C$ 165 Find Cheap Flights 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 Canada to the Cayman Islands departing on 29/11. 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

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Best Cayman Islands Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
George Town
George Town1 stopC$ 375
Cayman Brac
Cayman Brac2 stopsC$ 1,433
George Town
George Town1 stopC$ 375
Cayman Brac
Cayman Brac2 stopsC$ 1,433

Book Cheap Cayman Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights 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 to the Cayman Islands

Wed, 17 Dec - Wed, 24 Dec
United Airlines Logo
11:10 a.m. - 4:00 p.m.YOW-GCM
28h 50m2 stops
United Airlines Logo
5:45 p.m. - 9:18 p.m.GCM-YOW
27h 33m2 stops
C$ 375United Airlines
Find Deal
Thu, 27 Nov - Fri, 12 Dec
United Airlines Logo
6:20 a.m. - 4:30 p.m.YOW-GCM
34h 10m2 stops
United Airlines Logo
5:45 p.m. - 10:26 a.m.GCM-YOW
40h 41m2 stops
C$ 376United Airlines
Find Deal
Wed, 21 Jan - Wed, 28 Jan
Porter Airlines Logo
9:35 a.m. - 2:00 p.m.YOW-GCM
4h 25mdirect
Porter Airlines Logo
3:00 p.m. - 7:15 p.m.GCM-YOW
4h 15mdirect
C$ 409Porter Airlines
Find Deal
Thu, 20 Nov - Thu, 27 Nov
WestJet Logo
9:25 a.m. - 1:44 p.m.YYZ-GCM
4h 19mdirect
WestJet Logo
2:50 p.m. - 6:56 p.m.GCM-YYZ
4h 06mdirect
C$ 410WestJet
Find Deal
Thu, 22 Jan - Fri, 30 Jan
Porter Airlines Logo
12:15 p.m. - 4:25 p.m.YYZ-GCM
4h 10mdirect
Porter Airlines Logo
3:00 p.m. - 8:00 a.m.GCM-YYZ
17h 00m1 stop
C$ 421Porter Airlines
Find Deal
Sun, 23 Nov - Thu, 27 Nov
WestJet Logo
9:25 a.m. - 1:44 p.m.YYZ-GCM
4h 19mdirect
WestJet Logo
2:50 p.m. - 6:56 p.m.GCM-YYZ
4h 06mdirect
C$ 426WestJet
Find Deal
Tue, 18 Nov - Tue, 25 Nov
American Airlines Logo
2:29 p.m. - 12:05 p.m.YUL-GCM
21h 36m1 stop
American Airlines Logo
12:59 p.m. - 10:40 p.m.GCM-YUL
9h 41m1 stop
C$ 457American Airlines
Find Deal
Thu, 22 Jan - Fri, 30 Jan
American Airlines Logo
7:30 a.m. - 8:25 p.m.YYZ-GCM
12h 55m2 stops
American Airlines Logo
8:45 a.m. - 9:51 p.m.GCM-YYZ
13h 06m2 stops
C$ 461American Airlines
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Fri, 9 Jan - Sun, 11 Jan
Air Canada Logo
8:15 a.m. - 12:25 p.m.YYZ-GCM
4h 10mdirect
Air Canada Logo
1:30 p.m. - 5:35 p.m.GCM-YYZ
4h 05mdirect
C$ 486Air Canada
Find Deal
Fri, 9 Jan - Sun, 18 Jan
Air Canada Logo
8:15 a.m. - 12:25 p.m.YYZ-GCM
4h 10mdirect
Air Canada Logo
1:30 p.m. - 5:35 p.m.GCM-YYZ
4h 05mdirect
C$ 488Air Canada
Find Deal
Booking Insights

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

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

What is the cheapest flight to the Cayman Islands?

These are the best round-trip prices found by users searching on KAYAK in the last 72 hours.

The cheapest ticket to the Cayman Islands from Canada found in the last 72 hours was to George Town, at C$ 390 round-trip. The most popular route is Ottawa (YOW) to George Town (GCM) and the cheapest round-trip airline ticket found on this route in the last 72 hours was C$ 390.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Canada 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 Canada to the Cayman Islands is November, when tickets cost C$ 578 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is C$ 1,037 and C$ 933 respectively.

How far in advance should I book a flight from Canada 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 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 Canada to the Cayman Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Which is the cheapest airport to fly into in the Cayman Islands?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in the Cayman Islands is George Town Owen Roberts Intl Airport (GCM), with an average flight price of C$ 376.

Good to know

Low seasonSeptember
Cheapest flightC$ 165
Best time to beat the crowds (21% less expensive on average)
Most popular time to fly (19% more expensive on average)
Flight from Ottawa to George Town

FAQs - booking Cayman Islands flights

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Canada to the Cayman Islands is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Canada 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 Canada 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 Canada 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 Canada to the Cayman Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest day to fly to the Cayman Islands?

    Based on KAYAK data, the cheapest day to fly to the Cayman Islands is Tuesday when round-trip tickets can be as cheap as C$ 604. On the other hand, the most expensive day to fly is Friday, when round-trip prices are C$ 745 on average.

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

    The cheapest time of day to fly to the Cayman Islands is generally in the afternoon, when round-trip flights cost C$ 325 on average. Morning departures are around 29% more expensive than evening flights, 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 C$ 600.

Top tips for finding cheap flights to the Cayman Islands

  • Looking for cheap airfare to the Cayman Islands? 25% of our users found round-trip tickets to the Cayman Islands for the following prices or less: From Toronto Pearson Intl C$ 345, from Ottawa C$ 646
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Cayman Islands flight deals.

Reviews of the top 5 airlines flying to the Cayman Islands

 
Need help choosing which airline to fly with from Canada 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
Porter AirlinesOverall score based on 388 reviews
8.2Boarding
7.6Food
8.0Comfort
7.0Entertainment
8.6Crew
Airline reviews

Smaller plane. Food and bar service for free is amazing. Drinks were in glass not plastic cups.

10.0 ExcellentMike, Oct 2025YYC - YYZ
Read more Porter Airlines reviews

Smaller plane. Food and bar service for free is amazing. Drinks were in glass not plastic cups.

Poor landing as we overshot the runway and had to re land the plane. Lost both of my luggage not found as of yet. Had to pay extra money for my luggage in USD, now great my luggage is gone. Will not fly with Porter again.

This flight to St. Johns was really good. Boarding was a breeze. We left spot on time. Seats were actually pretty good. Recliner further than I expected. Three more flights to go we will see if this is the status quo for Porter.👍

I was not happy with AirfareAssist, the agency that kayak advised me would be handling my booking. I was advised by porter airlines that I had been overcharged for the Basic express , a option that I had asked airfare assist to help arrange after I realized that the basic fare I had chosen with porter did not include a carryon. At each checkin porter advised I had been overcharged for this . They advised that money would be refunded to my credit card, however, this is not likely to happen as it is not my name and credit card that appeared on the porter invoice, but that of another individual/agent. When airfare assist was arranging the basic express with porter on my behalf, they asked me to confirm that I agreed to pay $263 USD for this. I did agree, as I was advised this was needed to proceed. When I checked the invoice on the porter website and saw that it was not my name and credit card on the invoice, I was advised that this was how airfareassist processed the payment. The Porter invoice indicated a billed amount of $126USD I will not use Kayak or their designated AirfareAssist again

Our flight was delayed by a bit. I appreciated that we were kept informed on why periodically. Boarding was fine. I overheard one flight attendant sounding very rude to a passenger who was not paying attention to the safety demonstration. The snacks were minimal as it was a short flight. There was no entertainment. Overall the flight was good back to LGA.

The flight was fine see earlier note for the problem

All good the seats a little tight and no I pad screen

Everything was good except the fact you charge more for a carry on bag vs a check in bag and to top it off in US$ that was not impressive

Our flight was cancelled at the last minute for maintenance reasons and we were rebooked on a late flight when we purposefully booked our flight to be home early due to work.

Seemed like an old plane. Very noisy. The seat cushions were so old that the metal bracing of the seats were poking through. There was plenty of leg room though.

The food quality sucks. One must starve if they do not eat flesh Or wheat based products Some variety would be expected. The trivial amount of snacks and or food is inhumane

We Left Calgary 1/2 hour late and that made for a tight connection in Denver. After arriving everything was done to help us make our connection. That was a great effort. Thank You United

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

Overall, it was good. I was seating next to a wonderful lady and did not notice how time flew. Thanks

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

The experience was great, the crew was very polite and hospitable. I will definitely make if my go to airlines.

It was all good flight was on time, service was good I enjoyed a few movies and everything was smooth

Efficient, calm when things were delayed and kept us regularly informed of what was happening.

Airbus plane, nice and polite staff, entertainment even as it was a short flight.

Very nice and clean plane. Transit time between flights was tight though

Most things were ok but the main problem was the cabin staff; they were very abrupt and not very friendly. They were busy and often rushed, snatching drinks off people before finished and bossing them about.

Lost luggage stuck no clothes and no word after 2 days leaving on cruise no stuff or clothes

The flight was on time and crew were nice, seats were tight and there was entertainment available

Good service, friendly staff. Food was average for airlines and the seats were small.

Worst flight ever. I was suppose to have a 3 1/2 hour layover in Chicago but got to the gate 4 minutes before boarding.

The comfort of the seats was great, the crew eased my child’s anxieties and the fact that I had full cans of my beverage choice was great.

The plane was broken so we had to change planes.

A cookie and a soda, packed like sardines, will never be a positive experience. Also, boarded a 5:30 flight at 7:45pm

They cancelled my flight and downgraded me to economy and only gave me $250 for the downgrade

Very helpful ground crew after an earlier flight delay and being rebooked on a different flight.

Food good . No entertainment. Need to use wifi to access your own apps. Eg Amazon Prime, YouTube. They don't tell you unless you ask.

The check in was quick but the counter person didn’t inform me that the flight was delayed. I was also not informed of the boarding gate. When the plane landed there was a mixup at the gate with the ramp crew which delayed the flight further. All in all the experience didn’t meet the standard I’ve come to expect from WestJet

When flying premium on a two our flight a light lunch would have been nice considering the price you pay. A Kit Kat bar and bag of chips is rather cheap service.

I was seated near a "stinky" person. That's not the fault of Westjet🙁😶‍🌫️

The only thing I can't give good or really good is the fact that we didn't have food ,just a packet of pretzels or cookies which is normal,and ofcourse there isn't any entertainment. I've always flowen WestJet ..I really like the airlines..this plane was smaller one ,pretty tight seating.

Again, flight was late. It’s expected of this airline now i guess.

The ceiling leaked water on me. The toilets smelled very bad in the rear cabin

Counter representative refused to check my luggage despite paying for it in advance

We landed 26 min early. It was awesome! Smooth ride too.

When I purchased the flights I included the luggage, the luggage was not added and got charged the full price anyway. Had to pay for the luggage at check in. Initial flight was delayed, we missed our 9am connection (flew with my wife), then the airline rebooks us to the next flights, putting my wife in at 1.40pm and me at 4pm, what a crazy wait time. We managed to fix it with customer service and they put me in the 1:40pm flight too, but they left my baggage behind in the 4pm flight. When arrived to my destination, of course no luggage. It was delivered to the address thankfully late at night. The experience sucked.

it was hours late with a fake story about the high wind

I accidentally touched a cabin steward as she passed by and she reacted harshly yelling in a loud voice “don’t touch me”. It was embarrassing and uncalled for. I would characterize a few of the cabin crew as pretentious and aloof. Not at all what is expected. That was the first leg of our trip from Montreal to Munich. The second leg from Munich to Nice was more in keeping with the service I expected.

Would have preferred a better food menu. Other than that, no complaints.

Flight was excellent. The staff was a great comfort with the Captain meeting everyone on board The delay was unforeseen but an inconvenience.almost 3hours was too long to sit in the plane before the flight.

Good but need to be better with the flight times.

The staff could not have been any friendlier. Lots of usb ports on our aircraft.

The staff was great and made the long trip easy peasy!

Air Canada cancelled our flight and reschedule it 26 hours later that completely interrupted my family's long waited Japan trip, it wasn't due to natural reason such as weather but under the company's control. On the day we wasted 9 hours of our time from 6am to 3pm, including a few hours in the customer counter waiting for supervisor to handle our rescheduling. When we came to the counter for rebooking help there were at least 4 employees on the counter but we were told they were not trained to handle customer rebooking, we were also told the supervisor could come 10:30 to handle our rebooking, but she showed up more than one hour later, the end result was exactly the same so the few hours we spent waiting for her was completely wasted; We already prepaid hotel and all the tickets for the our stay in Tokyo so all of the cost for the first day is completed wasted; The $80 meal voucher issues was far less than our financial loss due to the financial cancellation, and it was not surprisingly invalid (as Your company screw up everything possible along the flight), the vouchers were supposed to last 72 hours, when we tried to used it at our lounge next day less than 24 hours from its issuing at a designated restaurant, the worker there couldn't scan the vouchers after multiple tries on all 4 vouchers issued, so we had to pay the food from our own money; For the two return flights they were also full of unfortunate events that caused bad experience and further delay and waste of our time, both flights departed late and the last leg had another significant delay of more than half an hour after touchdown, the gate was for some reason not available so we waited more than half an hour, when we got out of plane it was almost one hour later than the supposed arrival time; The gate you arranged is the farthest in Vancouver airport, also was the luggage pickup location in Seattle airport; We also called customer service for rescheduling help and after a long time wait (more than an hour) we got a call back but the CS representative was equally clueless and unhelpful. Other than a fatal crash, your company couldn't do anything right and provided the worst service possible among the tons of flights we have taken in our lives.

I like the free air Canada wifi and being able to watch things on there. The basic snacks are good, just wish I could have both. If I’m being really picky, the flight attendant who filled my drink, filled it half with fizz and didn’t take the second to let it go down and add more, so I got maybe half a cup of pop.

Seats too small and too cramped, I have stomach cancer and I threw up after the flight . No advance boarding for disabled people. No aisle seats available for disabled people who have to use the washroom frequently. No space for cabin baggage for disabled people who have to carry bulky medications or equipment to use on the flight. Baggage rules and fees are ridiculous. I have been an aeroplan member for 30 years and I fly frequently, but from now on I will choose offshore carriers. .

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

Cabin class types available on flights to the Cayman Islands

Cabin classes available on flights to the Cayman Islands. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.