Find flights
Deals
When to book
FAQs & Tips
Airlines

Find cheap flights to Caribbean Islands from $46

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from the United States to Caribbean Islands departing on 9/10. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Wed 7/10
Wed 7/17

Search hundreds of travel sites at once for deals on flights to Caribbean Islands

In the last 7 days travelers have searched 42,898,604 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Best Caribbean Islands Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Punta Cana
Punta Cananonstop$178
Montego Bay
Montego Baynonstop$201
Santo Domingo
Santo Domingononstop$185
Oranjestad
Oranjestad1 stop$245
Nassau
Nassaunonstop$227
Kingston
Kingstonnonstop$295
Simpson Bay
Simpson Bay1 stop$171
Providenciales
Providencialesnonstop$280
Port of Spain
Port of Spain1 stop$171
Bridgetown
Bridgetown1 stop$187
George Town
George Townnonstop$301
Aguadilla
Aguadillanonstop$104
Willemstad
Willemstad1 stop$358
St. John's
St. John'snonstop$363

Good to know

Low season

September

High season

December

Cheapest flight

$46
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 22% increase in price.
Flight from Orlando Airport to San Juan Airport

FAQs - booking Caribbean Islands flights

  • How long is the flight to Caribbean Islands?

    An average nonstop flight from the United States to Caribbean Islands takes 3h 56m, covering a distance of 1560 miles. The most popular route is Newark - San Juan with an average flight time of 3h 52m.

  • What is the cheapest flight to Caribbean Islands?

    The cheapest ticket to Caribbean Islands from the United States found in the last 72 hours was $78. The most popular route is Newark to San Juan Luis Munoz Marin Intl and the cheapest round-trip airline ticket found on this route in the last 72 hours was $104.

  • Which airlines fly to Caribbean Islands?

    JetBlue, Qatar Airways & Delta fly the most frequently from the United States to Caribbean Islands. The most popular route is from New York to San Juan, and Air Canada, United Airlines and JetBlue fly this route the most.

  • What are the most popular destinations in Caribbean Islands?

    Based on KAYAK flight searches, the most popular destination is Punta Cana (16% of total searches to Caribbean Islands). The next most popular destinations are Montego Bay (12%) and Santo Domingo (9%). Searches for flights to Oranjestad (9%), to Santiago de los Caballeros (7%) and to Nassau (6%) are also popular.

  • How does KAYAK’s flight Price Forecast tool help me choose the right time to buy?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a given destination and date is likely to change within 7 days, so travelers know whether to wait or book now.

See more FAQs

Top tips for finding cheap flights to Caribbean Islands

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Caribbean Islands flight deals.

Top 5 airlines flying to Caribbean Islands

Need help choosing which airline to fly with from the United States to Caribbean Islands? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 10295 reviews
8.2Boarding
8.0Entertainment
8.6Crew
7.9Comfort
7.4Food
Airline reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

2.0 MediocreCraig, Jun 2024CVG - LGA
Read more about Delta reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

terrible. Because I felt very unwell during the flight. How do they leave a woman alone in the middle of 2 men? an obese man who was falling on top of me.

They put me on a chair in between two men, one overweight who was almost falling on top of me, and the other was even uncomfortable because I was half falling because of what the other was pushing me. I stayed with. my feet were swollen from fluid retention and from being unable to accommodate myself. it was very uncomfortable. I asked for help but they told me that the flight was full and they couldn't help me. I got off the plane almost unable to walk due to the inflammation. and then at FLL airport I asked for help because I couldn't go to my next flight, which was a connection.

The walk from baggage claim to the taxi is very difficult for older people I will never fly into JFK again. It is physically challenging

Overall fine but both ways for this trip was delayed.

Flight was delayed by almost 5 hours. Suitcase was not loaded despite the flight being near empty (my colleagues’ suitcases did reach JFK, unlike mine). Had to argue on phone to get JetBlue to deliver the case to my hotel. Never again

The flight was excellent. The crew was welcoming and attentive.

Great! I love Jet Blue. My favorite airline! Very efficient, clean and timely.

Run out of snack choices. Why are the seats not padded for your butt? Are we sitting on blocks of wood or metal for $250-300 a pop? This ain’t spirit. Let’s get it together people

We were told that our flight would be delayed for 90+ minutes because of weather, so we went to get something to eat only to have them randomly start boarding 15 minutes after the announcement, with no warning.

Entertainment... No earphones passed out. Many including me couldn't use the TV. Legroom was good. Crew was indifferent and a bit surly. Free wifi was a nice convenience. Check in desk location was unknown. Gate number on the boarding passes was wrong.

