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Cheap flights from Caribbean Islands to Calgary 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 22/4. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — YYC
10 Apr — 17 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 11 March 2026.

Thu 26/33:20 p.m.
SXM
-
YYC
2 stops17h 33m
Multiple Airlines
Mon 30/32:20 p.m.
YYC
-
SXM
1 stop21h 15m
Multiple Airlines
Deal found 10/3C$ 751
Sat 30/54:10 p.m.
SJU
-
YYC
1 stop26h 50m
Multiple Airlines
Fri 5/611:50 p.m.
YYC
-
SJU
2 stops22h 57m
Multiple Airlines
Deal found 7/3C$ 786
Sat 30/57:00 a.m.
SJU
-
YYC
2 stops18h 38m
American Airlines
Fri 5/66:15 a.m.
YYC
-
SJU
2 stops14h 30m
American Airlines
Deal found 7/3C$ 824
Wed 1/44:10 p.m.
AUA
-
YYC
2 stops21h 34m
American Airlines
Wed 8/412:45 p.m.
YYC
-
AUA
2 stops22h 45m
American Airlines
Deal found 10/3C$ 892
Thu 2/77:20 a.m.
SJU
-
YYC
2 stops18h 22m
American Airlines
Tue 7/76:15 a.m.
YYC
-
SJU
1 stop14h 36m
American Airlines
Deal found 7/3C$ 930
Fri 17/47:40 a.m.
SJU
-
YYC
2 stops16h 08m
United Airlines
Mon 20/46:00 a.m.
YYC
-
SJU
1 stop9h 38m
United Airlines
Deal found 10/3C$ 945
Fri 17/73:05 p.m.
AUA
-
YYC
2 stops18h 15m
WestJet
Sat 25/78:40 p.m.
YYC
-
AUA
2 stops39h 35m
WestJet
Deal found 8/3C$ 952
Sun 26/77:25 a.m.
SJU
-
YYC
2 stops18h 15m
American Airlines
Mon 3/86:45 a.m.
YYC
-
SJU
1 stop14h 55m
American Airlines
Deal found 9/3C$ 984
Sat 25/49:10 a.m.
POS
-
YYC
2 stops27h 50m
Multiple Airlines
Tue 28/41:20 p.m.
YYC
-
POS
1 stop13h 20m
Multiple Airlines
Deal found 8/3C$ 986
Thu 16/41:00 a.m.
SJU
-
YYC
1 stop18h 30m
Air Canada
Mon 20/41:53 p.m.
YYC
-
SJU
1 stop28h 45m
Air Canada
Deal found 8/3C$ 995
Tue 7/76:00 a.m.
SJU
-
YYC
2 stops17h 43m
American Airlines
Fri 17/76:15 a.m.
YYC
-
SJU
1 stop15h 36m
American Airlines
Deal found 8/3C$ 1,002
Fri 17/73:05 p.m.
AUA
-
YYC
1 stop11h 39m
Multiple Airlines
Fri 24/712:55 a.m.
YYC
-
AUA
1 stop11h 20m
Multiple Airlines
Deal found 8/3C$ 1,029

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 11 March 2026.

Round-trip from

C$ 751

One-way from

C$ 269
Air Canada
  • Air Canada
  • 26/3-30/3
  • 3 total stops
  • 38h 48m total
  • Caribbean Islands to Calgary
Search Deals
22/4
  • 22/4
  • 3 total stops
  • 35h 47m 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 11 March 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

Cheapest round-trip

Simpson BayCalgary

SXM - YYC

SXMYYC

Simpson Bay Princess Juliana

Thu 26/3

3:20 p.m.-6:53 a.m.

2 stops17h 33m

Calgary

Mon 30/3

2:20 p.m.-1:35 p.m.

1 stop21h 15m

C$ 751
Quickest round-trip

San JuanCalgary

SJU - YYC

SJUYYC

San Juan Luis Munoz Marin Intl

Fri 17/4

7:40 a.m.-9:48 p.m.

