Monitoring prices and rebooking can be one of the highest-return plays
/For experienced travel hackers, the game can sometimes feel a bit mechanical: you earn the most valuable points you can at the lowest cost you can, and periodically re-evaluate which points are the most valuable, and how to earn them at the lowest cost. This doesn’t necessarily make it easy (electrical engineering is also “mechanical” — but it’s still hard!), since earning and redemption opportunities are constantly changing, but when you have a framework in mind it makes it relatively simple to calculate which miles and points are worth earning and when.
But travel hacking isn’t just about earning miles and points efficiently; it’s about paying as little as possible for the trips you want to take. When business class awards are available, or hotel rooms during peak demand periods like the Kentucky Derby are bookable with points, that can often mean saving hundreds or thousands of dollars booking awards. But the cheapest way to book a room, flight, or rental car may well be with cash, and monitoring those prices can save you with a few clicks hundreds of dollars that would take hours of manufactured spend to earn.
The bad old days: Southwest, hotels, and car rentals
These are the three buckets I put the best-behaved companies from the pre-pandemic days into.
Southwest Airlines would allow you to change or refund Rapid Rewards points into your account up until your flight’s departure, so monitoring the price of your flights from the time you book up until your flight time would allow you to shave down the price a few hundred or thousand points at a time. Paid flights were slightly more restrictive, since any price difference would be deposited in an eventually-expiring travel bank account that could only be used by the original ticketed passenger, which created some urgency to plug more money into the Southwest Airlines ecosystem.
Hotels have long had flexible rates which require no upfront payment and cancellation policies between 1 and 5 days before arrival. This creates an obvious incentive to immediately book every hotel you’re even considering staying at. If prices fall, rebook at the lower price, and if prices rise, cancel the more expensive reservations and keep the cheapest. If you have high-level status in multiple hotel loyalty programs, this also allows you to monitor for upgrades as you approach your travel date: at the same price point, you might prefer a Globalist suite upgrade at the Park Hyatt Vienna over a standard room at the Hilton Vienna Park, but access to the Hilton executive lounge over a standard room at the Park Hyatt. Booking both in advance lets you pick the one you end up wanting more. And no, I’m not comparing the two hotels in terms of price or quality, but if a family of 4 is deciding whether to book one room at the Park Hyatt (hoping for a suite upgrade that accommodates them all) or two rooms at the Hilton, the prices can sometimes end up fairly close.
Rental cars are even better, since they don’t even require billing information to book most rates, and Autoslash exists to both find the cheapest rates and monitor existing reservations to alert you when rates fall and you should rebook. Purely as a courtesy to the overworked rental car company staff I usually cancel my prior reservations when I rebook, but it’s not strictly necessary.
Other than those obvious examples, before the pandemic opportunities to rebook and save money were fairly limited. Mid-level airline elite status usually allowed you to redeposit awards tickets for a full refund, so if flights were expensive enough to meet whatever your threshold is to book using airline miles (and everyone’s threshold is different!), but subsequently dropped below that threshold, you could cancel your award tickets and rebook using cash.
Likewise, schedule changes that move your departure or arrival by more than an hour could be refunded to the original form of payment, so if you booked your flights far enough in advance you had a good chance of having an opportunity to request a penalty-free refund, as I did in May, 2020.
The opportunity set has greatly expanded
All of the tools I described above still exist, but the new “permanent” (where I have I heard that before?) policies adopted by US airlines have increased the number of opportunities to save money by booking early and continuing to monitor prices afterwards. However, while they sound similar and were announced around the same time frame, to take advantage of them you need to understand the key differences between airline policies.
Which fares are eligible? United, American, and Delta exempt Basic Economy fares from their no-change-fee policy, as Alaska does with its Saver fares and JetBlue with its Blue Basic fares. If you’re trying to play fares against each other, be sure not to book a fare that’s non-changeable and non-refundable! Note that these non-changeable fares are still eligible for refund under Department of Transportation rules if there’s a significant schedule change.
What happens when you cancel? For paid fares, unless you’re eligible for a refund due to a schedule change, or booked into a refundable fare class, you’ll usually be given a “flight credit” (United), “travel credit” (American, JetBlue), “eCredit” (Delta) or “Wallet” (Alaska). These funds expire, so it’s important to keep a close eye on them.
Who can use the ticket value? I believe (but correct me in the comments if I’m wrong) Alaska is the only airline that allows you to deposit “Wallet” funds into your own Wallet or, by requesting a voucher be e-mailed to you, any other Mileage Plan account. This is notably a way to share Companion Fares without sharing the cardholder’s credit card information, since Companion Fares can be paid for in full using Wallet funds, even if the person booking the ticket is not an Alaska Airlines credit cardholder (if Wallet funds don’t cover the full cost, any residual must be paid for with an Alaska Airlines credit card).
What are your expected flight needs? This is a highly individualized calculation. For example, my partner and I fly to the Pacific Northwest on Alaska and the Midwest on American and Delta at least once or twice per year, so any travel credit, eCredit, or Wallet funds I receive by cancelling a flight on those airlines is absolutely certain to be used. Conversely, it appears I have not flown on United since October, 2017 (although I may be breaking that streak this summer!), so I would never book a paid United flight as a “backup” since there’s virtually no chance I would ever use the flight credit.
Conclusion: use flexibility to your advantage, but don’t get too clever
Especially with respect to hotels and rental cars, making multiple reservations as far in advance as possible and then monitoring prices for opportunities to rebook has always made sense. But the added flexibility of pandemic airline policies makes this is a meaningful way to save money on all the main components of travel planning.
Still, as the voice of caution, I have to remind my beloved readers not to bite off more than they can chew. While rental cars don’t typically charge no-show fees, airlines and hotels absolutely do, so if you don’t trust yourself to keep a close eye on all your reservations as your travel date approaches, don’t bother, since a single no-show penalty is going to wipe out any savings you may have been counting on in advance.
