C$ 383 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 10/6. 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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Cheap Flight Deals 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.

Recent round-trip flight deals from Caribbean to Calgary

KAYAK's recommended round-trip deals from the most popular airlines that fly from Caribbean to Calgary.
Discover the best prices for you by selecting your travel dates on KAYAK.
United Airlines Logo
4:30 p.m. - 6:21 p.m.AUA-YYC
27h 51m2 stops
United Airlines Logo
8:30 a.m. - 12:40 p.m.YYC-AUA
26h 10m2 stops
C$ 689United Airlines
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Thu, 22 May - Sat, 31 May
 Logo
1:10 a.m. - 11:19 a.m.SJU-YYC
12h 09m1 stop
 Logo
7:00 a.m. - 12:12 a.m.YYC-SJU
15h 12m2 stops
C$ 739
Find Deal
Mon, 21 Jul - Tue, 29 Jul
American Airlines Logo
3:00 p.m. - 11:29 p.m.SJU-YYC
10h 29m1 stop
American Airlines Logo
6:45 a.m. - 12:05 a.m.YYC-SJU
15h 20m2 stops
C$ 778American Airlines
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Thu, 21 Aug - Mon, 25 Aug
Delta Logo
7:00 a.m. - 9:07 p.m.SJU-YYC
16h 07m1 stop
Delta Logo
9:45 a.m. - 11:59 p.m.YYC-SJU
12h 14m1 stop
C$ 868Delta
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Thu, 17 Jul - Tue, 29 Jul
American Airlines Logo
3:23 p.m. - 11:29 p.m.SJU-YYC
10h 06m1 stop
American Airlines Logo
6:45 a.m. - 9:55 p.m.YYC-SJU
37h 10m2 stops
C$ 880American Airlines
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Thu, 17 Jul - Sat, 2 Aug
Air Canada Logo
3:56 p.m. - 10:53 p.m.SJU-YYC
32h 57m1 stop
Air Canada Logo
12:55 a.m. - 11:57 p.m.YYC-SJU
21h 02m2 stops
C$ 919Air Canada
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Wed, 21 May - Thu, 29 May
Delta Logo
7:00 a.m. - 9:07 p.m.SJU-YYC
16h 07m1 stop
Delta Logo
9:45 a.m. - 11:59 p.m.YYC-SJU
12h 14m1 stop
C$ 925Delta
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Wed, 16 Jul - Tue, 29 Jul
Air Canada Logo
1:05 a.m. - 1:03 a.m.SJU-YYC
25h 58m2 stops
Air Canada Logo
7:15 a.m. - 11:57 p.m.YYC-SJU
14h 42m1 stop
C$ 929Air Canada
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Tue, 20 May - Fri, 30 May
WestJet Logo
1:06 p.m. - 10:15 p.m.SJU-YYC
11h 09m1 stop
WestJet Logo
10:00 a.m. - 4:36 p.m.YYC-SJU
28h 36m1 stop
C$ 1,053WestJet
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Sat, 19 Jul - Wed, 30 Jul
WestJet Logo
6:15 a.m. - 10:15 p.m.SJU-YYC
18h 00m1 stop
WestJet Logo
6:30 p.m. - 10:23 p.m.YYC-SJU
25h 53m2 stops
C$ 1,062WestJet
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Sat, 19 Jul - Wed, 30 Jul
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Good to know

Low seasonOctober
High seasonDecember
Best time to beat the crowds (4% less expensive on average)
Most popular time to fly (19% 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 8696 reviews
7.3Comfort
7.7Boarding
7.1Entertainment
6.6Food
8.1Crew
Airline reviews

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.

10.0 ExcellentDr. Joseph, Apr 2025ORD - YUL
Read more United Airlines reviews

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.

In general ok, my only issue is that they had no hot items for purchase. I had very little time in my connection due to baggage/customs/TSA, thag I barely even had a chance for a stop at the washroom and buy water, to make it to my gate when they started boarding. I had nothing to eat because the trip started early, so I was ready to purchase, and they had nothing except for dry items like snacks. I had to purchase a mediocre, overpriced cheese and fruit board, instead of at least a pizza or sliders that I was planning on getting. Other than that, it was fine. But that’s typical Air Canada, to not have enough.

Most disapointing experience. We were rerouted to Toronto, after a 7 hours flight , where we sat on the tarmac for a little over 4 hours, in a full airplain with no air. We were given a tiny cup of water twice during that wait. After the long wait we taxi out of toronto to wait another 30 min. Many people missed their conections including my kids and I. We were promised a hotel room in Montreal on the aircraft and at the exit of the aircraft, then directed to a desk after custom where me and my two kids were told that we do not get a room for the night and that we were on our own, after a back and fourth and stating what was told to us, the agent at the counter says that we are right and that we should have a room. I ask the lady if she could look into a different flight for us for the next day as I was with two you g kids and wanted them to get some rest. The gentlemen next to her jumps in and said there wss nothing without even (pretending) looking at their system, I insist and say that they could look for the kids. They seemed to have trouble with our reservation so they gave up. I told them that I needed to talk to a manager, they said there were no managers and that no one can do anything, to which I responded that there must be someone that could do something and that it does not make sense for them to repeat the same think as we are not undestanding each other. She threatns to call security and says I am rude. I say I will go, just give me the vouchers and ger response is “ not giving you the vouchers because you are rude”. I was not rude. It is normal to want to talk to a manager. I even said that the people at the counter were not resoonsible for the long journey and that there was nothing they could have done. But to threten and himiliate someone just because they ask for someone else to talk to ? I understand they are overwhelmed, but you know the quality and calibre of a company in the bad times not the smooth ones. I ended up leaving and paying for my own room and board.

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).

Scrooge airlines spoiled my last chance at Christmas with my 95 and 92 year old folks. and rest of the family in Calgary. Ticket personnel would not let me on without a passport and I always visit Canada with my enhanced driver;s License when I travel from the US

Flight was delayed due to mechanical issues to the point that I missed my connection and had to wait for 6 hrs in Calgary... thankfully I wasn't in a rush or that would have been annoying

It was an awesome experience flying with Westjet. This was my first domestic flight experience in Canada.

The additional charge for the WiFi was not worth it. Streaming a football game was a joke as it continued to lag will be requesting a refund

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.

Flt was Vanc to Toronto. You don’t serve food and child behind me kicking the seat. Otherwise good.

Due to the approaching strike I have to admit Air Canada personnel showed empathy and compassion.Thank you for an enjoyable flight

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