$104 Find Cheap Flights from Philadelphia to the Cayman 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 the Cayman Islands departing on 5/30. 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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1 adult, Economy, 0 bags

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Book Cheap Philadelphia to the Cayman 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 the Cayman 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 the Cayman Islands

Sat, May 30 - Tue, Jun 2
JetBlue Logo
7:00 am - 1:00 pm
PHL
-
GCM
7h 00m
1 stop
JetBlue Logo
2:05 pm - 10:47 pm
GCM
-
PHL
7h 42m
1 stop
$313JetBlue
Sat, Jun 20 - Tue, Jun 30
American Airlines Logo
8:35 am - 11:40 am
PHL
-
GCM
4h 05mnonstop
American Airlines Logo
5:12 pm - 10:41 am
GCM
-
PHL
16h 29m
1 stop
$317American Airlines
Fri, May 29 - Mon, Jun 1
Delta Logo
6:35 am - 11:54 am
PHL
-
GCM
6h 19m
1 stop
Delta Logo
1:19 pm - 10:12 pm
GCM
-
PHL
7h 53m
1 stop
$321Delta
Fri, May 29 - Mon, Jun 1
United Airlines Logo
7:45 pm - 12:30 pm
PHL
-
GCM
17h 45m
2 stops
United Airlines Logo
1:35 pm - 9:45 am
GCM
-
PHL
19h 10m
2 stops
$326United Airlines
Wed, Jun 3 - Wed, Jun 10
American Airlines Logo
6:00 am - 4:11 pm
PHL
-
GCM
11h 11m
1 stop
American Airlines Logo
5:12 pm - 7:25 am
GCM
-
PHL
13h 13m
2 stops
$331American Airlines
Fri, May 29 - Mon, Jun 1
United Airlines Logo
8:41 pm - 1:30 pm
PHL
-
GCM
17h 49m
1 stop
United Airlines Logo
1:35 pm - 9:45 am
GCM
-
PHL
19h 10m
2 stops
$356United Airlines
Sat, May 23 - Sat, May 30
American Airlines Logo
8:35 am - 11:40 am
PHL
-
GCM
4h 05mnonstop
American Airlines Logo
12:40 pm - 5:28 pm
GCM
-
PHL
3h 48mnonstop
$361American Airlines
Sat, May 23 - Sat, May 30
American Airlines Logo
7:35 pm - 11:30 am
PHL
-
GCM
16h 55m
1 stop
American Airlines Logo
12:40 pm - 5:28 pm
GCM
-
PHL
3h 48mnonstop
$365American Airlines
Sat, May 30 - Sat, Jun 6
Multiple Airlines Logo
7:00 am - 1:00 pm
PHL
-
GCM
7h 00m
1 stop
Multiple Airlines Logo
10:55 am - 2:48 pm
GCM
-
PHL
26h 53m
2 stops
$370Multiple Airlines
Sat, May 23 - Thu, May 28
American Airlines Logo
8:35 am - 11:40 am
PHL
-
GCM
4h 05mnonstop
American Airlines Logo
12:01 pm - 7:38 pm
GCM
-
PHL
6h 37m
1 stop
$371American Airlines
Booking Insights

KAYAK's insights & trends for Philadelphia to the Cayman Islands flights

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

What is the cheapest Philadelphia to the Cayman Islands flight route?

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

The cheapest ticket to the Cayman Islands from Philadelphia found in the last 72 hours was to George Town, at $319 round-trip. The most popular route is from Philadelphia (PHL) to George Town (GCM), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $319.

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

The average price for all round-trip flights from Philadelphia to the Cayman 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 the Cayman Islands is generally in the morning, when round-trip flights cost $690 on average. The most expensive time of day to fly to the Cayman Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $690.

Can I save money by flying with a layover from Philadelphia to the Cayman 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 $553, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Philadelphia to the Cayman 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 the Cayman Islands is December, when tickets cost $185 (return) on average. On the other hand, the most expensive months are October and November, when the average cost of round-trip tickets is $540 and $520 respectively.

How far in advance should I book a flight from Philadelphia to the Cayman 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 the Cayman 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 the Cayman Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$104
Best time to beat the crowds but there is an average 6% increase in price.
Flight from Philadelphia to George Town

FAQs - booking Cayman Islands flights

  • How does KAYAK find such low prices on flights from Philadelphia to the Cayman 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 the Cayman Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Philadelphia to the Cayman 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 the Cayman 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 the Cayman 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 the Cayman 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 the Cayman Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 4 airlines serving from Philadelphia to the Cayman Islands

 
Need help choosing which airline to fly with from Philadelphia to the Cayman 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
SouthwestOverall score based on 4302 reviews
8.0Comfort
8.6Crew
7.0Food
8.1Boarding
7.5Entertainment
Airline reviews

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

2.0 MediocreJoshua, May 2026
TPA - LAS
Read more Southwest reviews

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

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.

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

Kayak sucked. You gave me a confirmation number that was not useable by the jet blue system. Nor did you send any check in emails. I’ll not be using your site again. Nice work.

Direct tv did not work on flight Short flight so no good service offered Arrived early to destination and had to wait for gate to open. Deplaned LATER than if we arrived on time!! Poor planning Jet blue has had something go wrong on every flight I’ve taken with them in last five years. Terribly run airline

Given us a free miles or free flight for waiting for 9 hours I didn’t get home till 5am in the morning and I was supposed to be home at 9:30 touch down.

Excellent price. Everything on time. two bad parts. Kayak said I couldn't sign in for the flight online, but I got an email at the same time from Jet Blue and they let me sign in online. Second bad part was that, although I had provided my known traveler number, neither of my boarding passes, for this flight and the previous one, had TSA pre-check showing.

Jet blue was great But the Jayak system Wasa pure nightmare and wasted so much of my time and energy by not giving me a way to access jet blue to check in the flight back I didn’t even get the number confirmation code 24 hours before. Because I didn’t receive the email with the confirmation code I could NoT CHECk IN. I spoke to a kayak third party and they informed me I could not carry a carry on, on the flight which caused me so much extra stress it was just too much. You can be sure I will not be using it recommending your site. Again.

There was a screen but no earphones that could use the older input so I could listen to anything.

My experience with JetBlue was fine BUT I am very upset with Kayak! JetBlue had delayed our scheduled departure by an hour and you NEVER notified me of the change. I did not hear directly from JetBlue because the trip was booked through Kayak, a mistake I will not repeat. Your reminder of the our trip last week still had the WRONG departure time. Our return trip has also changed, and again no notice from you.

Jet blue just had great service overall! Only a little turbulence heading out of Austin, otherwise the jet stream helped the speed of the trip!

Boarding was quick and efficient. The flight crew were friendly. There were limited food options available on the flight. The pocket guide said there would be salad and sandwich sections available on flights over 3.5 hours. The only food available were snack boxes. And those were limited as well. My flight was over 5 hours. The entertainment system worked well. I had both extra legroom seats and regular coach seats. The seats were not very comfortable. The entertainment controls in the armrest made it difficult to rest my arm without changing the channel on my neighbors TV. Overall, my experience was mediocre.

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.

Everything you need to know for your flight from Philadelphia to the Cayman Islands

Information on your arrival and departure airports