C$ 209 Find Cheap Flights from Calgary to Caribbean Islands

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 Islands departing on 23/4. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Calgary to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Calgary to Caribbean Islands, as well as popular online travel agencies
Travellers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Best Caribbean Islands Flight Deals from Calgary

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stopsC$ 502
Montego Bay
Montego Bay2 stopsC$ 442
Kingston
Kingston1 stopC$ 763
Oranjestad
Oranjestad2 stopsC$ 610
Nassau
Nassau1 stopC$ 453
Pointe-à-Pitre
Pointe-à-Pitre1 stopC$ 958
Simpson Bay
Simpson Bay2 stopsC$ 675
Fort-de-France
Fort-de-France1 stopC$ 1,184
Bridgetown
Bridgetown1 stopC$ 687
Puerto Plata
Puerto PlatadirectC$ 512
Willemstad
Willemstad2 stopsC$ 667
Port of Spain
Port of Spain2 stopsC$ 733
Providenciales
Providenciales1 stopC$ 667
George Town
George Town2 stopsC$ 583
St. George's
St. George's2 stopsC$ 914
Santo Domingo
Santo Domingo2 stopsC$ 855
Punta Cana
Punta Cana2 stopsC$ 502
Montego Bay
Montego Bay2 stopsC$ 442
Kingston
Kingston1 stopC$ 763
Oranjestad
Oranjestad2 stopsC$ 610
Nassau
Nassau1 stopC$ 453
Pointe-à-Pitre
Pointe-à-Pitre1 stopC$ 958
Simpson Bay
Simpson Bay2 stopsC$ 675
Fort-de-France
Fort-de-France1 stopC$ 1,184
Bridgetown
Bridgetown1 stopC$ 687
Puerto Plata
Puerto PlatadirectC$ 512
Willemstad
Willemstad2 stopsC$ 667
Port of Spain
Port of Spain2 stopsC$ 733
Providenciales
Providenciales1 stopC$ 667
George Town
George Town2 stopsC$ 583
St. George's
St. George's2 stopsC$ 914
Santo Domingo
Santo Domingo2 stopsC$ 855

Cheap Flights from Calgary to Caribbean Islands

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

Sat, 20 Jun - Tue, 23 Jun
WestJet Logo
11:45 p.m. - 6:30 p.m.
YYC
-
MBJ
17h 45m
2 stops
WestJet Logo
12:45 p.m. - 7:15 a.m.
MBJ
-
YYC
19h 30m
2 stops
C$ 442WestJet
Mon, 22 Jun - Mon, 6 Jul
WestJet Logo
8:40 p.m. - 11:45 a.m.
YYC
-
MBJ
14h 05m
2 stops
WestJet Logo
1:50 p.m. - 10:20 p.m.
MBJ
-
YYC
33h 30m
2 stops
C$ 443WestJet
Thu, 16 Apr - Thu, 23 Apr
Multiple Airlines Logo
6:30 a.m. - 7:25 p.m.
YYC
-
NAS
10h 55m
1 stop
Multiple Airlines Logo
3:15 p.m. - 11:22 p.m.
NAS
-
YYC
10h 07m
1 stop
C$ 453Multiple Airlines
Sat, 2 May - Sat, 23 May
United Airlines Logo
6:00 a.m. - 3:30 p.m.
YYC
-
PUJ
31h 30m
2 stops
United Airlines Logo
4:00 p.m. - 9:48 p.m.
PUJ
-
YYC
31h 48m
2 stops
C$ 502United Airlines
Mon, 20 Apr - Mon, 27 Apr
United Airlines Logo
1:53 p.m. - 1:47 p.m.
YYC
-
NAS
21h 54m
1 stop
United Airlines Logo
2:53 p.m. - 1:53 p.m.
NAS
-
YYC
49h 00m
2 stops
C$ 508United Airlines
Mon, 13 Apr - Thu, 16 Apr
Air Canada Logo
3:25 p.m. - 11:10 a.m.
YYC
-
GCM
18h 45m
1 stop
Air Canada Logo
11:55 a.m. - 12:23 a.m.
GCM
-
YYC
13h 28m
1 stop
C$ 634Air Canada
Thu, 16 Apr - Fri, 24 Apr
Air Canada Logo
6:00 a.m. - 5:25 p.m.
YYC
-
PLS
9h 25m
1 stop
Air Canada Logo
1:20 p.m. - 8:28 a.m.
PLS
-
YYC
21h 08m
1 stop
C$ 667Air Canada
Sun, 19 Apr - Thu, 30 Apr
Multiple Airlines Logo
10:35 a.m. - 12:33 p.m.
YYC
-
SJU
23h 58m
1 stop
Multiple Airlines Logo
12:57 p.m. - 3:44 p.m.
SJU
-
YYC
28h 47m
2 stops
C$ 701Multiple Airlines
Thu, 16 Apr - Thu, 23 Apr
American Airlines Logo
12:45 p.m. - 2:18 p.m.
YYC
-
GND
23h 33m
2 stops
American Airlines Logo
3:18 p.m. - 11:43 a.m.
GND
-
YYC
22h 25m
2 stops
C$ 914American Airlines
Thu, 9 Apr - Thu, 16 Apr
American Airlines Logo
6:45 a.m. - 2:18 p.m.
YYC
-
GND
29h 33m
2 stops
American Airlines Logo
3:18 p.m. - 11:43 a.m.
GND
-
YYC
22h 25m
2 stops
C$ 1,265American Airlines
Booking Insights

