Flight to Caribbean

View S$151 flight on Wed, 8 Apr, 2026Opens in a new window

Popular airlines to Caribbean

  • Frontier Airlines

  • American Airlines

  • United

  • Delta

  • JetBlue Airways

  • Spirit Airlines

  • Southwest Airlines

  • Be in the know

    Get alerts if flight prices drop or rise*

  • Book smarter

    Save up to 40% on select hotels after you book a flight*

  • Earn twice

    Earn your airline miles on top of our rewards
    Sign in

Cheap round-trip flights to Caribbean

Prices were available within the past 7 days and start at S$151 for one-way flights and S$351 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Fri, 24 Apr - Tue, 28 Apr
EWR
New York
SJU
San Juan
S$351 Return, found 4 days ago
S$351
Return
found 4 days ago
Select Delta flight, departing Fri, 24 Apr from New York to San Juan, returning Tue, 28 Apr, priced at S$351 found 4 days ago
Arajet
Mon, 13 Apr - Wed, 22 Apr
EWR
New York
SDQ
Santo Domingo
S$361 Return, found 4 days ago
S$361
Return
found 4 days ago
Select Arajet flight, departing Mon, 13 Apr from New York to Santo Domingo, returning Wed, 22 Apr, priced at S$361 found 4 days ago
Arajet
Thu, 30 Apr - Sat, 2 May
EWR
New York
SDQ
Santo Domingo
S$367 Return, found 6 days ago
S$367
Return
found 6 days ago
Select Arajet flight, departing Thu, 30 Apr from New York to Santo Domingo, returning Sat, 2 May, priced at S$367 found 6 days ago
Arajet
Mon, 13 Apr - Wed, 22 Apr
EWR
New York
SDQ
Santo Domingo
S$374 Return, found 4 days ago
S$374
Return
found 4 days ago
Select Arajet flight, departing Mon, 13 Apr from New York to Santo Domingo, returning Wed, 22 Apr, priced at S$374 found 4 days ago
JetBlue Airways
Fri, 29 May - Sat, 13 Jun
EWR
New York
SJU
San Juan
S$401 Return, found 20 hours ago
S$401
Return
found 20 hours ago
Select JetBlue Airways flight, departing Fri, 29 May from New York to San Juan, returning Sat, 13 Jun, priced at S$401 found 20 hours ago
Delta
Fri, 24 Apr - Tue, 28 Apr
EWR
New York
SJU
San Juan
S$416 Return, found 4 days ago
S$416
Return
found 4 days ago
Select Delta flight, departing Fri, 24 Apr from New York to San Juan, returning Tue, 28 Apr, priced at S$416 found 4 days ago
United
Fri, 10 Apr - Tue, 14 Apr
EWR
New York
SJU
San Juan
S$428 Return, found 4 days ago
S$428
Return
found 4 days ago
Select United flight, departing Fri, 10 Apr from New York to San Juan, returning Tue, 14 Apr, priced at S$428 found 4 days ago
American Airlines
Thu, 12 Mar - Mon, 16 Mar
EWR
New York
MBJ
Montego Bay
S$436 Return, found 5 days ago
S$436
Return
found 5 days ago
Select American Airlines flight, departing Thu, 12 Mar from New York to Montego Bay, returning Mon, 16 Mar, priced at S$436 found 5 days ago
JetBlue Airways
Wed, 4 Mar - Wed, 18 Mar
EWR
New York
SJU
San Juan
S$439 Return, found 20 hours ago
S$439
Return
found 20 hours ago
Select JetBlue Airways flight, departing Wed, 4 Mar from New York to San Juan, returning Wed, 18 Mar, priced at S$439 found 20 hours ago
Arajet
Thu, 5 Nov - Sun, 15 Nov
EWR
New York
PUJ
Punta Cana
S$441 Return, found 5 days ago
S$441
Return
found 5 days ago
Select Arajet flight, departing Thu, 5 Nov from New York to Punta Cana, returning Sun, 15 Nov, priced at S$441 found 5 days ago

