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Cheap flights from Calgary to Caribbean Islands from C$ 269

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 19/9. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — SJU
24 Aug — 31 Aug1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Calgary to Caribbean Islands

Enter your travel dates to find the best prices.

Cheapest flights from Calgary to Caribbean Islands
Explore the most affordable flight options available from Calgary to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 25 July 2026.

Sat 14/1110:00 a.m.
YYC
-
MBJ
Nonstop5h 24m
WestJet
Tue 24/112:50 p.m.
MBJ
-
YYC
Nonstop8h 08m
WestJet
Deal found 23/7C$ 485
Tue 17/1110:00 a.m.
YYC
-
MBJ
Nonstop5h 24m
WestJet
Tue 1/122:50 p.m.
MBJ
-
YYC
Nonstop8h 08m
WestJet
Deal found 20/7C$ 541
Tue 27/106:00 a.m.
YYC
-
SJU
1 stop9h 25m
United Airlines
Wed 4/117:40 a.m.
SJU
-
YYC
2 stops17h 13m
United Airlines
Deal found 25/7C$ 545
Sun 1/116:35 p.m.
YYC
-
MBJ
2 stops17h 19m
WestJet
Wed 16/125:35 p.m.
MBJ
-
YYC
1 stop16h 10m
WestJet
Deal found 24/7C$ 545
Sat 14/1110:00 a.m.
YYC
-
MBJ
Nonstop5h 24m
WestJet
Sat 28/113:25 p.m.
MBJ
-
YYC
1 stop29h 05m
WestJet
Deal found 23/7C$ 565
Sat 5/128:45 a.m.
YYC
-
PUJ
1 stop8h 00m
WestJet
Sat 12/128:45 p.m.
PUJ
-
YYC
1 stop16h 25m
WestJet
Deal found 25/7C$ 576
Thu 12/1112:05 a.m.
YYC
-
PUJ
Nonstop5h 52m
WestJet
Fri 20/1111:00 a.m.
PUJ
-
YYC
Nonstop9h 00m
WestJet
Deal found 24/7C$ 577
Fri 4/126:10 p.m.
YYC
-
SJU
1 stop17h 30m
Air Canada
Sat 12/123:35 p.m.
SJU
-
YYC
1 stop12h 15m
Air Canada
Deal found 23/7C$ 580
Thu 12/111:45 a.m.
YYC
-
PUJ
1 stop14h 00m
Air Canada
Fri 20/1112:35 p.m.
PUJ
-
YYC
1 stop15h 15m
Air Canada
Deal found 24/7C$ 583
Tue 1/121:45 a.m.
YYC
-
PUJ
1 stop14h 00m
Air Canada
Wed 9/127:45 p.m.
PUJ
-
YYC
1 stop24h 30m
Air Canada
Deal found 25/7C$ 585
Fri 4/126:10 p.m.
YYC
-
SJU
1 stop17h 30m
Air Canada
Fri 11/122:25 p.m.
SJU
-
YYC
2 stops24h 30m
Air Canada
Deal found 23/7C$ 586
Fri 27/119:50 p.m.
YYC
-
PUJ
1 stop18h 55m
WestJet
Fri 4/1211:00 a.m.
PUJ
-
YYC
Nonstop9h 00m
WestJet
Deal found 24/7C$ 589

Find flight deals from Calgary to Caribbean Islands

Keep the following information in mind while searching for Calgary to Caribbean Islands flight deals. Data was last updated 25 July 2026.

Round-trip from

C$ 485

One-way from

C$ 269

Popular in

August

Cheapest in

June

Average price

C$ 935
WestJet
  • WestJet
  • 14/11-24/11
  • Nonstop
  • 13h 32m total
  • Calgary to Caribbean Islands
Search Deals
WestJet
  • WestJet
  • 19/9
  • 2 total stops
  • 15h 40m total
  • Calgary to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 6% potential increase in price (C$ 82 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Calgary to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 25 July 2026.
Use the filters below to find and compare flights from Calgary to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

CalgarySan Juan

YYC - SJU

YYCSJU

Calgary

Tue 27/10

6:00 a.m.-11:36 p.m.

2 stops15h 36m

San Juan Luis Munoz Marin Intl

Wed 4/11

7:40 a.m.-10:53 p.m.

