$100 Find Cheap Flights from Philadelphia to Caribbean Islands - Compare and Save

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 8/16. 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.
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Cheap Flights from Philadelphia to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$466
Santo Domingo
Santo Domingo1 stop$419
Montego Bay
Montego Bay2 stops$440
Oranjestad
Oranjestad1 stop$550
Nassau
Nassau1 stop$386
Kingston
Kingston1 stop$463
Simpson Bay
Simpson Bay1 stop$377
Providenciales
Providenciales1 stop$446
Port of Spain
Port of Spain2 stops$516
Bridgetown
Bridgetown1 stop$407
George Town
George Town1 stop$391
Willemstad
Willemstad1 stop$537
Castries
Castries2 stops$701
Aguadilla
Aguadilla1 stop$312
St. John's
St. John's2 stops$600
Puerto Plata
Puerto Plata1 stop$645
Punta Cana
Punta Cana1 stop$466
Santo Domingo
Santo Domingo1 stop$419
Montego Bay
Montego Bay2 stops$440
Oranjestad
Oranjestad1 stop$550
Nassau
Nassau1 stop$386
Kingston
Kingston1 stop$463
Simpson Bay
Simpson Bay1 stop$377
Providenciales
Providenciales1 stop$446
Port of Spain
Port of Spain2 stops$516
Bridgetown
Bridgetown1 stop$407
George Town
George Town1 stop$391
Willemstad
Willemstad1 stop$537
Castries
Castries2 stops$701
Aguadilla
Aguadilla1 stop$312
St. John's
St. John's2 stops$600
Puerto Plata
Puerto Plata1 stop$645

Book Cheap Philadelphia to Caribbean Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Philadelphia to Caribbean Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Philadelphia to Caribbean Islands

Wed, Sep 9 - Sun, Sep 13
Frontier Logo
6:24 am - 10:13 am
PHL
-
SJU
3h 49mnonstop
Frontier Logo
12:59 am - 4:47 am
SJU
-
PHL
3h 48mnonstop
$198Frontier
Mon, Sep 14 - Sun, Sep 20
Frontier Logo
1:50 pm - 5:48 pm
PHL
-
SJU
3h 58mnonstop
Frontier Logo
6:55 pm - 10:56 pm
SJU
-
PHL
4h 01mnonstop
$198Frontier
Tue, Sep 29 - Thu, Nov 12
Multiple Airlines Logo
6:24 am - 10:13 am
PHL
-
SJU
3h 49mnonstop
Multiple Airlines Logo
6:12 pm - 12:32 pm
SJU
-
PHL
19h 20m
2 stops
$232Multiple Airlines
Mon, Sep 28 - Wed, Oct 7
Multiple Airlines Logo
11:23 am - 3:19 pm
PHL
-
SJU
3h 56mnonstop
Multiple Airlines Logo
8:45 am - 7:04 pm
SJU
-
PHL
10h 19m
2 stops
$237Multiple Airlines
Thu, Sep 3 - Mon, Sep 7
American Airlines Logo
6:15 pm - 10:24 pm
PHL
-
SJU
4h 09mnonstop
American Airlines Logo
7:03 am - 11:07 am
SJU
-
PHL
4h 04mnonstop
$247American Airlines
Fri, Aug 21 - Fri, Aug 28
American Airlines Logo
6:15 pm - 10:24 pm
PHL
-
SJU
4h 09mnonstop
American Airlines Logo
7:03 am - 11:07 am
SJU
-
PHL
4h 04mnonstop
$247American Airlines
Wed, Sep 9 - Wed, Sep 16
Delta Logo
3:54 pm - 10:19 pm
PHL
-
SJU
6h 25m
1 stop
Delta Logo
5:59 pm - 12:40 am
SJU
-
PHL
6h 41m
1 stop
$256Delta
Wed, Sep 9 - Wed, Sep 16
Delta Logo
12:06 pm - 10:19 pm
PHL
-
SJU
10h 13m
1 stop
Delta Logo
2:59 pm - 12:40 am
SJU
-
PHL
9h 41m
1 stop
$256Delta
Tue, Sep 22 - Tue, Sep 29
Southwest Logo
1:55 pm - 10:05 pm
PHL
-
SJU
8h 10m
1 stop
Southwest Logo
6:00 am - 5:35 pm
SJU
-
PHL
11h 35m
2 stops
$256Southwest
Wed, Sep 23 - Fri, Sep 25
Southwest Logo
1:55 pm - 10:05 pm
PHL
-
SJU
8h 10m
1 stop
Southwest Logo
5:00 am - 3:25 pm
SJU
-
PHL
10h 25m
1 stop
$256Southwest
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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean Islands from Philadelphia found in the last 5 days was to San Juan, at $158 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 $158.

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

The average price for all round-trip flights from Philadelphia to Caribbean Islands depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Caribbean Islands is generally in the afternoon, when round-trip flights cost $262 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 $372.

