I have started almost every flight search of the past 21 years in the same place. Kayak launched in February 2005, and it is still where I go first, for flights and increasingly for hotels. In my experience, it still has the widest inventory, the best prices, and the best interface for choosing a trip. That includes the new AI tools.
Last October, its owner, Booking Holdings, wrote it down by $457 million. In February, its co-founder and CEO of 22 years stepped down. And in May, Skift broke the news that Booking’s big AI travel bet is being built by Kayak’s founders, under a different name. Booking may be confusing a declining business model with a product people still want.
The founding story explains what Kayak got right. In late 2003, Steve Hafner had just resigned from Orbitz, which he helped start, and had dinner with Terry Jones, who founded Travelocity. Fast Company later reported what they admitted to each other that night: they did not enjoy using thei