Our biggest point gambles | Frequent Miler on the Air Ep374 | 9-4-26

Our biggest point gambles | Frequent Miler on the Air Ep374 | 9-4-26

September 4, 2026 · 58 min · Episode 374

About this episode

The episode discusses significant point gambles and travel deals, including high-value transfers and missed opportunities.

On today's episode, we'll talk about why Air Canada to Hyatt 2-to-1 transfers can be a good deal, how we won big on a 240x deal, the 250x deal that got away, and much more. Our apologies for Nick's lower-quality audio this week! We're working to fix it! Our biggest point gambles Giant Mailbag (01:04) - Josh: Is the Hyatt/Aeroplan deal good for Canadians? Main Event: Our biggest point gambles (07:54) - When we took big risks to earn big miles... (08:04) - Nordstrom 36X (2012) (15:32) - Convert 90K SPG points into a 7 night Marriott stay + 120K Southwest points + Companion Pass for 2 years (2017) (19:43) - Marriott Travel Packages (2018) (23:40) - Iberia 90K (2018) (27:54) - Conservation International 240 AA miles per dollar (2021) (34:40) - Amex 20% transfer bonus to Hawaiian Airlines (2024) (39:28) - SAS: Fly 15 SkyTeam, earn 1M SAS Miles (2024) (44:50) - JetBlue 25/25 (2025) (48:42) - Kate Spade 250X via British Airways portal (2026) Subscribe and Follow Visit https://frequentmiler.com/subscribe/ to get updated on in-depth points and miles content like this, and don’t forget to like and follow us on social media. Music Credit – “Ocean Deep” by Annie Yoder Check out all of our…

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