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Find cheap flights from Philadelphia to Caribbean Islands from $44

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Philadelphia to Caribbean Islands departing on 5/25. 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 5/26
Sun 6/2

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Best Caribbean Islands Flight Deals

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

Punta Cana
Punta Cana1 stop$183
Montego Bay
Montego Bay1 stop$232
Santo Domingo
Santo Domingononstop$196
Oranjestad
Oranjestad1 stop$377
Nassau
Nassau1 stop$371
Kingston
Kingston1 stop$312
Simpson Bay
Simpson Bay1 stop$238
Providenciales
Providencialesnonstop$348
Port of Spain
Port of Spain2 stops$465
Bridgetown
Bridgetown2 stops$439
George Town
George Town1 stop$428
Aguadilla
Aguadilla1 stop$158
Castries
Castries3 stops$944
Willemstad
Willemstad2 stops$491
St. John's
St. John's1 stop$525

Good to know

Low season

September

High season

July

Cheapest flight

$59
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly with an average 4% increase in price.
Flight from Philadelphia to Simpson Bay

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Philadelphia to Caribbean Islands?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Philadelphia to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Philadelphia to Caribbean Islands?

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

  • What is the Hacker Fare option on flights from Philadelphia to Caribbean Islands?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Caribbean Islands with an airline and back to Philadelphia with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Philadelphia to Caribbean Islands?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Caribbean Islands from Philadelphia up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Caribbean Islands

  • Looking for a cheap flight? 25% of our users found tickets from Philadelphia to the following destinations at these prices or less: San Juan $109 one-way - $232 round-trip

Top 5 airlines serving from Philadelphia to Caribbean Islands

 
Need help choosing which airline to fly with from Philadelphia 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 10966 reviews
7.4food
8.0entertainment
7.9comfort
8.6crew
8.2boarding
Airline reviews

Delta is one of the best airlines I have flown

10.0 ExcellentKellie, Apr 2024ANC - SEA
Read more about Delta reviews

Delta is one of the best airlines I have flown

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

I always fly with Delta. My friends tell me their horror stories of flying with other airlines. I just smile and say, “You should fly Delta”

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

This flight was ridiculous. I had to have a connecting flight from New York to orlando Florida??? The flight left late and because it was a short flight there was no first class amenities. I had one alcohol drink. The flight crew was fine, but it sure did not feel like first class. Delta to me dropped the ball by giving me a connecting flight. By the time we got to Raleigh we would have missed the next flight. Lucky for me the flight never came so now I was stuck waiting for a later flight that came in late also.

Our flight was delayed in Atlanta. The staff could have gave us an explanation for the delay and how long it would be.

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive. I also upgraded to comfort + , I didn’t feel it was worth it. There was no benefit

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive.

Nothing beats ANA customer service on my opinion. Maybe because of their Japanese culture (and food). Arigatō

So so. Terrible aircraft choice for that leg of the flight.

Due to one crew member not showing up to work, our flight was significantly delayed causing us to miss our connecting flight in Houston to Mississippi causing us to be delayed by more than 6 hours and missing our event all together. Very disappointing. All because ONE crew member called in sick. United did grant us a $15 meal voucher, which was a small but appreciated concession that I wasn’t able to use because I ordered my lunch and paid for it before applying the concession, and the staff said it was too late to use it. Ugh! We also had a TWO delay coming back from Mississippi, but that was on American Airlines and it was due to weather, so not their fault. Anyway, not at all impressed with United’s handling of our flight and the HUGE disappointment of missing our important family event for our 90 year old mother. All that money and all that stress and emotions for nothing. Having to wait the hour to bring an employee from LAX seemed like something that should not have happened. Why don’t you have a local back-up? Santa Ana is not a little airport in a rural area.

Flight delayed from Cape Town to Washington then got diverted to miami and in miami we had to fend for ourselves , im still trying to get to Shreveport now

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

I just wrote a text which was supposed to be for the flight from Denver to spokane not Frankfurt to Denver.

On time every leg of the journey and exceptional staff at counter, gate, and on board. I haven’t travelled in US for a long time and was genuinely surprised how pleasant this was.

Hated every minute of it. This flight should have only taken 1.5hrs but was delayed over 10hours. Now I am being told I cannot be compensated or refunded my ticket price or extra leg room, which I purchased but did not receive, because the airline is throwing the blame on the 3rd party I purchased tickets through and 3rd party putting the blame on airline. No one wants to help. They received their money and that's all they care about. Im going on 3 days of still trying to get to my final destination, had to cancel car rental, car insurance and hotel. Currently staying in airport until hotels open up. Thank you Lufthansa, Kayak, Underpricer and United for making this trip the worst ever.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

flight delays, staff only communicating when pushed, food service lasting a grand total of 7 minutes, stuck in seat from 45mins into flight until landing

Same basket of unhealthy prepackaged snacks (junk food) which was depleted by the time it got to my row!!

