C$ 269 Find Cheap Flights from Calgary to Caribbean – Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Calgary to Caribbean departing on 19/9. 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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1 adult, Economy, 0 bags

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Flight Deals

Best Caribbean Flight Deals from Calgary

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stopC$ 648
Montego Bay
Montego BaydirectC$ 541
Kingston
Kingston2 stopsC$ 800
Oranjestad
Oranjestad1 stopC$ 649
Nassau
Nassau1 stopC$ 576
Pointe-à-Pitre
Pointe-à-Pitre1 stopC$ 877
Fort-de-France
Fort-de-France2 stopsC$ 766
Simpson Bay
Simpson Bay1 stopC$ 593
Bridgetown
Bridgetown2 stopsC$ 683
Willemstad
Willemstad1 stopC$ 705
Puerto Plata
Puerto PlatadirectC$ 657
Port of Spain
Port of Spain2 stopsC$ 695
George Town
George Town1 stopC$ 653
Providenciales
Providenciales1 stopC$ 700
St. George's
St. George's1 stopC$ 736
Santo Domingo
Santo Domingo2 stopsC$ 878
Kingstown
Kingstown2 stopsC$ 1,116
Punta Cana
Punta Cana1 stopC$ 648
Montego Bay
Montego BaydirectC$ 541
Kingston
Kingston2 stopsC$ 800
Oranjestad
Oranjestad1 stopC$ 649
Nassau
Nassau1 stopC$ 576
Pointe-à-Pitre
Pointe-à-Pitre1 stopC$ 877
Fort-de-France
Fort-de-France2 stopsC$ 766
Simpson Bay
Simpson Bay1 stopC$ 593
Bridgetown
Bridgetown2 stopsC$ 683
Willemstad
Willemstad1 stopC$ 705
Puerto Plata
Puerto PlatadirectC$ 657
Port of Spain
Port of Spain2 stopsC$ 695
George Town
George Town1 stopC$ 653
Providenciales
Providenciales1 stopC$ 700
St. George's
St. George's1 stopC$ 736
Santo Domingo
Santo Domingo2 stopsC$ 878
Kingstown
Kingstown2 stopsC$ 1,116

Cheap Flights from Calgary to Caribbean

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

Tue, 17 Nov - Tue, 1 Dec
WestJet Logo
10:00 a.m. - 4:24 p.m.
YYC
-
MBJ
5h 24mdirect
WestJet Logo
2:50 p.m. - 9:58 p.m.
MBJ
-
YYC
8h 08mdirect
C$ 541WestJet
Tue, 20 Oct - Thu, 22 Oct
United Airlines Logo
6:00 a.m. - 5:38 p.m.
YYC
-
SJU
9h 38m
1 stop
United Airlines Logo
2:00 p.m. - 9:48 p.m.
SJU
-
YYC
9h 48m
1 stop
C$ 545United Airlines
Tue, 20 Oct - Wed, 21 Oct
United Airlines Logo
6:00 a.m. - 11:50 p.m.
YYC
-
SJU
15h 50m
2 stops
United Airlines Logo
1:00 a.m. - 11:28 a.m.
SJU
-
YYC
12h 28m
2 stops
C$ 548United Airlines
Tue, 17 Nov - Tue, 1 Dec
WestJet Logo
10:00 a.m. - 4:24 p.m.
YYC
-
MBJ
5h 24mdirect
WestJet Logo
2:50 p.m. - 9:58 p.m.
MBJ
-
YYC
8h 08mdirect
C$ 552WestJet
Tue, 17 Nov - Tue, 1 Dec
WestJet Logo
10:00 a.m. - 4:24 p.m.
YYC
-
MBJ
5h 24mdirect
WestJet Logo
2:50 p.m. - 9:58 p.m.
MBJ
-
YYC
8h 08mdirect
C$ 560WestJet
Sat, 14 Nov - Sat, 28 Nov
WestJet Logo
10:00 a.m. - 4:24 p.m.
YYC
-
MBJ
5h 24mdirect
WestJet Logo
3:25 p.m. - 7:30 p.m.
MBJ
-
YYC
29h 05m
1 stop
C$ 565WestJet
Sat, 5 Sep - Fri, 11 Sep
WestJet Logo
4:50 p.m. - 11:10 a.m.
YYC
-
NAS
16h 20m
1 stop
WestJet Logo
12:00 p.m. - 10:30 p.m.
NAS
-
YYC
12h 30m
2 stops
C$ 576WestJet
Fri, 4 Dec - Sat, 12 Dec
Air Canada Logo
6:10 p.m. - 1:40 p.m.
YYC
-
SJU
17h 30m
1 stop
Air Canada Logo
3:35 p.m. - 1:50 a.m.
SJU
-
YYC
12h 15m
1 stop
C$ 580Air Canada
Fri, 4 Dec - Fri, 11 Dec
Air Canada Logo
6:10 p.m. - 1:40 p.m.
YYC
-
SJU
17h 30m
1 stop
Air Canada Logo
2:25 p.m. - 12:55 p.m.
SJU
-
YYC
24h 30m
2 stops
C$ 586Air Canada
Wed, 2 Sep - Wed, 9 Sep
American Airlines Logo
6:45 a.m. - 11:59 p.m.
YYC
-
SJU
15h 14m
2 stops
American Airlines Logo
7:00 a.m. - 11:29 p.m.
SJU
-
YYC
18h 29m
2 stops
C$ 594American Airlines
Booking Insights

