$99 Cheap flights to Caribbean
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Top places to visit in Caribbean
Cheap flights to Caribbean from $99 One Way, $298 Round Trip
$298 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 4 to October 9 | $298 |
| EWR | San Juan | October 4 to October 9 | $298 |
| JFK | Punta Cana | October 4 to October 15 | $414 |
| EWR | Montego Bay | October 2 to October 4 | $423 |
| JFK | Montego Bay | October 4 to October 8 | $426 |
| EWR | Nassau | October 2 to October 6 | $429 |
| EWR | Punta Cana | October 3 to October 15 | $431 |
| JFK | San Juan | October 4 to October 9 | $437 |
| EWR | Santo Domingo | October 4 to October 14 | $466 |
| EWR | Piarco | October 2 to October 6 | $468 |
| JFK | Santiago de los Caballeros | October 4 to October 13 | $472 |
| JFK | Santiago de los Caballeros | October 4 to October 13 | $472 |
| EWR | Kingston | October 3 to October 6 | $493 |
| JFK | Oranjestad | October 2 to October 4 | $566 |
| JFK | Kingston | October 4 to October 11 | $678 |
Find The Perfect Hotel For After Your Flight
Score Epic Caribbean Accommodation Deals
Comfort Suites Paradise Island
Coral by the Sea Hotel
"Clean room"
Reviewed on Sep 27, 2026
Breezes Resort Bahamas All Inclusive
"Breezes resort is a compact hotel. Everything within a short walk distance not too big and huge like a lot of your resorts. Workers friendly and all staff are very helpful. Will return next year."
Reviewed on Sep 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
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
Eagle Aruba Resort
Score Epic Caribbean Accommodation Deals
Hotel El Convento
British Colonial - Nassau
Hotel Rumbao, a Tribute Portfolio Hotel
The Reef at Atlantis
"Food wasn’t great but the amenities and scenery more than made up for it!"
Reviewed on Sep 27, 2026
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
"Most workers didn’t speak or understand English well. Food at the restaurants were the same everyday, mediocre at best and never any specials. Every bar should have top shelf liquors as they advertise. Most of top shelf liquors were hidden. Adult pools were great. The main pool had many tiles missing ..."
Reviewed on Sep 27, 2026
Need a Car For After Your Flight?
Economy
Compact
Midsize
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Caribbean
Orbitz provides convenient, one-stop shopping for travelers looking for budget flights to Caribbean or any other low fare domestic or international air travel.
Innovative Orbitz Tools for the Trip Planner on the Move
Now it is even faster to find exclusive deals and book cheap Caribbean flights from any location with our new Orbitz apps. These cutting-edge mobile tools are available free to anyone with an Android device, iPad, or iPhone. Look up Caribbean's most popular attractions, best restaurants, and entertainment venues or check on your flights to Caribbean and make changes to your itinerary while waiting in line for your latte.
Stay on Budget, Earn Miles with Bargain Caribbean Flights
You can find amazing discount fares with Orbitz’s guaranteed low prices or take advantage of last-minute sales and special travel packages. You can also earn points towards your airline frequent flyer programs when you book qualified flights to Caribbean. That means you can rack up money-saving points and miles for future use while saving money now.
We Are Just a Phone Call Away If You Need Us
Booking, changing, or canceling your Caribbean flights is a breeze with Orbitz’s online and mobile tools, but that doesn't mean that we leave you hanging if you want to speak with one of our representatives. If you need help, just contact our Customer Service by email or phone. To enjoy a less stressful trip, be sure to sign up for instant alerts so we can send you any updates or delays relating to your flights to Caribbean to your mobile phone or email.
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.