August 2020

Disclosure: This content is not sponsored or endorsed by any of the card brands described here and is accurate as of the posting date, but some of the offers mentioned may have expired. Money with Katie is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as MileValue.com. This compensation may impact how and where links appear on my site, and this site does not include all financial companies or all available financial offers.

Once you’re fully entrenched in the world of travel rewards and credit cards points with hundreds of thousands burning a hole in your pocket, your focus shifts to the second half of the equation: redemption.

Redeeming your points seems like it would be straightforward enough – after all, they’re a currency, and we’re all used to price-comparing a little bit before buying something – but I think most of us tend to believe that things just cost what they cost. Shopping for a hotel room on the hotel’s site, Expedia, or Booking.com usually doesn’t reveal a substantial difference in price (because of rate parity), but when you throw points into the mix, you’re walking onto the field of an entirely different ballgame.

As such, it’s important to assess all your options before burning your precious, hard-earned points.

Of course, you can always redeem travel in the Chase travel portal, but sometimes transferring is a more valuable approach (e.g., a flight might cost 80,000 points in the Chase portal but 40,000 points by booking directly with the airline – this is why you should always check).

General rules of thumb

These are just a few starting points to consider before we start talking about the specifics, but keep in mind that these are by no means always true (yay, #ambiguity):

• Generally speaking, the best redemption values (in the literal sense of a dollars-to-points conversion) are going to be business class flights, and usually just flights in general.

  • Example | A roundtrip United flight in November from DFW to Tokyo is $1,386 for Economy or 35,000 points, making each point worth almost 4 cents. You can transfer Chase points to United on a 1:1 basis – and remember, we usually value a Chase point at about 1.5 cents, so this is a great value.

• Transferring your points to a hotelier (e.g., converting Chase points to Bonvoy points) is generally a bad redemption value.

  • Example | Let’s extend our example above and find a 35,000-point Bonvoy room in Tokyo for November. The Aloft Tokyo Ginza costs 35,000 points per night or 27,440 yen, which equates to roughly $260. See what I mean? You can transfer 35,000 Chase points to United and book a $1,400 roundtrip flight or transfer 35,000 Chase points to Marriott and book a $260 hotel room.

Scenarios like this are the main reason I write about credit cards and travel hacking – because it feels like there should be some sort of safeguard in place to prevent you from royally f***ing up that badly. But there isn’t! There’s no pop-up window that asks you, “Yo, are you sure you want to blow 35,000 points on a $260 hotel room when you could transfer them somewhere else and get $1,400 of value from them?” And you know what? Sometimes you’re going to choose to accept a poor redemption value, because maybe you have 250,000 Chase points and you simply don’t want to spend $300 on a hotel room – but it should be a choice, not a mistake.

It does take trial and error, and we’ve all made stupid redemption decisions. My goal is to make yours (and mine!) few and far between.

• The last general rule of thumb is more so an equation you can always use to determine how valuable a redemption is:

[cost of flight or hotel in dollars] ÷ [number of points required] * 100 = [value of one point, in cents]

So, for the examples above, I did:

$1,386 ÷ 35,000 points * 100 = 3.9 cents

$260 ÷ 35,000 points * 100 = 0.7 cents

If you’re unsure or skeptical, just run a potential redemption through that formula and see how it nets out. Generally, anything under 1 cent is a poor redemption and anything over 1.5 cents is good.

Getting to know your transfer options

The two main travel rewards portals worth giving a shit about are Chase and American Express, as you can probably tell if you’ve spent more than 12 seconds on this site. Other banks have them, but they’re either underdeveloped, devalued, or still in their infancy.

(Citi used to have some pretty dope benefits for the Prestige, including, I believe, a fourth night free at a hotel every time you used it to book three nights, but they’ve since stripped that card of most of it.)

So my main strategy (as outlined in the Travel Hacking tab that provides an overview) is to acquire Chase cards, American Express card(s), and then cards at each of the hoteliers and airlines I use the most. Because while transferring 35,000 Chase points to Bonvoy is a bad idea, getting 100,000 Bonvoy points from their credit card for the $95 annual fee is a great idea.

Chase Ultimate Rewards

Chase Ultimate Rewards points, earned with cards like the Chase Sapphire Preferred [$95 annual fee; 100,000-point sign-up bonus right now] and the Chase Ink Business Preferred [$95 annual fee; 100,000-point sign-up bonus right now] can be transferred to these airlines and their respective loyalty programs. They are, as you’re about to learn, mindblowingly versatile.

