C$ 391 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 20/12. 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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Everything you should know

Cheapest round-trip
C$ 611
Typical prices: C$ 1,707-C$ 1,761
Multiple Airlines
Thu 22/1Fri 23/1
SJU - YYC • 1 stop
Cheapest one-way flights
C$ 461
Multiple Airlines
Sat 20/12
AUA - YYC • 3 stops
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Flight Deals

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

Thu, 22 Jan - Fri, 23 Jan
Multiple Airlines Logo
11:05 a.m. - 9:19 p.m.SJU-YYC
13h 14m1 stop
Multiple Airlines Logo
9:00 a.m. - 10:47 a.m.YYC-SJU
22h 47m2 stops
C$ 611Multiple Airlines
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Sat, 17 Jan - Fri, 30 Jan
Multiple Airlines Logo
5:00 p.m. - 6:25 p.m.SJU-YYC
28h 25m2 stops
Multiple Airlines Logo
9:00 a.m. - 6:54 p.m.YYC-SJU
30h 54m1 stop
C$ 638Multiple Airlines
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Thu, 11 Dec - Mon, 15 Dec
Multiple Airlines Logo
6:00 a.m. - 5:06 p.m.SJU-YYC
14h 06m1 stop
Multiple Airlines Logo
12:30 a.m. - 12:16 a.m.YYC-SJU
20h 46m2 stops
C$ 642Multiple Airlines
Find Deal
Tue, 10 Feb - Mon, 16 Feb
American Airlines Logo
6:00 a.m. - 9:58 p.m.SJU-YYC
18h 58m2 stops
American Airlines Logo
1:30 p.m. - 5:00 a.m.YYC-SJU
12h 30m1 stop
C$ 842American Airlines
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Thu, 22 Jan - Fri, 23 Jan
American Airlines Logo
7:07 a.m. - 9:58 p.m.SJU-YYC
17h 51m1 stop
American Airlines Logo
6:30 a.m. - 10:26 p.m.YYC-SJU
12h 56m1 stop
C$ 859American Airlines
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Tue, 17 Mar - Thu, 19 Mar
WestJet Logo
3:30 p.m. - 4:15 p.m.AUA-YYC
26h 45m2 stops
WestJet Logo
12:15 p.m. - 2:35 p.m.YYC-AUA
24h 20m2 stops
C$ 932WestJet
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Tue, 16 Dec - Wed, 31 Dec
WestJet Logo
4:30 p.m. - 7:42 a.m.AUA-YYC
18h 12m2 stops
WestJet Logo
12:15 a.m. - 3:40 p.m.YYC-AUA
12h 25m1 stop
C$ 940WestJet
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Wed, 15 Apr - Sat, 18 Apr
Air Canada Logo
1:20 p.m. - 9:08 a.m.PLS-YYC
21h 48m2 stops
Air Canada Logo
4:45 p.m. - 5:25 p.m.YYC-PLS
46h 40m2 stops
C$ 947Air Canada
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Wed, 15 Apr - Sat, 18 Apr
Air Canada Logo
1:20 p.m. - 12:03 a.m.PLS-YYC
12h 43m1 stop
Air Canada Logo
11:40 p.m. - 12:10 p.m.YYC-PLS
10h 30m1 stop
C$ 1,007Air Canada
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Fri, 6 Mar - Tue, 10 Mar
United Airlines Logo
2:25 p.m. - 9:38 p.m.SJU-YYC
10h 13m1 stop
United Airlines Logo
6:20 a.m. - 5:25 p.m.YYC-SJU
9h 05m1 stop
C$ 1,131United Airlines
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Useful Info

Good to know

Low seasonOctober
Best time to beat the crowds (20% less expensive on average)
Most popular time to fly and prices are also 42% lower 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.

Reviews of the top 3 airlines flying 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 9007 reviews
7.1Entertainment
6.6Food
8.1Crew
7.7Boarding
7.3Comfort
Airline reviews

Not the fault of United—weather, reroute around weather, time sitting on tarmac, arrived couple hours late, too late for train into city necessitating a much pricier cab but weather…can’t be helped.

8.0 ExcellentBrad, Oct 2025ORD - YYZ
Read more United Airlines reviews

Not the fault of United—weather, reroute around weather, time sitting on tarmac, arrived couple hours late, too late for train into city necessitating a much pricier cab but weather…can’t be helped.

Flight was good but there are way to many announcements for credit cards etc.

I had no checked baggage but was required to hand over carry on baggage at the door of the plane. There was a lot of overboard space in the plane and I was one of the last ones. I ran to get my carry on but it was gone. I was given back at the plane door in Toronto, so the wait was not as long as it would have been at the carousel.