2 stops17h 13m

C$ 545

CalgarySan Juan

YYC - SJU

YYCSJU

Calgary

Tue 19/1

6:00 a.m.-5:25 p.m.

1 stop9h 25m

San Juan Luis Munoz Marin Intl

Fri 29/1

2:25 p.m.-8:45 a.m.

2 stops20h 20m

C$ 575

CalgaryNassau

YYC - NAS

YYCNAS

Calgary

Sat 10/10

11:50 p.m.-11:10 a.m.

1 stop9h 20m

Nassau Intl

Sat 17/10

12:00 p.m.-8:00 a.m.

2 stops22h 00m

C$ 608

CalgarySimpson Bay

YYC - SXM

YYCSXM

Calgary

Sat 5/9

11:25 a.m.-2:20 p.m.

2 stops24h 55m

Simpson Bay Princess Juliana

Sun 20/9

3:20 p.m.-8:20 a.m.

1 stop19h 00m

C$ 608
Quickest round-trip

CalgarySan Juan

YYC - SJU

YYCSJU

Calgary

Tue 20/10

6:00 a.m.-5:38 p.m.

1 stop9h 38m

San Juan Luis Munoz Marin Intl

Wed 21/10

1:00 a.m.-11:28 a.m.

2 stops12h 28m

C$ 624

CalgaryNassau

YYC - NAS

YYCNAS

Calgary

Sat 14/11

1:40 p.m.-9:25 a.m.

1 stop18h 45m

Nassau Intl

Sun 22/11

4:50 p.m.-6:20 p.m.

2 stops26h 30m

C$ 627

CalgaryNassau

YYC - NAS

YYCNAS

Calgary

Wed 11/11

6:35 p.m.-9:25 a.m.

1 stop13h 50m

Nassau Intl

Sun 15/11

8:30 p.m.-6:20 p.m.

2 stops22h 50m

C$ 628

CalgaryMontego Bay

YYC - MBJ

YYCMBJ

Calgary

Thu 14/1

2:06 p.m.-3:24 p.m.

2 stops48h 18m

Montego Bay Sangster Intl

Fri 22/1

2:48 p.m.-12:54 p.m.

1 stop23h 06m

C$ 631

CalgaryMontego Bay

YYC - MBJ

YYCMBJ

Calgary

Fri 28/8

6:00 a.m.-1:30 p.m.

2 stops30h 30m

Montego Bay Sangster Intl

Fri 2/10

12:52 p.m.-11:28 a.m.

2 stops23h 36m

C$ 631

CalgaryMontego Bay

YYC - MBJ

YYCMBJ

Calgary

Mon 26/10

6:00 a.m.-1:14 p.m.

2 stops30h 14m

Montego Bay Sangster Intl

Sat 31/10

4:21 p.m.-12:35 p.m.

2 stops21h 14m

C$ 631

Flights are sorted by cheapest round-trip flights first.

Deals found on 22/7

Showing 1-10 of 60 resultsSorted by cheapest first
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6

Best time to book a flight from Calgary to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Calgary with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Calgary to Caribbean Islands

What is the cheapest month to book a flight from Calgary to Caribbean Islands?

Currently, September is the cheapest month in which you can book a flight from Calgary to Caribbean Islands (average of C$ 724). Flying from Calgary to Caribbean Islands in July is currently the most expensive (average of C$ 941). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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

The best time to book flights from Calgary to Caribbean Islands is 58 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean Islands. Reviews last updated 25 July 2026.
Read through reviews of airlines operating flights from Calgary to Caribbean Islands, such as Air Transat,United Airlines, andWestJet. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Air Transat
7.8
Good
568 reviews
Check prices

Entertainment

7.1

Overall

7.8

Comfort

7.3

Crew

8.5

Boarding

8.0

Food

6.8

Reviews

1 / 20
8.0
Excellent

Paul,Jul 2026

YUL - LGW

Had to bus to the plane which made priority boarding at the back of the bus
Air Transat
7.8
Good
568 reviews
Air Transat
7.8
Good
568 reviews
Check prices

Entertainment

7.1

Overall

7.8

Comfort

7.3

Crew

8.5

Boarding

8.0

Food

6.8

Reviews

1 / 20
8.0
Excellent

Paul,Jul 2026

YUL - LGW

Had to bus to the plane which made priority boarding at the back of the bus
United Airlines
7.4
Good
10,038 reviews
Air Transat
7.8
Good
568 reviews
Check prices

Entertainment

7.1

Overall

7.8

Comfort

7.3

Crew

8.5

Boarding

8.0

Food

6.8

Reviews

1 / 20
8.0
Excellent

Paul,Jul 2026

YUL - LGW

Had to bus to the plane which made priority boarding at the back of the bus
WestJet
7.2
Good
3,415 reviews
Air Transat
7.8
Good
568 reviews
Check prices

Entertainment

7.1

Overall

7.8

Comfort

7.3

Crew

8.5

Boarding

8.0

Food

6.8

Reviews

1 / 20
8.0
Excellent

Paul,Jul 2026

YUL - LGW

Had to bus to the plane which made priority boarding at the back of the bus
American Airlines
7.1
Good
11,850 reviews
Air Transat
7.8
Good
568 reviews
Check prices

Entertainment

7.1

Overall

7.8

Comfort

7.3

Crew

8.5

Boarding

8.0

Food

6.8

Reviews

1 / 20
8.0
Excellent

Paul,Jul 2026

YUL - LGW

Had to bus to the plane which made priority boarding at the back of the bus
Air Canada
7.1
Good
11,386 reviews
Air Transat
7.8
Good
568 reviews
Check prices

Entertainment

7.1

Overall

7.8

Comfort

7.3

Crew

8.5

Boarding

8.0

Food

6.8

Reviews

1 / 20
8.0
Excellent

Paul,Jul 2026

YUL - LGW

Had to bus to the plane which made priority boarding at the back of the bus

Related info for your journey

Find useful and relevant information for your journey from Calgary to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Calgary to Caribbean Islands?

    If you book a flight to Caribbean Islands from Calgary, you will be flying from Calgary, which is the city’s only airport. Calgary (YYC) is located 9.3 km from the centre of Calgary.

  • How long is the flight from Calgary to Caribbean Islands?

    For as low as C$ 608, United Airlines can have you in Caribbean Islands from Calgary in 9h 20m. The distance between Calgary and Caribbean Islands is about 4239 km. Both multi-stop and direct flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Calgary to Caribbean Islands one-way?

    For one-way options, check prices for WestJet. According to our data, you can fly for as low as C$ 162. Users have also found prices from C$ 251 and C$ 321 on United Airlines and Air Canada, respectively.

  • What are the most popular routes from Calgary to Caribbean Islands?

    While some choose either Calgary - Punta Cana or Calgary - Montego Bay Sangster Intl, Calgary - Oranjestad Reina Beatrix is the most popular route from Calgary to Caribbean Islands.

  • Can I find deals for flights from Calgary to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Calgary to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Calgary to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Calgary to Caribbean Islands.

  • Can I find deals for business class flights from Calgary to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Calgary to Caribbean Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Calgary to Caribbean Islands?

    Currently, September is the cheapest month in which you can book a flight from Calgary to Caribbean Islands (average of C$ 724). Flying from Calgary to Caribbean Islands in July is currently the most expensive (average of C$ 941). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Top 5 airlines flying from Calgary to Caribbean Islands

Discover the top 5 airlines that operate flights from Calgary to Caribbean Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 25 July 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 303AverageC$ 837FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 439AverageC$ 875FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 518AverageC$ 1,104FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Air TransatCheapestC$ 575AverageC$ 1,290FlexibilityNo cancel feeOn-time50%
Search Air Transat flights
American AirlinesCheapestC$ 630AverageC$ 858FlexibilityNo cancel feeOn-time71%
Search American Airlines flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Calgary to Caribbean Islands?

When you search for this flight from Calgary to Caribbean Islands, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

Why should you use Cheapflights to find cheap flight tickets from Calgary to Caribbean Islands?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Caribbean Islands from Calgary.

Can Cheapflights find flights from Calgary to Caribbean Islands with no change fees?

Certainly. Search results for flights to Caribbean Islands from Calgary shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Calgary to Caribbean Islands become cheaper?

Of course! You can now track prices for flights from Calgary to Caribbean Islands and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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