C$ 285 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

Wed, 2 Dec - Tue, 8 Dec
Multiple Airlines Logo
5:01 a.m. - 12:05 p.m.San Juan  San Juan Luis Munoz Marin Intl-Calgary Calgary
33h 04m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
1:25 a.m. - 1:07 a.m.Calgary  Calgary-San Juan San Juan Luis Munoz Marin Intl
21h 42m1 stop Atlanta Hartsfield-Jackson
C$ 708Multiple Airlines
1 day ago
Wed, 2 Dec - Tue, 8 Dec
Multiple Airlines Logo
5:01 a.m. - 9:45 p.m.San Juan  San Juan Luis Munoz Marin Intl-Calgary Calgary
18h 44m2 stops Atlanta Hartsfield-Jackson Las Vegas Harry Reid Intl
Multiple Airlines Logo
1:25 a.m. - 1:07 a.m.Calgary  Calgary-San Juan San Juan Luis Munoz Marin Intl
21h 42m1 stop Atlanta Hartsfield-Jackson
C$ 728Multiple Airlines
1 day ago
Tue, 13 Apr - Wed, 21 Apr
United Airlines Logo
1:00 a.m. - 1:56 p.m.San Juan  San Juan Luis Munoz Marin Intl-Calgary Calgary
14h 56m2 stops Newark Denver Intl
United Airlines Logo
6:20 a.m. - 5:38 p.m.Calgary  Calgary-San Juan San Juan Luis Munoz Marin Intl
9h 18m1 stop Denver Intl
C$ 811United Airlines
14 hours ago
Sat, 1 May - Sat, 8 May
Delta Logo
6:15 a.m. - 8:54 p.m.San Juan  San Juan Luis Munoz Marin Intl-Calgary Calgary
16h 39m2 stops Atlanta Hartsfield-Jackson Minneapolis St Paul
Delta Logo
7:45 a.m. - 10:25 p.m.Calgary  Calgary-San Juan San Juan Luis Munoz Marin Intl
12h 40m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson
C$ 866Delta
9 hours ago
Tue, 1 Dec - Tue, 8 Dec
Multiple Airlines Logo
3:43 a.m. - 6:55 p.m.San Juan  San Juan Luis Munoz Marin Intl-Calgary Calgary
17h 12m2 stops Orlando Atlanta Hartsfield-Jackson
Multiple Airlines Logo
1:25 a.m. - 2:13 a.m.Calgary  Calgary-San Juan San Juan Luis Munoz Marin Intl
22h 48m2 stops Atlanta Hartsfield-Jackson Orlando
C$ 876Multiple Airlines
1 day ago
Mon, 1 Feb - Thu, 11 Feb
Multiple Airlines Logo
2:30 p.m. - 12:45 a.m.Montego Bay  Montego Bay Sangster Intl-Calgary Calgary
11h 15m1 stop Toronto Pearson Intl
Multiple Airlines Logo
12:50 a.m. - 6:50 p.m.Calgary  Calgary-Montego Bay Montego Bay Sangster Intl
17h 00m1 stop London
C$ 880Multiple Airlines
1 day ago
Wed, 25 Nov - Sun, 29 Nov
Air Canada Logo
7:45 p.m. - 12:50 a.m.Punta Cana  Punta Cana-Calgary Calgary
31h 05m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
6:10 p.m. - 11:35 p.m.Calgary  Calgary-Punta Cana Punta Cana
27h 25m1 stop Montreal Pierre Elliott Trudeau Intl
C$ 890Air Canada
1 day ago
Wed, 25 Nov - Sun, 29 Nov
Air Canada Logo
3:30 p.m. - 11:55 a.m.Punta Cana  Punta Cana-Calgary Calgary
22h 25m2 stops Toronto Pearson Intl Edmonton
Air Canada Logo
6:10 p.m. - 11:35 p.m.Calgary  Calgary-Punta Cana Punta Cana
27h 25m1 stop Montreal Pierre Elliott Trudeau Intl
C$ 896Air Canada
1 day ago
Fri, 26 Mar - Mon, 29 Mar
WestJet Logo
7:35 p.m. - 10:05 a.m.Montego Bay  Montego Bay Sangster Intl-Calgary Calgary
15h 30m1 stop Toronto Pearson Intl
WestJet Logo
8:10 a.m. - 12:35 p.m.Calgary  Calgary-Montego Bay Montego Bay Sangster Intl
27h 25m1 stop Toronto Pearson Intl
C$ 910WestJet
2 days ago
Fri, 26 Mar - Mon, 29 Mar
WestJet Logo
12:35 p.m. - 10:05 a.m.Montego Bay  Montego Bay Sangster Intl-Calgary Calgary
22h 30m1 stop Toronto Pearson Intl
WestJet Logo
9:50 a.m. - 12:35 p.m.Calgary  Calgary-Montego Bay Montego Bay Sangster Intl
25h 45m2 stops Edmonton Toronto Pearson Intl
C$ 911WestJet
2 days ago
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Good to know

Low season

May
Best time to beat the crowds (9% less expensive on average)
Most popular time to fly and prices are also 41% 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 3436 reviews
6.1Entertainment
7.4Boarding
7.1Comfort
7.9Crew
6.2Food
Airline reviews

It is stupid to have to go to Atlanta in order to get to Rochester NY. I was up for 36 hours because who can sleep on an airplane. I'll next do tht again.

6.0 GoodAnonymous, Sep 2026
Read more WestJet reviews

It is stupid to have to go to Atlanta in order to get to Rochester NY. I was up for 36 hours because who can sleep on an airplane. I'll next do tht again.

Our flight was delayed 3x and we were unaware until 15min of arriving at the airport so had we been made aware sooner we could have enjoyed possibly another 4hrs poolside. Very frustrating. Made the next day going back to work extremely tough too.

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.

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