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Stress free morning trip from Toledo to Madrid airport?

We are staying in Toledo for a few nights prior to leaving Madrid on a flight to Marrakech on a Sunday at 11:45. Would it be stress free to get a morning train into Atocha and then a bus or metro to the airport, or should we leave the day before and stay in Madrid overnight?

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You don't have enough time. The train between Toledo and Madrid is a commuter line, so there are no early trains on the weekends. The first train on Sunday is at 9.25, arriving at Atocha at 9.58. You'll have to get from the train to the Cercanias for the next train to Barajas. At best, you'll get the 10.15 train which arrives at Terminal 4 at 10.41, leaving no more than 45 minutes to check in for the flight, get through security and get to your gate before they close the doors. They may even close the flight for check-in before you get to the counter. Even if you were to get a taxi right away, google says it's a 20 minute drive with no traffic from the station to the airport.

The only way you can get to the airport in time from Toledo is by private transfer/taxi and mucho €.