How to Travel with Points & Miles without Ruining Your Life: 8 Expert Tips for Easy Wins

1. Start with a flexible currency.

Points and miles come in many currencies. Delta Skymiles are one currency, for example, but they’re only good at Delta Airlines (not flexible). 

But American Express “Member Rewards” points (Amex points, for short) or Chase “Ultimate Rewards” points can be transferred to dozens of partners (flexible!). 

These are the main flexible currencies you have to choose from: 

(According to Victoria and Brad Parks – the points and miles bloggers known as Parks on Rec – from their excellent session on points and miles for beginners.)

• Capital One miles
• Chase Ultimate Rewards points
• Amex Member Rewards points
• Citi Thank You points 
• Bilt Points (the only currency you can earn without a credit card. More on that below.)

A flexible currency is almost always better, especially if you’re just getting started or don’t predominantly fly one airline, or stay in one brand of hotel chain. (Or if, like me, you never stay in chain hotels if you can avoid them.) 

So get a card that earns at least one of those currencies. 

Tip:

Even if you do always fly Delta, for example, it might be worthwhile to have a Delta “co-branded” credit card for the perks (like free checked bags, or access to Delta lounges, depending on which card you get). But that card won’t be the best place to spend every dollar. 

Why? Because you can earn more points or miles on most purchases with other types of cards. 

EXAMPLE: 

Take the Amex Gold card, for example, which I currently have, because it gets me 4 points for every dollar I spend at any restaurant in the world, and any grocery store in the US. (That’s the best deal for restaurant spending from any card.) 

If I put those meals on a Delta Amex credit card, I’d only earn one Delta Skymile per dollar. But I can still transfer my 4 Amex points per dollar to Delta at a one-to-one value, because Delta is one of the Amex transfer partners.

You see? 

Tip: 

If there is one airline you fly often (or want to fly), before you choose a flexible points earning card, make sure it’s on the list of transfer partners for that card’s currency. 

2. Do the basics to earn points!

Some people go WILD with points and miles strategies, but you do NOT have to. There is a lot of value for the taking without going overboard. 

There’s no reason not to set up the basic systems that will let you participate in the points and miles world. It’s basically free money. 

These are the basics that I recommend everyone should do:

• Get at least one good credit card that earns a flexible rewards currency, and makes sense for your current spending habits. 

• Pay off the card in full every month, earn points, and use them for something that brings you a little joy. It could be upgrading a flight to business class and getting a taste of luxury, or it could be taking a trip home to see your family in coach for free. Use your points for what you want. 

• Open a free Bilt account and link your credit or debit card. In short, Bilt Points are the most valuable points currency out there. And you don’t need a new card to earn them. Bilt Points stack on top of other rewards you earn, and they have an excellent list of hotel and airline transfer partners.
  • I know this might be new to you, so more info on Bilt Rewards will be in my “easy wins” for points and miles blog post – coming soon!

That’s it. That’s all it has to be. You can take advantage of this system without stressing or handing over your life to it. 

3. Check your options BEFORE you redeem

Just about everyone I talked to at the conference agreed that before you book a ticket with points, you should check both the bank’s travel portal (where you can book travel directly through Chase or Amex, for example) AND the airlines’ websites, to see which one offers the best deal. It won’t always be the same!

(You can start your search with Kayak, Skyscanner or Google Flights – whichever you prefer – to figure out which flight you want. Then you figure out where to book it.)

If that idea of checking your options isn’t clear, let me take a step back:

Once you get a few points or miles accumulated, it’s time to decide what to do with them! 

You basically have three options. Here are the general rules on what kind of value you can expect from each (again, from the beginner points tips from Parks on Rec): 

• Worst Value: Cash back on your card statement, or redeeming points for gift cards or Amazon purchases. These redemption options for points usually get you just 1 cent in value. This is better than nothing (see number 6 on this list) but…

• Better Value: Booking flights or hotels through the bank’s travel portal. These portals cap the value you can get from your points, usually at 1.5 to 2 cents per point. Two cents per point is a perfectly reasonable value. So we’re getting better, but…

• BEST Value (usually): Transfer those flexible points to a hotel or airline program! (AFTER you’ve found something you want to book directly on the airline or hotel website.) They’ll often be worth ~ 3 cents each or more. 

