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Can Hilton’s new AI planning tool help you find the perfect hotel? We put it to the test
Tanner Saunders is a Webby Award-winning senior hotels reporter for TPG based in Brooklyn. He covers everything from breaking hotel news to in-depth features on the world’s best hotels.
Katie Genter is a digital nomad who has traveled full time since June 2017. She writes and edits stories about points and miles, and loyalty programs, often letting her personal experiences color these stories.
Andrea M. Rotondo has traveled to 50+ countries using points and miles. She's a luxury, small-ship cruise expert and hotel maven who can share the not-to-be-missed spots in her adopted home state of Florida. She will also talk all day long about her ancestral homeland: Italy.
also contributed to this story
March 10, 2026 • 7 min read
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By commenting, you agree to our Community Guidelines to help create a positive space for conversation. The responses below are not provided or commissioned by the bank advertiser, our partners, or The Points Guy (“TPG”). They have not been reviewed, approved, or otherwise endorsed by any of these parties. All responses are submitted by individual contributors, and neither the bank advertiser, our partners, nor TPG are responsible for ensuring that all posts and/or questions are answered.
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Quick summary
Hilton has introduced Hilton AI Planner, a generative AI-powered digital concierge designed to help travelers find and compare hotels within its global portfolio.
The tool offers real-time responses and curated recommendations, aiming to streamline the hotel search and booking process beyond traditional filters.
Early testing found the AI helpful for narrowing down options and suggesting properties based on specific interests, though it struggled with complex requests and could not display the best award rates directly.
Hilton AI Planner is currently in beta and available to a limited group of users, with further enhancements expected.
What to consider
The tool cannot show the lowest award rates or identify the best dates for points redemptions, directing users to calendar views for this information.
Some recommendations may not fully match highly specific requests, particularly for niche amenities or property types.
As a beta product, features and accuracy may improve over time as Hilton gathers feedback and refines the tool.
What you'll miss from the article
Detailed user experiences highlighting the AI's strengths and limitations when planning trips to destinations like Europe, Japan and the Maldives.
Generated by AI with support from our editorial team.
If you haven't noticed, artificial intelligence is working its way into nearly every aspect of human life, from AI-powered drive-thrus at Taco Bell to AI models setting airline flight pricing.
Now, Hilton is entering its AI era with the beta launch of Hilton AI Planner, "a generative AI–powered digital concierge that helps travelers explore the company’s global portfolio of hotels and plan memorable stays with Hilton," the company said in a statement.
Initially rolling out to "a small pool of site traffic" on hilton.com, Hilton AI Planner "uses conversational intelligence to help travelers navigate every stage of the shopping journey — whether identifying the right destination, comparing properties or exploring amenities. With real-time responses and curated recommendations, the tool delivers a streamlined experience that goes beyond traditional search filters," Hilton explained.
"The launch of the Hilton AI Planner marks another step forward in our journey to reimagine the travel experience for Hilton guests," said Michael Leidinger, Hilton's senior vice president and chief information officer. "This is just the beginning and a preview of where we’re going, as we continue to focus on providing thoughtful, purposeful innovation that empowers travelers."
Ahead of Hilton AI Planner's beta launch, TPG was given access to explore the tool. TPG writers Tanner Saunders and Katie Genter put it to the test to see how useful it is when booking a hotel.
HILTON
Tanner's jaunt to Europe
First, I (Tanner) told the planner that I was looking for a European capital city with cultural activities and great food. After recommending Paris, Rome and Barcelona, it dug deeper, asking what draws me the most: "ancient history, artistic masterpieces, or modern creative energy?"
After a bit of surface-level back-and-forth, I landed on a spring trip to Paris rooted in culture and great neighborhoods with easy access to major landmarks. One thing I noticed was that as I kept getting more specific in the search — to the point of making sure the hotel had a fitness center and a bar or restaurant — the standard Hilton search page kept changing in the background.
HILTON
While I found the tool handy to quickly find helpful details about individual properties, it wasn't the most useful for finding the cheapest dates to book. After narrowing the search to two hotels, the tool couldn't show me the cheapest dates with points, though it did organize a list of hotels by lowest starting rate. To see actual award rates, it kept telling me to "explore the calendar view to compare points rates across different dates and find the best value for your stay."
HILTON
Despite not being able to do the heavy lifting of finding the best award rates, I appreciated the ease of pinpointing hotel options that met my needs, and I can see how the tool can be helpful for people inundated with choices in big cities or tourist destinations — though I would recommend still doing your own research on the individual properties it recommends.
