertalk, where you can ask questions and read about what’s going on in the ever-changing points world. Other things listed are through my own trial and error. There are a lot of travel sites out there that explain the points game, so take some time to search around. It may be time consuming, but it’s worth it! We currently have almost 500,000 miles at our disposal, enough for 20 domestic Saver Award tickets!

Interested in Earning Your Own Credit Card Points?
If you're interested in signing up for any of the American Express cards Ben talked about, AWESOME! You're on the track to travel bliss! If you sign up through me, you can even get me a referral bonus. Just shoot me an email with your first and last name, and you'll receive an introductory email from American Express (no obligation, you just get a link in your email and you can use it if you want, delete it if you don't). We are in no way affiliated with Amex, just regular ol' customers :)

That's all for now, travelers! Join us next week for tips on how to occupy little kiddies on the actual flight!

And, if we're not already connected, find me on Pinterest, Facebook, and Google+, and Bloglovin so we can start sharing ideas together!

Looking for more family-friendly TRAVEL TIPS? Check out these post below:

Sharing at:
From Dream to Reality
Wow Us Wednesdays 
Moonlight and Mason Jars 
Life of the Party  
Wowza Weekend 
Making the World Cuter 


  1. We have been doing a lot of reward travel lately, and 4 of us will be heading to Florida for Spring Break for a whole whopping $25! Still more miles in our account too!

    1. Thanks amazing, Diana!!! How great is that warm sun going to be?!


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