C$ 228 Find Cheap Flights from Calgary 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 Calgary to Caribbean Islands departing on 31/10. 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

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

Best Caribbean Islands Flight Deals from Calgary

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stopsC$ 529
Montego Bay
Montego Bay1 stopC$ 647
Oranjestad
Oranjestad2 stopsC$ 647
Kingston
Kingston1 stopC$ 742
Nassau
Nassau2 stopsC$ 521
Pointe-à-Pitre
Pointe-à-Pitre2 stopsC$ 982
Simpson Bay
Simpson Bay2 stopsC$ 591
Bridgetown
Bridgetown1 stopC$ 655
Puerto Plata
Puerto Plata1 stopC$ 573
Port of Spain
Port of Spain2 stopsC$ 602
Willemstad
Willemstad2 stopsC$ 1,413
Providenciales
Providenciales1 stopC$ 506
George Town
George Town1 stopC$ 667
Santo Domingo
Santo Domingo2 stopsC$ 611
St. John's
St. John's1 stopC$ 1,286
Kingstown
Kingstown2 stopsC$ 1,518
Punta Cana
Punta Cana2 stopsC$ 529
Montego Bay
Montego Bay1 stopC$ 647
Oranjestad
Oranjestad2 stopsC$ 647
Kingston
Kingston1 stopC$ 742
Nassau
Nassau2 stopsC$ 521
Pointe-à-Pitre
Pointe-à-Pitre2 stopsC$ 982
Simpson Bay
Simpson Bay2 stopsC$ 591
Bridgetown
Bridgetown1 stopC$ 655
Puerto Plata
Puerto Plata1 stopC$ 573
Port of Spain
Port of Spain2 stopsC$ 602
Willemstad
Willemstad2 stopsC$ 1,413
Providenciales
Providenciales1 stopC$ 506
George Town
George Town1 stopC$ 667
Santo Domingo
Santo Domingo2 stopsC$ 611
St. John's
St. John's1 stopC$ 1,286
Kingstown
Kingstown2 stopsC$ 1,518

Cheap Flights from Calgary to Caribbean Islands

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

Sat, 18 Oct - Thu, 23 Oct
Multiple Airlines Logo
9:00 a.m. - 2:59 p.m.YYC-SJU
27h 59m1 stop
Multiple Airlines Logo
4:04 p.m. - 11:20 a.m.SJU-YYC
21h 16m1 stop
C$ 471Multiple Airlines
Find Deal
Sat, 18 Oct - Thu, 23 Oct
Multiple Airlines Logo
12:15 p.m. - 10:56 a.m.YYC-SJU
20h 41m2 stops
Multiple Airlines Logo
4:04 p.m. - 11:20 a.m.SJU-YYC
21h 16m1 stop
C$ 497Multiple Airlines
Find Deal
Fri, 31 Oct - Fri, 7 Nov
United Airlines Logo
2:13 p.m. - 5:00 p.m.YYC-PLS
48h 47m2 stops
United Airlines Logo
5:06 p.m. - 2:21 p.m.PLS-YYC
47h 15m2 stops
C$ 515United Airlines
Find Deal
Thu, 30 Oct - Thu, 6 Nov
WestJet Logo
9:35 p.m. - 3:50 p.m.YYC-NAS
16h 15m2 stops
WestJet Logo
4:50 p.m. - 5:30 p.m.NAS-YYC
26h 40m2 stops
C$ 521WestJet
Find Deal
Thu, 30 Oct - Thu, 6 Nov
WestJet Logo
6:30 p.m. - 3:50 p.m.YYC-NAS
19h 20m1 stop
WestJet Logo
4:50 p.m. - 6:57 a.m.NAS-YYC
16h 07m2 stops
C$ 526WestJet
Find Deal
Sat, 8 Nov - Tue, 18 Nov
Air Canada Logo
6:15 p.m. - 5:20 p.m.YYC-PUJ
20h 05m2 stops
Air Canada Logo
12:50 p.m. - 11:44 p.m.PUJ-YYC
13h 54m1 stop
C$ 529Air Canada
Find Deal
Mon, 13 Oct - Tue, 21 Oct
Air Canada Logo
1:10 a.m. - 9:45 p.m.YYC-PUJ
18h 35m1 stop
Air Canada Logo
2:25 p.m. - 11:16 p.m.PUJ-YYC
10h 51m1 stop
C$ 537Air Canada
Find Deal
Mon, 15 Dec - Thu, 15 Jan
United Airlines Logo
6:15 a.m. - 6:18 p.m.YYC-PUJ
9h 03m1 stop
United Airlines Logo
2:05 p.m. - 9:53 p.m.PUJ-YYC
10h 48m1 stop
C$ 572United Airlines
Find Deal
Sat, 18 Oct - Tue, 21 Oct
American Airlines Logo
1:29 p.m. - 10:00 a.m.YYC-NAS
18h 31m2 stops
American Airlines Logo
7:45 a.m. - 9:54 p.m.NAS-YYC
16h 09m2 stops
C$ 600American Airlines
Find Deal
Mon, 12 Jan - Mon, 26 Jan
American Airlines Logo
1:40 p.m. - 1:25 p.m.YYC-SJU
20h 45m2 stops
American Airlines Logo
6:50 p.m. - 11:23 a.m.SJU-YYC
19h 33m2 stops
C$ 601American Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for Calgary to Caribbean Islands flights

