Find cheap flights from Philadelphia to Caribbean Islands - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 25% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Philadelphia to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana1 stop$440
Santo Domingo
Santo Domingo1 stop$374
Montego Bay
Montego Bay1 stop$588
Oranjestad
Oranjestad1 stop$531
Nassau
Nassau1 stop$324
Kingston
Kingston1 stop$519
Simpson Bay
Simpson Bay1 stop$458
Providenciales
Providenciales1 stop$414
Port of Spain
Port of Spain1 stop$638
Bridgetown
Bridgetown1 stop$563
George Town
George Town1 stop$387
Willemstad
Willemstad2 stops$428
Aguadilla
Aguadilla1 stop$208
Puerto Plata
Puerto Plata1 stop$646
St. John's
St. John's2 stops$671
Punta Cana
Punta Cana1 stop$440
Santo Domingo
Santo Domingo1 stop$374
Montego Bay
Montego Bay1 stop$588
Oranjestad
Oranjestad1 stop$531
Nassau
Nassau1 stop$324
Kingston
Kingston1 stop$519
Simpson Bay
Simpson Bay1 stop$458
Providenciales
Providenciales1 stop$414
Port of Spain
Port of Spain1 stop$638
Bridgetown
Bridgetown1 stop$563
George Town
George Town1 stop$387
Willemstad
Willemstad2 stops$428
Aguadilla
Aguadilla1 stop$208
Puerto Plata
Puerto Plata1 stop$646
St. John's
St. John's2 stops$671
Booking Insights

KAYAK's insights & trends for Philadelphia to Caribbean Islands flights

Get data-powered insights and trends into flights from Philadelphia to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Philadelphia to Caribbean Islands flight route?

The cheapest ticket to Caribbean Islands from Philadelphia found in the last 5 days was to San Juan, at $126 round-trip. The most popular route is from Philadelphia (PHL) to San Juan Luis Munoz Marin Intl Airport (SJU), and the cheapest round-trip airline ticket found on this route in the last 5 days was $126.

What is the cheapest time of day to fly to Caribbean Islands?

The cheapest time of day to fly to Caribbean Islands is generally in the afternoon, when round-trip flights cost $275 on average. Morning departures are around 5% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the evening, which is peak travel time and where the average cost of a ticket is $366.

Can I save money by flying with a layover from Philadelphia to Caribbean Islands?

No, with an average price for the route of $667, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Philadelphia to Caribbean Islands?

The cheapest month for flights from Philadelphia to Caribbean Islands is January, when tickets cost $569 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $721 and $708 respectively.

What’s the cheapest day of the week to fly from Philadelphia to Caribbean Islands?

If you are looking for a flight deal from Philadelphia to Caribbean Islands, look for departures on Mondays and avoid leaving on a Saturday, as it's usually the priciest day. When flying back from Caribbean Islands, Friday is the cheapest day to fly and Sunday is the most expensive.

How far in advance should I book a flight from Philadelphia to Caribbean Islands?

To get a below average price on the flight from Philadelphia to Caribbean Islands, you should book around 2 weeks before departure, which saves you about 9% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Good to know

Low season

September
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 16% increase in price.

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 from Philadelphia to Caribbean Islands 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 from Philadelphia to Caribbean Islands with an airline and back 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 from Philadelphia to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

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 $104 one-way - $206 round-trip

Reviews of the 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.
7.8
DeltaOverall score based on 8691 reviews
7.8Comfort
7.2Food
8.5Crew
7.8Entertainment
8.1Boarding
Airline reviews

Love Delta. I'll take connections to stay on Delta even if another airline has a direct flight.

10.0 ExcellentJennifer, Oct 2026
Read more Delta reviews

Love Delta. I'll take connections to stay on Delta even if another airline has a direct flight.

The main issue was the quantity of the drink. The hostess gave only half cup full of the soft drink. I was thirsty and was expecting full glass like every other time.

This a short easy flight. No food or drink but that was not an issue since we were only in the air for 35 minutes.

No Internet, no backseat screen, no nothing. I bought a Delta ticket and ended up on American Airlines. How did that happen?

Connection flights should be spaced out farther because too close I missed my connection.

The flight was way too HOT! And the plane did not have any in-flight TV entertainment.

The gate attendants and the crew were terrible. Because of high winds, they needed to carry more fuel, so they had to get volunteers to take the next flight at 6 am the next day. They did a terrible job of it - our flight ended up taking off just under 3 hours of the scheduled time. I hope to never fly Delta again.

Great service. Great staff. Boarding was a little slow, but I think there was a service dog slowing things down.

We splurged and decided to fly first class. Seats were roomy. But flight crew arrived late to the airport. That delayed our flight. Most of the passengers had to try to make connections flights. I felt bad for them. We checked 4 bags. We got three from the baggage claim carousel. 4th one was lost. Delta online help wasn’t good. Baggage claim staff were sympathetic and nice but we waited around for almost 2 hours and it had t been found. They did find it several hours later and we had to drive back to airport to retrieve it. I won’t be splurging on 1st. Lass again anytime soon. I think we got worse service. I am also not a huge fan of delta but we have family in ATL so we don’t have a ton of choice. What should have been an easy flight turned into a stressful event due to flight crew tardiness and baggage mishandling.

My flight consistently said it was on time and the plane didn’t arrive until after 30 minutes after take off and nothing was announced to passengers

The last 3 hours it was freezing cold in row 56. Multiple people had their winter coats on and were utilizing the blankets provided by the airline. I also did not have easy access to figure out how to book my food allergy and advance for my meals. Most of everything I received was something I couldn't eat. This needs to be made more accessible. Also, I'm 5'10 which is the average height of the American male. I flew from Philadelphia to Toronto and then to Tokyo and the seats were absolutely unbearable. For that long of a flight it is impossible to get comfortable when doing anything. Flights need to have more space and stop prioritizing costs over people.

Was delayed at every point/ connection. Luggages missing for 5days. Had no medications for diabetes and high B/p. when bags where finally delivered on the 30th, the insulin and ozempic were no longer patent, as the ice pack had since dissolved and the authenticity of the med is now questionable, since they must be refrigerated. Please have them refund my bag fees. I should sue them for all the inconveniences caused to me.

Plane was packed but flew on-time, and the comfort level was great! All planes are a bit cramped, but the in flight entertainment was superb, snacks were nice, and the crew was polite. Got into Calgary on schedule...all we could ask for

I am very tall. All airline seats are a bit uncomfortable.

Lots of announcements that no wheeled carry on bags were allowed on the flight, yet the overhead bins were totally full and made it uncomfortable trying to get through and significantly held up departure. Why were they allowed on when they said that they weren't? Trash only came by soon after service and I wasn't ready to dispose of it. I had to first hold on to it and after flagging and attendant was told to stuff it in the seat back! I have never run into the need to walk outside in northern winter weather at an international airport and wasn't dressed to do so in the cold pouring rain! I'm not thinking that I'll be back unless I hear things have changed.

No complaints l will always do Air Canada once they are flying where I want to go

Flight was delayed an ultimately cancelled. Took me close to 45 mins with an Air Canada staff to be put on another flight.

Boarding was particularly poorly done with disregard for courtesy, professionalism, and efficiency. Think mid 70’s bus station.

My trip was ruined by the restrictions hidden in their "basic economy" plan. I'd flown hundreds of times and never encountered a program that does not allow changes of any kind. I don't know whose interface hid this information more, but I'm unlikely to use Kayak or Air Canada again after that experience.