Katie's search for ski resorts
Having just returned from a ski trip to Niseko, Japan, where I (Katie) redeemed Hilton Honors points for a stay at Hilton Niseko Village, my first Hilton AI Planner request was for ski resorts in Japan. I was pleased to see the AI tool return the three Hilton properties in Niseko Village that offer ski-in, ski-out access.
Then I gave it a slightly more complicated request: Show ski resorts in Europe. It gave me some true ski resorts, some hotels near ski resorts (such as the Hilton Garden Inn Davos in Switzerland, which might be an underrated option if you don't need ski-in, ski-out access) and some options I'm not sure are appropriate for a ski trip at all. When I asked it to narrow my options to just ski-in, ski-out properties, it sadly still returned at least one property that didn't fit the parameters (Le Grand Bellevue, part of Small Luxury Hotels of the World).
HILTON
For my final query, I gave it a task I didn't expect it to succeed at: Display Hilton properties near Ikon Pass resorts. Interestingly, it did surprisingly well and, in fact, recommended hotels near Ikon Pass resorts. None were ski-in, ski-out options, but I honestly didn't expect it to be able to understand which hotels are near Ikon Pass resorts in the first place.
Katie's comparison of Maldives properties
Besides skiing in Japan, my (Katie's) favorite place to redeem Hilton points and free night certificates is the Maldives. I've stayed at four Hilton Honors properties in the Maldives, so, of course, I had to ask the AI tool about Maldivian resorts.
HILTON
I started by asking it for historic Maldives resorts, a query for which I expected it to highlight Baros Maldives, an SLH hotel, as it is one of the oldest Maldives resorts and steeped in history. Instead, it returned a list of "beautiful Hilton properties in this tropical paradise," with Baros near the bottom, noting its "Classic Maldivian elegance." The results gave me little more information than I would have gotten if I'd just searched for the Maldives as a destination, though the short descriptions for each property were accurate based on my experiences.
Andrea's Italian expectations
“I’ll be honest. I went into my experiment with Hilton’s new AI Stay Planner with a jaundiced eye. In the past, I’ve tried a variety of chatbots from some of my favorite retail brands and was often frustrated by their inability to answer my questions. This was not the case with Hilton’s new trip planner.”
In fact, I tried to “trick” the bot with a question I thought it couldn’t fully answer. I told the AI assistant that I wanted to visit somewhere off the beaten path (not a big city) in Southern Italy, preferably somewhere with ancient ruins or historical monuments.
I had a very specific idea of what I wanted the result to be because it’s a trip I’ve mapped out for myself and several friends. I hoped the AI assistant would suggest the Valley of the Temples in Agrigento, Sicily. The art and architectural ruins are Greek, built by settlers between the 8th and 5th centuries BCE.
Not only did Hilton’s new tool suggest a Small Luxury Hotels of the World property, Villa Athena Resort, with spectacular views of the ruins, but it also asked if I wanted to pair that visit with any other Sicilian destinations. I said, ‘Sure,’ and it included Syracuse for Neapolis Archaeological Park and the nearby historic center of Ortygia. Perfect additions to this itinerary.
After Hilton’s AI Stay Planner helped me review my options in Sicily, it suggested that I also consider a visit to the UNESCO World Heritage Site Matera in Italy’s Basilicata region, home to ancient cave dwellings carved into limestone cliffs. After that, a stop in Alberobello, in nearby Puglia, would be essential to view the area's unique conical, whitewashed stone huts called trulli. I love this part of Italy and was thrilled that Hilton's AI Planner suggested it. It proved to me that this planner was programmed with high-quality, targeted travel intel. I was impressed.
Bottom line
As AI becomes more enmeshed in everyday life, hospitality companies are making big moves to integrate the technology into the travel experience. Hilton's AI Planner tool was created to help streamline the booking experience — and at the moment is a handy way to narrow down destinations and hotels, depending on the experiences and amenities you want out of a trip.
Despite not being able to tell us the specific best dates to book with points and having some difficulty with more complicated parameters, it did a nice job of leading us (for the most part) to hotels worth further exploration.
But it's worth noting that Hilton AI Planner is still in beta and is likely to become more sophisticated over time.
By commenting, you agree to our Community Guidelines to help create a positive space for conversation. The responses below are not provided or commissioned by the bank advertiser, our partners, or The Points Guy (“TPG”). They have not been reviewed, approved, or otherwise endorsed by any of these parties. All responses are submitted by individual contributors, and neither the bank advertiser, our partners, nor TPG are responsible for ensuring that all posts and/or questions are answered.
