$90 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 11/18. 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 Cana1 stop$315
Santo Domingo
Santo Domingo1 stop$351
Montego Bay
Montego Bay1 stop$432
Oranjestad
Oranjestad3 stops$503
Nassau
Nassau1 stop$289
Kingston
Kingston1 stop$348
Simpson Bay
Simpson Bay1 stop$289
Providenciales
Providenciales1 stop$358
Port of Spain
Port of Spain1 stop$433
Bridgetown
Bridgetown2 stops$393
George Town
George Town1 stop$270
Willemstad
Willemstad1 stop$328
Castries
Castries2 stops$780
St. John's
St. John's2 stops$538
Puerto Plata
Puerto Plata1 stop$441
Aguadilla
Aguadilla1 stop$281
Punta Cana
Punta Cana1 stop$315
Santo Domingo
Santo Domingo1 stop$351
Montego Bay
Montego Bay1 stop$432
Oranjestad
Oranjestad3 stops$503
Nassau
Nassau1 stop$289
Kingston
Kingston1 stop$348
Simpson Bay
Simpson Bay1 stop$289
Providenciales
Providenciales1 stop$358
Port of Spain
Port of Spain1 stop$433
Bridgetown
Bridgetown2 stops$393
George Town
George Town1 stop$270
Willemstad
Willemstad1 stop$328
Castries
Castries2 stops$780
St. John's
St. John's2 stops$538
Puerto Plata
Puerto Plata1 stop$441
Aguadilla
Aguadilla1 stop$281

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, Nov 19 - Mon, Nov 24
Frontier Logo
7:30 am - 12:16 pmPHL-SJU
3h 46mnonstop
Frontier Logo
2:25 am - 5:32 amSJU-PHL
4h 07mnonstop
$174Frontier
Find Deal
Fri, Nov 28 - Tue, Dec 9
Frontier Logo
8:08 pm - 12:55 amPHL-SJU
3h 47mnonstop
Frontier Logo
1:59 am - 5:04 amSJU-PHL
4h 05mnonstop
$175Frontier
Find Deal
Sun, Jan 25 - Thu, Jan 29
Spirit Airlines Logo
8:05 pm - 12:28 pmPHL-STT
15h 23m1 stop
Spirit Airlines Logo
1:33 pm - 12:32 amSTT-PHL
11h 59m1 stop
$252Spirit Airlines
Find Deal
Wed, Dec 3 - Sat, Dec 6
Spirit Airlines Logo
5:25 am - 12:55 pmPHL-STT
6h 30m1 stop
Spirit Airlines Logo
3:54 pm - 11:34 pmSTT-PHL
8h 40m1 stop
$263Spirit Airlines
Find Deal
Sat, Nov 8 - Wed, Nov 12
JetBlue Logo
12:00 pm - 4:56 pmPHL-NAS
4h 56m1 stop
JetBlue Logo
2:22 pm - 10:55 pmNAS-PHL
8h 33m1 stop
$289JetBlue
Find Deal
Fri, Jan 9 - Fri, Jan 23
JetBlue Logo
7:00 am - 3:20 pmPHL-SXM
7h 20m1 stop
JetBlue Logo
4:25 pm - 11:34 pmSXM-PHL
8h 09m1 stop
$311JetBlue
Find Deal
Fri, Nov 28 - Fri, Dec 5
American Airlines Logo
8:30 am - 1:26 pmPHL-PUJ
3h 56mnonstop
American Airlines Logo
5:40 pm - 8:46 pmPUJ-PHL
4h 06mnonstop
$359American Airlines
Find Deal
Tue, Nov 11 - Thu, Nov 13
American Airlines Logo
7:00 am - 11:55 amPHL-PUJ
3h 55mnonstop
American Airlines Logo
5:47 pm - 8:50 pmPUJ-PHL
4h 03mnonstop
$363American Airlines
Find Deal
Thu, Feb 5 - Mon, Feb 9
Delta Logo
5:40 am - 3:20 pmPHL-BGI
8h 40m1 stop
Delta Logo
4:30 pm - 12:23 amBGI-PHL
8h 53m1 stop
$443Delta
Find Deal
Tue, Dec 9 - Sat, Dec 13
Delta Logo
5:30 am - 12:45 pmPHL-PLS
7h 15m1 stop
Delta Logo
3:10 pm - 12:36 amPLS-PHL
9h 26m1 stop
$444Delta
Find Deal
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 $169 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 $169.

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 $523, 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 October, when tickets cost $231 (return) on average. On the other hand, the most expensive months are December and April, when the average cost of round-trip tickets is $379 and $298 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 Wednesdays and avoid leaving on a Thursday, as it's usually the priciest day. When flying back from Caribbean Islands, Wednesday 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 2 weeks before departure, which saves you about 20% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 2 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$90
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 23% 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.

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

    The cheapest time of day to fly to Caribbean Islands is generally at night, when round-trip flights cost $278 on average. Morning departures are around 7% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $359.

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 $153 one-way - $288 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 7998 reviews
8.2Boarding
8.5Crew
7.9Comfort
7.9Entertainment
7.3Food
Airline reviews

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

8.0 ExcellentJulie, Oct 2025LAX - SFO
Read more Delta reviews

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

The aircraft interior is old and tired on this aircraft. The entertainment system never worked despite the crews attempt to reset the system.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Old plane and old configuration/seats but still comfortable for a morning flight

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

Delays to take off and to leave the plane after landing added a lot of time to this flight.

The Phildalphia to Allentown portion was a BUS, not a plane. All was as expected.

Excellent - explanations were clear staff was nice and flight was comfortable

Airport in MXP is crazy. Get there at least 2 hours before flight.

Flight was delayed not sure why no explanation given and no apologies either. Otherwise the flight was fine

Did not get the seat I selected and paid for.

The flight was canceled 3 hours after original take off time

Plane was delayed for 6 hours, at first by weather, which is understandable, but was further delayed with NO given reason for 2 1/2 hours more. We had no clue when we were going to depart actually until they opened the ramp. VERY POOR to ZERO COMMUNICATION!!!

Flight was delayed and after being in the airport for like seven hours, it was canceled.

Flight delays numerous times. Everytime we would get close to boarding it would be delayed again. Strung along the entire time.

The flight was two hours late due to a computer fault and resulting maintenance. Nothing was offered as compensation beyond bottles of water during the time we were deplaned and waiting in the terminal.

Very pleasant flight attendants. Gate crew rather loud chatting with each other.

Four plus hour flight delay in New York caused us to take off after 11:30pm. We didn’t arrive at our hotel until five hours after check in. Started the trip off feeling exhausted.

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

There was a fowl odour coming from the lavatory the entire flight

Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.

I don’t usually fly budget airlines or airlines in the United States. It was as good as any other airline. The seats are comfortable and the airline attendants are not rude & surly. Very nice flight (s).

No internet on a flight over three hours in this age is criminal. Staff inattentive and dismissive

They have the most inexperienced / rude flight staff I’ve encountered

very difficult boarding process - aggressive passengers not the friendliest crew

the plane was not full so the flight attendant had me move to an empty row which made for a good flight. The software for logging on and booking and confirming the flight is much too cumbersome.

Always comes in handy when I want a quick weekend getaway.

For the price I could have taken a “name brand” airline. No drink no snack and constant emails trying to get addition money for EVERYTHING other airlines include in the price. It looks cheaper but it’s Judy bait and switch and emails non stop!

The gate agents for spirit at EWR wouldn’t give me my ticket to board when I arrived 50 min from the flight, saying that I wouldn’t make my flight. They tried to reschedule me to arrive at my destination 14 hours after the original flight, which included a 10 hr layover in another city. I rebooked with another airline and it took me a total of 5 min to go through security. Then I see a charge on my card for a $100 change fee that I did not approve. Beware of this horrible place and these horrible people

Excessive fees for flight delays. What a Scam. I was not able to attend the wedding I needed to go.

Waited at the airport for over 4 hours to board this flight. Terrible airline

Was supposed to take off 8:00 last night. Got delayed till 8:00 this morning

It was terrible, we had to board and unboard the flight with a hour delay that caused me to miss an appointment and a surprise for my wife

When the flight ticket is expensive and you have to purchase check in luggage and there is no snacks, no entertainment, tight seats stuffed in the back of the plane not such good experience. I would like some to reach out to me . I paid for check luggage when I bought the ticket they made me pay again on the return flight extra $70. Very frustrating.

Excellent experience when I am looking for a budget airline where the main expectation is getting me from point A to point B with no frills.

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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