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

What is the cheapest Calgary 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 Calgary found in the last 72 hours was to Punta Cana, at C$ 509 round-trip. The most popular route is from Calgary (YYC) to Punta Cana (PUJ), and the cheapest round-trip airline ticket found on this route in the last 72 hours was C$ 509.

Can I save money by flying with a layover from Calgary 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 C$ 561, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Calgary to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Calgary 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 Calgary to Caribbean Islands is June, when tickets cost C$ 641 (return) on average. On the other hand, the most expensive months are December and February, when the average cost of round-trip tickets is C$ 873 and C$ 862 respectively.

What’s the cheapest day of the week to fly from Calgary to Caribbean Islands?

The average price of all round-trip flights from Calgary to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

When flying from Calgary to Caribbean Islands, you should consider leaving on a Sunday and avoid Mondays if you are looking for the best rates. For your return to Calgary, you’ll find the best rates on Wednesdays and the most expensive ones on Saturdays.

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

Good to know

Low seasonSeptember
Cheapest flightC$ 228
Best time to beat the crowds (21% less expensive on average)
Most popular time to fly (41% more expensive on average)
Flight from Calgary to Montego Bay

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Calgary 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 Calgary to Caribbean Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Calgary to Caribbean 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 Calgary 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 Calgary 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 Calgary 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 Calgary 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 in the afternoon, when round-trip flights cost C$ 489 on average. Morning departures are around 37% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is C$ 803.

Reviews of the top 5 airlines flying from Calgary to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Calgary 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 Calgary 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.
7.7
Air TransatOverall score based on 438 reviews
7.0Entertainment
7.9Boarding
7.3Comfort
8.4Crew
6.7Food
Airline reviews

This has been the worst experience I’ve ever had. Basically, I lost my round-trip tickets because one of my last names was missing, and you didn’t allow me to correct it. I had to purchase a full ticket again. Once I get home, I will start legal proceedings against you.

2.0 MediocreAnonymous, Sep 2025YYZ - ZAG
Read more Air Transat reviews

This has been the worst experience I’ve ever had. Basically, I lost my round-trip tickets because one of my last names was missing, and you didn’t allow me to correct it. I had to purchase a full ticket again. Once I get home, I will start legal proceedings against you.

The crew were polite and courteous. The Pilot did an excellent landing. It was very smooth and gentle. My only regret is that I was charged twice for my luggage . The attendant gave me no receipt . I didn't realize until I was about to board. How can this be resolved? Thank you.

Very smooth flights Toronto to Rome and return. Crews were great, food was fine but very narrow seats and limited leg room. Aisle seats on our return helped with a bit more space.

YUL AIRPORT is the worst. 1 Hr to Get out of the plane, 1 Hr To Cross the Border. 1Hr waiting to be pick up curbside. Trafic is ubeliveble.

It’s ok just the boarding point is far too far

Check in slow even though completed online check in, there was no bag drop available so had to query for 90mins as only 2 staff on desks.

Flying to a far away destination is a miracle in itself, so please take these with a grain of salt. The seats are a bit tired, and need a freshen up. The entertainment could be a bit newer, especially with all services available now. The food really is where we need help. But again, flying is a privilege, so all is good.

Not so much porter it's your site! Not good

They are a sister company with Air Transat and the two companies do not work well together. If you have any issues the two companies will blame each other and you will miss your flights. The help line does not help

Never book through a third party. Book through Air transats website. Terrible process to get help and many issues happen with them and sister companies because half the flights you book with them aren’t even through air transat.