Why does it have to be painful to fly long distances?

It is a modern tragedy that any airline expects you to travel for 14 hours in such discomfort and that the only way to add comfort is exorbitant prices. I was in pain by the time we landed. Shameful.

Original plane sidelined. Had to wait an hour for replacement.

Crew was very cooperative and professional. Passenger's first checked in bag should be free.

No real agent onsite helping you for missing luggage there. Not like the other airline next to UA desk, they have staff attending in their desk assisting answer/helping luggage issue, even after midnight.

Horrible, the flights kept delaying, so it is obvious that we won't be able to make it to the next connection. No easier/real agent on site to help you figure this out. UA agent on other counters refuse to assist you and direct us to use the QR code/call customer service. So inefficient and poor. While technology seems convenient, but it's not the best interest/experience for customers need help while there is active issue need assistance.

Food is very bad and entertint not too many options ... flight attendet service is not good

After the morning frenzy of 35 min wait through CLT security at 4;30 AM, it was nice to have a smooth pleasant boarding experience. This 6:30 AM flight was not full. We were able to get seated swiftly and took off promptly. Nice touch they distributed the old fashioned headsets with 8 mm jacks. Snacks were decent and arrival was uneventful.

My window shade didn’t work. So I missed coming into my city. ☹️

Flight was delayed in the gate by 5 hours and ultimately cancelled- rebooking service by United agents was terrible

This is by far the worst experience I have had with American Airlines. The start of this trip was a complete disaster. I purposely planned my trip so that I would weather any delays so that I could make very important meeting at the Pentagon. My flight was cancelled because of maintenance and I was put on the first flight the next day but I was late to the meeting. After a long week at the Pentagon I just wanted to go home and my flight home which was early in the day was delayed. Eventually the flight was delayed until the next day. I was not authorized a hotel room because DCA was my point of origin. So I paid for a hotel out of pocket. The flight this morning was boarded then deplaned because the aircraft was hot. The flow of information was not happening in DCA and made it worse when the news was bad. I am going to take a break from American for my next few military flights. Hopefully whatever has been going on with American Airlines will be resolved.

We had a 2 hour delay. The seats were smaller than most other airlines. The person in front of us wanted to lay back and we had to stop her because she was pressing against my girlfriend’s legs. We had to ask her to sit up and not lay back due to the lack of room.

Information when booking said the flight would be with American Airlines but the flight was actualy with British Airways. Check in from Orlando was nice and quick. I agreed to put my cabin case in the checked luggage as it was a full flight. Case came back damaged (unable to put the handle down) so will have to dispose of it. Seats were quite cramped with very little leg room, even for economy. This was the experience of both the outgoing and return flight. Cabin crew were ok and flight time was punctual.

Everything was fine once we actually got on our flight. It was more then annoying they canceled (delayed) our flight. We lost out on a day of our trip along with money on our stay. Plus we had to book another hotel. So expensive.

This flight was canceled and delayed several times without explanation. The plane was freezing cold and no wifi for messaging. Getting off the plane was terribly unorganized and felt like it took forever….

The flight was delayed several times without explanation. The seats were terribly uncomfortable and wifi isn’t included. All these make for a less than ideal flight.

The flights was delayed by hours and it was the firmest landing I have experienced in my life. My back is still sore.

Internet service was erratic. Crew service was poor and slow. My luggage on this non-stop flight was lost and not recovered

Terrible. I didn’t fly and I had an important meeting the next day.

Missed this flight due to the first AA flight delay

Flight was canceled less than 6 hours before takeoff, rebooked on a flight that was twice as long and left earlier so we couldn’t make it, when using text support option took over 2 hours to speak with someone.

Not enough help at airport during boarding process. Flight was delayed. Overall WORST flying experience I’ve ever had. Will NEVER FLT SPIRIT AGAIN

Terrible legroom, seats do not recline, tray table the size of an iPhone, delayed flight, have to pay 5$ to get a cup of water onboard.

Could have TV/Movie and some water ou soda free

Flight was good and clean but delayed over an hour on the return flight.

The non stop flight and able to go into Atlantic City airport. They could lower the prices. It starts out low but then if you want to bring luggage and pick your seat the price goes up quite a bit.

Flight got diwngraded last minute and left us stranded. I was told I’ll be given credit for my luggage and seat upgrades but haven’t got anything yet

We can’t predict circumstances like this ahead of time, but I give your staff a hats off for immediately giving us updated informations.

It was nice! There was a very unhappy child in front of us and the flight attendant did a great job calming the child. I was impressed.

The plane was not on time for boarding or departure or arrivals.

