In Milan, Putting an A.I. Travel Assistant to the Test

I wasn’t exactly sure what to expect from the itinerary my travel adviser had put together in a mere five seconds, but when I arrived in Milan’s central Piazza del Duomo, the cathedral glistening under the midday sun, I anticipated being swept into the city’s frenetic rhythm. Instead, I found myself in the middle of a relatively empty square, surrounded by shuttered stores and cafes.

“Why didn’t you tell me today was a public holiday in Milan?” I texted my adviser.

“I’m sorry, I didn’t realize that you were planning to visit Milan on May 1,” the adviser responded. “As a virtual travel assistant, I try to provide as much information as possible, but sometimes I miss something. I apologize for any inconvenience this may have caused you.”

I felt bad, as if I had hurt someone’s feelings, and had to remind myself that I wasn’t talking to a human. It was my first trip to Milan, and I was using the opportunity to try out the beta version of Expedia’s travel-planning chatbot powered by ChatGPT.

Travel companies are already using artificial intelligence to help with customer service and bookings, but now services like Kayak and Expedia are experimenting with A.I. assistants to help people find places to go and stay. I decided to put Expedia’s service to the test by comparing its itinerary with one prepared by a human adviser. “I have one day to visit Milan. Where should I go?” I asked it. “What should I see?”

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