KAYAK's insights & trends for Calgary to Caribbean flights

Get data-powered insights and trends into flights from Calgary to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Calgary to Caribbean flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean from Calgary found in the last 5 days was to Montego Bay, at C$ 443 round-trip. The most popular route is from Calgary (YYC) to Montego Bay (MBJ), and the cheapest round-trip airline ticket found on this route in the last 5 days was C$ 443.

What is the cheapest time of day to fly to Caribbean?

The average price for all round-trip flights from Calgary to Caribbean depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Caribbean is generally at night, when round-trip flights cost C$ 852 on average. The most expensive time of day to fly to Caribbean is generally at night, which is peak travel time and where the average cost of a ticket is C$ 852.

Can I save money by flying with a layover from Calgary to Caribbean?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of C$ 821, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Calgary to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Calgary to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Calgary to Caribbean is September, when tickets cost C$ 709 (return) on average. On the other hand, the most expensive months are July and December, when the average cost of round-trip tickets is C$ 916 and C$ 916 respectively.

How far in advance should I book a flight from Calgary to Caribbean?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Calgary to Caribbean, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below-average price on a flight from Calgary to Caribbean, you should book around 2 weeks before departure, which saves you about 8% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 21 weeks before departure.

Good to know

Low season

October

Cheapest flight

C$ 269
Best time to beat the crowds (9% less expensive on average)
Most popular time to fly (12% more expensive on average)
Flight from Calgary to Nassau

Flights from Calgary to Caribbean: the best tips from KAYAK users

Insights shared by verified travellers who flew the route from Calgary to Caribbean 
Verified travelerFlew with WestJet
YYC
-
NAS
Feb 2026
Buy food to take on board the plane
Verified travelerFlew with WestJet
YYC
-
PUJ
Dec 2023
Be prepared for not seating together with your loved ones, you can not book seats in advance and when the time comes that you got your seats automatically assign and want to change them then it's to late because nothing will be available.

FAQs - booking Caribbean flights

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

    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 Calgary to Caribbean.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Calgary to Caribbean is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Calgary to Caribbean?

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

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

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

Reviews of the top 5 airlines flying from Calgary to Caribbean

 
Need help choosing which airline to fly with from Calgary to Caribbean? 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.
7.8
Air TransatOverall score based on 566 reviews
8.0Boarding
7.3Comfort
6.8Food
8.5Crew
7.1Entertainment
Airline reviews

The crew was great. There was no entertainment and the internet wasn't working. We sat in the run way for a LONG time which is always so upsetting. The seats are very close together and the flights are completely full which makes for a tough flight. Flying is just an uncomfortable experience.

