C$ 244 Find Cheap Flights from Calgary to Caribbean – Compare and Save

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Best Caribbean Flight Deals from Calgary

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana2 stopsC$ 456
Montego Bay
Montego BaydirectC$ 470
Kingston
Kingston1 stopC$ 702
Nassau
Nassau1 stopC$ 469
Oranjestad
Oranjestad1 stopC$ 560
Fort-de-France
Fort-de-France2 stopsC$ 787
Pointe-à-Pitre
Pointe-à-Pitre1 stopC$ 891
Simpson Bay
Simpson Bay2 stopsC$ 524
Willemstad
Willemstad2 stopsC$ 546
Bridgetown
Bridgetown2 stopsC$ 562
Puerto Plata
Puerto PlatadirectC$ 535
Port of Spain
Port of Spain2 stopsC$ 702
George Town
George Town2 stopsC$ 521
Providenciales
Providenciales2 stopsC$ 597
St. George's
St. George's1 stopC$ 805
Santo Domingo
Santo Domingo2 stopsC$ 845
Kingstown
Kingstown2 stopsC$ 1,017
Punta Cana
Punta Cana2 stopsC$ 456
Montego Bay
Montego BaydirectC$ 470
Kingston
Kingston1 stopC$ 702
Nassau
Nassau1 stopC$ 469
Oranjestad
Oranjestad1 stopC$ 560
Fort-de-France
Fort-de-France2 stopsC$ 787
Pointe-à-Pitre
Pointe-à-Pitre1 stopC$ 891
Simpson Bay
Simpson Bay2 stopsC$ 524
Willemstad
Willemstad2 stopsC$ 546
Bridgetown
Bridgetown2 stopsC$ 562
Puerto Plata
Puerto PlatadirectC$ 535
Port of Spain
Port of Spain2 stopsC$ 702
George Town
George Town2 stopsC$ 521
Providenciales
Providenciales2 stopsC$ 597
St. George's
St. George's1 stopC$ 805
Santo Domingo
Santo Domingo2 stopsC$ 845
Kingstown
Kingstown2 stopsC$ 1,017
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?

The cheapest ticket to Caribbean from Calgary found in the last 5 days was to Montego Bay, at C$ 630 round-trip. The most popular route is from Calgary (YYC) to Punta Cana (PUJ), and the cheapest round-trip airline ticket found on this route in the last 5 days was C$ 718.

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

The cheapest time of day to fly to Caribbean is generally at night, when round-trip flights cost C$ 857 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$ 857.

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

No, with an average price for the route of C$ 733, prices are generally cheapest when you fly direct.

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

The cheapest month for flights from Calgary to Caribbean is January, when tickets cost C$ 738 (return) on average. On the other hand, the most expensive months are July and February, when the average cost of round-trip tickets is C$ 904 and C$ 885 respectively.

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

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 26% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Good to know

Low season

May

Cheapest flight

C$ 244
Best time to beat the crowds but there is an average 1% increase in price.
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-Feb 2026
Buy food to take on board the plane
Verified travelerFlew with WestJet-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 573 reviews
6.8Food
8.5Crew
7.3Comfort
8.0Boarding
7.1Entertainment
Airline reviews

Flight was really good, with no middle section on an A321neo for an international flight, from Ottawa directly to London. Staff was friendly. The food was okay, and entertainment amenities could be better.

10.0 ExcellentTony, Aug 2026
Read more Air Transat reviews

Flight was really good, with no middle section on an A321neo for an international flight, from Ottawa directly to London. Staff was friendly. The food was okay, and entertainment amenities could be better.

The flight was terrible based off the temperature in the plane and the air smelled so stale and gross. I have never wanted to hosed lore in my life after I got off. The food was disgusting and seemingly low quality. The staff was friendly. The bathrooms were so gross after a couple of hours. I will definitely never book with them again.

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.

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.

I'm so frustrated my flight was canceled they give flight on August 5 which is not sure. Its was big mistake I booked my ticket from kayak.

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

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