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

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $613, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Philadelphia to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Philadelphia to Caribbean Islands is September, when tickets cost $537 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $682 and $649 respectively.

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

The average price of all round-trip flights from Philadelphia to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Philadelphia to Caribbean Islands, look for departures on Mondays and avoid leaving on a Friday, 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 calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Philadelphia to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Philadelphia to Caribbean Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Good to know

Low season

September

Cheapest flight

$100
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 15% increase in price.
Flight from Philadelphia to San Juan Airport

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 $138 one-way - $252 round-trip

Reviews of the top 5 airlines serving from Philadelphia to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Philadelphia to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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 8491 reviews
7.8Comfort
8.5Crew
7.8Entertainment
7.2Food
8.1Boarding
Airline reviews

Delta is always late. Ruined our first day of a short vacation. Timing is important. We pay to stay on an itinerary

4.0 OkayAnonymous, Jul 2026
LAX - SFO
Read more Delta reviews

Delta is always late. Ruined our first day of a short vacation. Timing is important. We pay to stay on an itinerary

First flight was delayed which resulted in missing our connecting. As a result class was downgraded to economy on a later flight.

My son’s suitcase was left behind at SFO and did not make the flight.

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

Very good, boarded and took off on time and landed early

Boarding and Delays The boarding process for my American Airlines flight from Copenhagen to Philadelphia was a bit tricky. We experienced a gate change that required a long walk to a new area of the airport. Additionally, boarding was not via a jet bridge; we had to take a shuttle bus to the plane and then carry our luggage up the stairs ourselves. Furthermore, the bag drop didn't open until about 12:20 PM, which was only three hours before our scheduled departure. This meant I couldn't drop my bag off early and had to wait outside of security in order to drop off my bag and use the kiosk. The bag drop self-service kiosks also didn't open until about 12:00 PM when an American Airlines employee unlocked them so that we could print out our boarding passes and bag tags, which further created a backlog. The flight was delayed by over an hour because we had to wait for one of the tires on the plane to be changed. Flight Attendant Professionalism On a positive note, the flight attendant was very professional when handling a passenger who was sitting in the wrong seat. Even though the passenger was persistent and reluctant to move, the flight attendant calmly ensured the assigned passenger could take their seat. Kudos to the flight attendant for keeping his calm and composure, not allowing the issue to escalate, and handling it well under pressure while a line of passengers waited in the aisle to board. In-Flight Service The in-flight service was also fast, prompt, and efficient, although service had to be suspended for the last two hours of the flight due to weather and turbulence, which was outside of the crew's control. Limited Flight Options Please note that American Airlines only operates one flight per day in and out of Copenhagen. This means there are limited options available if your flight is delayed or canceled, which is something to take into consideration when booking.

Not much space for someone 6 feet high in normal economy seat. My knee hurt

Getting to Scotland with no luggage (no medicine, no clothes and no club) on golf trip very disappointed

Quick flight again no one illness why there were multiple delays and changing of the gate number.

The check in agents in PHL and gate agents had to have been the rudest women that I have ever encountered; the agent weighing the bags at check in screamed continuously at all of the guests as did the woman at the gate.I have Executive Platinum status with AA and fly a lot with AA but these ladies were the absolute worst I had the displeasure to encounter!

Delayed delayed. Poor professionalism. Our seats changed and we pay for them

Fine. Nothing to write home about. The plane left on time, and arrived on time.

Flight left early and arrived 30 MINUTES early at the destination. Smooth trip.

Flight was 3 hours delayed. They gave our plan to two other routes. Need to knock that off.

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.

Plane was delayed multiple times. I would like to request a refund. Was due to arrive Thursday evening ended up arriving Friday morning.

The seats were roomier than other airplanes I’ve been on.

The crew and the pilots. The pilots were amazing. The landing in Cancun was excellent.

The security line at JFK was one of the longest I’ve ever experienced - probably 45 minutes. I don’t know if JetBlue has control over it, but it detracted from the overall experience. Entertainment had good options, but the volume control was a bit small to tap on and the screen had a fair amount of interference blips. Clearer picture would have been better.

I liked the entertainment on JetBlue, the service from JFK to JAX was terrible at best

I usually dont fly JeTBlue and I dont think I will ever do it again. The flight was delayed fee time, nobody was giving us any info at at the airport, gate changing, the slowest and poorly organized boarding ever, rude staff.. huh

The flight was delayed. I upgraded to more room. I can't imagine how small the regular seats are I haven't upgraded for my return flight yet.

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.

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!

Booked direct in July '24. Turned into a 14 hr layover (both ways) in Denver. My 5 day vaca turned into a 1 day . Not good, BUT,... Thank you for the people @ Frontier who were professionally friendly & approachable.

$80 fee for a backpack as a personal item is robbery.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports