In this post, I discussed how we earn miles and points in order to travel for “free” (or, at least, very cheap) with our kids. Earning points is only half of the equation, though. Learning where to find the best value for your redemptions for your situation can really help you either get a lot more out of your miles or stretch them further, depending on your priorities.

Any miles or points blog out there will probably tell you that you will get far more value by redeeming your points and miles for business class or first class tickets. It’s true that, because of the extremely high cost of first class paid tickets, you will get more value per point with that type of redemption. You get to fly in comfort and have a lay-flat bed for your child to sleep on. However, as a family of four (though we’re still currently only buying three tickets and flying with Panda as a lap infant) with little disposable income, I personally find more value in saving those points for future trips. You need to make the best decision for your situation, taking into account the number of tickets you need to buy, how many points you can earn in a year, and how many trips you want to take.

2015-11-01 11.18.46

Kotor, Montenegro in 2015.

I will preface this by saying that the information below just skims the surface of redemption strategies. To be honest, I find a lot of the redemption side to be a bit confusing, but I’m trying to learn more to help us stretch our miles and points. I sometimes see people talk about their amazing redemptions and would love to get to that point. Until then, though, here are some basics:

Where to redeem

As I mentioned in my last post, flexible point currencies (like Chase Ultimate Rewards or American Express Membership Rewards) allow you to transfer your points to a wide range of partners including hotels and airlines. Generally, I have found that I get more value out of airline transfers.


I used to be a die-hard United fan because I flew them almost exclusively since they have big hubs in DC (where I live) and San Francisco (where I’m from) and direct flights to many places I used to travel (Geneva, Tokyo, etc.). I amassed a huge amount of points and still have some, despite relying quite a bit on United redemptions over the last several years. Before really diving into the world of travel hacking, I probably would have elected to transfer all my points to United.

Nowadays, I shop around a bit more. The great thing about United is that you know in advance exactly how many points your trip will cost on a saver award as well as a standard award. You can take a look at a reward chart and see what zone you’re in, what zone you’re going to, and what the award tickets cost. Within the lower 48 states, for example, a roundtrip ticket will cost 25,000 points on a saver award or 50,000 on a standard award. I’ve been able to get saver award tickets from DC to San Francisco for 25,000 points when a cash ticket would have cost $500, getting me 2 cents per mile which is a pretty good redemption value. However, when looking at a flight from DC to Tampa, that saver ticket still cost 25,000 points but only cost $220 cash, which isn’t nearly as cost efficient.

For traveling within the United States on points, especially on short-haul flights, I have to advocate for Southwest. Chase transfers to Southwest which has some of the best domestic (and limited international) redemptions. Southwest bases the point redemptions on the actual cost of the ticket, so if the flight itself costs less, so will the cost of your saver award. For the same dates looking at flights from DC to Tampa on Southwest, I was able to find roundtrip tickets for less than 15,000 points. We ended up basically saving 30,000 points by choosing Southwest, instead. While I don’t cover it here (and you can’t do it by transferring points), I do want to mention that if you are able to earn a Southwest Companion Pass either through miles flown or sign-up bonuses/credit card spend, that pass works on both paid cash tickets as well as award tickets. This pass is great because you get a free second flight with your companion on the same flight using a relatively small amount of points.

Using alliances

Sometimes, the best way to stretch your points and money is to look at where you can book through alliances or award partners. For example, United is part of the Star Alliance which has tons of partners, including Air Canada, Air China, Air New Zealand, Avianca, Lufthansa, Singapore Air, South African Airways and quite a few others. Because United does not charge fuel surcharges on its award tickets, you can book through United for a flight to Italy through Lufthansa without worrying about the extra surcharge. To be honest, this is the area that I’m most deficient in knowledge-wise and I’m always so impressed when I read about awesome redemptions (most often in business or first class). Instead, I suggest reading this post on redeeming United miles, this one for American AAdvantage miles, this one for American Express membership rewards, and this one for Chase ultimate rewards as starting points. Various travel hacking forums are also a gold mine if you have the time and interest.

Choosing where to fly

When you fly using miles and points, your tickets will be almost free compared to the cash price of the ticket. However, you’ll still pay taxes and fees, some of which might actually be quite high. The airline you select might have different rules on what taxes and fees are charged; British Airways, for example, has notoriously high fees because of a fuel surcharge. Also, where you’re flying in and out of, regardless of the air carrier you choose, may affect the total amount. London Heathrow’s airport has a high airport tax. On international flights I’ve traveled on (or looked into), the award ticket fees have ranged from $80 per ticket (domestic flights I usually pay between $6 and $15) to more than $500 a ticket; with such a huge range, it’s obviously worth figuring out how to avoid these surcharges. One of the reasons I still like flying with United or Star Alliance partners is that United does not charge for fuel surcharges, which usually make up the bulk of the higher costs.

When to fly

Timing can be a big factor. Just as there are peak and off-peak seasons for cash prices, the same is true for award tickets. You’re much more likely to find saver awards on flights during off-peak dates, which are often half the cost of standard awards. Even better than the traditional saver awards, though, are when the airlines offer promotions. For example, a roundtrip saver award ticket from the United States to Europe will typically cost 60,000 miles on United. Each year, I’ve seen United run at least one promotion offering some type of discount on saver awards. Last year in June, for example, United announced that any flights booked that week for travel between August 23, 2016 and March 31, 2017 from the United States or Canada to Europe would save 25% on the saver awards. Thus, instead of paying 60,000 miles for a roundtrip saver award ticket, the cost would only be 45,000. That savings really adds up when you’re buying three or four tickets! Keep an eye out for these deals and be ready to pounce when they’re offered.

Where to book

I generally book directly with the airline, but more recently I’ve been looking at booking through the Chase Ultimate Reward Portal now that I have two cards earning ultimate rewards points. What’s great about booking award travel through the portal is you can do all points or a mixture of cash and points (or all cash, if you want to). There are discounts in booking through the portal if you have certain Chase branded cards like the Chase Sapphire Preferred or Sapphire Reserve. With the Preferred card, you get a 20% bonus, while the Reserve card offers a 50% bonus on your points (meaning that 50,000 ultimate rewards points are worth $750 instead of $500 in travel). You also earn miles when booking on flights booked through the portal, whereas a transfer of points to an air carrier directly will mean you don’t earn any miles on that flight. You can stretch your points this way if you find good redemptions on the portal.


I have a decent number of Hilton points from a past life where I traveled a lot and got to keep my hotel points (I now often go to conferences where the rooms are booked under a corporate block and my company gets the points), but I don’t redeem them very often. Honestly, more than anything, I just have a mental block against using them because the cents per point valuation isn’t as good as miles, so I often just want to pay the cash price. I need to get over that because free is better than a bank of points that I’m never going to use! I know that some other hotel groups, like those using Starwood Preferred Guest points, give more value per points and we may try to start collecting those at some point. For now, though, we typically use our miles and points for flights only.

That said, there are a number of ways to travel cheaply or make good use of points for your hotel stays. Some of the credit cards, which I briefly covered in Part 1, come with bonuses to cover hotel stays. The IHG card, for example, has an annual fee of $49 and comes with one free night stay at any IHG hotel anywhere in the world each year. Others allow for one weekend stay (2 nights) or free nights at certain category hotels.

Stay tuned for Part 3 which is a long roundup of my favorite travel hacking resources.


Brighton, England in 2007.