The Data Days at ETH Zurich closed with a 24-hours Machine Learning hackathon on May 15, 2022, and I was a jury member in one of the four competitions. Being a jury member of such a competition gives the privilege of gaining a lot of insights. Besides the solution per se, there are several learnings about how the different teams approach the problem-solving and their journey during the hackathon. In our competition, the teams had to build a travel insurance chatbot helping the travelers to guide through the different challenges in a COVID-19-driven world with several requirements per country, travel options, and insurance coverage and assistance in all these situations. These nicely framed questions come to your mind when you think about a chatbot for travel insurance.