Frequent Miler on the Air
Frequent Miler
Do we book speculatively, hoping for a schedule change? | Question of the Week Ep8 | 7-5-26
In this episode of Frequent Miler on the Air, the hosts explore the strategy of booking speculative flights with the hope that a future airline schedule change will allow for a free adjustment to a more convenient route. The discussion centers on whether travelers should book less ideal, cheaper award tickets in advance, anticipating that minor modifications by the airline will grant them the flexibility to rebook onto a preferred flight without additional fees or requiring award availability on the desired route. The hosts share personal anecdotes, including experiences with Southwest, American Airlines, and United, noting that while this tactic can be highly effective for securing better itineraries, it requires diligence. Key takeaways include the importance of researching desired routings ahead of time and being aware that airline policies regarding schedule changes can vary by carrier and representative. Ultimately, the hosts remain somewhat lukewarm on the practice due to the mental bandwidth required to manage multiple bookings. They emphasize that while it is a legitimate tool for savvy travelers, one must weigh the potential benefits against the risks of mismanaging complex travel schedules.
Updated Jul 5, 2026
About This Episode
Do we book speculatively, hoping for a schedule change? Reader "LR" sent us the following question:
"I was intrigued by a recent post about schedule changes in another group that I follow. This particular person noted that anytime United or AA makes a schedule change of any type, you can change your flight at no additional cost to your preferred route. Sometimes you may even have flexibility within several days of the original flight. So my question is, is this a tactic that you all use if you book flights far in advance? Pick the cheapest award price from one city to another, and then hope for a schedule change in order to change it to your preferred route? And then on an even more complicated note- have any of you had success following a schedule change, of changing from a flight in “first class (non-lay-flat seats)” to a different flight on “Delta One” or AA’s “flagship business” or United Polaris (etc, all of which have lay-flat seats)? I assume these are considered different classes and would require a fee upgrade. I’m trying to book flights home from Hawaii next March, and I’m wondering if this kind of tactic may work."
We’ve been answering a reader or listener question at the end of each Frequent Miler on the Air podcast episode. Now, we’ve turned the question of the week into its own weekly episode. Tune in every Sunday at 5pm for our Question of the Week podcast. And if you have your own question you’d like to submit, you can send it to mailbag@frequentmiler.com.
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More Episodes
Which Hyatt Milestone Reward should I pick? | Coffee Break Ep113 | 7-7-26
In this episode of Frequent Miler on the Air, the hosts tackle the common dilemma of selecting Hyatt Milestone Rewards. Using a personal example, the team explores the pros and cons of various choices available to elite members after hitting thirty nights. They analyze specific benefits, including two-thousand-point bonuses for select brands, club access awards, Find Experience credits, and American Airlines preferred seat coupons. The discussion highlights the importance of checking upcoming travel plans and elite status before making a selection to ensure the reward provides actual value. Moving beyond the thirty-night mark, the hosts provide a strategic breakdown of the best options at higher milestones. They evaluate the trade-offs between suite upgrade awards, bonus points, airline elite status, and the highly coveted Miraval extra night. Throughout the conversation, the hosts offer insights into maximizing these perks, weighing the benefits of short-term rewards versus long-term status advantages. The episode serves as a practical guide for frequent travelers looking to navigate Hyatt’s loyalty structure and extract the most utility from their hard-earned milestone selections.
12 things to know about Hyatt's devaluation | Frequent Miler on the Air Ep365 | 7-3-26
In this episode of Frequent Miler on the Air, the hosts conduct an in-depth analysis of the recent Hyatt loyalty program changes. Following Hyatt’s shift to a new award chart featuring five tiers per category, the team utilized hotel data to determine the actual impact of the devaluation. Their findings indicate that the median point value has dropped to 1.54 cents, a decrease from the previous 1.7 cents. While the decline was less severe than their initial projections, they warn that the situation will likely worsen as Hyatt gradually increases property pricing. The hosts also break down how point value fluctuates by brand, noting that Hyatt Regency properties currently offer some of the best redemption values, whereas Mr. & Mrs. Smith and all-inclusive brands, such as Ziva and Dreams, tend to provide significantly lower returns. Additionally, the episode covers a variety of other travel news, including an update on airline credit card spending bonuses, a quirky discrepancy between Chase business and consumer card benefits, and tips for optimizing Southwest Airlines seat selection and promo codes using the mobile app.
Speculative Bilt transfer bonuses | Coffee Break Ep112 | 6-30-26
In this episode of the Coffee Break series, the hosts challenge the long-standing conventional wisdom that travelers should only transfer credit card points to loyalty programs when they have an immediate, specific redemption in mind. With the evolution of the Bilt Rewards program—which now offers significantly more ways to earn points through rent, mortgage payments, and neighborhood rewards—the hosts explore whether the strategy of speculative transferring has become viable. A central point of discussion is how Bilt’s frequent transfer bonuses, often capped at 100,000 points, shift the calculus for members who are accumulating larger balances. The hosts walk through a variety of Bilt’s airline and hotel transfer partners, debating whether they would move points speculatively if a 100% transfer bonus were available. While they reach a consensus on high-value partners like Alaska Airlines and Hyatt, they express differing levels of enthusiasm and caution regarding programs like Flying Blue, Avianca LifeMiles, and various hotel chains. Ultimately, the conversation highlights how earning power and specific travel goals necessitate a more nuanced approach to point management than in years past.
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