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Flying from Calgary to Rome to Athens

I am flying Westjet from Calgary, Canada to Rome, then changing airlines to fly to Athens on Italian Airline (ITA). I will have to go through customs and pick up my luggage as it is not a connecting flight. I have a 3 hour and 20 minute layover. Will I have to leave security and go back through security to check into my Italian Airline (ITA) flight?

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As I recall you have to pick up your luggage then go through passport control. After that you go to departures, drop off your bags and go through security. Hopefully ITA will allow you to print your boarding pass before you depart Calgary.