KAYAK's insights & trends for Calgary to Caribbean Islands flights

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

What is the cheapest Calgary to Caribbean Islands flight route?

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

The cheapest ticket to Caribbean Islands from Calgary found in the last 72 hours was to Montego Bay, at C$ 221 round-trip. The most popular route is from Calgary (YYC) to Nassau (NAS), and the cheapest round-trip airline ticket found on this route in the last 72 hours was C$ 243.

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

The average price for all round-trip flights from Calgary to Caribbean Islands 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 Islands is generally at night, when round-trip flights cost C$ 783 on average. The most expensive time of day to fly to Caribbean Islands is generally at night, which is peak travel time and where the average cost of a ticket is C$ 783.

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

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$ 643, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Calgary to Caribbean Islands, 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 Islands is September, when tickets cost C$ 586 (return) on average. On the other hand, the most expensive months are February and November, when the average cost of round-trip tickets is C$ 820 and C$ 811 respectively.

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

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 Islands, 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 the flight from Calgary to Caribbean Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.

Good to know

Low seasonOctober
Cheapest flightC$ 209
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly (5% more expensive on average)
Flight from Calgary to Montego Bay

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

Insights shared by verified travellers who flew the route from Calgary to Caribbean Islands 
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 Islands flights

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

    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 Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Calgary to Caribbean Islands 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 Islands?

    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 Islands 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 Islands?

    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 Islands 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 Islands

 
See real verified KAYAK customer reviews for airlines flying from Calgary to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Calgary to Caribbean Islands? 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.
7.7
Air TransatOverall score based on 521 reviews
7.3Comfort
6.8Food
7.9Boarding
8.5Crew
7.0Entertainment
Airline reviews

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.

4.0 OkayMarcel, Mar 2026
YUL - LIS
Read more Air Transat reviews

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.

I was very nice to arrive earlier than scheduled. Very much appreciated. No issues with flight. All was good.

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 crew and entertaining Captain. Seats were not what we had expected based on my booking but things worked out in the end. Of course, like all airlines these days not enough leg or elbow room.

The entertainment system was down; food by purchase only; several people did not receive their luggage. No one answers at the local office or online about the luggage.

The Turkish was good . I had a problem with air Transat terrible experience for me

I did not like I have been charged for my carry on

Onward flight was okay. return from Lisbon was poor as we missed our flight due to a long line at the passport control. Air Transat made no effort to accommodate us even though we were at the passport control 40 minutes prior to the departure.

It was very good but no tv but the experience was great

Hopped on time for the flight only to get deplaned and delayed another 2.5 hours.

Given I (and I’m assuming most people) have both carry in and a personal item included in their fare, I find it very unfair that on neither of my flights I was able to use the overhead for my small backpack because they were completely rammed with luggage, people personal items, jackets, hats and other items. So the only item I brought in had to be stuffed under my seat while they had their leg room and sat comfortable with all of their items in the overhead. This has to stop because I was uncomfortable on both flights when I only had one smaller item that could not be checked due to its contents (medication etc). Plenty of people could have checked theirs but chose not to and then took up the space allotment for 2 people.

