In this week’s Midweek Mini, we’re breaking down one of the biggest and best deals in the entire world of points and miles — the Southwest Companion Pass. Whether you’re new to travel hacking or already a seasoned Southwest flyer, this episode walks you through exactly how to earn and maximize this incredible perk.

We share two main strategies to earn the pass — the classic two-card combo (personal plus business) and the real-life “no business card” approach — and explain how to time your spending perfectly so your pass lasts nearly two full years. You’ll also hear why this perk is so special for families and frequent travelers, along with a few important warnings about timing your spend before and after January 1.

We also dive into recent and upcoming Southwest changes, from assigned seating and new card perks to controversial snack and accessibility policy updates. Despite the changes, we both agree that if you fly Southwest even a few times a year, this is still one of the most valuable deals you can grab in travel.

If you’ve ever wondered how to earn 135,000 qualifying points the smart way, when to open your cards, or how to make your pass last the longest, this episode has everything you need to know. We’re sharing our own Companion Pass experiences, what worked, what didn’t, and why this deal continues to be one of our all-time favorites for families who love to fly for nearly free.

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Episode 47

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This week on the Wonderland on Points podcast, we’re joined by Jenna from @TravelersinLaw for one of the most sporty trips we’ve ever talked about — her points-and-miles-fueled adventure to Milan for the Formula 1 Italian Grand Prix. We go behind the scenes on how it all happened, from locking in flights right when the availability opened to booking last minute puddle jumpers and hotels using points.

Jenna shares what it’s like attending an F1 race in Italy as a super fan. We talk about how she booked her flights and where she stayed, plus what the experience was actually like once she was there — the atmosphere, the food, the people, and the chaos that only Italy can deliver.

We also chat about how this trip fits into the bigger picture of the dreams that points and miles can make possible.

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Mary Ellen | Jo

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We receive a small commission when you choose to use any of our links to purchase your products or apply for your cards! We SO appreciate when you choose to give back to the podcast in this way!

This week, we begin with some less than thrilling news in the points and miles world. We love to keep you up to date but it's not always fun to share. THEN- we’re pulling back the curtain on how a trip actually comes together — from that first spark of inspiration to locking in the flights. It started with an Instagram video, a great transfer bonus, and some unbelievable business class redemptions, and by the end of the day, we had a surprise trip booked.

We walk through the entire process of figuring out where to go, how to get home, what the taxes and fees really looked like, and how we turned a spur-of-the-moment idea into a birthday trip of a lifetime.

If you’ve ever wanted to see what it looks like to build a trip with points in real time — the thought process, the strategy, and the excitement — this episode is for you.

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Mary Ellen | Jo

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Wonderland On Points Blog

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Rakuten- Mary Ellen (Get 5000 AMEX POINTS)

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Chase/Capital One/Amex Card Links

30% off the CardPointers subscription!

FlyKitt- the BEST Jet Lag Solution!

Tripiamo Driving Tutorials

Our Favorite Travel Necessities

We receive a small commission when you choose to use any of our links to purchase your products or apply for your cards! We SO appreciate when you choose to give back to the podcast in this way!