Caribbean Islands Beach Holidays
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See all available trips from Chicago to Caribbean Islands
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Majestic Elegance Punta Cana - All Inclusive
Playa Bavaro - Punta Cana Punta Cana La Altagracia
- 13 hours drive from Oyster Bay Marina
Stay at this luxury resort in Punta Cana. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the pool and the restaurant in their reviews. ...
Majestic Colonial Punta Cana - All Inclusive
Carretera El Macao Punta Cana La Altagracia
- 13 hours drive from Oyster Bay Marina
Stay at this beach resort in Punta Cana. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. Popular ...
Holiday Inn Resort Aruba - Beach Resort & Casino by IHG
J E Irausquin Boulevard 230 Noord
- 22 hours drive from Oyster Bay Marina
Stay at this beach resort in Noord. Enjoy free Wi-Fi, free parking and 3 outdoor pools. Our guests praise the breakfast and the pool in their reviews. Popular ...
8.4/10 Very good! (1,892 reviews)
Travellers like: on the beach, sunloungers, beach bars, beach umbrellas
Travellers say...
"Had a ocean front king room in the Palm tower and it was amazing. Didn’t spend much time in the room other than to sleep. Walking distance to everywhere you need and the bartenders at the small bar in the lobby were our favorite. Can’t wait to come back and stay here again. We didn’t eat much food ..."
Reviewed on 10 Aug 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Things to do
St. Croix’s Forts, Freedom, and Beaches: A Self-Drive Audio Tour
€22
per traveller
St Croix Tiki Tours Frederiksted’s Tiki Boat Experience
€70
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
