Cheat Sheet [updated Apr 2019]

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Do you want to know all the shit I’ve figured out about earning the best and most free travel? Yes, you do, and it’s all summarized in this post.

Here’s the somewhat short answer. Or, if you’re just insufferably impatient, you can instead read the very short answer.

Unless you’re dedicated to one airline, and one airline only, you want a credit card that earns you reward points, rather than a credit card that earns you frequent flyer miles. You earn miles slowly, and you can use yours alone, on a single airline, and that’s it. (You could also consider a card that earns cash back if you want something simpler, but with less potential upside.)

But you can use points on several different airlines, or as cash, and combine them with your family members. Compared to a frequent flyer program credit card, you earn more points for the same spending, and the points you earn are worth more, and can be used more flexibly. Get it? Points > miles. The best points are Chase Ultimate Rewards points, especially if you have household members to combine them with.


Chase Ultimate Rewards Points (good for United and others): good

Are you able and willing to fly United? Swell. Get a Chase Sapphire Reserve card, andChase Freedom Unlimited card. Don’t get one. Get both. Listen to me. I am right. When you use the Freedom Unlimited, you’ll earn 1.5 Chase Ultimate Rewards points per dollar spent (though they will call this “1.5% cash back”). When you combine the points to your Sapphire Reserve, each point is worth a minimum of 1.5 cents towards travel on nearly any flight on any airline, so you’re talking a minimum of 2.25% travel back on all your spending. If you want to do even better, use your Sapphire Reserve for restaurant, travel, lodging, and transportation charges (including taxi, Uber, MTA, AirBnB, parking, etc); you’ll earn 3 points per dollar spent, yielding a minimum of 4.5% travel back for those purchases. That doesn’t suck.

If you want to do really well, like scoring an international business class ticket that would otherwise cost you five grand or more, and you are blessed with patience, you can instead send the points from your Sapphire Reserve to frequent flyer programs at United, Southwest, JetBlue, British Airways, Virgin Atlantic, Air France/KLM, Singapore, Aer Lingus, and Iberia, and redeem them for a frequent flyer award ticket, possibly on yet another airline who’s partnered with one of the above programs. (You can also send them to hotel loyalty programs at Hyatt, Marriott, and IHG, where they can be redeemed for free stays, but Marriott and IHG are bad deals.)

Though the Sapphire Reserve seems to cost $450/year, it’s really $150/year, because you automatically receive a statement credit each year for your first $300 worth plane tickets, taxis, hotels, etc. (If you’re still scared, then wade into the water with the Chase Sapphire Preferred, which is free the first year, though it only earns 2 points where the Reserve earns 3. If you’re sold on the merits of your new life, you can convert it to a Reserve when it’s due for renewal.) The Freedom Unlimited has no annual fee.

Chase Ultimate Rewards points are better than other points because you don’t need as many kinds of cards to earn them quickly, they’re worth a lot, they’re very flexible, and it’s trivial to pool them with family members. I wish they could be transferred to a few more airlines, though.

(more details on Chase Ultimate Rewards points)


American Express Membership Rewards Points (good for Delta and others): good

If you’re a Delta loyalist, or are primarily an international flyer, you might want the American Express Blue Business Plus card. (Don’t be afraid if you don’t own a business. Just say you’re a sole proprietor who earns $1,000 a year selling cigarettes on the street. They don’t care.) This card earns 2 Amex Membership Rewards points per dollar spent for the first $50,000 spent per year, and it costs nothing. Who says the best things in life ain’t free.

Alternatively, if the whole business card thing puts you off, consider the $95/year Everyday Preferred card. If you make at least 30 charges per month, you’ll earn 1.5 Amex Membership Rewards points per dollar spent, or 3 points for gas, or 4.5 points for groceries (for the first $6,000 in groceries per year).

You might also want to think supplementing one of the above with the American Express Gold card. The swell thing about this card is that you get 4 dollars per point at supermarkets and US restaurants, and 3 for travel when booking with airlines, so you can rack up points pretty quickly. It’s $250/year, which can be reduced to $150 by buying $50-$75 airfare gift cards from American or Delta by selecting one of those airlines as your yearly chosen airline for your travel credit benefit. You also get $10 a month towards Seamless/Grubhub, so if you’d normally be spending that, it lowers the cost of the card further.

If you get one or more of the above Amex cards, you might still also consider also getting the American Express Business Platinum card, because it has a unique feature in which you can, in economy class on a yearly designated domestic airline, or business class on any airline, pay with points for any flight at one cent per point, but then receive 35% of those points back a month later as a rebate. That makes each point worth 54% more (1.54 cents per point) than if paying with points on any other Amex card (including the personal Platinum).

