$89 Cheap flights to Caribbean
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Top places to visit in Caribbean
Cheap flights to Caribbean from $89 One Way, $177 Round Trip
$177 return flights and $89 one-way flights to Caribbean were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Deals For This Weekend's Flights
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| JFK | San Juan | May 30 to June 5 | $332 |
| JFK | San Juan | May 30 to June 5 | $332 |
| JFK | Montego Bay | May 29 to June 23 | $337 |
| JFK | Montego Bay | May 29 to June 23 | $337 |
| EWR | San Juan | May 29 to June 9 | $377 |
| JFK | Nassau | May 30 to June 3 | $402 |
| JFK | Nassau | May 30 to June 3 | $402 |
| EWR | Oranjestad | May 30 to June 6 | $403 |
| JFK | Oranjestad | May 30 to June 1 | $435 |
| EWR | Montego Bay | May 29 to May 30 | $458 |
| JFK | Santiago de los Caballeros | May 30 to June 5 | $461 |
| JFK | Santiago de los Caballeros | May 30 to June 5 | $461 |
| JFK | Santo Domingo | May 31 to June 7 | $483 |
| EWR | Santo Domingo | May 31 to June 7 | $570 |
| EWR | Nassau | May 30 to June 1 | $599 |
Find The Perfect Hotel For After Your Flight
Score Epic Caribbean Accommodation Deals
Comfort Suites Paradise Island
"Customer service was top tier. Darrens made sure we had everything we needed at check-in."
Reviewed on May 26, 2026
Coral by the Sea Hotel
"Great staff!"
Reviewed on May 27, 2026
Breezes Resort Bahamas All Inclusive
"Excellent value for money, rooms are a bit out dated, but staff was extremely helpful food was pretty good and amenities on the property are nice. And of course the view overlooking the pool and ocean is Bahama Beautiful."
Reviewed on May 27, 2026
Meridian Inn
"Stayed 2 nights while waiting for flights after a cruise. Wonderful place on the Ocean. Great pool and friendly staff. Comfortable bed. Would certainly stay here again as it’s a great price when you do not want an all inclusive resort. I gave cleanliness a 5* even though the bathroom had tiny ants ..."
Reviewed on Apr 25, 2026
Our Top Caribbean Apartment Hotels
Simpson Bay Resort, Marina & Spa
"Simpson Bay Resort is a great place to stayt, the breakfast buffet is very good, we recommend that you include it in your reservation. The beaches are beautiful, comfortable to swing. The pools are very clean and warm. Overal, we liked it and we would stay here again in our next trip to St. ..."
Reviewed on May 25, 2026
Amsterdam Manor Beach Resort
"Great staff. Jennifer was great."
Reviewed on May 24, 2026
Divi Aruba Phoenix Beach Resort
"Everything was great. The staff was friendly and helpful"
Reviewed on May 26, 2026
Eagle Aruba Resort
"Nice hotel"
Reviewed on May 26, 2026
Score Epic Caribbean Accommodation Deals
Hotel El Convento
"Friendly staff… Very clean…"
Reviewed on May 26, 2026
British Colonial - Nassau
"Hotel was centrally located for good activities during the day. Hotel offered limited activities and venues."
Reviewed on May 27, 2026
Hotel Rumbao, a Tribute Portfolio Hotel
"Great location in the heart of Old San Juan. Clean rooms, friendly staff, and a comfortable stay. We enjoyed our visit and would definitely stay here again."
Reviewed on May 25, 2026
The Reef at Atlantis
"It was incredible trip, I came with my husband and daughter and we stayed at the reef. So much to do. So many amazing activities to do."
Reviewed on May 26, 2026
Family Friendly Hotels in Caribbean
Barceló Bávaro Palace - All Inclusive
Majestic Colonial Punta Cana - All Inclusive
"Overall it was a good stay..."
Reviewed on May 20, 2026
Dreams Rose Hall Resort & Spa - All Inclusive
Families like: Outdoor pools, free waterpark access, kids club, playground
"All was good"
Reviewed on Jan 15, 2026
Majestic Elegance Punta Cana - All Inclusive
Families like: Outdoor pools, waterslide, kids club, playground
"Beautiful and large resort with a lovely beach and lots of swimming pools and restaurant options"
Reviewed on May 26, 2026
Need a Car For After Your Flight?
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Caribbean
Snag some “suite” deals when you add cheap hotel rooms to Caribbean flights at Orbitz. You can score tickets to ballgames, concerts and other activities while planning your low fare flights. For non-stop air tickets or planned layovers, Orbitz is your discount travel resource.
Budget Prices, Luxury Life
Find mobile-only bargains on your home away from home with Orbitz cutting-edge mobile tools. Search domestic and international hotels at Orbitz On the Go. Find free travel planning apps for your iPhone, Android or iPad. You’ll always get our guaranteed low prices on your favorite hotels and flights to Caribbean.
Fun for All
While shopping Orbitz sales on Caribbean flights, remember to throw in some fun. Ticket sales for music, theatre, sports and more can be found on the Activities page. Just tell us what you want to do, and Orbitz will save your seat.
Non-Stop or Stop and Visit
Will you be flying round-trip or one-way? Going directly from Point A to Point B? Maybe you’d like to have dinner with family and friends along the way. Whether you need non-stop flights to {destination.name} or lowest cost layovers on Caribbean flights, you will always find the best air travel prices at Orbitz.
All in One
Now you can custom design the perfect travel package with Orbitz and save more when booking your flights to Caribbean. Do you have a favorite airline, hotel or car rental company? Every page at Orbitz gives you complete freedom to create your travel plans according to your unique wants and needs. Orbitz is designed to meet your discount travel planning needs completely and conveniently.
Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.