We experience delays on departure and connecting flights resulting in 14 hour to our next departure. We were accommodated with a night's stay but was only provided a 12 dollar meals accommodation. The airlines rules state.at least 50 dollars. In any case, it can not make up for the whole day missed on our vacation in Sydney Australia.

Flight from PHL to PHX arrived 50 minutes early and a gate was available. First class flight attendant Stephanie was very friendly and polite. Sanitizing wipes should be provided with meals in addition to refresher towels.

flight delayed so missed connection and this had to rebook for next day

Flight departed PHL one hour late due to late arrival of aircraft. On board services were okay. First class menu does not offer any new items; same desserts (cheese & crackers or Mango sorbet). At least there were no credit card promotions during the flight.

After sitting on plane for 7+ hours, flight was canceled. And to makes matters worse, my suitcase is in baggage hell!

Some of the crew members were rude for no good reason

Terrible Ticketing and Check in process. I learned that AA unilaterally cancelled my premium seating from PHL to CLT and from CLT to JAN. They did, however, refund my money, but my seating was subsequently severely downgraded. They didn’t have a seat for my unless I paid for it! Not cool! Consequently, Check-in took 45 min. AA is usually great, but this was my worst experience with AA ever. Appalling they they arbitrarily cancel my seats threatening loss of flight if I didn’t pay for a seat!!!! -John

We liked quick boarding and on time departure. Seats were very uncomfortable.

Great flight. Quick boarding and departure. No problems. Flight crew were very friendly and professional.

Not much seat room, but that was unexpected. But the seat headrest was very uncomfortable.

First the good, everyone was friendly and efficient. Flight was smooth and plane was very clean and new. Now the bad, seats have almost no padding on your behind. I was in exit row so I had tons of leg room for a 6' 2" bean pole with long legs. Everything was extra - water, soda, snacks everything besides oxygen. Ya get what you pay for, and my flight was cheap as you could ever want it, so no worries.

First the good, everyone was friendly and efficient. Flight was smooth and plane was very clean and new. Now the bad, seats have almost no padding on your behind. I was in exit row so I had tons of leg room for a 6' 2" bean pole with long legs. Everything was extra - water, soda, snacks everything besides oxygen. Ya get what you pay for, and my flight was cheap as you could ever want it, so no worries. They dont really bother you about carry-on size, I brought a descent sized backpack and they didnt even check.

Spirit canceled the flight in March and never notified me!

Seats suck, not enough room, overcrowded planes, hectic situation all together.

Pretty good. Would’ve been excellent if we would have left on time and the crew wasn’t late.

I do not like the customer service, I had an emergency and needed to cancel a pet reservation right after I had booked it and they would not do anything but issue a credit. I haven't flown in years as I have 7 kids and don't have spare time. I want my $125 back on my card please

Spirit airline tries to screw you at every opportunity. Spirit wanted 65$ for an extra pound in the suitcase Made me open the suitcase at the counter to remove 1 pound. Staff very cold and rude Will never fly spirit again and will recommend same to family and friends

Delayed..4 times...completely disorganized boarding. After 5 hours they scrambled to move ppl off plane bc they overbooked. Then they didn't have a cabin crew. WiFi on plane didn't work. Zero amenities. Once we boarded we sat on tarmac for an hour. Explore all alternate options including purchasing a pair of hiking boots and walking to your destination instead of flying spirit.

what I like about Spirit is that the pilot and crew are good communicators. The plane itself - well, its a budget airline and you get what is expected, But I generally just feel safer, somehow, when I know more about what is going on - and Spirit has always done a good job of telling me what is going on: why the delay, why the turbulence, why this and that... and that means a lot to me.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

Not have to pay for every single item to take a flight. Seating and delays sucked.

Flight was cancelled and I had to spend the night in the airport lugging my suitcase around

If you don’t check in 24 hours in advance, they will charge you $110 to check your bag instead of the $30. I did not get an email with this information and did not check in. In addition, my flight home was cancelled at layover and I had to spend the night in the airport, and then have another layover at another airport before making it home. Will not fly frontier again.