The Business Platinum is $595/year, but you can reduce that to effectively $195 by making your designated domestic airline either American or Delta, and then buying $200 worth of $50-$75 airline gift cards from their web sites; and by activating the $200 yearly Dell benefit, and buying $200 worth of electronics a year, which I know you do, from the Dell web site. If you do need to buy a plane ticket with cash, you’ll get 5 points per dollar spent if you buy at, but for other purchases, it only earns 1 point per dollar spent, so instead use the Blue Business Plus or Everyday Preferred or Gold. But you can enjoy the Business Platinum for its perks, the best of which is the amazingly nice Centurion lounge, if you’re in one of the nine airports that has one; or you can the Delta lounge when flying Delta. Getting 10 Gogo wifi passes per year isn’t bad either. Also, cashiers and waiters everywhere will be very impressed by your blingy card.

While it’s possible to buy tickets on any airline with Amex points, it’s a shitty deal (unless you have a Business Platinum card, per above, which makes it decent). If you want to get yourself a nice a business class award ticket, you can transfer your Amex points to frequent flyer programs for Delta, JetBlue, British Airways, Air France/KLM, Virgin Atlantic, Alitalia, Air Canada, ANA, AeroMexico, El Al, Emirates, Etihad, Hawaiian, Iberia; or hotel loyalty programs for Hilton, Marriott, and Choice. Most of these are decent deals, but not all (El Al and Marriott are especially bad).

Amex Membership Rewards points are nice to have, because they earn quickly and are flexible, but I don’t like them as much as Chase points, because to get the most from them, you need more kinds of cards, at greater expense. And the points themselves are they’re more difficult for family members to pool, aren’t quite as flexible or valuable (especially when using points as cash for a ticket), plus Amex charges a small but dickish fee when sending points to domestic airlines. But Amex points do transfer to more airlines than Chase points do, and United’s award prices look as though they are on the way to eventually becoming as expensive as Delta’s, so Chase’s advantage here is less than it used to be.

(more details on Amex Membership Rewards Points)


American and Alaska: boo

If you primarily fly American or Alaska, you might want to have a hard talk with yourself, because your options for earning free travel are kind of sucky. You could get a branded credit card, of course, but then your miles are stuck at American or Alaska, and can only be used for award tickets on them, or one of their partner airlines, giving you many fewer options, which defeats the whole fucking point. The points also earn fairly slowly, and can’t be pooled between family members, and can’t be used as cash-equivalent for any airline at any time. So I’m not that much of a fan, though if what you really want from life is American or Alaska miles, then it is what it is.

You do have a few options. You could instead earn Chase or Amex points on the cards above, at a faster clip than you’d earn with an airline branded card, and then use the points as cash to buy American or Alaska tickets. Further, both Chase and Amex let you send points to British Airways, and when there are saver-level tickets available, it’s often possible to fly American or Alaska domestically via a BA award ticket. (It’s a super pain for Alaska, though, because you have to search on to see what Alaska flights are available, and then call BA to book, because the Alaska flights can’t be seen or booked directly at Personally, if I were stuck with one of these airlines, I’d do the Chase combo.

Your other choice is to collect Marriott points, by spending on one of their branded credit cards. These can be sent to frequent flyer programs for forty-five fucking airlines, including American and Alaska, which is sweet, and they can also be used as cash-equivalent for purchasing tickets. But, as of August 2018, you only earn 0.67% of what you’d earn on an American or Alaska card, and even worse on Chase and Amex cards, so I can’t really recommend it. If you value the flexibility for other airlines, you can consider it.

But I really just think you should fly other airlines that are compatible with Chase or Amex points. If you already have some kind of elite status on American or Alaska and that’s what’s keeping you there, you may be able to get United or Delta to match it, if you call and ask. If you’re near an American hub, consider moving. You don’t want to be in Phoenix or Charlotte anyway.

(more details on Alaska and American)



If you fly JetBlue (their Mint business class is sick! Try to sit in row 2 or 4, where you get your own pod with a door!), you can earn their points really quickly from their branded credit cards, though then you have JetBlue points, which you can mostly only use on JetBlue. I’d rather just earn Chase points from the Chase cards above, and buy JetBlue tickets with them. (In fact, that’s what I do.) But if you really want maximum free JetBlue travel, then you probably want a Barclays JetBlue Plus or Barclays JetBlue Business card.


Cash Back: yay if you like shit to be super simple

If you just want something that’s easy and not tied to any one airline, consider a Citi Double Cash card. It costs nothing, and gives gives you 2% cash back on everything, which is pretty dece for moderately priced tickets, but won’t get you kick ass deals if a ticket is expensive, like an award ticket will.

An alternative is the Synchrony PayPal Cashback card, which also earns 2% cash on everything, but, unlike the Double Cash, it doesn’t have a foreign transaction fee when used overseas. The downside is that, rather than getting a statement credit, you have to claim the cash back to your PayPal account, from where you can transfer it to your checking account.