6.0 GoodAnonymous, Jul 2026
YYZ - SFO
Read more Air Transat reviews

The crew was great. There was no entertainment and the internet wasn't working. We sat in the run way for a LONG time which is always so upsetting. The seats are very close together and the flights are completely full which makes for a tough flight. Flying is just an uncomfortable experience.

Very kind crew. Vegetarian food better than usual. Prompt take off. Entertainment worked well. Could always do with more room!

I liked the reliability. I liked less the chair comfort...

The dinner was bland and boring, but the economy seats were surprisingly comfortable. The flight was very packed.

I didn't have any problems during my flight. My main issue is with airlines in general, they keep offering less and less every year, AirTransat is no different.

We are a senior couple (70+) and chose emergency exit seats so we would have 2 seats together and neither of us had to sit in a middle seat. My husband is type 1 diabetic on an insulin pump and I monitor his blood sugar levels. I am 5'9" and 250 lbs and found the seats extremely uncomfortable. Toward the end of the flight I developed diarrhea which lasted a full 24 hours.

We were treated well by the staff at the airport and on board aircraft. Delay was uncontrollable due to the weather. Had to wait for another gate as we were late landing in Fort Lauderdale.

I was supose to have a carrey on incluided for each passenger and they made me paid 75$ each at the gate.

Great flight great seats will absolutely fly with you again

Porter airlines was good. I didn't have the best experience when booking through airfare assist however, as I got no final confirmation from them that the flight was booked until I called them. Even then, the confirmation code they gave me was incorrect and couldn't be used for check in. On a positive note airfare assist was actually picked up the phone relatively quickly when calling

They were fast and I like how they used to entertainment system to play video about the safety.

We Left Calgary 1/2 hour late and that made for a tight connection in Denver. After arriving everything was done to help us make our connection. That was a great effort. Thank You United

Plane 3 hours late. Missed connection. No help from gate staff. App horrible. Lost connection repeatedly. No service desk. Finally got help from young girl driving cart.

Horrible; seating was atrocious - inadequate leg room and seat width tight even for a small individual. Profits shouldn’t be everything!

I flew basic economy, so it was what I expected. Crew was nice though, and flight was quick. Would recommend for flights under 6 hours, otherwise would upgrade to something with more leg room.

Airline staff was good the checkin process was ok but the plane itself was very bad the comfort was worst it was worst and the most stiff 5 hours of my life i felt claustrophobic

Calgary desperately needs a star alliance lounge in the transborder area for United.

Leg room was lacking. Legs crammed into seat in front.

Flight was delayed but reasonable notice and communication was always there for the passengers.

I think it would have been better to get a heads up to download the app before getting on the plane as I only had wifi in the airport and didn’t realize the plane was an older one. Maybe a little more communication before hand would be lovely. The seats as always were crammed and uncomfortable and trying to convince people to spend an extra 150 so that we have an extra foot of leg room was less then ideal.

Average flight, comfort was as expected for a 10 hour flight. The service was fine.

Despite travelling ultra basic for the first time due to such increased rates we both managed with one bag each. Even boarding last wasn’t SO bad.

Food was not inspired but was satisfying. Same for infotainment selection. You’d think business class would come with complimentary WiFi. Crew was uniformly attentive and excellent.

Better movie options. More diligence on the size and amount of bags people bring on board. Lady across aisle from me had a bucket style bag that would only go so far under the seat in front of her. She was not told once that the whole bag is supposed to be under the seat. Crew is very hardworking however.

I didn’t have any food but my Prosecco hit the spot. We left on time and the crew was friendly.

Flight didn’t happen because both my connections were lost and Toronto wouldn’t let me board. I was checked in to all 3 flights at the check-in fest in Dublin.

I wasn’t able to book or pay for a seat and they forgot to check me in for my third flight so I spent 24 hours in Toronto waiting for another one.