The Annual Holiday Sale

Members save up to 40% on hotels. Plan this year’s big trip and save.
Book now

Trending flights to Caribbean

These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Sun, 12 Apr - Tue, 14 Apr
SIN
Singapore
SJU
San Juan
S$1,551 Return, found 1 day ago
S$1,551
Return
found 1 day ago
Select United flight, departing Sun, 12 Apr from Singapore to San Juan, returning Tue, 14 Apr, priced at S$1,551 found 1 day ago

Frequently asked questions

Can I cancel my flight booking to Caribbean due to COVID-19?
If you haven't booked yet, scan the terms and conditions of the airline you're considering. If you've already secured your flight to Caribbean, head to our Customer Service Portal. It will help determine which COVID-19 policies apply to your booking and provide advice on the next steps.
What's the best way to find cheap flights to Caribbean that have flexible change policies?
When it comes to flying these days, flexibility is important. That's why we've added a "No change fee" search function to help you track down flexible, low-priced tickets to Caribbean. It's to the left of your screen just below the "Flexible change policies" subheading.
What are some of the general tips for travelers to Caribbean during the COVID-19 outbreak?
The COVID-19 outbreak has resulted in big changes to how we travel. If you plan to visit Caribbean, these tips will help you navigate these new challenges and rules:

  • Before you book a flight, see if any travel restrictions apply — in both your origin and destination. Keep informed with the latest updates by reviewing government travel advisories.
  • Keep your face mask on during airport screening. A TSA employee will ask you to lower your mask temporarily for ID purposes.
  • To avoid cross-contamination, position your boarding pass on the reader yourself and then hold it up for inspection. Do not hand your pass directly to a TSA employee.
  • TSA now permits passengers to take one container of hand sanitizer, up to 12 oz (350 ml) in size, in carry-on luggage. This will have to be removed from your bag for X-ray scanning.
  • To minimize handling during screening, place personal items such as your phone, wallet and keys into your carry-on rather than the bins.
  • Transport any food items in a clear plastic bag and also place them in a screening bin. Keeping food separate from your carry-on makes it less likely that a TSA officer will need to open and touch your bag for inspection.

How much is a flight to Caribbean?
There were lots of inexpensive fares up for grabs in the last seven days, with the cost of a return ticket to Caribbean ranging between S$351 and S$1,551. Many lucky vacationers purchased one-way flights from New York (EWR) for as low as S$151.
When is the cheapest time to fly to Caribbean?
Jet off on a Tuesday to boost your odds of bagging the cheapest flight to Caribbean. Mondays are usually the next most affordable day to depart. Saturday is generally the most expensive day to fly anywhere.
How much is a plane ticket to Caribbean?
In the last seven days, ticket prices to Caribbean ranged from S$351 to S$1,551.
What are the best things to do in Caribbean?

  • With so much to see and do in Havana, it's little surprise that most travelers kick off their Caribbean getaway in this happening city. Spend your first couple of days going to see famous attractions like Hotel Nacional de Cuba before taking a look at some of this place's lesser-known highlights.
  • Havana features a tropical savanna climate. But before you take off, study what the weather will be up to while you're there. Hot, cold, wet or dry, it's smart to arrive prepared.
  • Make Camaguey the next place you go. It's around 483 kilometres to the east of Havana and where you'll discover Casa Natal del Mayor, one of this city's top tourist sights.

What months are the cheapest to book a flight to Caribbean?
February is a cheap month to book your Caribbean trip. Airfares are at their most expensive during the festive month of December, so avoid this time if possible.

Book with confidence

About Caribbean

Expedia offers flights to Caribbean to meet every traveller's needs. Whatever your flight need - Expedia has the flight for you. So choose from flights to Caribbean or destinations around the world and discover how easy it is to make your flight reservations on Expedia.
About Caribbean

Travel information

Caribbean Flights Information

Airlines serving
Delta, Air Canada, Arajet, American Airlines, United, JetBlue Airways
Roundtrip price
from S$351
Caribbean Flights Information

Explore a world of travel with Expedia

*Available to Expedia members.