If you can manage two cards in your life, consider also getting the Barclay Uber Visa, which also has no annual fee, and put dining (4% cash back!) and airfare/hotel (3% cash back) only on that. It has no foreign transaction fee. If you have a Double Cash, use the Barclays card when overseas to avoid foreign transaction fees.

Alternatively, you can jump through a few hoops to get the Alliant Visa Signature card, which yields 3% on everything cash back the first year, and 2.5% thereafter, for a $99 annual fee (waived first year), or the Bank Of America Premium Rewards card, which offers 2.6%-3.5% back, but only if you hold $100K in assets with them.

Don’t bother with Barclay Arrival Plus, or similar cards. They earn points which are cash-equivalent for travel, but that’s not as good as, you know, cash, and the points can’t be sent to mainstream frequent flyer programs. These cards also have annual fees, and don’t earn better than cash back cards. So, fuck ‘em.

I’m not particularly excited about cash back or travel back cards, but they’re simple and flexible, like this girl I once knew. Thank you, I’ll be here all week.

(more details on cash back cards)


You still might want a United or Delta branded card, even if you shouldn’t spend on it

If you’re flying United regularly, for many of the perks of elite airline status without having to actually fly enough to earn it, get a Chase United Explorer card or Chase United Club card. You get more options for award tickets if you have one of these, even if you don’t have elite status, as well as other status-like perks. And if you do have elite status, having one of these cards makes you eligible for cabin upgrades on award tickets. Because these cards earn miles rather than points, don’t use them for purchases, except to maybe to buy tickets on United (which is required to get free bag check). Be sure to enjoy the gnashing of teeth of the various wannabe George Clooneys who resent your crass appropriation of their hard-flown privileges. (more details)

Same goes for Delta branded cards from Amex if you regularly check bags, and don’t have elite status. Some Delta branded cards also let you earn elite status qualifying miles, if that’s something you want to chase.


Flying airlines you to which you can’t send Chase or Amex points

If you can’t transfer your points directly to the airline you want to fly, and you’ve got nothing better to do with your life, you might be able to figure out how to book the same flight indirectly, via airline partners. For example, if you wanted to use your Chase or Amex points to fly American, you could send the points to British Airways, once BA confirms they can do it. Or you can use Air France miles to fly Delta. Or Air Canada to fly United. My brother says this doesn’t work, but I say it does, so who are you going to believe? I’ve made some of the above plays, as well as shit like flying SWISS, by transferring Amex points to Air Canada and booking the flight as an Air Canada ticket.

In a lot of cases you can’t actually see or book an award ticket on a partner airline from the web site of the airline where you can send your miles. Also, sometimes the web sites will lie and say a seat is available on a partner airline when it isn’t. Call the airline to where you can send your miles, and confirm availability before you move your points from Chase or Amex, because there ain’t no moving them back.


Signup bonuses: hooray

Most of the above cards come with major signup bonuses, worth up to $1,000 or more, if you spend some amount of money, usually $3,000-$5,000, in the first three months. Don’t be an asshole and blow it. Time your application before you have to spend a bunch of dough on dental surgery so that you feel like you’re getting something for your pain.

If you haven’t spent enough, buy an Amazon gift credit — it won’t expire, so you’ll eventually burn through it.

If Amazon credit doesn’t appeal, then check out Plastiq, which charges you 2.5% for using your credit card to write checks to businesses. Some cards are limited to paying certain kinds of businesses, so check the site. I’ve used Plastiq many times when the signup bonus is large enough to make it worth it. (more details)

And always, always, always, always, always, always, always, always pay your dumb credit cards on time and in full. If you don’t, the interest and/or late fees nuke whatever benefit you got from your rewards, and the bastards win. If, like me, you’re shaky on this kind of thing, set up each card to pay itself out of your bank account automatically, or every Sunday just log in and pay the cards off, wherever they’re at. Hint: get the apps for the cards. Makes it easy and painless.



That’s all you really need to know, but if you don’t savor every last word I write in the future, you may live the rest of your life vaguely haunted by wondering what you still don’t know. So come back later, or subscribe via email, and spare yourself the worry.

(Note: if there are links for the cards above, they’ll take you to the card application page, and I’ll get a referral bonus. I appreciate it!)


6 thoughts on “Cheat Sheet [updated Apr 2019]

  1. Jojo

    Hi Ivan, thank you for doing this!! I’ve been clueless all these years about my credit cards –if only I read this sooner! Can’t wake to take advantage. You are crazy and brilliant.

    1. Ivan X Post author

      Thanks for the comment! If padawan learners are getting benefit from it, then that’s why I wrote it. In fact you motivated me to update a couple of minor things. I’ll get some new posts up soon.


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