Max Craig, the mastermind behind Points-to-the-Max and a miles-and-points expert, joins to unravel the secrets of earning the Southwest Companion Pass for 2026. He shares top credit card strategies and the ideal timing to maximize points efficiency. Listeners will discover the impacts of recent program changes, how to navigate hub routes, and when to avoid chasing the Companion Pass. With practical tips for both beginners and seasoned travelers, Max provides a roadmap to travel savings like no other!
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insights INSIGHT
Maximize Companion Pass Timing
The Companion Pass gives buy-one-get-one flights for at least a year and can extend into the following year if earned late.
Max emphasizes timing the pass early in the year to maximize nearly two years of value.
volunteer_activism ADVICE
Use Points Or Cash Equally
The pass applies to both cash and points bookings, so you can redeem points and still bring a companion for only taxes.
Max advises redeeming points as you go because your qualifying tracker only increases.
insights INSIGHT
Companion-Only Points Boost Explained
Southwest added a companion-pass-only qualifying points boost for cardholders that doesn't create spendable points.
That boost effectively lowers the hurdle for cardholders to reach the 135,000 qualifying threshold.
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Earn the Southwest Companion Pass in 2026
In this Hurdy Gurdy Travel Podcast episode, Justin sits down with Max Craig from Points to the Max to break down exactly how to earn and maximize the Southwest Companion Pass for 2026.
We cover the best timing for points, which cards to open (and when), stacking strategies, and what recent program tweaks mean for your plan.
Whether you’re brand-new to points or already flying regularly, you’ll get a practical, step-by-step gameplan to secure the companion pass and squeeze maximum value from it, plus intel on routes, hubs, and event meetups to level up your travel.
What you’ll learn
The cleanest timeline to lock the 2026 Southwest Companion Pass
Which credit cards to consider and how to sequence them
Points vs. flights: the math to qualify efficiently
Recent Southwest program changes (and what still works)
Hubs, routes, and positioning strategies
Opportunity cost: when not to chase it
Chapters
00:00 Intro
00:45 Meet Max Craig (Points to the Max)
02:50 Companion Pass, explained (eligibility & value)
04:49 Credit-card strategy & timing for 2026
06:10 What changed at Southwest (and what didn’t)
07:49 Qualifying: points vs. flight segments
11:22 App strategy: rules, pacing, and denials
23:35 Events, meetups, and community resources
28:47 Music City Miles & Points shoutouts
29:37 Frequent Traveler University notes
30:33 Fine print of the Companion Pass
32:55 Hubs, routes, positioning flights
34:53 Opportunity cost & alternative plays
43:10 Program benefits recap & pitfalls to avoid
43:36 Where to find Max (site & socials)
45:31 Trip planning tips & closing thoughts
51:31 Outro
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