When we have to catch a flight for something really important: a job interview, a wedding, a funeral. How can we know the chances of the airline failing us? Of overbooking? Of the flight being late or even getting cancelled?

I understand that the overbooking info might be kept under wraps by the airline companies, but is there a historical public database of flights cancelled? And, if we know what flights landed with how many passengers, we could also guess that airlines with flights that are always full could tend to overbook more aggressively.

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    You can often get on-time and cancellation statistics by airline, route, and flight number; either from the airline itself, a government regulator, or a third-party data service. Availability may vary depending on the airline and the government. Of course, it's often hard to know what this implies for your upcoming flight; past performance does not necessarily indicate future results. Jun 15 '18 at 16:54

Short answer: You can't.

To address your scenarios: Plan enough time to accommodate any disruptions. The airlines really, really want to run everything on time. But external unforeseeable circumstances can change this such as extreme weather, volcanos, union strikes. Overbooking is less of a concern now as flexible passengers are quite willing to take the compensation and fly later.

For example, cruise passengers are near universally advised to plan to arrive at the port the day before. If something goes wrong, they still have a day to catch up and not miss the ship. Same goes for weddings or other one-time events.

You will typically have the option to choose itineraries with extra long connection times which can handle delays after you've departed.

Background: Airline performance information is widely available from various commercial and government sources. The problem is, it's all generalized and the past performance of any given flight doesn't mean.

You can find recent flight histories here: Flight Aware

General airline stats are nicely summarized here: Flight Stats

  • It's worth noting that the one time overbooking algorithms can still go wrong is when large, time sensitive events happen in small cities. At that point there sudden aren't any flexible travellers to volunteer.
    – origimbo
    Jun 15 '18 at 17:15

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