$99 Cheap flights to Caribbean
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Top places to visit in Caribbean
Cheap flights to Caribbean from $99 One Way, $270 Round Trip
$270 return flights and $99 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* |
|---|---|---|---|
| EWR | San Juan | October 3 to October 17 | $332 |
| EWR | San Juan | October 3 to October 17 | $332 |
| EWR | Punta Cana | October 4 to October 8 | $385 |
| JFK | Montego Bay | October 4 to October 8 | $426 |
| JFK | Montego Bay | October 4 to October 8 | $426 |
| EWR | Nassau | October 2 to October 5 | $429 |
| EWR | Nassau | October 2 to October 5 | $429 |
| EWR | Oranjestad | October 4 to October 17 | $444 |
| JFK | Santo Domingo | October 4 to October 7 | $487 |
| JFK | Santo Domingo | October 4 to October 7 | $487 |
| JFK | Santiago de los Caballeros | October 4 to October 8 | $501 |
| JFK | Santiago de los Caballeros | October 4 to October 8 | $501 |
| JFK | Piarco | October 4 to October 5 | $544 |
| EWR | Piarco | October 4 to October 12 | $752 |
| JFK | Nassau | October 3 to October 7 | $792 |
Find The Perfect Hotel For After Your Flight
Score Epic Caribbean Accommodation Deals
Comfort Suites Paradise Island
"Very convenient location to Atlantis and because buffet breakfast and entrance to Atlantis was included for everyone in your room, this is the best value on Paradise Island. Parking was also complimentary."
Reviewed on Sep 28, 2026
Coral by the Sea Hotel
Breezes Resort Bahamas All Inclusive
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
"Loved everything would stay here again"
Reviewed on Sep 28, 2026
Amsterdam Manor Beach Resort
"I didn’t like how I could hear my room neighbor coughing all night, and how loud was the air-circulating exhaust was with no off switch. Besides those two things, the hotel was perfect."
Reviewed on Sep 26, 2026
Divi Aruba Phoenix Beach Resort
"Liked how it was located between Palm beach and Eagle beach. Walkable each way. Dislikes: Room generally clean but I found an old contact lens on the floor in the bathroom One or the knives had breadcrumbs on it I booked my room to be ocean view and my view was the vacation center; basically resort ..."
Reviewed on Sep 29, 2026
Eagle Aruba Resort
"This resort is perfect. Fun activities, very clean, and close to lots of fun things to do. Would absolutely stay here again."
Reviewed on Sep 29, 2026
Score Epic Caribbean Accommodation Deals
Hotel El Convento
"Such a beautiful and unique stay. The open area in the middle is a great spot for drinks and dinner in the restaurant didn't feel like we were eating at a hotel. We'd love to come back!"
Reviewed on Sep 27, 2026
British Colonial - Nassau
Hotel Rumbao, a Tribute Portfolio Hotel
"Excellent location, excellent and friendly staff."
Reviewed on Sep 27, 2026
The Reef at Atlantis
Family Friendly Hotels in Caribbean
Barceló Bávaro Palace - All Inclusive
Majestic Colonial Punta Cana - All Inclusive
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
Need a Car For After Your Flight?
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Caribbean
Start your search for cheap flights to Caribbean on Orbitz. Orbitz is where you will discover guaranteed low prices on Caribbean flights, as well as all of the following conveniences:
Travel Updates on Your Mobile Device
Orbitz offers cutting-edge mobile tools for your smartphone. Whether you own an iPhone or an Android phone, you can benefit from Orbitz’s flight status updates and even book your future Caribbean flights. You can also review and reserve hotel rooms for when your Caribbean flights land and see other special offers.
Low Prices Guaranteed on Flights to Caribbean
Orbitz offers large discounts on a wide range of Caribbean flights. Through our easy-to-use site, you can find, plan, and reserve your desired flights to Caribbean while taking advantage of the lowest fares around.
Customer Care When You Need It
Orbitz is dedicated to making your flight booking experience as stress-free as possible. If you need to cancel your reservation, you can do so at your own convenience by going to the Orbitz website. If you need to change your flights to Caribbean to another time or date, you can contact our customer service representatives by phone, and they help you make the flight adjustments you need.
Loyalty Program Participation Opportunities
Orbitz lets you add your loyalty or frequent flyer account numbers when you book qualifying flights to Caribbean. So don’t worry about missing out on earning miles or points simply because you aren’t booking with the airline directly. You can save on your flights, and rack up miles too.
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.