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Southwest just made one of the best deals in travel much harder to get. And United Airlines isn't making elite status any easier—or cheaper.

This week, Ed is joined by Leslie Harvey of Trips With Tykes and Disney Deciphered to break down Southwest's major Rapid Rewards overhaul coming in 2027. The biggest change? Credit card welcome bonuses will no longer help travelers earn the coveted Southwest Companion Pass, ending a strategy that families have used for years to bring a companion along for nearly free.

Leslie explains the new Silver, Gold and Platinum status levels, how Companion Pass qualification will work, and why some Southwest loyalists may need to rethink their entire strategy. There are a few new milestone rewards and some transitional protections, but are they enough to offset what travelers are losing?

The conversation also explores whether Southwest is still worth flying if you can no longer earn Companion Pass the old-fashioned way. Leslie shares why she's sticking with Southwest for many trips—but may be much more willing to fly American Airlines in the future.

Then Ed heads to Las Vegas for a conversation with Adam Duckworth, founder and CEO of Travelmation, about the remarkable comeback of travel advisors. They discuss why travelers are spending more on once-in-a-lifetime experiences, a unique Five Guys Las Vegas wedding partnership, and a Disney cruise dedicated to pin trading that has attracted nearly 500 guests.

Adam also shares the inspiring work of Funding Love, an organization that helps adoptive families and birth mothers create memories at Walt Disney World, along with Travelmation's efforts to support Jamaica's tourism recovery.

Finally, Ed and Leslie tackle another unwelcome airline announcement: United is raising the cost of elite status in 2027 and eliminating the flight-segment qualification path. With United 1K requiring $32,000 in qualifying spending, and upgrades becoming increasingly unpredictable, Ed asks whether chasing top-tier status makes sense anymore.

Maybe it's time to stop chasing airline status and start choosing flights based on price and schedule.

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✈️ What We Cover in This Episode

✈️ Southwest's massive Rapid Rewards overhaul

  • A-List and A-List Preferred are being replaced by Silver, Gold and Platinum

  • Credit card welcome bonuses will no longer count toward Companion Pass qualification beginning in 2027

  • The new 140,000 tier-qualifying-point threshold for Platinum and Companion Pass

  • A remaining opportunity to earn Companion Pass through 2027 under the existing rules

  • New milestone rewards and transitional benefits

✈️ Is Southwest loyalty still worth pursuing?

  • Reduced earning rates on certain higher-priced fares

  • Why the new qualification rules could be particularly tough for occasional flyers

  • Leslie's strategy for flying Southwest after her existing Companion Pass expires

  • Why Southwest's onboard hospitality still matters

  • An unexpectedly good assigned-seating experience

✈️ The travel advisor comeback

  • Why premium and multigenerational travel continues to grow

  • Travelmation's expansion and its Las Vegas partnership with Five Guys

  • Why more travelers are hiring professionals to plan complex vacations

  • The value of having a travel advisor when something goes wrong

✈️ Disney pin trading at sea

  • How a casual idea turned into the Pins and Ports cruise

  • Nearly 500 Disney pin enthusiasts participating

  • Exclusive merchandise, dedicated trading sessions and special activities

  • Why Adam believes the concept could grow

✈️ Travel that gives back

  • Funding Love's Walt Disney World experiences for adoptive families and birth mothers

  • Travelmation's involvement with Give Kids The World

  • The Think Jamaica initiative and the importance of restoring tourism

✈️ United makes elite status more expensive

  • The elimination of the Premier Qualifying Flights qualification path

  • United Gold requiring $12,000 and 1K requiring $32,000 in qualifying spending

  • Why PlusPoints are becoming harder to value

  • Whether United Gold is now the smarter target

  • Why price and schedule may matter more than elite status

Plus, Leslie shares her upcoming Arizona adventure, Ed reflects on airline loyalty, and the two debate whether the benefits travelers are chasing are still worth the price.

⏱️ Episode 459 Timestamps

 

0:47 Leslie Harvey returns to discuss Southwest's big changes

3:54 Southwest overhauls Rapid Rewards and Companion Pass

7:57 New milestone rewards and reduced points earning

15:10 Is Southwest still worth flying without Companion Pass?

19:42 Ed's surprising Southwest assigned-seating experience

26:18 Adam Duckworth on Travelmation, Las Vegas and Five Guys

31:45 Pins and Ports: the Disney pin-trading cruise

36:24 Why premium travel and travel advisors are booming

40:19 Funding Love and Travelmation's charitable initiatives

47:38 United raises elite status requirements for 2027

 

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