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Flights from Athens to Islands and back

I am planning to fly from Athens to Milos on May 11th and back to Athens from Santorini May 25th. How far in advance should I start looking for flights and booking them? Also, which airlines would you recommend?

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Aegean had a seat sale on recently. Now is a good time to be looking for flights. Having said that Milos is a subsidized route so you will have to pay full price no seat sales. Also flights are on 30 passenger Dash 8 turboprops so they fill up fast. You should book that one right now.