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Increasingly difficult to hold on to both....

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Do you have Global Entry? Are you flying from an airport that already has US customs?
It's for my British relative coming from Dublin. Will have gone through customs at Dublin Airport but doesn't have global entry.
Correct me if I'm wrong, but I don't believe you have to recheck bags when coming from Dublin. If so... Should be similar to a domestic flight in all regards? I've flown from Dublin many times, but my first US airport was my final destination.
Wrong. All bags must be picked up at first port of entry
Pushing it big time. I have even missed connections within JFK from international flts. You need more time to transfer between JFK and LGA.
I’d say no, or cutting it *very* close.. they’re 30-45 mins apart at best, 60-90 at worst. Add to that clearing customs and maybe picking up bags, you’re not giving yourself enough time
Secondly, he was actually held up at us customs in Dublin Airport, resulting in him missing his connection. The airline refused to put him on the next flight but we finally got them to agree. They said they'll send him to jfk instead of ord and we have to pay 150 euros plus we have to arrange our own flight from jfk to ord. It's that normal procedure?
Yeah he had his passport. They went to customs together and he needed further questions. The agent told his brother to go ahead and even called the gate to ask them to wait and said that it's in their best interest to wait a few minutes or put him on the next one. Turned out to not be the case
No way - you need to go through immigration, wait for your luggage, take a cab to LGA, check in again, and go through security. It will take min 4h...
Won't have any immigration coming from Dublin. You clear there.
Oh wow sorry OP. I missed the LGA part!! Hard no then from me
Considering customs will have been done in Dublin, is 3 hours reasonable to make the transfer?
Possible ONLY if no checked-in luggage. Otherwise forget it