Consider the advantages of the size of $129 billion Booking Holdings. While smaller companies might be content launching a single consumer-facing AI product, Booking has five major ones in the works simultaneously.
Among its brands, Priceline and Booking.com have chatbots, while Agoda will debut one shortly. And they take various approaches in terms of starting at the top of the marketing funnel or from the bottom and working up.
Then there are two internal, native AI startups. Details about them are relatively sparse. One of them, Lola, is being led by Kayak co-founder Steve Hafner, and the other is based on the West Coast and that’s about all we know about it so far.
Booking has the luxury to evaluate the divergent approaches, seeing what works, what doesn’t and where to invest. That’s a pretty good position to be in.
STRIPE + SKIFT
For hospitality and travel companies, modernizing payments infrastructure has become an essential input for revenue growth and guest satisfaction. A new report from Skift and Stripe reveals how profitability hinges on innovative payment strategy, which is essential for driving guest experiences, revenues, and boosting operational efficiencies.
EDITOR’S PICKS
With Booking’s Etraveli Deal Still Blocked, Expedia Has the Edge in M&A
September 10, 2026
Skift Data + AI Summit Europe
Bernstein's case for Airbnb rests on AI search and loyalty paying off as envisioned. The harder question is which AI actually ships, operates, and holds up once the regulators, the languages, and the market get involved.
That is the entire day in London on October 6, with the CEOs of KAYAK and Skyscanner, the Chief AI Scientist of International Airlines Group, and product leaders from Amadeus and Travelport on how AI gets built and run across Europe.
SKIFT PODCAST NETWORK
AI agents are starting to book travel, chase reservations, and monitor openings faster than humans can.
Sarah Kopit and Seth Borko discuss why tools like Instinct could change who gets access to the best tables, tickets, and trips and why platforms are already pushing back. This episode is brought to you by ZS.
SKIFT TRAVEL 200
How are public travel tech companies performing around the world? The Skift Travel 200 pulls the data you need to know to understand the market. Paid subscribers get full access here.
