Booking Holdings has quietly launched a startup designed to compete with itself. It's called Lola, and it's an AI assistant that acts as a full online travel agency: you describe a vague trip idea in chat, and Lola handles everything from inspiration to a confirmed booking. The operation is led by Kayak co-founders Steve Hafner and Paul English, funded wholly by Booking Holdings, and reports directly to CEO Glenn Fogel. After five months of work, the team stands at roughly 20 people split between New York and Cambridge, Massachusetts — deliberately small and built on a separate tech stack from Booking.com, Priceline and Agoda.
The interesting twist is how Lola makes money. Instead of quietly pocketing hotel and flight commissions like every other agency, it offers three membership tiers: a free plan, Plus at $5 a month and VIP at $25 a month, with the paid tiers on 12-month commitments. In exchange, Lola passes its commission back to members. Booking's own example: a four-night Miami Beach stay priced at $783 for a VIP member versus $997 for the same stay on Booking.com or Expedia. Even accounting for the subscription fee, that's a meaningful gap on a single booking.
Inventory isn't limited to the Booking empire, though that's where it starts. Lola also taps OpenTable, ResX, SeatGeek, GetYourGuide, FareHarbor, BLADE, Aero and Nuitée, with talks underway with Ticketmaster/Live Nation, AEG, SevenRooms and Resy. So restaurant tables, event tickets, tours and even helicopter transfers sit alongside the usual hotels and flights.
There's a human safety net too. Concierge firm Ten Group handles the trickier requests — the sort of thing an AI might fumble — with usage metered by your tier. Ten Group also brings direct enhanced-benefit relationships with roughly 5,500 to 6,000 hotels, meaning perks like room upgrades and late checkout that the AI can request on your behalf.
Hafner is candid about the maths: he expects around 90% of active users to stay on the free tier. The subscription model is really a bet that a subset of travellers will happily pay a small monthly fee to recoup commissions on big-ticket trips, plus get better hotel perks and access to human concierges. And the ambition is obvious — the stated goal is for Lola to grow into a brand as large as Booking.com itself.
For travellers, this is one to watch rather than immediately switch to. If you book several trips a year and value perks like late checkout or an actual human sorting out problems, the $25 VIP tier could pay for itself on one booking. If you travel once a year, the free tier gets you the same AI planning and the inventory without commitment. Either way, the big agency groups are clearly no longer treating AI chat as a gimmick — they're building entire businesses around it.
