I can fly out of either Reagan National, Dulles or BWI airport. I have heard that stopping off in a city outside of Italy and then taking a smaller/budget plane to Sicily is cheaper than flying straight into Rome and then traveling to Siciliy from there.
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Messina does not operate an airport with scheduled passenger traffic. Your nearest airport would be in Reggio Calabria, Italy (REG). Routing is usually dependent on the airline which you chose to fly and the locations of its hubs. Looking at prices on a Feb 1 departure, your cheapest routings seem to go to a US hub for a foreign carrier (such as Boston or NYC) and from there onto Rome before hitting Sicily.
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