We had a layover from YVR to Denver. We bought 4 bottles of Absolut Vodka at the YVR Duty Free for $116.20, after going through security and American Customs Pre Clearance at YVR, Vancouver. When we landed in Denver, United put us behind the American Customs as well as TSA again for some reason. We were forced to go through American Customs and TSA again. TSA confiscated our rightfully owned Duty Free Absolut Vodka bottles. Because United incorrectly forced our flight behind American border and TSA again, we missed the connecting flight. After United put us on a later flight, we eventually arrived in Chicago very late, with hardly any sleep. I am looking for compensation from United for our incorrectly confiscated Absolut Vodka bottles worth $116.20, as well as compensation for incorrectly putting us behind American Customs and TSA again, causing us to miss our connecting flight, making us arrive extremely late in Chicago.

From the first moment you interact with United Airlines, you can expect nothing less but extreme frustration. The baggage handler at the bag drop seems completely unbothered by the presence of customers waiting in line. No help was extended to load the baggage whatsoever. And if any of your bags is overweight by 0.01 pound they will make you re-distribute everything in your suitcase just to play power trip. When it was time to board no help was extended to customers to locate their seats. Moreover. It was a chaotic mess at the gate when it was unclear who should board first and everyone just bunched up, trying to get on the plane. I am sure the crew was doing their best to perform their jobs while being paid their wages however it shouldn’t be that hard to smile once or twice when you’re in the business if serving customers. It is a shame for the United States of America to have a flagship carrier of such low caliber. Our flight was also delayed by about an hour and a half due to further delays prior to our inbound flight. Being someone who has travelled for both business and leisure in Asia, Europe, and South America I have never experienced such poor quality of service.

The pilots were late and it made us 1 hour late. The meat was tough and bok choy was also tough.

the delay for 3 hours was understandable due to weather conditions but the flight should’ve provided some on flight compensations or at least provide more food.

Flight was actually on Air Canada. The flight itself was fine. Nothing special. Food was pretty pathetic except for cookies. They offered plenty of food and drinks but just wasn't very good. Even for airline food.

Boarding experience was smooth. Flight attendants were friendly and helpful. Entertainment system on the Houston-Edmonton flight did not function for passengers on the left side of the aisle. On the bird's eye flight from Quito to Houston, they should not serve a meal. No one needs to eat after midnight and it is disturbing for those passengers trying to sleep.

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.

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

I rated westjet poor on food for not accepting debit to make in flight purchases. This is dumb.

Delayed 8 hours, This is the 2nd time in a month that my flight was not on time.

The snacks could have been better, and maybe some warm drinks instead of just water cause it was very very cold.

I like and appreciate the attention and patience from all west jet personal to my senior mother. Thank you!!!!

Our first flight from LAX to Winnipeg was changed but you never informed us at all. It went from a nonstop flight to a stay at Calgary. This impacted our trip negatively as we arrived much later than we planned to. Our returning flight was horrible. The flight was delayed 6 hours!! And we were NOT going to wait that long. The only way we got on our original flight was running there. However all of our suitcases were now coming on the delayed flight. It was the worst experience we ever had flying. I want my money back.

Please make more option. And be more precise on the type of food you giving. Diner and breakfast can be different

It was generally pretty good, but the check-in and boarding process were a little difficult. Check in was in terminal 2F, but there was a shuttle required to get to the gate, which added significant time. The gate was changed 30 minutes before boarding, which took us by surprise - we did not get the notice until boarding had started. The check in line moved very slowly - the agent was friendly, but did not seem very efficient/urgent given the growing line.

Delays and missed connections were very hard the crew were wonderful but 1 1/2 hours late from Abbotsford to a 4 hour wait in Calgary was too much. I am 79 years old and I didn’t get to my destination until after 1 in the morning. They could have offered a seat in the lounge or a meal. I was very disappointed in the treatment

No dogs! Can we have no dogs in the cabin? Why was there a yappy little dog behind me? Lucky I had ear plugs. Sorry for others without

Very nice staff members are very nice and friendly helpful

The internet connection was perfect, and the updated entertainment systems that allow me to connect my Bluetooth earbuds was excellent

Just the stress of possible cancellations on flights from Air Canada, but all went as planned and everything was perfect! Thank you

It was good to receive a card for my birthday

It got cancelled and they haven't given me a flight back yet!!

It would have been better if it wasn’t cancelled

Awful. As we were boarding we were told the flight was cancelled. Then had to stand in a queue for 3 hours to talk to someone at the kiosk of Air Canada. They were not helpful at all. No empathy. My issue is not with them striking but the total disregard for the chaos and distress late notice caused. No thought on the impact this has caused.

Flying in the Dreamliner is always comfortable. Though the food options for Air Canada aren't great.

No TV's. Seats are super uncomfortable. Crew was great!

This flight was canceled at the last moment and I was stranded in the Vancouver International. I spent the night there without compensation and the staff looked annoyed and wanted to get rid of the passengers without offering much help.

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