$75 Find Cheap Flights from Philadelphia to Caribbean Islands

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
1 adult, Economy, 0 bags

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

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Philadelphia to Caribbean Islands.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Philadelphia to Caribbean Islands.
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Flight Deals

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 Cananonstop$337
Santo Domingo
Santo Domingononstop$327
Montego Bay
Montego Bay1 stop$389
Oranjestad
Oranjestad1 stop$389
Nassau
Nassau1 stop$385
Kingston
Kingston1 stop$416
Simpson Bay
Simpson Bay2 stops$443
Providenciales
Providenciales1 stop$505
Port of Spain
Port of Spain1 stop$461
Bridgetown
Bridgetown1 stop$388
George Town
George Townnonstop$315
Willemstad
Willemstad2 stops$448
Castries
Castries2 stops$763
Aguadilla
Aguadilla1 stop$204
Puerto Plata
Puerto Plata1 stop$582
St. John's
St. John's1 stop$470
Punta Cana
Punta Cananonstop$337
Santo Domingo
Santo Domingononstop$327
Montego Bay
Montego Bay1 stop$389
Oranjestad
Oranjestad1 stop$389
Nassau
Nassau1 stop$385
Kingston
Kingston1 stop$416
Simpson Bay
Simpson Bay2 stops$443
Providenciales
Providenciales1 stop$505
Port of Spain
Port of Spain1 stop$461
Bridgetown
Bridgetown1 stop$388
George Town
George Townnonstop$315
Willemstad
Willemstad2 stops$448
Castries
Castries2 stops$763
Aguadilla
Aguadilla1 stop$204
Puerto Plata
Puerto Plata1 stop$582
St. John's
St. John's1 stop$470

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

Tue, May 12 - Sat, May 16
Frontier Logo
2:55 pm - 3:59 pm
PHL
-
SJU
25h 04m
1 stop
Frontier Logo
5:15 pm - 7:12 am
SJU
-
PHL
13h 57m
1 stop
$178Frontier
Mon, May 11 - Fri, May 15
Frontier Logo
8:29 pm - 12:21 am
PHL
-
SJU
3h 52mnonstop
Frontier Logo
11:00 am - 12:46 am
SJU
-
PHL
13h 46m
1 stop
$179Frontier
Sat, May 2 - Wed, May 6
Multiple Airlines Logo
7:30 am - 11:24 pm
PHL
-
SJU
15h 54m
1 stop
Multiple Airlines Logo
6:30 am - 10:41 am
SJU
-
PHL
4h 11mnonstop
$180Multiple Airlines
Thu, May 14 - Sat, May 16
Multiple Airlines Logo
8:30 am - 11:57 pm
PHL
-
SJU
15h 27m
1 stop
Multiple Airlines Logo
1:30 am - 5:35 am
SJU
-
PHL
4h 05mnonstop
$182Multiple Airlines
Sat, May 16 - Thu, May 21
Spirit Airlines Logo
6:45 am - 12:47 pm
PHL
-
STT
6h 02m
1 stop
Spirit Airlines Logo
1:52 pm - 11:58 pm
STT
-
PHL
10h 06m
1 stop
$337Spirit Airlines
Mon, May 11 - Fri, May 22
Spirit Airlines Logo
6:45 am - 12:47 pm
PHL
-
STT
6h 02m
1 stop
Spirit Airlines Logo
1:52 pm - 11:58 pm
STT
-
PHL
10h 06m
1 stop
$343Spirit Airlines
Sun, Jul 12 - Fri, Jul 17
JetBlue Logo
6:00 am - 1:34 pm
PHL
-
AUA
7h 34m
1 stop
JetBlue Logo
2:39 pm - 11:51 pm
AUA
-
PHL
9h 12m
1 stop
$397JetBlue
Mon, Aug 17 - Wed, Aug 26
JetBlue Logo
6:00 am - 1:34 pm
PHL
-
AUA
7h 34m
1 stop
JetBlue Logo
2:39 pm - 11:51 pm
AUA
-
PHL
9h 12m
1 stop
$398JetBlue
Sat, May 30 - Sat, Jun 6
Air Canada Logo
6:00 am - 2:15 pm
PHL
-
AUA
8h 15m
1 stop
Air Canada Logo
3:05 pm - 9:48 am
AUA
-
PHL
18h 43m
1 stop
$402Air Canada
Sat, May 30 - Sat, Jun 6
Air Canada Logo
6:00 am - 2:15 pm
PHL
-
AUA
8h 15m
1 stop
Air Canada Logo
3:05 pm - 2:48 pm
AUA
-
PHL
23h 43m
2 stops
$405Air Canada
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 72 hours was to San Juan, at $148 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 72 hours was $148.

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 $268 on average. On average, there is no price difference when choosing to fly in the morning or the evening on this flight route. 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 $327.

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 $611, 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 April, when tickets cost $594 (return) on average. On the other hand, the most expensive months are September and December, when the average cost of round-trip tickets is $703 and $703 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 Monday 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 3 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$75
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 19% 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 $114 one-way - $256 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.
7.9
DeltaOverall score based on 8465 reviews
8.1Boarding
7.8Entertainment
8.5Crew
7.9Comfort
7.2Food
Airline reviews

The flight was operated by Latam. The aircraft had a technical issue and the flight was delayed for the next day. They grounded other passengers to get their airplane assigned to my flight. Most of he ground staff don't speak English (Orlando Airport), but were very polite.The crew on the other hand could speak English and Portuguese. On board service was good.

