Skift Daily Travel Briefing

The AI Assistant Race, Southwest's New Promise and Booking.com Revelations


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Southwest Airlines has scrapped its signature free-checked-bag perk, instituting $35 and $45 fees for first and second bags, moving toward assigned seating with extra charges, and framing the changes as essential for competitiveness and profit. OpenAI, meanwhile, is forming a hardware company to build AI-native devices that could become travelers’ primary booking assistants, giving the startup a chance to rethink consumer tech from the ground up and challenge incumbents like Apple and Google. Finally, the 2021 investigative book The Machine chronicles Booking.com’s tumultuous rise, revealing cultural rifts, leadership shake-ups, and a long-standing resistance to sharing data and resources with other Booking Holdings brands.

  • Inside Booking.com: Ousted CEOs, Power Struggles and Local Backlash
  • Southwest’s Overhaul: New Bag Fees, Seating Changes – What's at Stake

  • OpenAI’s New Device Company and the Race for the Ultimate Travel Assistant

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