Travel companies such as Kayak, Hipmunk, Expedia and Skyscanner have all recently launched ‘bots’ with artificial intelligence to help customers book trips online. Ben Brown decides to put Kayak’s to the test and book a holiday.

Users interact with the chat bots through Facebook Messenger, giving them the feeling of talking to a human about what they want, when and where. As Business Insider says: “Rolling out bots for the travel industry is one way for agencies to provide the semblance of a live agent’s help but cuts back on costs for actually adding them to the payroll.”

It adds: “In addition to launching bots, multiple online travel agents have launched profiles on Facebook Messenger that provide live help and customer service. Hyatt Hotels, KLM Royal Dutch Airlines, and all currently have profiles on Messenger that let users perform a variety of tasks including asking general customer service inquiries, checking availability, check-in for flights, and confirm reservations.”

I open Facebook Messenger with a certain degree of scepticism. Kayak – the online travel aggregator and booking site – has a new Facebook bot that helps travelers find flights and hotels; I want to see if I can use it to book an upcoming visit to Milan.

I recall once using an automated, speech-recognition bot to book a flight, and it took every fibre of my being not to throw my phone at the wall in frustration. Will Facebook bots fare any better?

Well, ten minutes later, my scepticism has evaporated and I have hotel and flight confirmations in my inbox. Here’s how the exchange played out.

Step 1. Getting started

First of all, I have to “like” the Kayak page on Facebook, and begin a message with its bot. I was a little confused about who would start the conversation, but a slew of information immediately comes my way.

Kayak bot conversation 1

It’s perhaps more information than you need all at once, but it looks straightforward.  I click “flights…

Kayak bot conversation 2

Step 2. Booking flights

Picking the airports is simple enough, but I thought I’d try to catch it out with the dates. I’m flexible on the departure date, so I ask for flights on the 17th or 18th August.

Unfortunately, this seemed to outfox the bot, as it showed me all the flights from now until the 18th August.

Lesson number 1: be specific when using the Kayak bot.

Kayak bot conversation 3

I try again with the specific date, and enter a return option.

I select two flights that work for me, and it brings up a full price and the operator. I also run a quick price check on the Kayak website, Skyscanner,, and directly through the Easyjet website. This really is cheaper or equal to any other price I find.

The only small niggle at this point is that the bot brings up flights into Milan Linate airport, despite specifying Malpensa at the start of the search. It’s a small glitch, and you can skip past the options you don’t want.

Clicking on the final price sends you to the tour operator, in this case Opodo, to complete the booking. The price is true to the advertised figure.

Step 3: Booking a hotel

With the flights booked, I ask the bot to help me find a hotel. At this point, I’m feeling confident, and forget “lesson number 1: be specific.”

I slip into a conversational tone, and it tries to book a hotel at its own headquarters. This is definitely my fault, so I ask specifically for a hotel in Milan. Strangely it interprets this as Milan Mela, which is a convention center in Kolkata.

I correct myself with more specificity.

Kayak bot conversation 4

This time it brings up the correct location, and a carousel of great options. Again, I check the price against competitors, and eventually book it through their suggested third party.

I’m informed that Kayak will also send me my any flight updates, check-in opening times and information through messenger as the trip gets closer.

Kayak bot conversation 5

That was easy.

Aside from a couple of small glitches – that were partly my fault – the bot works efficiently and quickly. It’s also friendly. It doesn’t feel automated, it feels like chatting to a real travel agent.

It feels collaborative. Strangely, I’m also a little more confident in the booking. After booking through an online aggregate site, I often have a sense of uncertainty. Is the flight definitely confirmed? Will the hotel be okay?

This almost feels more secure, like a recommendation from an expert. I know this is irrational, but I like it.

Step 4: Where can I go for £1,000?

My trip is booked, so I decide to have a little fun with the bot. The intro message tells me I can use the service for inspiration, so I ask it where I can go for £1,000.

This is a fantastic feature. It shows me potential trips to Victoria, Taipei, the Seychelles, St Lucia and Chengdu. I spend a few minutes browsing through, before I realise that I’ve been drawn in by the process… Exactly what they want.

Kayak bot conversation 6

The Kayak bot removes a certain barrier to the booking process, making it more likely that you’ll book a trip.

Step 5: When’s the best time to fly to Amsterdam?

I have another trip coming up, this time to Amsterdam, but without a specific date yet. I ask Kayak when the cheapest time to fly is.

Kayak bot conversation 7

Great. A simple and immediate answer. I don’t book the flights just yet, but I am likely to use this tool when I do.

With Facebook Messenger on my phone, I now have a virtual travel agent in my pocket.

Could artificial intelligence bots become a replacement for travel agents? Kayak’s Facebook Messenger service is certainly the first step towards this future.

Skyscanner, Expedia, and Hipmunk each have similar Facebook bots, although Kayak’s is the most intelligent.

With a few tweaks, it’s not difficult to imagine linking a credit card and having the bot actually make the booking for me. It’s easy to imagine the bot suggesting and booking local restaurants or tours.

Are the bots taking over? Maybe, but I kinda like it.Kayak bot conversation 8

For travel trends delivered straight to your inbox, sign up for the Globetrender newsletter.