What happens when AI starts booking your flights?
New tools promise to put your trip on autopilot. But they're far from perfect.
Ignore the usual year-end predictions—the hot destinations, the airfare trends, the hidden travel fees. The only thing you need to know about travel in 2026 is this: Agentic AI will touch every trip you take.
What’s that? Well, think of agentic AI as the next version of today’s chatbots. Generative AI summarizes but agentic AI acts. It’s the difference between a map that shows the route and a self-driving car that takes you there.
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These tools will do more than suggest an itinerary. They’ll book flights, reserve hotels, and manage your trip—in other words, they’ll put your entire vacation on autopilot.
“Travelers will ask AI to book a trip that suits their preferences,” says Ross Borden, CEO of Matador Network. “And the AI will do it. This vision will become reality in 2026.”
But as these autopilot vacations take off, a question remains: When a robot plans your trip, who answers for the rookie mistakes, the security risks, or the flight simply invented by an algorithm?
AI is already planning your vacations—sorta
AI is already part of the travel process, of course. Barbara Alexander recently used ChatGPT to plan trips to Scandinavia and Japan. For a 24-hour stopover in Helsinki, she asked the AI bot to maximize public transportation to get her to an overnight ferry on time.
“It took some refining,” says Alexander, who works for a nonprofit in Washington, D.C. Eventually, the bot gave her a perfect schedule. “It’s fun, like talking to a smart travel agent.”
But Cleo Parker, a retired advertising executive from Livonia, Mich., found AI unready to take the wheel. She used Google’s Gemini to plan a 12-hour road trip to a dog show in Perry, Ga. The AI bot generated a 20-page document. It looked impressive. It was wrong.
It suggested rest stops on the northbound side of the highway while she drove south. It trusted her car’s manufacturer’s highway mileage claims, leaving her low on gas in Tennessee.
“You have to check the AI’s work,” says Parker.
So much for an autopilot vacation.
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The industry doubles down on AI bots
Still, everyone seems to be betting on bots. IDC predicts that by 2030, 45 percent of organizations will use AI agents. Capgemini is even more bullish, estimating that agentic AI could generate up to $450 billion in economic value within two years. Despite the hiccups, travel companies are pushing their chips into the pot.
Steve Hafner, CEO of Kayak, says his company is building software to plan, book, and manage trips in real time.
“We envision some travelers using a Kayak AI agent directly,” Hafner explains. “Others will rely on assistants powered by our data. As this technology grows, our goal is simple: make AI do the hard work.”
The risks of relying on algorithms for travel
Should you trust a robot with your vacation? Squaremouth, a travel insurance comparison site, recently surveyed thousands of travelers about their 2026 plans. While 47 percent have used AI to build itineraries, one-third reported receiving false or misleading information.
“As AI grows, its convenience can obscure the risks,” warns Lauren McCormick, a spokeswoman for Squaremouth. “We recommend proceeding with caution.” She notes that most travel insurance policies won’t cover you if your AI agent hallucinates a flight.
There are security risks, too. Frank Harrison, regional security director for World Travel Protection, warns that by 2026, AI will know a lot more about you than you realize—or than you want. Convenience has a cost.
“As the digital footprint grows, so does a traveler’s exposure,” Harrison says. “Cyber hygiene, once a niche concept, has become a foundational duty of care.”
The human element isn’t dead yet
Before you fire your travel advisor in favor of an autopilot vacation, listen to Susan Sherren, founder of Couture Trips. She’s seen the AI itineraries clients bring her. They often miss the subtleties of travel—the road closures in Big Sur, the unreliable Greek ferries in windy weather, or the fact that a “hiking trip” might be a bad idea for someone with a heart condition.
“Unless you become sophisticated with your AI inputs, you’re going to miss the nuance,” Sherren warns.
Jessica Parker, founder of the agency Trip Whisperer, is even more blunt.
“AI tools are designed to fill rooms and chase the cheapest or fastest option, not to curate your best experience,” she says. “AI can get you a room, while relationships get you the experience.”
AI cannot replace everything. You want a real person answering the phone when you call your insurance company with a problem.
“In a real medical emergency abroad, no traveler is looking for an algorithm,” says Nicole Perrault, COO of AXA Partners North America. “They want a human expert.”
How to use AI to plan your trip in 2026
Agentic AI remains theoretical, but it will become real in 2026. If you let a bot plan your next vacation, proceed carefully.
Start small. Don’t ask the AI to book a month-long expedition to Antarctica. Use it for discrete tasks: finding a hotel near a landmark or comparing flight prices. Resist the urge to let it book. Take baby steps.
Verify everything. As Parker discovered in Georgia, AI doesn’t always know which side of the road a rest stop is on. Double-check routes, opening times and prices. AI bots are subject to what are known as “hallucinations”—simply inventing facts.
Guard your data. Ensure you understand how the agent stores your credit card and passport information. “Cyber hygiene” is the new hand-washing. The last thing you need is a bot going on a spending spree with your credit card.
Use it for logistics, not taste. Agentic AI excels at action. In 2026, these tools will do more than compare prices. They will monitor flights for delays and rebook your connecting flight before the first flight lands. They will negotiate refunds by analyzing the fine print of your insurance policy. They can coordinate multi-leg journeys, syncing your rental car pickup time with your actual flight arrival. But they can’t tell you if the neighborhood is cool.
You may be able to book an autopilot vacation in 2026, but that doesn’t mean you should. Use AI for the homework; don’t let it take the final exam.
Remain in charge of your vacation. The robot is the navigator—but sometimes it holds the map upside down.
Would you let AI book your trip in 2026?
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