Hilton’s CIO: Building the AI Trip Planner and Grappling With ‘Tokenomics’
Photo Credit: Michael Leidinger, chief information officer at Hilton, speaking at Skift Data + AI Summit on June 3, 2026 in New York City. Skift
Skift Take
A live AI tool with early conversion gains is one Hilton story. The cost of running AI across the wider company is another.
Hilton’s AI trip planning tool is delivering “slightly higher” conversion rates three months after launch, and the hotel group is preparing to roll the tool into the Hilton Honors loyalty app this month.
The planner lets travelers describe a trip in conversational prompts rather than picking a city and dates, but it took a few tries to get it right.
“The first iteration, it would allow one prompt and then immediately ask for dates,” said Michael Leidinger, Hilton’s chief information officer, at the Skift Data + AI Summit on Wednesday.