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Cheap flights from Caribbean Islands to Calgary from C$ 280

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 18/5. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — YYC
30 Mar — 6 Apr1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Caribbean Islands to Calgary

Enter your travel dates to find the best prices.

Cheapest flights from Caribbean Islands to Calgary
Explore the most affordable flight options available from Caribbean Islands to Calgary. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 28 February 2026.

Thu 14/53:18 p.m.
SJU
-
YYC
2 stops31h 07m
Multiple Airlines
Sun 17/512:30 a.m.
YYC
-
SJU
1 stop11h 38m
Multiple Airlines
Deal found 26/2C$ 621
Tue 12/53:08 a.m.
SJU
-
YYC
2 stops20h 47m
Multiple Airlines
Wed 13/512:30 a.m.
YYC
-
SJU
1 stop11h 38m
Multiple Airlines
Deal found 26/2C$ 809
Sun 12/71:25 a.m.
POS
-
YYC
2 stops22h 35m
Multiple Airlines
Tue 21/712:30 p.m.
YYC
-
POS
2 stops33h 45m
Multiple Airlines
Deal found 25/2C$ 817
Tue 5/51:35 p.m.
SXM
-
YYC
2 stops23h 57m
United Airlines
Wed 27/512:28 p.m.
YYC
-
SXM
2 stops22h 05m
United Airlines
Deal found 24/2C$ 830
Wed 13/56:45 a.m.
SJU
-
YYC
1 stop16h 59m
American Airlines
Thu 14/56:45 a.m.
YYC
-
SJU
1 stop19h 47m
American Airlines
Deal found 26/2C$ 834
Thu 14/54:30 p.m.
SJU
-
YYC
2 stops22h 29m
American Airlines
Mon 18/512:45 p.m.
YYC
-
SJU
2 stops18h 28m
American Airlines
Deal found 26/2C$ 840
Thu 7/52:55 p.m.
SXM
-
YYC
2 stops22h 52m
Air Canada
Mon 1/66:45 a.m.
YYC
-
SXM
1 stop29h 58m
Air Canada
Deal found 24/2C$ 845
Thu 7/52:40 p.m.
SXM
-
YYC
1 stop19h 55m
WestJet
Wed 27/57:10 p.m.
YYC
-
SXM
1 stop16h 40m
WestJet
Deal found 24/2C$ 848
Sat 9/53:50 p.m.
SXM
-
YYC
2 stops23h 04m
United Airlines
Fri 29/56:00 a.m.
YYC
-
SXM
2 stops28h 33m
United Airlines
Deal found 24/2C$ 849
Wed 6/51:35 p.m.
SXM
-
YYC
1 stop29h 55m
Air Canada
Fri 29/56:05 p.m.
YYC
-
SXM
1 stop17h 55m
Air Canada
Deal found 24/2C$ 852
Thu 7/52:55 p.m.
SXM
-
YYC
2 stops19h 33m
Air Canada
Sun 31/512:40 p.m.
YYC
-
SXM
2 stops24h 03m
Air Canada
Deal found 24/2C$ 856
Mon 4/51:35 p.m.
SXM
-
YYC
2 stops34h 13m
United Airlines
Thu 28/512:28 p.m.
YYC
-
SXM
2 stops22h 05m
United Airlines
Deal found 24/2C$ 910

Find flight deals from Caribbean Islands to Calgary

Keep the following information in mind while searching for Caribbean Islands to Calgary flight deals. Data was last updated 28 February 2026.

Round-trip from

C$ 621

One-way from

C$ 280
14/5-17/5
  • 14/5-17/5
  • 3 total stops
  • 42h 45m total
  • Caribbean Islands to Calgary
Search Deals
18/5
  • 18/5
  • 3 total stops
  • 58h 45m total
  • Caribbean Islands to Calgary
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean Islands to Calgary 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 28 February 2026.
Use the filters below to find and compare flights from Caribbean Islands to Calgary that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

San JuanCalgary

SJU - YYC

SJUYYC

San Juan Luis Munoz Marin Intl

Thu 14/5

3:18 p.m.-8:25 p.m.

2 stops31h 07m

Calgary

Sun 17/5

12:30 a.m.-2:08 p.m.

1 stop11h 38m

C$ 621

Simpson BayCalgary

SXM - YYC

SXMYYC

Simpson Bay Princess Juliana

Tue 5/5

1:35 p.m.-11:32 a.m.

2 stops23h 57m

Calgary

Sun 31/5

8:30 a.m.-12:33 p.m.

2 stops26h 03m

C$ 830

Port of SpainCalgary

POS - YYC

POSYYC

Port of Spain Piarco Intl

Sun 12/7

1:25 a.m.-10:00 p.m.

2 stops22h 35m

Calgary

Tue 21/7

8:05 p.m.-12:15 a.m.

1 stop26h 10m

C$ 880

Simpson BayCalgary

SXM - YYC

SXMYYC

Simpson Bay Princess Juliana

Mon 4/5

1:35 p.m.-1:53 p.m.

2 stops26h 18m

Calgary

Sat 30/5

8:30 a.m.-12:33 p.m.

2 stops26h 03m

C$ 910

Simpson BayCalgary

SXM - YYC

SXMYYC

Simpson Bay Princess Juliana

Mon 4/5

1:35 p.m.-9:48 p.m.

2 stops34h 13m

Calgary

Thu 28/5

12:28 p.m.-12:33 p.m.

