Find flights
Deals
When to book
FAQs & Tips
Airlines

Find cheap flights to Caribbean Islands from $39

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 6/12. 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
Sun 6/9
Sun 6/16

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

In the last 7 days travelers have searched 43,895,468 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$179
Montego Bay
Montego Baynonstop$198
Santo Domingo
Santo Domingononstop$165
Oranjestad
Oranjestad1 stop$188
Nassau
Nassaunonstop$228
Kingston
Kingstonnonstop$277
Simpson Bay
Simpson Bay1 stop$193
Providenciales
Providencialesnonstop$304
Port of Spain
Port of Spain1 stop$227
Bridgetown
Bridgetown1 stop$215
George Town
George Townnonstop$313
Aguadilla
Aguadillanonstop$136
Willemstad
Willemstad1 stop$353
St. John's
St. John'snonstop$319

Good to know

Low season

September

High season

December

Cheapest flight

$39
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 Philadelphia 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 55m, covering a distance of 1546 miles. The most popular route is Newark - San Juan with an average flight time of 3h 54m.

  • 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 $79. 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 $103.

  • 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 (10%). Searches for flights to Oranjestad (8%), to Santiago de los Caballeros (6%) 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 10768 reviews
7.9Comfort
8.6Crew
8.0Entertainment
8.2Boarding
7.4Food
Airline reviews

West Jet has a horrible boarding process and the seats have no cushion.

4.0 OkayDouglas, May 2024MSP - YEG
Read more about Delta reviews

West Jet has a horrible boarding process and the seats have no cushion.

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

Delayed departure. Delayed after landing pulling into gate. Delay due to sky bridge malfunction

Great. Loved that there was WiFi on flight to keep in touch and excellent service of beverages and snacks.

Business class is great. New airplane, very comfortable, better than some of the major airlines I am used to

Terrible. Flight was cancelled due to the weather in the east and sout east(florida). Did not get any compesation of any kind. According to them, it was not under their control so I lost all the money paid for the 2 fairs from Raleigh, NC to Orlando, Fl.

great flight. Pilot was communicative, flight attendants were excellent. Really nice experience except my tv didn’t work.

Overall, the flight was better than the flight I took to go to Florida, which had a bunch of problems. The crew is really nice and the plane was new so it had a small problem when we were on the runway, but the flight itself was great. They even made some time back up, which is always a good thing.

at the time for boarding the lady just call Group A and no other goups and everybody from A to F go inside without the right turn,and when we get in theres no more spsce for carry on , the ones that get in at not correct group from the back occupy our space !!!!! a mess !!!!

There were multiple delays but JetBlue tried to make the boarding and departure process as quick and efficient as possible. The crew was as detached from reality as could be, meaning: not very friendly and just doing things by the numbers.

I had back trouble prior to my flight and everyone was great about helping me.

Jetblue needs to improve on Onboarding as it seems to always be behind on departing. It never leaves on time. I would recommend to have an earlier Onboarding in order to leave on time and respect your customers time as well.

Check in etc was very good. As for on the plane, it was like flying in a freezer. It was so cold, i have flown for years and never been so cold on a plane. Staff on board said its always cold when flying which is a load of rubbish. They wouldnt put any heating on and now i have the flu because of this .

I’ve had a couple flights this week on United that were delayed by an hour or more

Flight was delayed 2.5 hours - a big deal on an overnight when you plan to sleep.

I feel like they have upgraded the app since I last flew United and I found it to be super helpful. I had stopped flying United unless absolutely necessary and my experience on this trip indicates they have been working hard to improve their services.

Surprisingly easy! I was hesitant to try this, but the cost swayed me. I actually felt like I had less stress than all the taxiing and possible delays that occur with short regional flights where you spend less time in the air than getting to and from the plane..

This flight was delayed multiple times and eventually canceled around 2-3ish. Original take off time was around 10:30am. By 3, there were no other options out of Houston, so stuck in Houston for from 3pm - 11am the next day.

