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Cheap flights from Caribbean Islands to Calgary from C$ 274

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 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — YYC
27 nov. — 4 dic.1
1 adult
1 adult, Economy, 0 bags

Cheap 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 octubre 2025.

Round-trip from

C$ 694

One-way from

C$ 274
10/2-16/2
  • 10/2-16/2
  • 3 total stops
  • 33h 05m total
  • Caribbean Islands to Calgary
Search Deals
9/11
  • 9/11
  • 2 total stops
  • 25h 12m total
  • Caribbean Islands to Calgary
Search Deals

Find 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 octubre 2025.

mar. 30/124:20 p.m.SXM - YYC
2 stops18h 22mWestJet
dom. 4/18:15 p.m.YYC - SXM
2 stops40h 06mWestJet
Deal found 28/10C$ 1,007
dom. 21/124:20 p.m.SXM - YYC
2 stops28h 00mWestJet
dom. 28/1211:40 p.m.YYC - SXM
2 stops36h 41mWestJet
Deal found 27/10C$ 1,185
mar. 30/124:20 p.m.SXM - YYC
2 stops18h 22mMultiple Airlines
dom. 4/18:25 a.m.YYC - SXM
3 stops26h 50mMultiple Airlines
Deal found 25/10C$ 1,266
mar. 30/125:00 p.m.SXM - YYC
1 stop18h 43mAir Canada
dom. 4/13:25 p.m.YYC - SXM
1 stop21h 35mAir Canada
Deal found 26/10C$ 1,490
dom. 21/123:40 p.m.SXM - YYC
1 stop11h 04mAir Canada
dom. 28/123:25 p.m.YYC - SXM
1 stop21h 35mAir Canada
Deal found 27/10C$ 1,513
sáb. 20/125:00 p.m.SXM - YYC
1 stop18h 43mAir Canada
dom. 28/126:15 p.m.YYC - SXM
1 stop18h 45mAir Canada
Deal found 27/10C$ 1,522

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 octubre 2025.
Use the filters below to find and compare flights from Caribbean Islands to Calgary that are best for you.

Fly from

Caribbean Islands

Fly to

Calgary

Route

Depart

Return

Price

San JuanCalgary

SJU - YYC

SJUYYC

San Juan Luis Munoz Marin Intl

mar. 10/2

10:59 a.m.-7:09 p.m.

1 stop11h 10m

Calgary

lun. 16/2

9:00 a.m.-9:55 a.m.

2 stops21h 55m

C$ 694

Simpson BayCalgary

SXM - YYC

SXMYYC

Simpson Bay Princess Juliana

mar. 17/2

1:25 p.m.-12:05 a.m.

1 stop13h 40m

Calgary

dom. 1/3

8:20 a.m.-3:10 p.m.

2 stops27h 50m

C$ 799

San JuanCalgary

SJU - YYC

SJUYYC

San Juan Luis Munoz Marin Intl

mar. 10/2

6:00 a.m.-9:58 p.m.

2 stops18h 58m

Calgary

lun. 16/2

1:30 p.m.-5:00 a.m.

1 stop12h 30m

C$ 835

Simpson BayCalgary

SXM - YYC

SXMYYC

Simpson Bay Princess Juliana

mar. 17/2

1:25 p.m.-12:05 a.m.

1 stop13h 40m

Calgary

mar. 24/2

12:15 a.m.-3:17 p.m.

1 stop12h 02m

C$ 866

ProvidencialesCalgary

PLS - YYC

PLSYYC

Providenciales

mié. 15/4

3:55 p.m.-11:08 a.m.

2 stops21h 13m

Calgary

sáb. 18/4

1:13 p.m.-10:00 a.m.

2 stops18h 47m

C$ 867

OranjestadCalgary

AUA - YYC

AUAYYC

Oranjestad Reina Beatrix

mar. 17/3

3:30 p.m.-10:16 p.m.

2 stops32h 46m

Calgary

jue. 19/3

6:30 a.m.-2:35 p.m.

2 stops30h 05m

C$ 925

ProvidencialesCalgary

PLS - YYC

PLSYYC

Providenciales

mié. 15/4

1:20 p.m.-11:21 a.m.

2 stops24h 01m

Calgary

vie. 17/4

12:55 a.m.-5:25 p.m.

1 stop14h 30m

C$ 938

ProvidencialesCalgary

PLS - YYC

PLSYYC

Providenciales

mié. 15/4

2:35 p.m.-1:56 p.m.

2 stops25h 21m

Calgary

sáb. 18/4

2:00 p.m.-11:29 a.m.

2 stops19h 29m

C$ 979

Simpson BayCalgary

SXM - YYC

SXMYYC

Simpson Bay Princess Juliana

mar. 17/2

4:20 p.m.-7:36 a.m.

2 stops18h 16m

Calgary

mar. 3/3

3:00 p.m.-3:17 p.m.

2 stops21h 17m

C$ 986

Simpson BayCalgary

SXM - YYC

SXMYYC

Simpson Bay Princess Juliana

mié. 18/2

4:20 p.m.-3:58 p.m.

1 stop26h 38m

Calgary

mar. 3/3

7:35 p.m.-3:17 p.m.

2 stops16h 42m

C$ 986

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/10

Showing 1-10 of 49 results
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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, December is the cheapest month in which you can book a flight from Caribbean Islands to Calgary (average of C$ 298). Flying from Caribbean Islands to Calgary in March is currently the most expensive (average of C$ 757). 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 octubre 2025.

When flying from Caribbean Islands to Calgary, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 52% versus a flight in the afternoon.

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 octubre 2025.
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
9,001 reviews
Check prices

Boarding

7.7

Overall

7.4

Comfort

7.3

Food

6.6

Entertainment

7.1

Crew

8.1

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
9,001 reviews
United Airlines
7.4
Good
9,001 reviews
Check prices

Boarding

7.7

Overall

7.4

Comfort

7.3

Food

6.6

Entertainment

7.1

Crew

8.1

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
3,148 reviews
United Airlines
7.4
Good
9,001 reviews
Check prices

Boarding

7.7

Overall

7.4

Comfort

7.3

Food

6.6

Entertainment

7.1

Crew

8.1

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
10,371 reviews
United Airlines
7.4
Good
9,001 reviews
Check prices

Boarding

7.7

Overall

7.4

Comfort

7.3

Food

6.6

Entertainment

7.1

Crew

8.1

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 18h 58m. The distance between Caribbean Islands and Calgary is about 5541 km. Both multi-stop and direct flights can be found to your destination and back.

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

    When deciding which route to take from Caribbean Islands to Calgary consider Oranjestad Reina Beatrix - Calgary, Providenciales - 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, December is the cheapest month in which you can book a flight from Caribbean Islands to Calgary (average of C$ 298). Flying from Caribbean Islands to Calgary in March is currently the most expensive (average of C$ 757). 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
Drumheller
Kananaskis

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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 octubre 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 335AverageC$ 818FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 336AverageC$ 799FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 486AverageC$ 921FlexibilityNo cancel feeOn-time60%
Search WestJet 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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