Madrid Barajas Airport T2 arrival to T1 Depature with luggage one person 2 hours and 45 minutes, is it enough time?

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Aegean doesn't sell tickets to Cancun, so I assume these are two different tickets.

I know nobody knows for sure, but generally speaking is this a HUGE gamble?

This really depends on your personal risk tolerance. The "likelihood" of missing the connection is low. However the "impact" of missing it is high: you are a no-show for your second flight and at the mercy of the airline. In the worst case, they will cancel your entire ticket and you have to buy a new one on the spot at "same day" prices.

If all goes well, this should be fine. Your first flight is Schengen to Schengen so there will be only minimal or no passport control involved. You will have to wait for your baggage, but it shouldn't take more than an hour from arrival to the check in counter of your second flight. Aer Europa, for example, closes check in 60 minutes before departure, so you would have 45 minutes to spare. Once you are checked in, you should be good. Even if security is unusually long they will most likely wait for you since otherwise they will have to unload your bags.

Things that can go wrong:

  1. Your first flight is significantly delayed, cancelled, rebooked or the schedule is changed
  2. They loose your bag. In this case you have to wait until the carrousel is empty before you can file a missing bag report.
  3. Schedule change for your second flight.

Everyone feels differently about risk, so you have to decide for yourself if you are comfortable or not.

Personally, I don't do self-connections with less than 4 hours. More if there are exacerbating circumstances.

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