Book cheap flights from Philadelphia to Caribbean Islands

Recent round-trip flight deals

5/11Sat
nonstopFrontier
3h 39mPHL-SJU
5/16Thu
nonstopFrontier
3h 46mSJU-PHL
$131
5/11Sat
nonstopFrontier
3h 39mPHL-SJU
5/15Wed
nonstopFrontier
3h 46mSJU-PHL
$132
5/7Tue
nonstopSpirit Airlines
3h 53mPHL-SJU
5/10Fri
nonstopSpirit Airlines
4h 01mSJU-PHL
$134
5/29Wed
nonstopSpirit Airlines
3h 50mPHL-SJU
6/6Thu
1 stopSpirit Airlines
12h 26mSJU-PHL
$136
5/17Fri
2 stopsAmerican Airlines
15h 15mPHL-STI
5/24Fri
1 stopAmerican Airlines
10h 30mSTI-PHL
$318
5/15Wed
1 stopAmerican Airlines
7h 15mPHL-STI
5/25Sat
1 stopAmerican Airlines
19h 26mSTI-PHL
$345
9/23Mon
1 stopDelta
6h 49mPHL-PLS
9/25Wed
1 stopDelta
25h 53mPLS-PHL
$370
9/22Sun
1 stopDelta
19h 42mPHL-PLS
9/24Tue
1 stopDelta
25h 53mPLS-PHL
$377
8/16Fri
1 stopUnited Airlines
7h 59mPHL-PLS
8/19Mon
2 stopsUnited Airlines
21h 30mPLS-PHL
$387
7/10Wed
1 stopUnited Airlines
5h 51mPHL-PLS
7/16Tue
2 stopsUnited Airlines
31h 14mPLS-PHL
$452

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Recent one-way flight deals

5/25Sat
1 stopFrontier
16h 05mPHL-SXM
$59
5/13Mon
3 stopsSpirit Airlines
23h 07mPHL-SJU
$80
5/3Fri
nonstopFrontier
3h 39mPHL-SJU
$81
6/4Tue
1 stopSpirit Airlines
12h 57mPHL-SJU
$82
5/14Tue
2 stopsAmerican Airlines
7h 51mPHL-SDQ
$126
5/2Thu
1 stopAmerican Airlines
12h 10mPHL-SDQ
$129
5/11Sat
1 stopJetBlue
7h 29mPHL-SJU
$217
5/11Sat
2 stopsUnited Airlines
23h 15mPHL-SJU
$252
7/18Thu
1 stopJetBlue
6h 25mPHL-SXM
$271
7/21Sun
2 stopsUnited Airlines
28h 55mPHL-AUA
$382

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Last minute flights from Philadelphia to Caribbean Islands

Last minute flight, train and bus deals

4/28Sun
nonstopSpirit Airlines
3h 53mPHL-SJU
5/4Sat
multi-stopSpirit Airlines
12h 09mSJU-PHL
$140
4/28Sun
nonstop
3h 53mPHL-SJU
5/16Thu
multi-stop
14h 02mSJU-PHL
$146
4/28Sun
nonstopFrontier
3h 39mPHL-SJU
5/3Fri
nonstopFrontier
3h 54mSJU-PHL
$156
5/1Wed
multi-stopFrontier
10h 07mPHL-SJU
5/16Thu
multi-stopFrontier
14h 02mSJU-PHL
$158
5/1Wed
multi-stopAmerican Airlines
9h 46mPHL-SDQ
5/5Sun
multi-stopAmerican Airlines
14h 23mSDQ-PHL
$275
5/1Wed
multi-stopAmerican Airlines
9h 43mPHL-SDQ
5/5Sun
multi-stopAmerican Airlines
14h 23mSDQ-PHL
$280
5/1Wed
multi-stopDelta
6h 35mPHL-NAS
5/8Wed
multi-stopDelta
8h 37mNAS-PHL
$628
5/1Wed
multi-stopUnited Airlines
18h 08mPHL-NAS
5/8Wed
multi-stopUnited Airlines
8h 15mNAS-PHL
$723
4/28Sun
multi-stopDelta
8h 55mPHL-AUA
5/3Fri
multi-stopDelta
7h 35mAUA-PHL
$896
4/28Sun
multi-stopUnited Airlines
18h 07mPHL-AUA
5/3Fri
multi-stopUnited Airlines
9h 13mAUA-PHL
$946

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Philadelphia - Caribbean Islands Flights

Departure:

Philadelphia (PHL)United States

Return flight deals:

Caribbean Islands - Philadelphia

Cabin classes:

$379
$435
$368
$38

Browse destinations:

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