I have spent this exchange year in Milan, which means every trip home to Dublin starts with the same question: do I lock in the fare the second it looks decent, or do I hold off and let something cheaper surface? For two years I answered that with a browser, twelve tabs, and a lot of guessing. This spring I handed one trip to an agentic assistant that watches prices and books on my behalf, and kept the other trip for my own cold-blooded early booking, then compared what actually landed.
Where booking early still wins, and where the hype oversells
Common advice says the assistant will beat you because it never sleeps. That is true on exactly one kind of route: short-haul leisure with lots of capacity, where fares twitch all day and a bot catching a €4 drop at 3am is genuinely worth something. My Milan to Dublin return for Easter, booked six weeks out by hand, came to €61 each way with one cabin bag on Ryanair. The assistant, given the same route two weeks later, found €58. Three euros. I had spent an afternoon feeding it my calendar, my bag rules, my refusal to take a 6:20am departure, and it saved me the price of a coffee at Malpensa.
Where it breaks is long-haul and school-holiday dates. In February I watched it chase a Milan to New York fare for the July window and it kept waiting for a drop that never came, because those seats sell to people who book in January. Agentic tools are patient; the inventory is not. A bot cannot manufacture a cheaper seat class that has already closed, and if you tell it “find me the cheapest” without a ceiling, it will quietly book you onto a 23-hour connection through Lisbon with a four-hour layover, which I let it do once and will not let it do again.
Here is what I now check before letting anything book on my behalf:
- A hard price ceiling, not “as cheap as possible”
- A maximum number of stops and a minimum connection time
- A bag rule, because a €39 fare with a €45 cabin bag is not a €39 fare
- A deadline, so it stops waiting for a ghost
- Whether it can actually pay, or just tells me it found something
If you are the sort of person who wants the machine to do the watching while you still press the button, Kupi is the kind of tool I keep open in a second tab, mostly because it tells me when a route I am tracking has moved rather than pretending it knows the future.
The flexible half, and the train that beat both of us
The assistant’s real gift is not price, it is permission to be late. On a Milan to Naples run in March I had no fixed date, and it held four candidate departures while I waited to see whether a friend could join, then grabbed a €29 one-way on Italo when one opened up. Booking that early by hand would have cost me €45 and locked me in. So: flexible wins when your dates are soft and the route is short; early wins when your dates are hard and the route is long.
The honest alternative on the Milan to Dublin leg is not another flight, it is the whole question of flying at all. There is no train under the Irish Sea, but there is a coach to Bergamo, a €12 airport bus, and a Ryanair or Aer Lingus fare that with a bag lands near €90 return. The train does not win that route and never will. Where it does win is Milan to Rome or Milan to Zurich, and if your actual trip is one of those, close the booking app and buy a rail ticket.
What decides it, in the end, is not how clever the assistant is. It is whether your dates can move at all, because a flexible traveller with a free tool beats a fixed traveller with the best one.