Remember, the actual redemption values always vary, so always check both the credit card travel booking portal and the airline BEFORE you transfer points. This is something I never used to do (I just booked my travel through the bank portals and was happy with my 2 cents per point) but now I will!

Tip:

Never transfer speculatively because, again, you never know.

To be clear:

With the cash-back option, I’m not talking about straight up “cash back credit cards.” Those are a different concept from travel credit cards that earn you miles, which you can use for cash back. (But don’t! The point of earning points is that they can be more valuable than plain cash back.) 

Details:

For more help choosing between a cash back card and a travel rewards card, see my post on answering your points and miles questions. (Coming soon!) 

4. Don’t expect EVERYTHING to be available with points. 

One problem that a lot of people have is that they expect “award flights” (flights booked with points and miles) to be available for any flight, any day, anywhere and at a good price.

That’s just not the way it works. 

Points and miles exist because the system also benefits airlines and banks. (And that’s why we have entire conferences on how to optimize and get the best value out of the system. If they made it easy, everyone would do it.)

And the airlines want your cash. That means they’ll only allow a flight to be bookable with points if they expect to have a hard time selling it. The most popular flight on the most popular day will never be available to book with your miles, and especially not a good redemption value. 

Flying to or from a small airport also usually makes it harder to get a good deal booking with points. 

Bottom Line: Points and miles are not an automatic free pass. It does take some effort to play this game. 

If you put in a bit of effort, you can get great value from it. But if you hate that idea, or you can’t ever be flexible on your flight times or dates, maybe a simple cash back card would be a better option for you. (More about that in my post answering my email list subscribers’ questions – coming soon!)

Get involved! 👇

I realized this was such an issue because a couple of people on my email list sent in questions along these lines when I told them I was going to this conference. I’m writing a whole blog post answering those readers’ questions, with the feedback I got from points and miles experts who I took the questions to. Coming soon! 

If you want to get in on that kind of opportunity, you should definitely sign up for my email list! 

5. Have a GOAL for your points. 

During the session on collecting points by using online shopping portals like Rakuten (totally fine if you have no idea what that means), I realized the experts in lots of sessions were always talking about having a “goal.” Something to collect points and miles for – like a specific trip you want to take, or being able to experience a first class flight. 

I think that’s a good way to think about it, and to make sure you don’t just let them collect digital dust forever. (See Number 6 for more on that.)

But having a goal in mind and finding the ticket are two different things. If you’re feeling overwhelmed, or don’t have time to figure out how to use your points, here’s help:

D.I.Y., but easier:

How much simpler would it be if you could search for flights that you can book with any points or miles, on any airline, all in one search? Seats.aero is the service all the pros at the conference recommended because it does just that. 

(More details on that in my blog about intermediate tips for points and miles – coming soon!)

D.I.-Someone Else:

Don’t want to do any searches yourself? These flight alert services do the hunting for you, and send you what you want when they find it.

I’d recommend choosing one based on the goal you have for your points.

First Class Goals? If your goal is experiencing a first class flight without having to sell a kidney, Going Elite is a flight alert service that sends you first class deals (including ones you can book with cash, points or miles). They send them to you ASAP, so you can book before the prices go up. 

First class, but hands-off? If you’re realizing you don’t even want to deal with the points and miles game, check out Ashley Gets Around – founded by my friend Ashley Peterson, who also started the TravelMore conference. (Yes, she made the pun on purpose.) 

She and her team dig up great deals on first class, business class and premium economy flights – but they’re usually flights you buy with cash.

Just looking for a good deal? If your goal is to fly somewhere for cheap, even if it’s not in first class, Going has a free version of their service for US domestic flight deals in economy class. 

But the free version won’t send you award flight options. You’ll need Going Premium for that. It also lets you set up custom flight alerts, so your inbox doesn’t get bombarded, at the price of a monthly coffee.