2 stops16h 08m

Calgary

Mon 20/4

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

1 stop9h 38m

C$ 945

OranjestadCalgary

AUA - YYC

AUAYYC

Oranjestad Reina Beatrix

Fri 17/7

3:05 p.m.-7:20 a.m.

2 stops18h 15m

Calgary

Sat 25/7

8:40 p.m.-2:15 p.m.

2 stops39h 35m

C$ 952

San JuanCalgary

SJU - YYC

SJUYYC

San Juan Luis Munoz Marin Intl

Thu 16/4

1:00 a.m.-12:23 a.m.

2 stops25h 23m

Calgary

Mon 20/4

2:20 p.m.-1:45 p.m.

2 stops21h 25m

C$ 1,012

San JuanCalgary

SJU - YYC

SJUYYC

San Juan Luis Munoz Marin Intl

Sun 26/7

7:25 a.m.-11:40 p.m.

2 stops18h 15m

Calgary

Mon 3/8

6:15 a.m.-10:59 p.m.

2 stops14h 44m

C$ 1,036

OranjestadCalgary

AUA - YYC

AUAYYC

Oranjestad Reina Beatrix

Wed 1/4

3:40 p.m.-6:22 p.m.

2 stops28h 42m

Calgary

Wed 8/4

4:30 p.m.-2:35 p.m.

1 stop20h 05m

C$ 1,064

Port of SpainCalgary

POS - YYC

POSYYC

Port of Spain Piarco Intl

Fri 24/4

12:30 a.m.-9:48 p.m.

2 stops23h 18m

Calgary

Tue 28/4

6:00 a.m.-11:23 p.m.

2 stops39h 23m

C$ 1,077

Port of SpainCalgary

POS - YYC

POSYYC

Port of Spain Piarco Intl

Sun 21/6

12:30 a.m.-11:15 p.m.

1 stop24h 45m

Calgary

Fri 31/7

6:00 a.m.-11:23 p.m.

2 stops39h 23m

C$ 1,108

Port of SpainCalgary

POS - YYC

POSYYC

Port of Spain Piarco Intl

Fri 19/6

12:30 a.m.-10:37 p.m.

2 stops48h 07m

Calgary

Thu 30/7

6:00 a.m.-11:23 p.m.

2 stops39h 23m

C$ 1,108

Port of SpainCalgary

POS - YYC

POSYYC

Port of Spain Piarco Intl

Thu 2/7

12:30 a.m.-10:37 p.m.

2 stops48h 07m

Calgary

Fri 10/7

7:15 p.m.-12:50 a.m.

2 stops27h 35m

C$ 1,111

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/3

Showing 1-10 of 28 resultsSorted by cheapest first
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, August is the cheapest month in which you can book a flight from Caribbean Islands to Calgary (average of C$ 338). Flying from Caribbean Islands to Calgary in April is currently the most expensive (average of C$ 669). 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 11 March 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 11 March 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
9,413 reviews
Check prices

Overall

7.4

Comfort

7.3

Entertainment

7.1

Crew

8.1

Food

6.6

Boarding

7.7

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
9,413 reviews
United Airlines
7.4
Good
9,413 reviews
Check prices

Overall

7.4

Comfort

7.3

Entertainment

7.1

Crew

8.1

Food

6.6

Boarding

7.7

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
3,288 reviews
United Airlines
7.4
Good
9,413 reviews
Check prices

Overall

7.4

Comfort

7.3

Entertainment

7.1

Crew

8.1

Food

6.6

Boarding

7.7

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
10,800 reviews
United Airlines
7.4
Good
9,413 reviews
Check prices

Overall

7.4

Comfort

7.3

Entertainment

7.1

Crew

8.1

Food

6.6

Boarding

7.7

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 16h 08m. 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 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$ 225), WestJet (C$ 248), and Air Canada (C$ 282).

  • 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 Providenciales - 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$ 338). Flying from Caribbean Islands to Calgary in April is currently the most expensive (average of C$ 669). 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 2 airlines flying from Caribbean Islands to Calgary

Discover the top 2 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 11 March 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 326AverageC$ 775FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 471AverageC$ 944FlexibilityNo 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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