Flight was delayed for 5hours. Food vouchers just aren’t good enough

Flight was early. That’s the only positive I can share. I paid for wifi on the flight and it didn’t allow me to use any streaming services so it was a waste of $20. West Jet also lost my ski equipment on my way to a ski vacation. They told me it would be delivered to the hotel as soon as it arrived at the airport. It was never delivered. I had to pick it up at the airport on my way home. I am completely disgusted with my experience on west jet

No kiosk to help pre boarding unlike other airlines, still lost the luggage despite its own crew/TSA or security tagging it, poor handling of lost luggage and possibly compensation is likely poor too.

This may have been the hottest cabin temperatures I have experienced on any flight prior to take off lasting for approximately 30 minutes. I am not typically one to complain but I was genuinely worried about the health of several passengers on the flight due to the extreme temperatures including a small toddler.

I got bumped by Qantas to American Airlines incurring a 6 hr layover at lax. I was not happy

Air conditioning was out for about 15 minutes that made it uncomfortable. WiFi went out halfway into the flight. Flight was about 45 minutes late.

Delayed due to weather in Dallas (arriving flight arrived late), then boarded the plane only to deboard immediately afterwards, tire needed to be replaced. Flight supposed to depart at 6:15pm but departed at 9:35pm.

Meals were not so good. Snack between the meals was very bad. Like Japan Airlines, they could eliminate the snack and make the second meal much better.

Baggage allowances are terrible and the experience of only being allowed one bag and paying so much to take sporting equipment to a known ski area should be addressed.

The flight was on time and crew were nice, seats were tight and there was entertainment available

Good service, friendly staff. Food was average for airlines and the seats were small.

Worst flight ever. I was suppose to have a 3 1/2 hour layover in Chicago but got to the gate 4 minutes before boarding.

A cookie and a soda, packed like sardines, will never be a positive experience. Also, boarded a 5:30 flight at 7:45pm

I was notified 8 hours before that my flight was cancelled due to mechanical issues and they would let me know when they put me on a new flight. Didn’t hear back for 6 hours and was never notified and had to log into the app to find out I was put on a new flight. First time flying with air Canada and won’t fly with them again.

My experience was good. On my return my screen had a glitch but the movie, show and internet options were good. Seats were comfortable, as comfortable as a plane could get in economy. Friendly service. Only complaint would be high price.

Every flight was canceled and they didn’t care much about their passengers

I was tired enough to fall asleep soon after takeoff and slept until "we are starting our descent to Toronto" announcement. That's not bad at all.

It was great to have a vegetarian meal option, but departure was delayed because they had oversold the flight. Air Canada, you’re in charge of how many tickets are sold: don’t oversell!

The lead flight attendent was outstanding. We were delayed waiting for a connection and she kept us up-to-date with a great sense of humor. She also made sure a passenger in the back of the plane was sble to get out first to make a connection. She needs to be recognized by your company! She is awesome!

My experience was good with United too But only not so good thing was that at Calgary airport I was not given lounge access despite of flying business. Aspire lounge denied it to me, which was unfair I feel

Very bed experience never want to travel air canada anymore

Was not sent a link to check in online. Tried to check in online using website. Site didn’t work. Called support line, was told it often didn’t work. Went to counter at airport to check bags and get boarding passes. Had to stand in a lineup. They were unable to tell me how much to pay. Had to take a paper to another counter, took a long time to be told what I owed. I fondly remember the days of checking in online, getting my boarding pass digitally, paying for my luggage on line, scanning my passport at the airport to get my luggage tags, and putting my luggage on the conveyor. Easy peasy. Air Canada has really taken a step back in time, and made what was an easy check in experience to one that seemed unduly long and frustrating.

Really out of Air Canada's control due to long delay because of mechanical issues. While doing their best, disappointed by their assumption that all passengers have smart phones. Should have communicated food voucher availability at gate area. Late arrival cost me an extra $51 because public transit was not available, Otherwise, feel Air Canada did their best dealing with their challenges. Will likely continue using them in the future.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports