C$ 306 Find Cheap Flights from Caribbean to Calgary

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Calgary departing on 27/7. 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

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Cheap Flights from Caribbean to Calgary

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

Tue, 15 Jul - Wed, 30 Jul
 Logo
1:37 a.m. - 9:08 p.m.SJU-YYC
21h 31m1 stop
 Logo
12:30 a.m. - 11:32 a.m.YYC-SJU
33h 02m2 stops
C$ 570
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Fri, 18 Jul - Wed, 30 Jul
 Logo
1:37 a.m. - 6:28 p.m.SJU-YYC
18h 51m1 stop
 Logo
12:30 a.m. - 11:32 a.m.YYC-SJU
33h 02m2 stops
C$ 573
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Wed, 15 Oct - Wed, 22 Oct
American Airlines Logo
6:30 a.m. - 9:55 p.m.SJU-YYC
17h 25m2 stops
American Airlines Logo
1:27 p.m. - 12:40 p.m.YYC-SJU
21h 13m2 stops
C$ 774American Airlines
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Tue, 14 Oct - Wed, 22 Oct
United Airlines Logo
1:05 a.m. - 11:38 a.m.SJU-YYC
12h 33m2 stops
United Airlines Logo
6:15 a.m. - 11:57 p.m.YYC-SJU
15h 42m2 stops
C$ 807United Airlines
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Wed, 20 Aug - Mon, 25 Aug
United Airlines Logo
1:05 a.m. - 4:03 p.m.SJU-YYC
16h 58m2 stops
United Airlines Logo
6:15 a.m. - 11:57 p.m.YYC-SJU
15h 42m2 stops
C$ 822United Airlines
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Tue, 22 Jul - Tue, 29 Jul
American Airlines Logo
6:04 a.m. - 9:57 p.m.SJU-YYC
17h 53m2 stops
American Airlines Logo
6:29 a.m. - 12:27 a.m.YYC-SJU
15h 58m2 stops
C$ 868American Airlines
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Sun, 10 Aug - Thu, 21 Aug
Air Canada Logo
2:20 a.m. - 1:15 a.m.POS-YYC
24h 55m1 stop
Air Canada Logo
12:25 a.m. - 1:20 a.m.YYC-POS
22h 55m1 stop
C$ 1,010Air Canada
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Sun, 10 Aug - Sat, 30 Aug
Air Canada Logo
2:20 a.m. - 1:15 a.m.POS-YYC
24h 55m1 stop
Air Canada Logo
6:55 p.m. - 1:20 a.m.YYC-POS
28h 25m1 stop
C$ 1,086Air Canada
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Wed, 15 Oct - Tue, 21 Oct
WestJet Logo
7:30 a.m. - 8:52 p.m.SJU-YYC
15h 22m2 stops
WestJet Logo
1:00 a.m. - 10:21 p.m.YYC-SJU
19h 21m2 stops
C$ 1,226WestJet
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Wed, 15 Oct - Tue, 21 Oct
WestJet Logo
7:30 a.m. - 8:00 p.m.SJU-YYC
14h 30m1 stop
WestJet Logo
12:30 a.m. - 4:18 p.m.YYC-SJU
13h 48m1 stop
C$ 1,282WestJet
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Useful Info

Good to know

Low seasonOctober
High seasonDecember
Best time to beat the crowds (22% less expensive on average)
Most popular time to fly (2% more expensive on average)

FAQs for booking flights from Caribbean to Calgary

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

    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 Caribbean to Calgary.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Calgary from Caribbean 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 Caribbean to Calgary?

    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 to Calgary with an airline and back to Caribbean with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean to Calgary?

    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 to Calgary from Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top 3 airlines serving from Caribbean to Calgary

 
Need help choosing which airline to fly with from Caribbean to Calgary? 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.
7.4
United AirlinesOverall score based on 8790 reviews
7.7Boarding
7.3Comfort
6.6Food
7.0Entertainment
8.1Crew
Airline reviews

Flight was late as pilot crew had to land at different airport in their previous flight. Passengers boarded and had to wait for pilots inside plane. Series of incomplete and unnecessary announcements by an annoying voice, rather than complete, informative announcements.

6.0 GoodAnonymous, May 2025SFO - YVR
Read more United Airlines reviews

Flight was late as pilot crew had to land at different airport in their previous flight. Passengers boarded and had to wait for pilots inside plane. Series of incomplete and unnecessary announcements by an annoying voice, rather than complete, informative announcements.

Delay and keep changing gates. I have to run around from B to C then to E.

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

My suitcase was completed destroyed. The top part is broken and unusable now.

When I booked it on Kayak it aaid that I wasn't allowed hamd luggage. I called United Airlines and it took them 6 minutes to figure out if I was allowed free hand luggage. Surely something that simple they should be able to tell me instantly.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

I love United was disappointed we had a two hour delay, however the Pilot did say safety first.

We were delayed in Toronto on the tarmac for THREE hours with no clear indication as to why except that it was not a safety hazard. Pilot did apologize more than once but even he was unable to explain why exactly we were delayed. I overheard the stewards saying that the captain was very frustrated with the situation as well because he was not able to explain why except it had something to do with water supply or system on the aircraft and now we needed to wait for an engineer to approve the aircraft for flight. It was very frustrating and distressing as a passenger and we should have been given complimentary meals at the very least.

All male crew was just too woke for me. I felt like a sardine. I will never take a window seat or the rearmost seat again. I booked early and did not pay for seat selection and that was a mistake. The security at IAH was atrocious. I was violated and radiated as I was in a hurry to connect to my other flight. I may have lost items under the seat in front of me that I couldn't see nor bend over to look.

Liked nothing. As per previous segment it was delay delay delay.

We purchased premium flex tickets for our overseas flight to London. I have food, allergies, so I knew I wouldn't be able to get a full meal. WestJet doesn't seem to provide any way for people like myself to register their allergies ahead of time. I was given one small package of crackers and cheese as my meal. I was told there were no more packages available and no other alternatives for food. The flight attendant seemed quite disinterested in providing service. That stands in stark contrast to other Westjet flights where the flight attendants have gone out of their way to provide service.

Lots of overhead storage and a good crew and service.

The flight was ahead of schedule. A half glass of juice and a cookie is pathetic! No entertainment possibilities. Not even a plug-in for phone or IPad if you wanted to watch a downloaded movie. Back to flying Air Canada!

The flight was ahead of schedule. A half glass of juice and a cookie is pathetic!

Our flight was delayed for almost 2 hours resulting in a rush to connect to our next flight

Good. Would be better if the carry on baggage was free.

Flight cancelled and Kayak switched our return flight to a red eye. Ridiculous.

Limited water service in a 6 hour flight offered at the very beginning and end of the flight.

They delayed flight because lack of staff then missed connection. Never flying with kayak or weather

WestJet claims that tickets purchased through a 3rd party (such as you kayak) they cannot make sure they mention the luggage situation. We purchased tickets that wouldn’t allowed any carry on. WHAT!? So ridiculous. We bought them and there was not one single place mentioning that. Then on our departure the WstJet attendant was a super nasty rude person. Very unprofessional, unpleasant. She should be reprimanded and given some sort of training but I believe that won’t change her nasty disposition. On our return was great, the front desk gentleman was really professional, friendly and helpful. He offered us to pay $18 usd each for our carry on backpacks as they were small (instead of $90 each at the departure, she could have mentioned but decided not to do so. Didn’t print my boarding pass with my full name as in the passport and made the flight delay because the crew needed to correct it).

Service Director cut all cabin lights and window screens defaulted to dark, but it was an afternoon flight going west. I spent hours trying to see what was reading as reading lights weren't working either. What the hell.

The food could have been better. The flight attendant was the friendliest and most helpful I have ever had.

it was great only downfall was that the tvs weren't working but the rest was great specially the wifi

The Entertainment system was nearly useless because videos kept stopping then jumping over segments at random but closely spaced intervals. About 75% of the plane gave up trying to watch and then the gaps and jumps became shorter, It was terrible and made it hard to know what was happening since it was not a normal buffering pause where you still get the cont6en t. Instead the video would pause then jump ahead missing short segments and dialog entirely! The economy class seats on all flights have less and less legroom. I’m tall and the upgraded seats are no better for the leg room, not worth it. I flew from Toronto to Calgary….The staff at YYZ was awesome and kind. My flight’s (prior) incoming plane from Liberia had been delayed over 3 hours and the attendant quickly and kindly transferred me to the earlier flight that got me in hours earlier. Such a great staff!! Every staff member on the plane was very-very Canadian/Kind . Great job and attitude you folks! The plane itself was new and in great condition, except the issue with the video streaming.

I did not like ANYTHING about Discover....see my previous comments regarding our trip. I will do everything possible never to fly with Discover again!!!

We were sent via the ac app to a wrong gate. And then got a boarding message to the original gate. Had to run through the airport to get to the gate just in time. Were they purposely trying to trick me? The day before flight was sent a message for free change of flight. Kinda suspect they oversold the flight.

The crew and food were very good. The plane was dirty..

Had to buy headphones. Which is sad. I did not so I listened to podcasts and slept. Free beer is excellent a d those pretzels are great too. Overall I feel Air Canada slightly exceeds Westjet for overall experience. But still more can be done. Like allowing guests to view a movie for free.

Flight was cancelled due to problems with the aircraft . Not much else to add . Itinerary was changed from yeg to Yule direct . Fine .

Both my flights from Calgary to Montreal were pleasant. I should also mention my gratitude to the two ladies at YYC who helped with my check in and went out of their way to assist me.

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