Book Cheap Caribbean Islands Plane Tickets

Recent round-trip flight deals

9/14Sat
nonstopFrontier
4h 05mEWR-SJU
9/18Wed
nonstopFrontier
4h 08mSJU-EWR
$95
8/27Tue
1 stop
9h 13mEWR-SJU
9/18Wed
nonstop
4h 08mSJU-EWR
$100
11/1Fri
nonstopJetBlue
2h 44mMCO-SJU
11/2Sat
nonstopJetBlue
3h 03mSJU-MCO
$183
9/6Fri
2 stopsAmerican Airlines
8h 59mJFK-SJU
9/18Wed
1 stopAmerican Airlines
12h 42mSJU-JFK
$224
8/6Tue
1 stopJetBlue
7h 12mJFK-SJU
8/13Tue
1 stopJetBlue
6h 47mSJU-JFK
$244
9/17Tue
nonstopDelta
3h 53mJFK-STI
10/5Sat
nonstopDelta
3h 45mSTI-JFK
$279
11/3Sun
nonstopUnited Airlines
3h 48mEWR-STI
11/16Sat
nonstopUnited Airlines
4h 05mSTI-EWR
$279
11/19Tue
nonstopDelta
3h 59mJFK-STI
12/14Sat
nonstopDelta
3h 59mSTI-JFK
$289
8/20Tue
2 stopsAmerican Airlines
10h 43mEWR-STI
9/20Fri
2 stopsAmerican Airlines
22h 14mSTI-EWR
$297
10/19Sat
nonstopUnited Airlines
3h 45mEWR-STI
10/26Sat
nonstopUnited Airlines
3h 58mSTI-EWR
$328

Search by stops

Search by airline

Search by price

Recent one-way flight deals

9/10Tue
1 stopSpirit Airlines
13h 14mMCO-SJU
$46
9/10Tue
1 stopSpirit Airlines
9h 15mEWR-SJU
$46
6/19Wed
nonstopJetBlue
2h 57mMCO-SJU
$107
7/2Tue
nonstopJetBlue
4h 04mEWR-SJU
$108
8/21Wed
1 stopAmerican Airlines
7h 15mJFK-SJU
$117
6/13Thu
1 stopAmerican Airlines
9h 19mJFK-SJU
$128
9/5Thu
nonstopDelta
4h 04mJFK-STI
$136
8/30Fri
nonstopDelta
4h 10mJFK-MBJ
$157
10/2Wed
nonstopUnited Airlines
3h 49mEWR-STI
$161
6/22Sat
nonstopUnited Airlines
3h 59mEWR-SJU
$162

Search by stops

Search by airline

Search by price

Last minute flights to Caribbean Islands

Last minute flight, train and bus deals

6/15Sat
multi-stopFrontier
22h 17mMCO-SJU
6/21Fri
multi-stopFrontier
30h 11mSJU-MCO
$155
6/11Tue
multi-stopSpirit Airlines
9h 49mMCO-SJU
6/26Wed
multi-stopSpirit Airlines
13h 16mSJU-MCO
$160
6/11Tue
nonstopJetBlue
2h 52mMCO-SJU
6/16Sun
nonstopJetBlue
3h 10mSJU-MCO
$233
6/15Sat
nonstopJetBlue
3h 01mMCO-SJU
6/18Tue
nonstopJetBlue
3h 08mSJU-MCO
$241
6/13Thu
multi-stopAmerican Airlines
11h 34mMCO-SJU
6/16Sun
multi-stopAmerican Airlines
13h 43mSJU-MCO
$275
6/13Thu
multi-stopAmerican Airlines
13h 33mMCO-SJU
6/16Sun
multi-stopAmerican Airlines
13h 43mSJU-MCO
$282
6/11Tue
multi-stopDelta
9h 49mMCO-SJU
6/14Fri
multi-stopDelta
11h 23mSJU-MCO
$319
6/12Wed
nonstopDelta
4h 05mJFK-STI
6/15Sat
nonstopDelta
3h 57mSTI-JFK
$325
6/11Tue
multi-stopUnited Airlines
6h 35mEWR-PUJ
6/12Wed
nonstopUnited Airlines
4h 20mPUJ-EWR
$335
6/15Sat
nonstopUnited Airlines
3h 59mEWR-SJU
7/13Sat
nonstopUnited Airlines
4h 09mSJU-EWR
$336

Search by stops

Search by airline

Search by price

Flights to Caribbean Islands

Return flight deals:

Caribbean Islands - United States

Cabin classes:

$94
$124
$62
$25

Browse origins:

View more

Browse destinations:

View more