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Airfare to St. Kitts???

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Hi,
We are a family of 6 that are interested in St. Kitts mainly for the info we have read on the board. My children love to snorkel, we have a 250 gal tropical fishtank, so its kinda there hobby. Anyways,we were wondering if its feasible to take a flight to san juan, which is roughly $300.00 ata from chicago. Then make our own connection with nevis express into St Kitts? Would that be too complicated with 4 kids with check in and check out of each flight?? We have never been to the caribbean so any help would be appreciated.
Susan

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