Sorry, saw this late.
There are a few AI components here:
1. ML based recommendation engine to suggest flights, hotels, activities/experiences, and even destinations based on profile (social data, interaction data, and booking data) and clusters based on certain components. (Currently works well for flights at 85% accuracy - top five results, for hotels, we are at 52% in top 10 results)
2/ Voice + NLP engine to handle more intuitive queries. One aspect of travel inspiration is that when people google, they dont ask the question they have. Like for a question like 'Where can I go for a beach trip next weekend' becomes a search query of 'Top beaches in US' or 'Top 10 exotic beaches'.
3/ 80% of the trip planning effort is spent on just finding the relevant info cos it is way too scattered. There is a way it can be made more concentrated, when we scrape more data from existing blogs, and create a graph network of information to serve a more relevant and contextual answer to the queries. Initial thoughts only on this, since we are still solving this. (Example would be, let's say you are planning a trip to Thailand, the product should be able to give contextual info keeping your preferences in mind. If you are an adventure lover, focus would only be on those activities, if you like a secluded beach to relax, you will be given those answers.)
3rd is the most complex and requires a lot more effort. This is not the same as itinerary building (cos that is the part of experience). We just want to take away the frustrating bits away from the planning part.
Apart from these, the usual features, like fare prediction, flight delay prediction, deals info, are also on the roadmap.