Southwest Just Killed One of the Best Deals in Travel

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. ⏱️ Episode 459 Timestamps Time Chapter 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