6.0 GoodSilvestre, Apr 2026
MCO - GRU
Read more Delta reviews

The flight was operated by Latam. The aircraft had a technical issue and the flight was delayed for the next day. They grounded other passengers to get their airplane assigned to my flight. Most of he ground staff don't speak English (Orlando Airport), but were very polite.The crew on the other hand could speak English and Portuguese. On board service was good.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

Purchased through 3rd party vendor which made everything difficult. Unable to check in online. Unable to get flight updates easily, tsa precheck information didn’t carry through, longer time to check in in person. Entertainment looked good but had to purchase conventional headphones to view.

Boarding was fast, easy, and we landed early. The entertainment system was very buggy and kept resetting throughout the flight.

Not having an assigned seat until boarding and then having to check my bag.

Flight emergency landed in Chicago due to “Odor” in back of plane . Had to buy ANOTHER TICKET to get to Boston cash out of my own pocket . Then they would notchange my return flight time without a 400. Charge!!!! Insulting.

I purchased ticket so our daughter ( a minor) can sit next to her mother. No help at gate after kayak insisted that this could be done. She ended sitting by herself

Flight was as expected. But it was delayed an hour. Also, my luggage got damaged. So that sucked especially since the damage made navigating the airport difficult. Walking to get ground transportation is sooo far away now and my checked bag was difficult to carry.

we were an hour delayed after boarding and given no reason. Headsets cost money. Also there were openrows with no one setting in them but we were told we were not allowed to swtich.

Crew was very friendly. Did not like being jammed in the back middle seat. Don’t understand why I can not select an aisle for free based on first come first serve. Also first time I’ve been on a flight which attempted land then circled Detroit airport multiple times.

Terrible. There was a lot of misleading information regarding ticketing, seat upgrades, & boarding group. I also expect my seat will recline. I have back problems & it is very painful for me of the seat doesn’t recline. In addition, when I choose a fare that allows me a carry-on bag, I expect to be able to carry it on. Not be forced to check it. Thos happened on my flight to MCO & back to Boston. Not sure I will ever fly JetBlue again. Further I bought the ticket through hat deal. I will NEVER do that again. They were incapable of providing an accurate record locator # for either leg of the trip. I had to call them before each flight with me VERY stressed about whether I would actually be able to get on my flight. Who does that? Who books flight & then FAILS to give an accurate record locator? Twice!

The flight was delayed 4 hours and the JetBlue people at the counter kept lying to us and telling us it was due to weather however all other flights were going in and out of NY and FL. Then they lied that the plane had to stop to refuel. Then they lied and said the plane needed a tire change. JetBlue is the worst. Then they gave a lot of people meal vouchers however I didn’t know they did that and they didn’t offer anything to me.

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 flight was on time and the landing was very smooth. The crew and flight attendants were all very friendly and professional.

Plane was super cold. No entertainment unless you were with mileage program Getting off the plane was super slow

I appreciate that I finally got the seat I paid extra for this time. Thank you

Half of the TSA checkpoints at PHL are closed. Also, there is no standby for first class passengers. You can only standby for coach. Very dated policy and inconsistent with peers.

It would have been nice if American tried to care.

Delayed initially because they couldn’t print the flight details. Poor instruction on delay. When I got on the plane the flight attendant argued with me about whether my carry on would fit (it did, although she didn’t acknowledge that). No greeting (other than arguing with me) getting on or off the plane.

Beverage service was not good. Also just one service in 5 hr 30 min flight. No ask fir water ir anything beside one time beverage service.

They are always late and seats was also not having working charger

The flight was delayed for over an hour. No one at the gate said anything about the flight being delayed. I had to rely on my phone for updates. Absolutely no communication at the gate.

The AC broke and we were onboard for 2 hrs waiting for them to fix it. It was so hot and we could not get any water or anything to drink. They finally let us off the plane after the second attempt and we boarded a new plane. We didn't land till 12:15am!

The boarding process was simple but the seats were very uncomfortable. The staff lady was also very hard to understand when she spoke over the intercom about procedures and updates. Other staff members seemed like they were just tired and didnt want to be on the plane. Im used to happy attendants and being able to understand what is said over the speakers.

There was no flight. Call the airline and confirmed. I have no idea why you think that I flew on the days that you say I did.

They canceled my flight and never told me. There was no follow up email. I had to buy another ticket the day of.

Easy to get our TSA pre check #added. Flight crew was great and entertaining and we landed early!

Flight was delayed 6plus hours Did not take flight Customer service was terrible Will never fly again and will spread how terrible you are You stink

I didnt have a flight. Kayak must be on drugs because I confirmed with spirit that I had no booked flight.

We were surprised to be charged $99 for a personal item. And of course everything offered on the flight was an additional charge. Other than that the pilot flew and landed the plane well and the attendants and fellow passengers were nice enough.

baggage drop off was a bit much. I felt like I worked for spirit airlines since I did all the work.

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports