$180 Find Cheap Flights from Philadelphia to the Cayman Islands - Compare and Save

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Price, demand and travel trends for Philadelphia to the Cayman Islands flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

What are the cheapest fares from Philadelphia to the Cayman Islands right now?

The cheapest fares from Philadelphia to the Cayman Islands on KAYAK in the last week were to George Town Owen Roberts Intl (GCM) from $479 round-trip, and to Cayman Brac Gerrard-Smith (CYB) from $628 round-trip.

What’s the cheapest month to fly from Philadelphia to the Cayman Islands?

May is the cheapest time of year to fly, with average fares of $347. Prices are highest in October, when average flight costs increase to around $972.

When is the best time to book flights from Philadelphia to the Cayman Islands?

Booking last-minute, within 2 weeks of departure, usually offers the lowest fares from Philadelphia to the Cayman Islands. It runs around 29% cheaper than the route's average fare over the last 12 months.

Which airport in the Cayman Islands is the cheapest to fly to from Philadelphia?

Based on KAYAK data from the past 12 months, the cheapest airports to fly into the Cayman Islands are:

• George Town Owen Roberts Intl (GCM) (avg. price $618)
• Cayman Brac Gerrard-Smith (CYB) (avg. price $1,216)

What’s the cheapest day to fly from Philadelphia to the Cayman Islands?

Wednesday tends to be the cheapest day to fly from Philadelphia to the Cayman Islands, while Monday is the most expensive. Fares run about 37% higher that day, based on the past 12 months of KAYAK data.

What's the cheapest time of day to fly from Philadelphia to the Cayman Islands?

Data from the past 12 months shows it's cheapest to fly to the Cayman Islands during the night with average prices of $370. The morning is the most expensive time to fly, with average prices of $630.

Key details for Philadelphia to the Cayman Islands flights

Low season

September

Cheapest flight

$180
Beat the crowds with an average 78% drop in travelers.
The most popular month to fly with an average 59% increase in travelers.
One-way flight from Philadelphia to George Town

Your Philadelphia to the Cayman Islands flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Philadelphia to the Cayman Islands?

    Fares from Philadelphia to the Cayman Islands are around their usual level right now. A round-trip under $378 is considered a good deal, so it's worth keeping an eye out, or setting a Price Alert to catch price changes.

  • How much should I budget for a flight from Philadelphia to the Cayman Islands?

    Over the past 12 months, round-trip fares from Philadelphia to the Cayman Islands have ranged from $378 to $839.

  • What airlines fly nonstop from Philadelphia to the Cayman Islands?

    Based on the flight schedule for the next 3 months, just one airline regularly flies nonstop from Philadelphia to the Cayman Islands: American Airlines.

  • Where in the Cayman Islands can I fly nonstop from Philadelphia?

    Based on the flight schedule for the next 3 months, you can only fly nonstop from Philadelphia to George Town.

  • Is it cheaper to fly with a layover from Philadelphia to the Cayman Islands?

    Yes, nonstop flights from Philadelphia to the Cayman Islands average $767 over the past 12 months, but flights with a layover can cost less. The most affordable connecting airports are:

    • Chicago O'Hare Intl (ORD) (avg. price $313)
    • Fort Lauderdale (FLL) (avg. price $391)
    • Toronto Pearson Intl (YYZ) (avg. price $434)

  • How long is a flight from Philadelphia to the Cayman Islands?

    Flights from Philadelphia to the Cayman Islands take 4h 01m on average.

  • Which cabin classes are available on flights from Philadelphia to the Cayman Islands?

    On flights from Philadelphia to the Cayman Islands you can book Economy Class, Business Class or First Class.

  • What are the earliest and latest flights from Philadelphia to the Cayman Islands?

    The earliest nonstop flight from Philadelphia to the Cayman Islands departs at 7:00 am and the latest departs at 8:27 am. Nonstop flights take about 4h 01m.

Your guide to booking Philadelphia to the Cayman Islands flights

Get tips on when to book, when to fly and what to know before your trip.
  • If you're flexible on timing, there's no need to rush. Booking last minute (within 2 weeks of departure) tends to be around 29% cheaper than the route's average fare over the last 12 months.

    Not ready to commit? Set a Price Alert and we'll let you know when prices change.
  • If your travel dates are flexible, book your trip for May when flights are typically cheapest and avoid October when prices are at their highest.
  • Flying on Wednesday is usually the cheapest. Flights on Monday cost about 37% more on average, so being flexible with your travel dates could help you save.
  • If you're looking to save, George Town Owen Roberts Intl (GCM) is the cheapest airport to fly into from Philadelphia. If you have onward travel, don't forget to factor in the cost of your journey by train, bus or domestic flight.
  • Start your trip in George Town, which is the most popular destination in the Cayman Islands. From there, it's easy to continue on to other popular destinations such as West Bay, East End and North Side.
  • If you want the shortest trip, choose the Philadelphia to the Cayman Islands nonstop route. If you'd rather save money, the route via Chicago O'Hare Intl (ORD) is usually the cheapest.

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.
8.0
SouthwestOverall score based on 4214 reviews
8.0Comfort
7.5Entertainment
8.6Crew
8.1Boarding
7.0Food
Airline reviews

They delayed my flight all day but didn't try to reschedule me until all other options were gone. Ended up on a red eye. Not happy. Lesson learned, don't book the last flight from SJC to RDU.

2.0 MediocreAnonymous, Nov 2026
Read more Southwest reviews

They delayed my flight all day but didn't try to reschedule me until all other options were gone. Ended up on a red eye. Not happy. Lesson learned, don't book the last flight from SJC to RDU.

Every single flight I take with southwest is delayed by at least one hour. Unbelievable

Just crazy with times being pushed and pushed and pushed and gate crew at Philly super rude and unprofessional with many under stress with delays.

My experience will Southwest was good. I wish there was more entertainment and the boarding process was slow at time but other than that my experience was great definitely will be flying with SouthWest again.

For my birthday trip this was my second time ever flying, this trip was the best.

I really wish that SW would ask anyone with a carry-on to wait while those who don’t have to access the overhead bins are boarded. Then, reverse that when the plane arrives. Those without the need to clog up the aisle retrieving their bags from the overhead bins wait for those exiting the plane without needing to clog up. The aisle.

We boarded the flight and set two and a half hours on the jetway. Would have been better if they had not boarded us at all. Plane was hot and it was limited ability to access the restrooms or get a drink of water. Very unpleasant experience

The actual flight was great! The 3 hour delay not so much.

Southwest is a garbage airline and the people who fly it are garbage people.

Boarding was easy. Plane wasn’t crowded. Plenty of space. Flight was on time. Crew was pleasant.

A 6hr delay is going to put a damper on all reviews. It was almost impossible to get into the Delta club also. Zero conveyance. I could not use my status for anything. Makes me wonder why am I loyal to delta?

I fly coach so there is always the feeling everyone up front has more space than me. Everything was fine - on time which is the most important thing!

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

Free wifi was almost impossible to get, kept dropping the connection

Not good - we boarded and taxied for an hour before they told us there were technical issues with the plane. They told us we were going to need to deplane, parked back at the gate but then didn’t tell us we didn’t have to anymore. There was just a lot of uncertainties with poor communication.

3.5 hour delay because of “mundane” mx issue. Aircraft had to be towed 3 times.

Overall great experience, though my screen for entertainment was not working and I could see that others were.

Plane was very comfortable,ore legroom, help yourself snack are so weren't disturbed by staff passing up and down cabin, gluten free food availability and really efficient and friendly staff . Boarding and good to time. Highly recommend t

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.

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…

Drinks and snacks provided. TV had a lot of entertainment options. Plane was fairly comfortable. Staff was less than pleasant.

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

The flight was delayed several times as they didn't have pilots. Then we were boarded on the plane and again waited on the tarmac for over 30-40 minutes waiting for pilots to board. The in flight entertainment was confusing at best on how to use it. It took multiple attempts to get wifi to connect and by the time it worked the flight was almost over.

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.

More options for your flight from Philadelphia to the Cayman Islands

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