When your leaving the US you don't have to worry about Customs untill you get to a diffrent country. On your way back as soon as you land in the US you have to go through Customs. Basically you have to go through customs every time you enter a new country and bring your bags through customs by hand (even if its a short lay-over) since you have to claim items according to that countries rules. There may be some exceptions and the airline would be able to tell you once you get on the plane
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