Southwest Companion Pass in 2026 with Max Craig
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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