2 stops22h 05m

C$ 910

Port of SpainCalgary

POS - YYC

POSYYC

Port of Spain Piarco Intl

Sun 12/7

1:25 a.m.-11:36 a.m.

1 stop12h 11m

Calgary

Tue 21/7

8:05 p.m.-12:15 a.m.

1 stop26h 10m

C$ 923

Simpson BayCalgary

SXM - YYC

SXMYYC

Simpson Bay Princess Juliana

Fri 8/5

1:35 p.m.-12:54 p.m.

2 stops25h 19m

Calgary

Sun 31/5

8:30 a.m.-12:33 p.m.

2 stops26h 03m

C$ 927

Simpson BayCalgary

SXM - YYC

SXMYYC

Simpson Bay Princess Juliana

Fri 8/5

1:35 p.m.-12:54 p.m.

2 stops25h 19m

Calgary

Mon 1/6

12:28 p.m.-12:33 p.m.

2 stops22h 05m

C$ 927

San JuanCalgary

SJU - YYC

SJUYYC

San Juan Luis Munoz Marin Intl

Fri 27/3

8:47 p.m.-5:59 p.m.

1 stop23h 12m

Calgary

Fri 3/4

8:55 a.m.-9:53 a.m.

2 stops46h 58m

C$ 944

Simpson BayCalgary

SXM - YYC

SXMYYC

Simpson Bay Princess Juliana

Wed 6/5

1:35 p.m.-11:32 a.m.

2 stops23h 57m

Calgary

Mon 1/6

6:00 a.m.-12:33 p.m.

2 stops28h 33m

C$ 1,024

Flights are sorted by cheapest round-trip flights first.

Deals found on 24/2

Showing 1-10 of 41 resultsSorted by cheapest first
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Best time to book a flight from Caribbean Islands to Calgary

Have a flexible travel schedule? Discover the best time to fly to Calgary from Caribbean Islands 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 Caribbean Islands to Calgary

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

Currently, August is the cheapest month in which you can book a flight from Caribbean Islands to Calgary (average of C$ 340). Flying from Caribbean Islands to Calgary in November is currently the most expensive (average of C$ 628). 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.

What is the cheapest time of day to fly from EPX to YYC?

Find hourly flight availability from Caribbean Islands to Calgary. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 28 February 2026.

When flying from Caribbean Islands to Calgary, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Calgary

Get insights into the airlines that provide service to Calgary. 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 Calgary. Reviews last updated 28 February 2026.
Get a feel of what it's like to fly with United Airlines,WestJet, andAir Canada from Caribbean Islands to Calgary by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,363 reviews
Check prices

Crew

8.1

Comfort

7.3

Overall

7.4

Boarding

7.7

Entertainment

7.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!
United Airlines
7.4
Good
9,363 reviews
United Airlines
7.4
Good
9,363 reviews
Check prices

Crew

8.1

Comfort

7.3

Overall

7.4

Boarding

7.7

Entertainment

7.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!
WestJet
7.2
Good
3,276 reviews
United Airlines
7.4
Good
9,363 reviews
Check prices

Crew

8.1

Comfort

7.3

Overall

7.4

Boarding

7.7

Entertainment

7.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!
Air Canada
7.1
Good
10,757 reviews
United Airlines
7.4
Good
9,363 reviews
Check prices

Crew

8.1

Comfort

7.3

Overall

7.4

Boarding

7.7

Entertainment

7.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!

Related info for your journey

Find useful and relevant information for your journey from Caribbean Islands to Calgary. 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 into for flights to Calgary from Caribbean Islands?

    Located just 9.3 km from the city centre, Calgary (YYC) is the airport most travelers will use when flying to Calgary from Caribbean Islands.

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

    Departing from Caribbean Islands to Calgary will take you 12h 11m. The distance between Caribbean Islands and Calgary is about 6540 km. Both multi-stop and direct flights can be found to your destination and back.

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

    The cheapest airlines for a one-way flight from Caribbean Islands to Calgary are United Airlines (C$ 226), WestJet (C$ 250), and Air Canada (C$ 284).

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

    When deciding which route to take from Caribbean Islands to Calgary consider San Juan Luis Munoz Marin Intl - Calgary, Oranjestad Reina Beatrix - Calgary or Port of Spain Piarco Intl - Calgary as they are the most popular.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Caribbean Islands to Calgary 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 Caribbean Islands to Calgary?

    Currently, August is the cheapest month in which you can book a flight from Caribbean Islands to Calgary (average of C$ 340). Flying from Caribbean Islands to Calgary in November is currently the most expensive (average of C$ 628). 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

Travelling to a place near Calgary?

Book flights to Calgary if you plan to visit one of these locations
Canmore
Radium Hot Springs
Airdrie
Kananaskis
Drumheller

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Top 3 airlines flying from Caribbean Islands to Calgary

Discover the top 3 airlines that operate flights from Caribbean Islands to Calgary. 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 28 February 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 328AverageC$ 780FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 474AverageC$ 949FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 760AverageC$ 895FlexibilityNo cancel feeOn-time67%
Search Air Canada 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 Caribbean Islands to Calgary?

Cheapflights makes it easy to find Caribbean Islands to Calgary flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

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

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Caribbean Islands to Calgary.

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

Certainly. Search results for flights to Calgary from Caribbean Islands 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 Caribbean Islands to Calgary become cheaper?

Not ready to book yet? You can track prices for flights from Caribbean Islands to Calgary on Cheapflights with our Price Alert feature and get notified when better prices are available.

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