C$ 246 Find Cheap Flights from Caribbean to Calgary – Compare and Save

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Cheap Flights from Caribbean to Calgary

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Caribbean to Calgary

Tue, 3 Nov - Wed, 25 Nov
WestJet Logo
4:20 p.m. - 2:55 a.m.SXM  Simpson Bay Princess Juliana-YYC Calgary
12h 35m1 stop Toronto Pearson Intl
WestJet Logo
10:05 p.m. - 2:25 p.m.YYC  Calgary-SXM Simpson Bay Princess Juliana
14h 20m2 stops Edmonton Toronto Pearson Intl
C$ 565WestJet
Tue, 3 Nov - Wed, 25 Nov
WestJet Logo
4:20 p.m. - 9:50 a.m.SXM  Simpson Bay Princess Juliana-YYC Calgary
19h 30m2 stops Toronto Pearson Intl Edmonton
WestJet Logo
6:15 p.m. - 2:25 p.m.YYC  Calgary-SXM Simpson Bay Princess Juliana
18h 10m2 stops Edmonton Toronto Pearson Intl
C$ 588WestJet
Tue, 3 Nov - Wed, 25 Nov
WestJet Logo
4:20 p.m. - 10:35 a.m.SXM  Simpson Bay Princess Juliana-YYC Calgary
20h 15m1 stop Toronto Pearson Intl
WestJet Logo
2:25 p.m. - 2:25 p.m.YYC  Calgary-SXM Simpson Bay Princess Juliana
22h 00m1 stop Toronto Pearson Intl
C$ 593WestJet
Tue, 3 Nov - Wed, 25 Nov
WestJet Logo
4:20 p.m. - 2:55 a.m.SXM  Simpson Bay Princess Juliana-YYC Calgary
12h 35m1 stop Toronto Pearson Intl
WestJet Logo
7:45 p.m. - 2:25 p.m.YYC  Calgary-SXM Simpson Bay Princess Juliana
16h 40m2 stops Winnipeg Toronto Pearson Intl
C$ 594WestJet
Tue, 3 Nov - Wed, 25 Nov
WestJet Logo
4:20 p.m. - 2:55 a.m.SXM  Simpson Bay Princess Juliana-YYC Calgary
12h 35m1 stop Toronto Pearson Intl
WestJet Logo
2:25 p.m. - 2:25 p.m.YYC  Calgary-SXM Simpson Bay Princess Juliana
22h 00m1 stop Toronto Pearson Intl
C$ 595WestJet
Thu, 24 Sep - Thu, 1 Oct
Multiple Airlines Logo
5:11 p.m. - 9:50 p.m.SJU  San Juan Luis Munoz Marin Intl-YYC Calgary
30h 39m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
9:00 p.m. - 3:19 p.m.YYC  Calgary-SJU San Juan Luis Munoz Marin Intl
16h 19m2 stops Vancouver Intl Atlanta Hartsfield-Jackson
C$ 608Multiple Airlines
Sun, 20 Sep - Sat, 3 Oct
WestJet Logo
3:20 p.m. - 10:20 a.m.SXM  Simpson Bay Princess Juliana-YYC Calgary
21h 00m2 stops Toronto Pearson Intl Regina
WestJet Logo
8:10 a.m. - 2:20 p.m.YYC  Calgary-SXM Simpson Bay Princess Juliana
28h 10m2 stops Winnipeg Toronto Pearson Intl
C$ 622WestJet
Sun, 20 Sep - Sat, 3 Oct
WestJet Logo
3:20 p.m. - 8:20 a.m.SXM  Simpson Bay Princess Juliana-YYC Calgary
19h 00m1 stop Toronto Pearson Intl
WestJet Logo
6:00 a.m. - 2:20 p.m.YYC  Calgary-SXM Simpson Bay Princess Juliana
30h 20m1 stop Toronto Pearson Intl
C$ 631WestJet
Sun, 20 Sep - Sat, 3 Oct
WestJet Logo
3:20 p.m. - 12:20 p.m.SXM  Simpson Bay Princess Juliana-YYC Calgary
23h 00m1 stop Toronto Pearson Intl
WestJet Logo
12:25 p.m. - 2:20 p.m.YYC  Calgary-SXM Simpson Bay Princess Juliana
23h 55m2 stops Winnipeg Toronto Pearson Intl
C$ 633WestJet
Mon, 12 Oct - Mon, 19 Oct
Multiple Airlines Logo
5:11 p.m. - 11:00 a.m.SJU  San Juan Luis Munoz Marin Intl-YYC Calgary
19h 49m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
1:15 p.m. - 9:18 a.m.YYC  Calgary-SJU San Juan Luis Munoz Marin Intl
18h 03m2 stops Nashville Intl Orlando
C$ 648Multiple Airlines
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Good to know