Air Canada staff needs to be trained in hospitality. Most flight attendants are with attitude. Air Canada needs to carry additional food on board especially vegetarian plates as this category of travellers are on the rise. This is necessary for long distance flights. Blankets are cheap. Seats are not designed well Lower back portion should be thicker. Everytime thr passenger at the back of me took stuff or put stuff in the pocket of the seat in front of them which is my seat, I could feel them pushing or hitting on my chair.

The boarding agent and checked bag agent were both rude. It only takes a second to be kind. However, the flight crew was amazing. I got a turkey sandwich and it wasn't bad---not great but not bad. The internet was my biggest problem. This was a work trip and I REALLY needed the internet to meet a deadline but it didn't work for 80% of the trip. Very disappointing.

I tried to check in beforehand from Ireland. The Jet Blue website sent me to the Aer Lingus website and vice versa. I tried to get a boarding pass at Dublin Airport as well, but they said they couldn't help me either. I had to wait until I arrived at the gate in Boston to secure a boarding pass...it was a bit nerve wracking.

Great flight. Best in years. Very clean craft. Easy boarding. Communicative pilot. Friendly flight attendants. Absolutely smooth take off, in flight and landing. Very comfortable seats. Smoothest flight I've experienced in years. THANK YOU JET BLUE!

I was asked to pony up an additional $239 (over the $735 paid originally) for a one way middle seat, which was very uncomfortable. Where did you expect me to sit?

Jet Blue sevice was good. Just don't understand why they charge for earphones to listen to flight entertainment. Other than that, everything was excellent.

Mostly good, flight take off in time and land earlier I can’t ask for more..

The crew was not nice this time. I asked for a drink one time and the girl didn’t say anything to me and just got me the hot drink while walking super fast to the back. We were sitting in the back and she wasn’t doing anything except socializing. She was upset I asked for something and she had to do her job. I also didn’t fully have it in my hands when she handed it to me so it was dangerous. She was abrupt and rude. She wouldn’t allow for people to spread out like previous flights we had been on if they were empty, and there were empty rows. It was strange and she enjoyed being angry at us.

They lost my luggage and refuse to help. Terrible airline. I've never experienced worse customer service in my life. Pretty much just told me too bad that I lost all my luggage, not caring that I am stuck in Europe for 2 weeks with absolutely nothing.

I especially liked the lead crew officer. His boarding and safety announcements were made with a bit of novelty and humor. The flight also left the gate 10 minutes early and we landed about 20 minutes early… It was a delightful flight…

As with all airline's seats, a little more padding would appreciated. Especially on longer flights.

It was a late flight; crew was invisible. Zero air flow - the tiny plane was a sauna; the left the lights on for 1/2 of the flight; there was no water. Never again.

What an amazing plane! We flew a 787 to Miami. Although the Internet was not functioning, it was a wonderful flight.

Plane was in good shape, multiple passes from the drink cart, and one of the smoothest flights I've had in a while.

Smell of jet fuel was overwhelming from inside the plane while on the ground at take off and landing. Gave me a sore throat and a headache. During boarding, de-planing, taxi-ing, waiting in line for take off, etc. Also, the vents didn't have enough cool air coming out (yes, off course I opened it all the way) so the whole flight was hot and stuffy. But just my vent - all the vents.

After lack of help in Philadelpha made us late to board our flight to akansas City, our flight to Kansas City was very good. And the flight attendants were also very good. The only thing that sucked was problems with assistance in Philadelphia caused our bags not to arrive.

AA needs to review it's policy whereby it's most tenured staff gets to pick their flights. This tends to place flight attendants with the most jaded customer service attitudes on long haul flights. Whilst I realize this is a generality I have experienced increasing levels of woefully poor customer service. One particular flight attendant on this flight was downright rude to several customers. After serving an awful meal they disappeared to their cots below deck and for the most part did not reappear until 1.5hrs before landing. A very disappointing flight.