Should have video screens Plane audio was poor and without wired connection hard to understand crew. Should serve more than just cups of water and pretzels on six hour flight. Did not see crew rest of flight. Fix charging sockets to retain charging blocks.

I paid $380 for my one-way ticket from California to Minnesota. The fair did not include online check-in. I received instructions from their app to check in at a kiosk. At the kiosk, the boarding pass would not print until an actual person came to verify that I had a personal item and not a carry-on item, On the plane, the person next to me was drunk and allowed to continue to order alcohol. United is garbage I’d rather fly spirit.

The plane was dirty and the in seat air wasn't blowing as planes usually do.

Generally good but there wasn’t any staff available when my luggage didn’t appear at baggage claim in Fresno. It took about half an hour to locate a staff member to open up the locked room where it was being kept.

Worst situation ever! I booked my tickets for this trip on Alaska Airlines. I guess AA is a partner and we flew nonstop from Eugene to PHX on an AA jet. I had to pay for luggage from PHX to EUG. And this was an Alaska Airlines reservation paid for with Alaska airlines credit card! Got to the PHX airport and was not able to check bags because of some weird issue with the AA software. My reservation had to be the-entered by the agent. I will never pick another American Airlines flight on the Alaska Airlines website. While on vacation, I tried to upgrade our seats for the trip home. The request just buffered and never went through. I tried four times and was charged four times on my credit card. The card was charged but the seats were never changed. What a wreck!

Left from gate 30 minutes before flight. Never been late to a flight ever. It says 15 minutes before explicitly on the ticket.

I like the boarding process, it was fast. The seat doesn’t have a TV for a long flight and food wasn’t served, just snacks.

Use planes with TVs on flights over 4 hours. The free entertainment was a cheap in between solution for a very long flight that you don't even bother providing meals or decent snacks.

Even though we left CMI late, we mostly made up the time.

Delayed almost 4 hours for a 45 minute flight with no explanation.

Again, multiple delays and I eventually just canceled and drove!

Great crew. Very comfortable business seats with nice bedding. Good food. We were delayed to let late passengers on the flight, but otherwise great experience.

Great crew. We were delayed so that late passengers could get on the flight. Love the bedding in business class. Good food. Great experience.

The CX617 from HK to BKK was delayed more than 1.5 hours.

Flight delayed then canceled! I will NEVER fly Spirit Airlines again and will tell all my friends!

Absolutely terrible. The boarding process had zero organization. Mobs of people trying to board. People were climbing over my child's stroller with her in it. No families were boarded first. Boarding was delayed with no reasoning or notification that it would be late. We were then stuck on the plane for 45 minutes after landing. Then waited over two hours for our luggage. There was zero communication with the travelers. Never have I experienced such I professionalism and disgrace of others. Extremely disappointed.

For it to have left on time! Instead of two hours early with zero notice

Flight kept delayed from morning to late afternoon so I had to make other arrangements

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

Terrible… missed our flight due to ridiculously long time to go thru baggage check-in!

The crew was not great or professional. It seemed like they didn't really want to be there. A true lack of effort for accommodating customers.

Everything was really good but the seats are not very comfortable.

I paid for WiFi, but it (WiFi) was very very slow, will never take again! Impossible open Utube 😤😤😤

I had no legroom, although I paid for extra legroom. I could barely put my bag in front of my feet and under the seat. The Wi-Fi was horrible. In fact the flight attendant said that they had to reboot it and see if it was going to work and never did.