Low season

February
Best time to beat the crowds but there is an average 54% increase in price.
Most popular time to fly and prices are also 38% 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 airline 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.
7.2
WestJetOverall score based on 3445 reviews
7.9Crew
6.1Entertainment
6.2Food
7.1Comfort
7.4Boarding
Airline reviews

Bumped from my connected flight, we arrived earlier than scheduled and I was bumped 4.5 hours later. There was no reason, they said my time I wouldn’t have connected in time. I had 41 minutes. None of Westjet customer service in airport could figure out why me and my 5 year old were bumped from flight we booked. We had 10 minutes to get to next gate after we got off the plane, one lady mentioned that’s not enough time to get to next gate. I was there in 3 minutes. Was originally suppose to fly out at 6:50 pm And was re scheduled to 11:45pm.

2.0 MediocreAnonymous, Aug 2026
Read more WestJet reviews

Bumped from my connected flight, we arrived earlier than scheduled and I was bumped 4.5 hours later. There was no reason, they said my time I wouldn’t have connected in time. I had 41 minutes. None of Westjet customer service in airport could figure out why me and my 5 year old were bumped from flight we booked. We had 10 minutes to get to next gate after we got off the plane, one lady mentioned that’s not enough time to get to next gate. I was there in 3 minutes. Was originally suppose to fly out at 6:50 pm And was re scheduled to 11:45pm.

Terrible. I was charged $75 for a checked bag when I only had a carry on. The lady at the desk said she couldn’t refund me the money and that I had to call westjet. I called the next day and they said they couldn’t refund me because there is no way to prove I didn’t have a checked bag.

WestJet employees were not properly informed about where my luggage was going causing extreme confusion and almost made me miss my flight

It would have been nice to know there was no on flight entertainment

Due to delays at SFO, my WestJet light missed its connecting WestJet flight. If they had held the plane in Calgary for 15 minutes, 2 families with children would not have been stranded in Calgary for more than 24 hours. I understand the need to be on-time, but when it is the same company, you would think they could make a phone call. Or maybe they could go to a higher altitude to make up for lost time? Instead of attempting to put us on another flight, they rescheduled us for the same connecting flight 24 hours later. We then had to scramble to find a hotel, which they state that they were not responsible for since the delay was not their fault and therefore became an additional out of pocket expense for us. The customer service is severely lacking here at this company. They also mentioned that if we purchased our tickets through a 3rd party site (Kayak) versus WestJet directly, that they couldn't help us. Seriously?? Additionally, we lost 2 days of travel and missed out on tours and taxis that were pre-booked. I will not be using WestJet again,

Everyone was extremely friendly and nice, from the front desk to the cabin crew!

This airline would not refund my money and I had a physician note that I could not fly. They are crooks

I like that we landed safely and that my dog was safe underneath as well. Outside of that, we were 45 mins late for a direct flight that is 1.5 hours long. And 2 of my 3 bags did not make the flight. Only my dog was onboard.

Decent entertainment although my wife was not offered any ear buds so couldn’t enjoy. Real issue was the appalling food. Presentation was unacceptable with cheap hard to open packaged bread, plastic cheese again in hard to open shrink wrap, main course in small cardboard box again hard to open, wooden utensils which lack substance making the whole experience poor. Surprised I didn’t cover myself or neighbour as the food moved all over the place. Breakfast calzone was dry and unappealing with the staff basically throwing them around. Very disappointed

The flight didn’t happen because they apparently lost my check in and wouldn’t let me board.

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Everything you need to know for your flight to Calgary

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