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Cheap flights from Caribbean Islands to Calgary from C$ 341

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 17/11. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — YYC
10 Dec — 17 Dec1
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 10 November 2025.

Round-trip from

C$ 746

One-way from

C$ 341
United Airlines
  • United Airlines
  • 15/4-18/4
  • 4 total stops
  • 45h 00m total
  • Caribbean Islands to Calgary
Search Deals
United Airlines
  • United Airlines
  • 17/11
  • 2 total stops
  • 22h 25m 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 10 November 2025.

Tue 25/114:20 p.m.SXM - YYC
2 stops23h 02mWestJet
Sat 29/119:45 p.m.YYC - SXM
2 stops38h 36mWestJet
Deal found 10/11C$ 661
Thu 27/116:01 a.m.SJU - YYC
1 stop16h 08mMultiple Airlines
Sun 30/117:00 a.m.YYC - SJU
2 stops37h 44mMultiple Airlines
Deal found 10/11C$ 744
Wed 26/1111:55 a.m.SJU - YYC
3 stops31h 21mMultiple Airlines
Sun 30/1112:40 p.m.YYC - SJU
3 stops28h 47mMultiple Airlines
Deal found 10/11C$ 889
Sun 23/114:20 p.m.SXM - YYC
1 stop30h 15mMultiple Airlines
Thu 27/117:30 a.m.YYC - SXM
2 stops27h 45mMultiple Airlines
Deal found 8/11C$ 947
Sun 23/114:20 p.m.SXM - YYC
2 stops17h 37mWestJet
Thu 27/119:50 a.m.YYC - SXM
2 stops26h 31mWestJet
Deal found 8/11C$ 1,021
Tue 25/114:20 p.m.SXM - YYC
2 stops19h 57mMultiple Airlines
Fri 28/111:00 a.m.YYC - SXM
3 stops16h 45mMultiple Airlines
Deal found 10/11C$ 1,094
Wed 24/125:00 p.m.SXM - YYC
1 stop20h 39mAir Canada
Sun 28/125:35 a.m.YYC - SXM
1 stop31h 25mAir Canada
Deal found 9/11C$ 1,129
Sun 21/123:40 p.m.SXM - YYC
2 stops18h 39mAir Canada
Sun 28/125:35 a.m.YYC - SXM
1 stop31h 25mAir Canada
Deal found 8/11C$ 1,143
Wed 24/124:20 p.m.SXM - YYC
2 stops28h 00mWestJet
Sun 28/124:15 p.m.YYC - SXM
2 stops44h 06mWestJet
Deal found 9/11C$ 1,153
Sun 21/124:20 p.m.SXM - YYC
2 stops17h 45mWestJet
Sun 28/1211:40 p.m.YYC - SXM
2 stops36h 41mWestJet
Deal found 9/11C$ 1,176

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 10 November 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

Simpson BayCalgary

SXM - YYC

SXMYYC

Simpson Bay Princess Juliana

Tue 25/11

4:20 p.m.-12:22 p.m.

2 stops23h 02m

Calgary

Sat 29/11

9:45 p.m.-3:21 p.m.

2 stops38h 36m

C$ 661

San JuanCalgary

SJU - YYC

SJUYYC

San Juan Luis Munoz Marin Intl

Wed 4/3

3:55 a.m.-12:05 a.m.

2 stops23h 10m

Calgary

Sun 8/3

4:20 p.m.-12:34 p.m.

1 stop18h 14m

C$ 719

ProvidencialesCalgary

PLS - YYC

PLSYYC

Providenciales

Wed 15/4

5:15 p.m.-11:37 a.m.

2 stops20h 22m

Calgary

Sat 18/4

1:27 p.m.-4:05 p.m.

2 stops24h 38m

C$ 746

San JuanCalgary

SJU - YYC

SJUYYC

San Juan Luis Munoz Marin Intl

Tue 24/2

2:25 p.m.-9:53 p.m.

1 stop10h 28m

Calgary

Tue 3/3

6:15 a.m.-6:25 p.m.

1 stop9h 10m

C$ 753

San JuanCalgary

SJU - YYC

SJUYYC

San Juan Luis Munoz Marin Intl

Thu 27/11

6:01 a.m.-7:09 p.m.

1 stop16h 08m

Calgary

Sat 29/11

1:05 a.m.-10:56 a.m.

2 stops30h 51m

C$ 823

San JuanCalgary

SJU - YYC

SJUYYC

San Juan Luis Munoz Marin Intl

Tue 24/2

2:31 p.m.-11:42 a.m.

2 stops24h 11m

Calgary

Tue 3/3

12:45 p.m.-1:33 p.m.

2 stops21h 48m

C$ 831

San JuanCalgary

SJU - YYC

SJUYYC

San Juan Luis Munoz Marin Intl

Tue 10/2

8:20 a.m.-9:58 p.m.

2 stops16h 38m

Calgary

Mon 16/2

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

1 stop12h 30m

C$ 838

OranjestadCalgary

AUA - YYC

AUAYYC

Oranjestad Reina Beatrix

Tue 17/3

3:30 p.m.-8:17 p.m.

2 stops30h 47m

Calgary

Thu 19/3

3:00 p.m.-2:35 p.m.

2 stops21h 35m

C$ 928

ProvidencialesCalgary

PLS - YYC

PLSYYC

Providenciales

Wed 15/4

1:20 p.m.-7:11 a.m.

2 stops19h 51m

Calgary

Fri 17/4

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

1 stop14h 30m

C$ 941

Simpson BayCalgary

SXM - YYC

SXMYYC

Simpson Bay Princess Juliana

Sun 23/11

4:20 p.m.-7:35 p.m.

1 stop30h 15m

Calgary

Thu 27/11

7:30 a.m.-2:15 p.m.

2 stops27h 45m

C$ 947

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/11

Showing 1-10 of 26 results
1
2
3

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$ 281). 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 10 November 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 10 November 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
9,012 reviews
Check prices

Comfort

7.3

Food

6.6

Crew

8.1

Boarding

7.7

Overall

7.4

Entertainment

7.1

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
9,012 reviews
United Airlines
7.4
Good
9,012 reviews
Check prices

Comfort

7.3

Food

6.6

Crew

8.1

Boarding

7.7

Overall

7.4

Entertainment

7.1

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
3,156 reviews
United Airlines
7.4
Good
9,012 reviews
Check prices

Comfort

7.3

Food

6.6

Crew

8.1

Boarding

7.7

Overall

7.4

Entertainment

7.1

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
10,429 reviews
United Airlines
7.4
Good
9,012 reviews
Check prices

Comfort

7.3

Food

6.6

Crew

8.1

Boarding

7.7

Overall

7.4

Entertainment

7.1

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 19h 51m. The distance between Caribbean Islands and Calgary is about 4851 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$ 341), WestJet (C$ 619), and American Airlines (C$ 638).

  • 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, Port of Spain Piarco Intl - Calgary or Oranjestad Reina Beatrix - 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$ 281). 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
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 10 November 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 337AverageC$ 822FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 337AverageC$ 802FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 488AverageC$ 925FlexibilityNo 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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