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I don’t know about Toronto but it seems a sensible thing if they have pre-clearance for travel to the US. Personally I always like Detroit since it’s such an easy airport to navigate although I don’t know whether you have any flights to there. Since your kid has already flown so extensively I’m sure he will be fine flying, I certainly wouldn’t have been ready for it at that age as I only picked up on flying when i was 24 but certainly made up for the missed years 🙂