I must admit that I'm dubious about A.I.. When I ponder the state of the world, I don't see a lot of what I consider to be intelligence at work. It would seem to me that to be of value artificial intelligence would have to be firmly anchored in the bedrock of incontrovertible intelligence, lest all of its product be somewhat suspect. Or, garbage in, garbage out. Caveat Emptor, IMHO! 😊
A.I.-powered tools can help you plan trips, squeeze value out of loyalty programs and translate languages. But don’t give up Google Flights just yet.
By Gabe Castro-Root
Aug. 19, 2025 - NY Times
Creators of travel technology powered by artificial intelligence say their tools can make your life easier by doing everything from planning your dream trip to maximizing your loyalty points to telling you about a cool building down the street.
But can they really?
The answer, after putting some of the biggest players to the test: Sort of.
Droves of seemingly identical A.I. trip planners can help you lay out an itinerary and find hotels and restaurants, with varying degrees of success. The best ones can match the conversational style of chatbots like OpenAI’s ChatGPT or Google’s Gemini.
Of course, travel planning tools also have the same shortcomings as any A.I. program: They don’t always have access to the latest data, they may not have the detailed information of sites like Google Flights, and, sometimes, they just make things up.
But there are ways to make the most of them. I got advice from experts and tested out these trip planners, as well as A.I.-powered tools to help you stretch your hotel and airline points and translate conversations. Here’s how they did.
A.I. Travel Tools Are Everywhere. Are They Any Good?
Greg
Quick and Dirty
Creators of travel technology powered by artificial intelligence say their tools can make your life easier by doing everything from planning your dream trip to maximizing your loyalty points to telling you about a cool building down the street.
But can they really?
The answer, after putting some of the biggest players to the test: Sort of.
Droves of seemingly identical A.I. trip planners can help you lay out an itinerary and find hotels and restaurants, with varying degrees of success. The best ones can match the conversational style of chatbots like OpenAI’s ChatGPT or Google’s Gemini.
Of course, travel planning tools also have the same shortcomings as any A.I. program: They don’t always have access to the latest data, they may not have the detailed information of sites like Google Flights, and, sometimes, they just make things up.
But there are ways to make the most of them. I got advice from experts and tested out these trip planners, as well as A.I.-powered tools to help you stretch your hotel and airline points and translate conversations. Here’s how they did.
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The task: Turn Instagram Reels into a vacation itinerary.
This well-designed travel planner is easy to use: When you see an Instagram Reel about a destination you’re interested in visiting, send it to Expedia via direct message, just as you would share it with a friend. The A.I. chatbot will strike up a conversation and ask you about your preferences — “Are you more into history, food, nature, nightlife or something else?” — and tailor its recommendations for that place based on your responses.
Jochen Koedijk, Expedia Group’s chief marketing officer, said Trip Matching was designed for people who are still toying with ideas and don’t already have a trip planned. “We wanted to give a service to travelers who see something and they’re like, ‘Hey, this looks amazing. What is it?’”
Trip Matching provides links to book hotels on the spot, in case you’re feeling impulsive.
Like other A.I. tools, Trip Matching has some issues to work out. It offered generic activity recommendations for my destinations, and it repeatedly suggested I stay at hotels that had little or no availability for the dates I wanted. When I asked it to find flights for an imaginary vacation in Central Asia, it suggested I consider a layover in Moscow, despite the ongoing war with Ukraine making travel there dangerous for Americans.
The task: Provide tailored trip suggestions based on your interests.
Great visuals give this ChatGPT-style trip-planning tool an edge. Its interface, a lively conversation with a chatbot, includes detailed maps and photos of each attraction or accommodation. Start by taking its short quiz to help tailor the bot’s suggestions to your interests. If you’re not sure what follow-up questions to ask, Mindtrip can help with that, too — its “You might want to ask” feature suggests prompts that can unlock more details about a place you’re interested in.
Once you’ve narrowed down your options, you can get the details from a human: Mindtrip features about 30,000 guides made by content creators and other users. You can reserve some hotels directly via Mindtrip, which earns a commission if you book through its site.
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Where Mindtrip falls short is flights. The site told me it did not have “specific flight pricing or availability” for certain routes, and an internet search quickly turned up cheaper airfare for several destinations, though the tool seemed to be more accurate for domestic flights than for international ones.
Mindtrip is free, but you’ll need to create an account after the first few messages.
The task: Offer trip planning advice with your emotions in mind.
To hear Layla’s chief executive, Saad Saeed, tell it, this tool works best when you share your feelings with it.
“A.I. really is good earlier in the journey when you don’t know exactly what you want, and you can be very expressive of what you are feeling and why you want to travel,” Mr. Saeed said.
“Spoiler,” he added, “searching for flights is still definitely better on Google Flights.”
Layla, with its curly-haired young woman avatar, has a similar design to Mindtrip — a conversational text interface plus a map and photo spread — though it sometimes takes Layla a few prompts to unfurl the visuals. Its $49-per-year membership also unlocks discounts of up to 20 percent at select hotels around the world.
The big difference: The tone of conversation. When I told Layla I was planning a trip to Vermont this fall, it asked a few questions, then said, “Hit me up with the deets, and I’ll cook up some wicked cool things to do!” Yikes.
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The other downside is that Layla gives you fewer than 10 messages before you hit its paywall. While you can still get a good amount of information before that — I found recommendations for where to rent a kayak on Lake Champlain and learned Vermont has 100 covered bridges — I wasn’t convinced Layla was worth paying for when other platforms offered a comparable product at no charge.
The task: Squeeze the most out of your loyalty points and miles.
Gondola offers to help you find the best deal in the confusing universe of loyalty programs.
Users can give Gondola permission to scan their email inbox for travel reservations, or enter information manually. If you have points with Marriott, Hilton and Hyatt, for example, you can search all three at once on Gondola and it will rank your options from best to worst value, showing the cash and points rates side by side, along with the points you’d earn from each option. You can book a hotel directly via Gondola.
The site also monitors airfare and room rates even after you book a flight or hotel, so if the price drops, you can rebook at a lower rate. But you can’t book flights directly on the site.
Gondola’s target audience is people who travel 10 or more times per year, said Skyler Erickson, a co-founder.
“Our goal is like, you are a traveler who knows they’re going to stay two nights in San Francisco,” he said. “What is the best way to do that?”
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Gondola does have an open-ended text box, but the site is primarily useful as a comparison tool rather than an ideas generator.
The task: Get travel information on the fly.
By this point, you’ve already taken your flights, checked into your hotel and headed out to see the sights. What’s that landmark in front of you? Just ask your glasses.
The Ray-Ban Meta glasses can use A.I. to tell you about objects like that historic-looking fountain in Rome you want to identify. All you have to do is say “Hey, Meta,” then ask it to take a look. You’ll get an instant audio response. It also has live audio translation between English, Spanish, French and Italian. That sounds impressive until you consider that Google Translate has around 250 language options.
The glasses, which start at $299, come in a range of frame and lens colors and can be purchased as sunglasses (polarized or not), blue light glasses or with transition lenses, as well as with a prescription. Battery life is around four hours for “moderate usage,” according to Meta, and you’ll need your phone’s internet connection for most A.I. features.
And, of course, the glasses have a camera. Photos and videos save to the Meta A.I. smartphone app, and a light on the glasses alerts others that they’re being recorded. But reasonable people could disagree whether it’s actually easier to take a photo with your glasses than to just pull out your phone.