The Condor via Alaska Stopover Hack

Note: This episode can be viewed with video on Youtube/Spotify.

Summary

In this episode, Tom Kim and Trevor Mountcastle welcome back Nick from The Frequent Miler to discuss the latest strategies in the award travel world. Nick breaks down his family’s massive undertaking of the JetBlue 25-for-25 promotion, his nuanced take on the Hyatt award chart changes, and his favorite tools for finding the best flight redemptions, including a surprising hack for Southwest Airlines.

Key Points From This Episode:

0:00 – Introduction

• Tom and Trevor welcome back Nick.
• Brief catch-up on Nick’s recent travel adventures since his last appearance.

0:43 – The JetBlue 25-for-25 Family Challenge

• How Nick completed the challenge for his entire family of four.
• The logic behind securing 25 years of airline status for his young children.
• Strategy: Using Amex Membership Rewards points and the Business Platinum 35% rebate to fund the flights.
• Leveraging partner bookings like Etihad Guest for high-value JetBlue redemptions.

7:16 – Hyatt Award Chart Changes: To Panic or Not?

• Nick’s take on the recent devaluation: Why Hyatt remains the strongest hotel currency despite the hit to top-tier redemptions.
• The strategy of speculative bookings for "bucket list" properties like Park Hyatt Kyoto before price hikes.
• Comparing the rising cash rates of luxury hotels to the increasing point requirements.

18:25 – Aeroplan and the Current State of Flight Awards

• The pros and cons of Air Canada’s Aeroplan, including their massive partner network.
• The frustration of dynamic pricing with partners like United.
• The difficulty of finding award space to Asia in the current travel climate.

23:14 – Advanced Award Searching & The "Condor Hack"

• Using Alaska Airlines to book Condor with a stopover in Frankfurt en route to Bangkok.
• Nick’s favorite tools: AwardTool, Seats.Aero, and the Points Path Chrome extension.
• Autopilot: A new tool for automatically repricing paid flights for credits.

29:16 – Southwest Airlines Strategies & IT Glitches

• The shift to assigned seating and the impact on Southwest's value proposition.
• A bizarre IT glitch: Why Nick’s 8-year-old son could see award seats that Nick (a premium cardholder) could not.
• The benefits of the Southwest Priority and Performance Business cards.

36:00 – Family Travel: World-Schooling & The Librea Tar Pits

• Nick’s experience homeschooling his kids for a quarter while traveling to the Bahamas, Los Angeles, and French Polynesia.
• The educational value of travel: From the aquariums in Atlantis to prehistoric history in LA.

41:40 – The Casino Status Match & Free Cruises

• How Nick turned casino status matches into 14 free cruises.
• Reviewing Margaritaville at Sea: Why it’s surprisingly great for families despite its budget reputation.
• Pro Tip: Using the casino "cage" for organic spend/cash advances on cruises.

51:00 – Lifemiles & Flying Blue Subscriptions

• Is the LifeMiles+ subscription worth $20/month? (Hint: The 10% discount and free cancellations might be).
• The new Flying Blue subscription model and whether it’s worth it for promo awards.

Keywords

Hyatt award chart, travel hacking, JetBlue 25 for 25, Family travel, Aeroplan, Southwest Airlines