Originally Posted by
monitor
I would not dare booking a flight into LGA leaving me 2h25 for an international flight. It could (god bless the Van Wyck

) take a half or even more of that 2:25 simply changing airports.
This OP should avoid all possible heartburn by booking into JFK the afternoon before with Plan B being that first DL flight the next morning. Nothing else makes much sense to me.
I agree with the first part, but if flying the day before, I would be pretty comfortable flying into either LGA or JFK (and I'd only rule out EWR because that ground transfer is too long and expensive for me).
Plan B would be the first flights into either LGA or JFK, giving 3-4 hours to transfer if arriving at LGA. If operating Plan B, OP would certainly want to check traffic and if there are major incidents, taking a cab to Woodside LIRR and then on to Jamaica/AirTrain is also an option to avoid the Van Wyck lottery.