Keeping your options open? Thrifty Traveler covers all your bases – flight deals you can book with points or cash, in either economy or fancy seats, plus useful news and tips on traveling with points and miles.

I use all three of these services. 

Remember, for any of these flight alert services to be worthwhile, you have to be flexible on both dates and destinations, and be able to book a flight immediately. (Usually within a day or two of when a deal hits your inbox, because it won’t last.)

6. Use. Your. Points.

Save them for your points goal, but don’t hoard them forever.

That might sound obvious, but it’s a step a lot of people forget. It’s easy to fall into the trap of just collecting points forever and never using them – which means the banks win the game! 

But points are not money. Points and miles will lose value over time. But like money, you can’t take ‘em with you. SO USE THEM. 

As Kelly Wright, AKA The Points And Miles Doc, said in her session about using award calendars to find better deals: 

“Even if it’s not the best deal, use your points how you want – you don’t always have to be optimizing.”

Dr. Kelly Wright, the Points and Miles Doc

Celeb Bio: 

Dr. Wright also has a course on points and miles, designed especially to “help medical professionals fight burnout,” which I think is lovely. (Yes, she’s a real doctor! And she makes the time to write papers about sustainability in hospitals, so you know she’s one of my favorites.)

I haven’t taken her course, but knowing her, I am 100% sure it’s excellent.

To give you an idea, her session at TravelMore was one of those simple but brilliant talks with good advice that I will probably always be too lazy to apply. But it didn’t make me want to run away from the points game. It made me feel knowledgeable and empowered. 

You can purchase the TravelMore conference session recordings to watch her talk, along with all the other sessions, or grab her free, 15-page points and miles guide.

7. Don’t let points & miles take over your life (unless you want to). 

I’m not gonna lie, there were some sessions at this conference that were inspiring and straight-forward, and made me want to actually play this game a bit more. 

And there were other sessions that made me want to run away into a forest and forget that I spent a weekend being sucked into a cult that wants me to spend my life strategizing every purchase and bean-counting with apps and spreadsheets instead of… you know, living. 

I’m kidding, it’s not a cult. Don’t sue me. That’s just my overwhelmed brain running in the opposite direction screaming I don’t have time for this. 

If you start to feel that, it’s okay. It’s fine to do less. Just do what feels fun and exciting and valuable, and ignore the rest. 

But, that being said, the superb travel-hacker (and entertainer) Janelle on a Jet made an interesting point when we were chatting about this after-hours at the conference: 

“When I had a lot of time and no money, it was worth it to totally gamify and strategize everything.”

Janelle on a Jet

True. If you want to dive all the way in, you have the time, and it sounds like fun to squeeze as much value as you can out of all this, go for it!

8. Hold on to your ethics and your logic.

I’m sure you can guess that this final point is 100% my own advice, not something from a rewards travel expert. But it’s important to remember, especially if you’re skeptical of the system, as I was. 

Don’t let the points and miles “game” change your shopping habits or make you stop voting with your wallet for the kind of world you want to live in. 

Keep your money in a bank like Green Fi, that doesn’t invest in fossil fuels, even if the credit card that makes the most sense for you is from a bank that does. You can make an effort (and an impact) by being mindful, even if you’re not perfect.

You don’t want to give up on buying from local businesses in favor of using “shopping portals” that give you bonus points for online shopping at chain stores? 

Then don’t. (That’s another reason I recommend signing up for Bilt Points – it’s the only currency that has opportunities for earning bonus points from purchases at small businesses, like local restaurants in your neighborhood, who also benefit from the program.)

As the Points and Miles Doc said:

“Spend your points with the evil corporations, and your cash with the good guys.”

Dr. Kelly Wright, the Points and Miles Doc

You don’t want to do “mileage runs” to burn fuel for no reason other than stacking up airline miles?

Then don’t.

You don’t plan to spend enough money in the next few months to earn a “welcome bonus” for a fancy rewards credit card?

Then don’t! (You can get a card with a lower minimum spend requirement that still gives you a hundred dollars or more back as a welcome. And hey, why say no to $100?)

There’s plenty to optimize, but you don’t have to optimize everything.