Quick note on the airlines: This collection of 10 direct transfer partners opens the doors to all three major airline alliances, Oneworld, SkyTeam, and Star Alliance. This will be a topic for a different day, but the point is: You can access many other airlines through these 10, and I listed them under the transfer partner so you can see, at a glance, how much the entire world has just been opened up to you via your tiny piece of blue plastic.

Aer Lingus – AerClub – Avios Points

• Good for flying to Ireland

Air France & KLM – Flying Blue – Miles

• Good for going to France, the Netherlands, and more

• Any SkyTeam airline can be booked with these

British Airways – Executive Club – Avios Points

• Good for getting to Western Europe

• Can also use these points for…

  • airberlin, Alaska Airlines, American Airlines, Aer Lingus, Cathay Pacific, Finnair, Iberia, Japan Airlines, LAN, Malaysia Airlines, OpenSkies, Qantas, Qatar Airways, Royal Jordanian, S7 Airlines and TAM Airlines.

Emirates – Skywards – Skywards Miles

• Mainly known for flying to the Middle East, Africa, and Asia

• Can also use these points for…

  •  Alaska Airlines, jetBlue, Copa Airlines, easyJet.

Iberia – Iberia Plus – Avios Points

• Good for flying to Spain

• Can also use these points for…

  • Iberia Group, British Airways, Aer Lingus.

JetBlue – TrueBlue – Points

• Great (domestically) for New York, Boston, Fort Lauderdale, LA, Orlando, and San Juan

• Their Mint Class is amazing and a fun points splurge if you have a cross-country flight

• Can also use these points for…

  • Hawaiian Airlines

Singapore Airlines – KrisFlyer – Miles

• The obvious choice for flying to Singapore, as expected

• Any Star Alliance airline can be booked with these miles

Southwest Airlines – Rapid Rewards – Points

• The best airline in the world and I am NOT biased whatsoever by my employment status

• Realistically, though, if you’re flying in the Southwestern part of the U.S., you really can’t beat Southwest – especially thanks to Companion Pass and the low point redemptions. I once booked a last-minute flight from Dallas to Seattle for 3,000 points.

United Airlines – MileagePlus – Award Miles

• United has generally good redemption values; however, I don’t fly them often because their network isn’t very strong in this part of the country

• Any Star Alliance airline can be booked with these miles

Virgin Atlantic – Flying Club – Miles

• I’d put Virgin in the same category as British Airways, network-wise, but like the cooler younger brother

• Can also use these points for…

  • Delta Air Lines, Virgin Australia, Hawaiian Airlines, Air China, Air New Zealand, All Nippon Airways, Gulf Air, Jet Airways, Scandinavian Airlines, Singapore Airlines and South African Airways

You can also transfer to these hotels…

• World of Hyatt (really, the only valuable transfer hotel option)

  • Your best bets for high-value redemptions at Hyatt are at the Park Hyatts, Grand Hyatts, and Hyatt Zilara/Ziva (the all-inclusives in Mexico, covered here)

• Marriott – Bonvoy (I’ve covered this one extensively, as it was my pick for hotel cards)

• IHG – IHG Rewards Club

  • Think Kimpton, Hotel Indigo, Holiday Inn, and more

  • I have PTSD from the origin story of my IHG Rewards Club membership – attempting to fly standby back from San Diego on a day where Texas was being rocked by storms, we had to fly to Austin instead (reasoning that we’d rent a car and drive the rest of the way) and were diverted to Corpus Christi (six hours south of Dallas) due to weather. We landed at 1 a.m. and sat on the tarmac for an hour before paying through the nose for a room at the Holiday Inn in Corpus. And that’s how I earned my first 2,000 IHG Rewards Club points!

In conclusion

Everyone approaches trip-planning differently, but my general approach that I’d recommend is starting with Google Flights. Search the routes you’re interested in (for example, JFK to Greece) and get a feel for which airlines fly where you want to go. Then, navigate to their sites, and see how many points it takes to get there. You’ll need to set up a frequent flier account with that airline’s loyalty program if you don’t already have one. Last, you can go into the Chase transfer portal and see if points are transferred on a 1:1 basis.

From there, it’s really just about using the equation at the beginning of this article to gauge your best options.

Another post is coming on the actual “how” of transferring and when you want to book say, an American Airlines flight via British Airways, but in the meantime, consider getting the Chase Sapphire Preferred card to begin banking your hella valuable, versatile Ultimate Rewards points!

Learn more about the Chase Sapphire Preferred Card

Editor’s Note: Opinions expressed here are mine alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved, or otherwise endorsed by any of the entities included in the post.