Book Cheap Caribbean Islands Plane Tickets

Recent round-trip flight deals

5/18Sat
nonstopFrontier
2h 59mMCO-SJU
5/21Tue
nonstopFrontier
3h 17mSJU-MCO
$103
5/18Sat
nonstopFrontier
3h 01mMCO-SJU
5/21Tue
nonstopFrontier
3h 17mSJU-MCO
$104
6/6Thu
1 stopAmerican Airlines
9h 19mJFK-SJU
6/9Sun
1 stopAmerican Airlines
13h 04mSJU-JFK
$216
5/25Sat
nonstopJetBlue
4h 00mEWR-SJU
6/1Sat
nonstopJetBlue
4h 13mSJU-EWR
$225
6/9Sun
nonstopJetBlue
4h 00mEWR-SJU
6/12Wed
nonstopJetBlue
4h 22mSJU-EWR
$228
5/14Tue
1 stopAmerican Airlines
12h 15mJFK-SJU
5/15Wed
1 stopAmerican Airlines
15h 48mSJU-JFK
$249
5/19Sun
nonstopUnited Airlines
3h 59mEWR-SJU
5/23Thu
nonstopUnited Airlines
4h 09mSJU-EWR
$263
5/12Sun
1 stopUnited Airlines
8h 39mEWR-PUJ
5/16Thu
nonstopUnited Airlines
4h 20mPUJ-EWR
$282
6/7Fri
nonstopDelta
4h 05mJFK-STI
6/12Wed
nonstopDelta
4h 01mSTI-JFK
$287
6/8Sat
nonstopDelta
4h 05mJFK-STI
6/29Sat
nonstopDelta
4h 01mSTI-JFK
$289

Search by stops

Search by airline

Search by price

Recent one-way flight deals

6/12Wed
1 stopSpirit Airlines
12h 45mPHL-SJU
$39
5/29Wed
1 stopSpirit Airlines
6h 22mPHL-SJU
$46
6/3Mon
nonstopDelta
4h 06mJFK-SJU
$89
6/6Thu
1 stopAmerican Airlines
6h 01mMCO-SJU
$101
6/5Wed
1 stopAmerican Airlines
7h 40mJFK-SJU
$102
6/8Sat
nonstopJetBlue
4h 00mEWR-SJU
$104
9/17Tue
1 stopJetBlue
6h 07mJFK-SJU
$113
5/15Wed
1 stopDelta
9h 43mEWR-SJU
$128
11/4Mon
1 stopUnited Airlines
6h 06mLGA-SJU
$138
5/26Sun
nonstopUnited Airlines
3h 54mEWR-SDQ
$179

Search by stops

Search by airline

Search by price

Last minute flights to Caribbean Islands

Last minute flight, train and bus deals

5/13Mon
nonstopFrontier
2h 54mMCO-SJU
5/18Sat
nonstopFrontier
3h 17mSJU-MCO
$120
5/13Mon
nonstopFrontier
2h 50mMCO-SJU
5/18Sat
nonstopFrontier
3h 17mSJU-MCO
$121
5/12Sun
multi-stopAmerican Airlines
7h 32mMCO-SJU
5/16Thu
multi-stopAmerican Airlines
6h 29mSJU-MCO
$240
5/12Sun
multi-stopAmerican Airlines
6h 35mMCO-SJU
5/16Thu
multi-stopAmerican Airlines
6h 29mSJU-MCO
$241
5/12Sun
nonstopJetBlue
2h 47mMCO-SJU
5/12Sun
nonstopJetBlue
3h 22mSJU-MCO
$278
5/14Tue
nonstopJetBlue
4h 08mEWR-PUJ
5/16Thu
nonstopJetBlue
4h 15mPUJ-EWR
$278
5/12Sun
multi-stopUnited Airlines
8h 39mEWR-PUJ
5/16Thu
nonstopUnited Airlines
4h 20mPUJ-EWR
$282
5/15Wed
nonstopDelta
3h 55mJFK-SJU
6/22Sat
nonstopDelta
4h 01mSJU-JFK
$283
5/15Wed
nonstopDelta
4h 06mJFK-SJU
6/21Fri
nonstopDelta
4h 16mSJU-JFK
$287
5/12Sun
multi-stopUnited Airlines
9h 39mEWR-PUJ
5/16Thu
multi-stopUnited Airlines
7h 09mPUJ-EWR
$292

Search by stops

Search by airline

Search by price

Flights to Caribbean Islands

Return flight deals:

Caribbean Islands - United States

Cabin classes:

$94
$124
$65
$23

Browse origins:

View more

Browse destinations:

View more