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Reasonable Baggage pick-up & re-check time at JFK

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I arrive at JFK on Delta at approximately 3:30 on a Tuesday afternoon in June. I depart JFK that evening at approximately 8 p.m. for LHR. I am booked on separate airlines with separate tickets. I will attempt to get direct luggage checking for my destination LHR. at my starting point RDM, a small wonderful airport. If II am unsuccessful is it reasonable to plan luggage claim at JFK and recheck with Iceland Air in that time period.

Normally I travel with a 21" and don't check it. This time I am meeting two women who will have been backpacking in Europe for the previous 3 weeks. After a week in London we are taking a transatlantic cruise to NYC. Thus the need for a second piece of luggage, I have their London and cruise clothes. I keep fearing "lost" luggage and no way to get the luggage as I will be in transit to LHR.

If I check luggage I know I will need to pass security again at JFK, I don't know if I need to change terminals. The time difference between arrival and departure is almost 6 hours which on paper appears to be more than enough time to go through the process.

I have considered a private luggage service and sending the extra piece separately. My concern with that procedure is the wait time in London. We have rented a flat and someone will need to wait for delivery instead of enjoying the wonders of London .

So Fodorites what path would you choose, or do you have even a better suggestion for me to consider?
Thanks and happy travels

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