Legroom was decent, but the seat comfort was horrible; I believe the seat cushions have lost their cushion. I was uncomfortable and had back pain throughout the nearly five-hour flight. WiFi did not work despite my attempts to get it up and running. This was very frustrating as passengers all around me were streaming football games, movies, and accessing email and text messages. One flight attendant suggested it was my seat, but that makes no sense, given WiFi doesn't work that way. On another note, I rarely have a good experience with aainflight.com.

Id like for them to not have lost my bag. And maybe be a little nicer to me, given the fact they lost my bag.

Seats are uncomfortable and my impressive barely 5’10” frame meant my knees were touching the seat in front of me. My 5’3” sweetheart found the seats equally uncomfortable The crew were transactional. The food edible. The entertainment manageable. The boarding process efficient. The experience okay.

Hey as long as you bring me back to earth in one piece I’m good! Otherwise great flight smooth take off and landing good staff Only thing is the staff at the back of the aircraft chatters a lot it’s annoying at times but I’ll let that go because they are very sweet overall.

Flight delayed and missed connection. Next available flight was a 10 hour delay.

Great flight, no problems. I wish they would increase the checked bag weight limit. Packing was very stressful.

First of all we hade waited 3 hours in the airplane waiting to leave. Second the return schedule was changed and it messed up my entire vaction. I won't buy never again another flight and recommend to nobody traveling with them.

I am writing to express my disappointment with my recent Frontier Airlines flight. I was charged $99 at the gate because my bag was said to be too large, yet once onboard there was no available overhead bin space, and I was required to place the bag under the seat in front of me anyway. This made the charge feel unnecessary and unfair. Additionally, before the flight even took off, I was asked to move from the seat I paid for into a middle seat so another passenger and her cat could have my seat to themselves. I was not offered compensation or an explanation for being moved from a paid seat. Between the unexpected bag fee and being forced to give up my seat, this experience fell well below acceptable customer service standards. I would appreciate a review of this situation and appropriate compensation.

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

Check in at Philadelphia international was absolutely terrible! I fly 2 to 3 times a month and avoid frontier at all cost and will never fly Frontier again! The night before travel, I tried checking in however, the app was giving me an error, so I went to the desktop, which instructed you that you need to use the app. The next day I presented at the check-in gate after trying at least a half dozen times prior to getting into the airport and continuing to getting the error in the app. I actually had rebooted my phone numerous times and reinstall the app just in case. My phone is only one generation older than the current model. It has no problems completing a frontier flight purchase or any other app issues. There was only three frontier employees working at check-in and a huge line while I was in line I continued to try and check in via the app. As I approach the desk, I was dreading dealing with the agent. He was extremely unprofessional, anti-semantic & very ignorant, and mean to the people in front of me, as well as the people who ended up being behind me. He literally told people “Man I don’t care bout y’all” in his native dialect! Maintaining my composure I approached and explained the situation. To which he replied, you’re gonna have to pay then! I don’t understand. It’s an issue with their app not allowing me to check in! Not my issue! He told me if I pay cash it would be $15, $25 if I pay credit card. I don’t understand a $10 difference for paying with a credit card? I am completely cashless so I continued to try using the app to avoid the $25 fee, Which I still don’t believe that I should be responsible for since it was Frontier’s technical issue!!! I continued to check in via the app a couple more times after he verified I was doing everything right he proceeded to continue to belittle the people behind me. Yelling at them saying I don’t care about you people! I cannot believe that this is the way that businesses would treat its customers! Unfortunately, the black mail with dreadlocks did not have a name tag all he had was a frontier sweater on! For the $25 fee that I ended up getting charged on my credit card. I should’ve just booked originally with Spirit or any other carrier! I have no problem paying fees that I should be responsible for, but when it’s due to a technical failure of a company, the customer should not be responsible for it! I cannot believe that it’s not frontier going out of business!

terrible cascading delays and unhelpful customer service. uncomfortable plane. crew was great, however!

More options for your flight to Caribbean Islands

Complete your trip to Caribbean Islands with a hotel stay or car rental