Should I transfer my points to take advantage of a bonus, even if I don't know where I'm traveling yet?
Welcome to Ask The Group Chat, where every week I am answering questions from my readers, trying to help you figure out the life stuff you think you’re already supposed to understand. This week’s message comes from Cowboy O, who wants to take advantage of credit card points transfer bonuses, but can never seem to time it right.
It feels like whenever I’m planning a trip, my travel portal has no relevant transfer bonuses. However, when I’m not booking a trip… my travel is rich with transfer bonuses. When there is a decent transfer bonus, I’m tempted to transfer points so that I’ll have them in the future, but I get cold feet because I don’t know if they’ll actually be relevant to my future travel plans. So I guess the question is- Are there specific transfer bonuses you always go for and bank for the future? Or is it best to save your points when you have something specific in mind and hope there’s a bonus when it comes? For personal context, I’ve been a Chase Sapphire girlie and now a recently upgraded Reservanista. But I feel like this is relevant to all cards. LMKKKKK!! - Cowboy O
The best thing to do with a credit card point is to use it. Hoarding your points is good, to a point. But over time, frequent travel programs will devalue the points, making redemptions more expensive. So there’s a delicate balance in conversions when you don’t have a planned trip. Instead of versatile Chase points, you could end up saddled with Marriott points and nowhere to actually spend them.
The sweet spot in transfers from a program like Chase or Amex is over to a travel program that has lower points rates for good redemptions, even without a bonus. The gold standard of this for hotels is Hyatt, which, even after some devaluations, still has great redemptions for half the price of Marriott or Hilton in the same cities. A standout example I’ve redeemed often is the Orlando options around Disney World. Hyatt has all Category 4 and below hotels in the area, with a maximum points per night redemption of 18,000. Compare that to Hilton or Marriott, which have a variety of hotels in the area, and those on par with the Category 4 Hyatts charge 50,000 - 90,000 points per night. If you’re transferring from Amex or Chase without a bonus, it’s at a 1:1 rate, so you’re getting double the hotel rooms from Hyatt. While you can often find Marriott or Hilton with a bonus transfer, you do best to wait until it’s an 80% one to really match the Hyatt transfer value. Hyatt rarely, if ever, runs a bonus, but the transfer rate as it stands for their redemptions is so good I’m not even mad about it.
For flights, you generally won’t get the most bang for your points with a transfer to a US-based airline, but partners like Flying Blue or Virgin Atlantic can offer great international redemption offers for a fraction of the points, even before lucrative bonus offers. With Virgin Atlantic recently, there were one-way London flights for 9000 points, which could be reduced to 7000 if you grabbed a transfer bonus. At that rate, a pretty standard signup bonus could equate to 7 or more roundtrips to the UK!
All that said, stockpiling points with these good deals is only a good deal if you can actually redeem the points for the trip you want. Here’s what I’d recommend you do before you click on the transfer confirmation.
First, do some research into the flight costs for potential future trips. See where the range is for a trip to London during the months when you’re most likely to want to travel. If you’re able to be flexible, you’ll have the most options, but it’s good to know what the worst-case scenario is on airlines. Compare a few — check Virgin and British Airways if you’re trying to get to London directly, try Flying Blue if you’re open to connecting in Amsterdam or Paris. Then, watch for a bonus to appear, 30% as a target. When that arrives, it’s a good time to try and make a flight plan. As tempting as it is, with airlines, I don’t recommend blindly transferring to take advantage of the bonus, especially if it’s an airline you don’t normally fly. It just traps your points somewhere new.
I have a slightly different approach to hotel transfers. Flight point redemptions can waver a lot from day to day, or even within flight times on the same day, based on demand. Hotels generally have a more rigid redemption chart, so you know how much a room will cost on a yearly basis in points, and can plan accordingly. Just like with the flights, you should do some research into each chain and what hotels they have in cities you’re interested in visiting. Domestically in the US, they all have various presences in major cities, but internationally it can be a gamble. I just returned from Sicily, and none of the three major chains has a presence in a city like Palermo, for example. In other tourist desintations like Cancun or London, you’ll have a lot of options. See what type of hotel speaks to you, and which brand you’re willing to explore.
Hotels also run bigger bonus offers throughout the year, and if you see a Hilton or Marriott transfer for 70 or 80%, it can be worth it to jump on that, which puts it at par with a Hyatt transfer in terms of worth. Hotels tend to adjust their points charts yearly, moving some hotels around at redemption levels or adjusting their point value altogether. Still, you can make an educated guess on how many points you’ll need for a full stay, and at the very least, you’ll have enough for some nights if not all when you do you do get to book your trip.
You can plan and prep forever, but the best point is a well-used point, and if the time comes to book your dream trip and there are no bonuses available, don’t hold back. My parting advice is to double-check what benefits you most — transferring the points to a partner or booking directly via a travel portal. Historically, transfers are the best, but there have been some targeted offers that incentivize portal booking. The big tip is don’t rush into what seems like a good deal without exploring all your options!
Quick Hits
Since I mentioned Disney above, I guess it’s time to remind you all that I love booking travel for people, especially theme park travel. I’m the kind of person who gets true joy out of telling you where all the different Dole Whip flavors are available on Disney property. Hit me up if you want to talk trip planning (at no cost to you!). Despite never having been on a cruise before, I am eyeing their European cruise lineup for 2026 (probably also because I just returned from Europe…) and plotting a visit to Universal’s new Epic Universe park before the end of the year.
Airbnb is in Midlife Crisis Mode. This is a few weeks old now, but a great read on the company’s next evolution.
I cannot stop watching old seasons (series? it’s British) of Taskmaster on YouTube. I got sucked into the current one, and then just started randomly watching different ones until I find a cast that compells me. For the uninitiated, it’s a competition show where 5 comedians are given truly unhinged tasks to compete in pre-taped segments and are awarded points by a grumpy comedian in front of a studio audience. Simple, yet has my in hysterics on my couch even if I don’t get all the UK references.
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Reminder: I’m not a licensed financial advisor, and this is not financial advice. I’m just sharing my personal opinions with my group chat.