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. And it will all be explained in excruciating detail in posts to come! Thank me later. (Updated July 2017)
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 your dumb miles slowly, and you can use yours alone, on a single airline, and that’s it. But you can use your points on several different airlines, or as cash, and easily combine them with your family members. Also, you can earn at better than 1 point per dollar spent, and redeem at under 100 points per cash price dollar, so compared to a frequent flyer card, you just earn more, and what you get is worth more. Get it? Points > miles. The best points are Chase Ultimate Rewards points, though if you never fly United, they’re not quite as great.
Are you able and willing to fly United? Yay for you. Get a Chase Sapphire Reserve card, and a Chase Freedom Unlimited card. Don’t get one. Get both. Listen to me. I am right. Either apply for both at once, or wait at least a month between applications. 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 transfer 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 double that when you can, then put restaurant, travel, lodging, and transportation charges (including taxi, Uber, MTA, AirBnB, parking, etc), on the Sapphire Reserve; you’ll earn 3 points per dollar spent. And you might be able to do even better if you transfer the points from your Sapphire Reserve to United, Southwest, five international airlines, or four hotel programs, and redeem them for an award ticket. Though the Sapphire Reserve seems to cost $450/year, it’s really $150/year, because you get automatically get credited $300 each year for plane tickets, taxis, hotels, etc. The Freedom Unlimited has no fee. (more details)
If you don’t ever fly United, and sometimes fly American or Delta, but want maximum transfer flexibility for 30+ other airlines, you could get the American Express Starwood Preferred Guest card and put all your spending on that. You get 5,000 bonus points when you transfer 20,000, so try to transfer to airlines in that increment. Bummers are that SPG points-to-miles transfers usually take a few days, and the points earn slowly, at one point per dollar spent. Also, what SPG points get you may change now that Starwood and Marriott have merged, but probably not until 2018 at the earliest. (more details)
If you’re a Delta loyalist or are primarily an international flyer, you might want the American Express Blue Business Plus card. It earns 2 Amex Membership Rewards points per dollar spent, up to $50,000 per year; it has no annual fee, and you don’t really have to have a business to get one. (Alternatively, consider the $95/year Everyday Preferred card. If you make at least 30 charges per month, you’ll earn at least 1.5 Amex Membership Rewards points per dollar spent, plus more for gas and groceries.) You can transfer the points to a few domestic airlines and several international airlines, or use them to pay for any ticket on any airline, where each point is worth one cent. You might also consider adding to one of these the Amex Business Platinum, because it has a unique feature in which you can, in economy class on a yearly designated airline, or business class on any airline, pay with points for any flight as usual, but then receive 35% of those points back a month later as a rebate. That makes each point worth 54% more. It’s $450/year, but you can reduce that to effectively $250 by buying $50-$75 airline gift cards, or contribute to an airline gift registry, on your yearly designated airline. Don’t spend on this card though; for most purchases, it only earns 1 point per dollar spent. Use the Blue Business Plus or Everyday Preferred. Instead, use the Business Platinum’s fairly nice perks, like the Centurion lounge, if you’re in an airport that has one. (more details)
If you just want something that’s easy and not tied to any one airline, if less rewarding, consider a Barclaycard Arrival Plus card, a Capital One Venture Rewards card, or a Citi Double Cash card. I like the Double Cash best because it has no annual fee, but it also has no bonus, unlike the other cards. These basically all just give you 2% cash back on your spending, which is pretty good for moderately priced tickets, but won’t get you kick ass deals if a ticket is expensive. The more it costs, the more points you have to use. I’m not that excited about them, but they’re simple and flexible, like this girl I once knew. Thank you, I’ll be here all week. (more details)
If you’re flying United regularly, for many of the perks of elite airline status without having to actually fly enough to earn it, add a Chase United MileagePlus Explorer card or (especially) MileagePlus Club card, or whatever the equivalent is for the dumb airline that you prefer. You get more dates for award tickets if you have one of these, but don’t have elite status. Because it earns miles rather than points, don’t use this card for purchases, except to maybe to buy tickets on United (which unlocks some of the status-equivalent perks like 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)
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 transfer the points to British Airways, once BA confirms they can do it. Or you can use Air France miles to fly Delta. My brother says this doesn’t work, but the internet says it does. I myself was able to fly American after transferring Amex points to BA and booking it as a BA ticket; I also was able to fly SWISS by transferring Amex points to Air Canada and booking the flight as an Air Canada ticket.
Most of the above cards come with major signup bonuses if you spend some amount of money in the first three months. Don’t be an asshole and blow it. If you haven’t spent enough, buy an Amazon gift credit — it won’t expire, so you’ll eventually burn through it. If you want to earn some extra United bonus miles on the same dime, for fucking free, buy the Amazon credit (and any other Amazon purchases) using the MileagePlus X app for your phone, rather than directly at Amazon. If Amazon credit doesn’t appeal, then check out Plastiq, which charges you 2.5% for to use your credit card to write checks to businesses of any kind. Might be worth it if that signup bonus is large enough. (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 once a week just log in and pay the cards off. 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.