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

Our flights got changed from United to Air Canada and our purchased seats did not get transferred so we had to pay for seats twice. I brought it up with Air Canada and they stated I had to go back and chase it with United. The united seats were $21 Canadian each and Air Canada were $56 each so we have paid $77 for each seat. Very unhappy

So far so good but food and entertainment are not available for this flight

Plane temperature was comfortable (not to hot) when boarding and waiting for takeoff.

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 flight had a delay that made me being in a real rush to take the second flight. The delay was almost for 2 hours. They moved us from gate to gate in 4 times. Once I arrived to Philadelphia, I got to run thorough all the airport, as the train was already closed by that time. So I got sick with asthma for all the running I had to do. And I was the last one to board, when it was almost closed. So irresponsable with the people

Overall very good, only complaint I have is the crew from CLT to SAT could have collected trash sooner.

This flight never occurred because AA couldn’t get their act together.

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

Everything was great except British airways lost our luggage that was gate checked all the way through to Italy. No one knows currently where one is and the other one may be in route to Amsterdam to meet us but not sure. If you can Hale’s it would be awesome. The website is not helpful.

Not very good , the stewardess were unfriendly and they don't like to be bothered. Cos was a night flight and they need to sleep.

Typical Canadian airline experience. Charger and tray were broken, food was poor quality, and yet you're still paying more than flights with equal to better service than elsewhere globally.

Not enough food option. And not enough advices or information about what we are gonna eat.

my carry-on bag was delayed and I did not receive it until the day of my return at the airport. This delay caused me significant inconvenience, as I did not have access to my personal belongings for the duration of my trip. I had expected to rely on my carry-on items, and being without them negatively impacted my travel experience.

Technology issues at the bag-check counter caused a delay, and we were unable to check out our bags, ultimately missing our flight. They offered no assistance other than telling us to book another flight out of Calgary. We arrived with plenty of time; if there hadn't been an issue with the kiosk and the length of the lines due to the technical issues, we could have made it home.

Worst check in and bag drop off experience. Staff were incredibly rude given that it’s the WestJet system that is faulty.

The staff at the airport and on the plane were wonderful I especially wanna acknowledge the staff who boarded us at the Calgary airport. The women who helped us board at the airport were incredible… they were so kind and sweet…I very happy with WestJet and I am hoping I can fly more often to Canada.

7 hour layover was a drag. Free internet on the long leg was great.

From vancouver go calgary nd vice vetsa fligjt was delayed

It was good! Short flight and it was on time!

Staff was nice, helpful, and did all they could. I understand economy seats are bottom of the barrel, but we're crammed in there with others in our row.

Really out of Air Canada's control due to long delay because of mechanical issues. While doing their best, disappointed by their assumption that all passengers have smart phones. Should have communicated food voucher availability at gate area. Late arrival cost me an extra $51 because public transit was not available, Otherwise, feel Air Canada did their best dealing with their challenges. Will likely continue using them in the future.

They canceled my flight, I had to rent a car, drive 14 hours. They tell to go on line for a refund, but only offer $24 for a $210 flight and you can’t get hold of anybody by phone and no help from staff at the airport.

I wish to travel with Air Canada for my next trip

They were very attentive, polite, professional and great customer service skills.

Business class was not worth the extra charge. Overpriced for slightly larger seat. Nothing special. Small older plane.

Pros: The airplane was new and had in-flight entertainment (tablet behind seats) with new movies instead of watching on personal devices. Cons: the flight time was changed without informing us. When I booked the flight, the time was 13:30pm (also in the email confirmation). However, when I reached the airport, the time was conveniently changed to 14:55pm. When I asked at the counter, they said the flight always took off at this time. The booking was made by Air Canada, but the flight was operated by United.

The app was great, service was wonderful, everything was quick and easy

On the flight from Montreal to Calgary the flight attendant we had was excellent. Unfortunately I did not get her name but she made the flight very comfortable and enjoyable.

Like- beer/wine for free Dis-like- all other aspects- customer service was horrible the entire trip. No help from Air Canada after they changed flight 6+ hours later. Also they put us on standby for no reason. Then almost 2 hours to get our bags after we arrived back at airport

Ground personnel in better mood. Sounded agressive wrt carry on bagage sizing.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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