Most people like traveling. But far fewer enjoy booking it.

A survey of more than 2,400 people who book their own travel arrangements found that 71% say the process is at least somewhat stressful for them, according to a 2024 survey by the consumer data company CivicScience. The percentage is even higher among parents of kids and teens, the survey showed.

Trip planning can involve an arduous slog through booking websites, star ratings, travel reviews and fine print — first to find what to book, then to find the best available price.

Artificial intelligence is set to change this, with ChatGPT already proving that generative AI can provide itineraries and recommendations in a matter of seconds.

But Booking Holdings CEO Glenn Fogel told CNBC Travel he wants to "go beyond" that.

Rather than leaving it to travelers to plan their trips from scratch, Fogel said, he wants Bookings' brands — which include Booking.com, Agoda, Kayak, Priceline and OpenTable — to anticipate their needs.

"I want us to be going to the traveler and saying, "Hi, we think, given everything we know, that you're probably thinking about wanting to go to, let's say, Naples in Italy. And using all the data we have, all we know about our customers, what they may want, trying to start that conversation."

"That's the difference," he said.

In effect, travelers with preferences — say, for connecting rooms, baby cribs or high floors in hotels — wouldn't have to repeatedly ask for those extras, because the AI would have anticipated the request.  

"It's just like it was many, many years ago, when there's a human travel agent that people dealt with, and that travel agent knew everything about you," he said. But "technology can do so much better than the human travel agent ever could."

Generative AI should also grow with travelers as they age, said Fogel, as they transition from post-collegiate trips to Ibiza in their 20s to Disney World trips in their 30s.

"It should know everything about you," said Fogel.

For example, the first time someone requests a baby chair will indicate the traveler likely had a child, and thus will need similar seats for future bookings, he said.

One-stop booking

On average, travelers spent more than five hours — reading some 141 travel-related webpages — in the 45 days before booking their trips, according to Expedia Group's "The Path to Purchase" report, conducted with Luth Research.

But it's not a pipe dream to book entire trips — from accommodations and flights to activities and meals — all in one sitting, Fogel said.

But "I want even more. I want suggestions coming to me," he said.

"Let's say I'm doing a very luxurious trip to London," he said. "Our generative AI for example will say there's this great steak place in Mayfair that we think you'd like [based on prior bookings]. And by the way, they would like to offer you an incredible discount on these beautiful red wines that we know you like. The personalization is going to be just fantastic."

How far off?

Everybody wants to know when these new advanced planning tools will be available, Fogel said.

But as with all revolutionary technologies, "the hype is always way in front of the actual usage."

Fogel said he may not know when, but he does know how these tools will arrive.

"It'll be incremental, step by step by step. New services will be added, new products will be added," he said. "More and more information will be into our models, and we'll know more and be able to provide better services."

The company rolled out a generative AI service on Booking.com called "Trip Planner," which is currently in beta-mode, said Fogel.

Still "it just gives you a little taste of what the future is going to be," he said.

As for when simple, all-in-one-go planning will arrive, "I can guarantee you it's not happening tomorrow," he said. "But it will come. That I do know."