29-05-2025
The AI Assistant Race, Southwest's New Promise and Booking.com Revelations
For today's pod we look at Southwest's break with the past, the AI travel assistant race, and a brief history of
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Listen to the day's top travel stories in under four minutes every weekday.
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Good morning from Skift. It's Wednesday, May 28. Here's what you need to know about the business of travel today.
Tuesday was the final day that flyers on Southwest Airlines were able to check bags for free. Airlines Reporter Meghna Maharishi examines the end of Southwest's most iconic perk and other major changes at the carrier.
Southwest is now charging customers $35 for their first checked-in bag and $45 for the second. Maharishi notes the baggage fees apply to those flying basic economy, along with Southwest's Wanna Get Away Plus and Anytime fares. In addition, Southwest expects to start operating flights with assigned seats next year and will also start charging seat selection fees.
Southwest executives have argued those changes are necessary for the carrier to remain competitive and shore up its profitability.
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Next, OpenAI is establishing its own device company. Travel Technology Reporter Justin Dawes explains what that development could mean in the race to create the ultimate travel assistant.
Dawes notes AI assistants could be the main way users purchase travel. Although Apple and Google are both taking steps toward that vision, it's tougher to overhaul an established suite of products.
Dawes adds that OpenAI has an opportunity to fully reimagine how devices operate, built from the ground up with AI at the center. OpenAI has said it's planning a 'family of products,' and the company aims to reveal more details next year.
Finally, Executive Editor Dennis Schaal delves into a book published four years ago that revealed details about the history of from its founding in Amsterdam in 1996.
Three Dutch investigative journalists wrote the 2021 book 'The Machine,' which documents the tensions between the American and Dutch employees, and then between the Dutch and the Brits; takes you behind closed doors where one CEO gets fired and another is forced to resign; and discusses local backlash and strategic decisions.
"The Machine" also shows execs' resistance to cooperating with other Booking Holdings brands. Until Glenn Fogel took over in 2019, there had been little sharing of data, resources or supply out of fear that it would dilute the brand and slow growth.