Flight attendants had a little attitude. Food tastes no good.

From pre boarding to flight attendant, crew and baggage handler, excellent. Didn’t lost my luggage like West jet.

Very poor. The flight was delayed from Toronto because some forget to do there job . I got to my connecting gate in San Francisco 10 minutes before the departure.but this didn’t let me board even though the flight was still there for an other 30 minutes. The the gentleman at the unite airline desk told me that they usually wait for passengers but air Canada called and told them not to we I been rerouted to Manila instead of Hong Kong . In San Francisco they mad me check in my carryon bag . I was told the it will directly go yo ho chi minn cuyt but I was told that by the Vietnams airline desk that’s not there I’m 10 hours behind my scheduled flight and looks like I I’m going without baggage. I don’t have a chance of catching ..

It was great. There were some issues prior to takeoff. The weather was poor so we had to go through deicing, and we were delayed a bit by the pilots' concern about one of the engines, but that's aviation. The pilots handled everything with aplomb, and kept us apprised

Reliable, nice crew, I fly often on that flight and I like it all.

l really enjoy very much the flight was very pleasant

The Sears in the 800s are not too good perfect Airbus why cant the new 737 fix that

Quick and seamless boarding. No entertainment but fast Starlink wifi for this short trip and the staff was really friendly.

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.

Everything was great until we had to get our bags. The bags came out in several different batches over 90 minutes after we landed maybe more we got our bags. So much for the old West Jet where they promised bags in 20 minutes. I Next time I will pack lighter and go with a carry-on.

The flight was full and good as could be expected. We arrived early which is always a good thing.

Not sure what happened, but for some reason we had to sit on the plane for an extra 10 minutes once we arrived in Abbotsford. Obviously, it was an engine issue.

It was disappointing to see the huge number of people who were allowed to board who were claiming to either be disabled or needed extra time to board who practically ran to the gate as soon as boarding opened. One of the female flight attendants in the premium economy section refused to let a lady with an infant use the toilet next to row 9 to change her baby even though the path back to the rear toilets was blocked by staff and trolleys and said she would have to carry the baby to the toilet during the descent phase when turbulence was present. The passenger refused and the baby had to wait until landing. It would have been no problem to allow this infringement of weathers petty rules. The flight was also very cold due to a cold draft throughout the flight from the bulkhead ceiling which was not controllable.

Food good . No entertainment. Need to use wifi to access your own apps. Eg Amazon Prime, YouTube. They don't tell you unless you ask.

I was seated near a "stinky" person. That's not the fault of Westjet🙁😶‍🌫️

Horrible experience upon landing. Probably more due to DCA utter incompetence than AA.

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

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.

Waited for oxygen tanks for 30 minutes after boarding was complete.

The accessible bathroom should be visible to people in Economy class.

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 app doesn't update with a gate number even when you are on the plane. The in flight food is only snacks. The charging ports on the seats are old, only for USB A when most devices today use USB C. This should be made known to customers.

We were upgraded to Business Class. So comfortable with great service and food options

The flight attendant use 1.5 hours to answer my call. My dirty food tray was unattended.

Original flight was canceled and rescheduled for the next day. Cancelation notice was sent in the middle of the night (only saw it in the morning), leaving no room to find other options. No offers to reimburse for the extra expenses or compensations. My flight to Rio on 12/12 was also delayed for 16 hours. This seems to be the new normal for AA.

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.

They canceled my flight, I had to rent a car, drive 14 hours. They tell to go on line for a refund, but only offer $24 for a $210 flight and you can’t get hold of anybody by phone and no help from staff at the airport.

I wish to travel with Air Canada for my next trip

They were very attentive, polite, professional and great customer service skills.

Business class was not worth the extra charge. Overpriced for slightly larger seat. Nothing special. Small older plane.

Pros: The airplane was new and had in-flight entertainment (tablet behind seats) with new movies instead of watching on personal devices. Cons: the flight time was changed without informing us. When I booked the flight, the time was 13:30pm (also in the email confirmation). However, when I reached the airport, the time was conveniently changed to 14:55pm. When I asked at the counter, they said the flight always took off at this time. The booking was made by Air Canada, but the flight was operated by United.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports