Find flights
When to book
Airlines
FAQs

Cheap flights from Caribbean Islands to Calgary from C$ 307

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 28/5. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — YYC
14 Feb — 21 Feb1
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 15 January 2026.

Round-trip from

C$ 735

One-way from

C$ 307
WestJet
  • WestJet
  • 30/1-3/2
  • 2 total stops
  • 49h 50m total
  • Caribbean Islands to Calgary
Search Deals
28/5
  • 28/5
  • 2 total stops
  • 22h 36m 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 15 January 2026.

Fri 30/14:20 p.m.
SXM
-
YYC
1 stop32h 03m
WestJet
Tue 3/26:30 p.m.
YYC
-
SXM
1 stop17h 47m
WestJet
Deal found 15/1C$ 735
Thu 2/44:05 p.m.
AUA
-
YYC
2 stops32h 18m
Air Canada
Fri 10/48:45 p.m.
YYC
-
AUA
2 stops40h 25m
Air Canada
Deal found 14/1C$ 764
Fri 23/18:10 a.m.
SJU
-
YYC
2 stops16h 43m
United Airlines
Tue 27/16:15 a.m.
YYC
-
SJU
2 stops15h 21m
United Airlines
Deal found 13/1C$ 813
Thu 2/43:30 p.m.
AUA
-
YYC
2 stops17h 23m
WestJet
Fri 10/411:40 p.m.
YYC
-
AUA
2 stops35h 30m
WestJet
Deal found 15/1C$ 873
Mon 13/71:25 a.m.
POS
-
YYC
1 stop13h 21m
Air Canada
Tue 21/73:50 p.m.
YYC
-
POS
2 stops30h 25m
Air Canada
Deal found 14/1C$ 919
Thu 24/95:35 p.m.
AUA
-
YYC
2 stops26h 05m
Multiple Airlines
Wed 14/1012:45 a.m.
YYC
-
AUA
1 stop11h 10m
Multiple Airlines
Deal found 15/1C$ 944
Sun 26/710:23 a.m.
SJU
-
YYC
2 stops15h 19m
American Airlines
Mon 3/812:52 p.m.
YYC
-
SJU
1 stop9h 25m
American Airlines
Deal found 14/1C$ 1,028
Tue 10/28:20 a.m.
SJU
-
YYC
2 stops16h 38m
American Airlines
Mon 16/26:30 a.m.
YYC
-
SJU
1 stop14h 01m
American Airlines
Deal found 14/1C$ 1,035
Sun 26/710:23 a.m.
SJU
-
YYC
2 stops15h 19m
American Airlines
Mon 27/76:45 a.m.
YYC
-
SJU
1 stop19h 47m
American Airlines
Deal found 14/1C$ 1,055
Fri 26/61:25 a.m.
POS
-
YYC
2 stops33h 06m
Air Canada
Sat 8/89:20 a.m.
YYC
-
POS
2 stops36h 55m
Air Canada
Deal found 12/1C$ 1,065
Tue 7/710:23 a.m.
SJU
-
YYC
2 stops15h 19m
American Airlines
Fri 17/76:15 a.m.
YYC
-
SJU
1 stop14h 36m
American Airlines
Deal found 14/1C$ 1,084
Sat 28/29:10 a.m.
POS
-
YYC
2 stops29h 33m
Multiple Airlines
Fri 6/31:05 a.m.
YYC
-
POS
1 stop25h 35m
Multiple Airlines
Deal found 14/1C$ 1,091

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 15 January 2026.
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

Fri 30/1

4:20 p.m.-9:23 p.m.

1 stop32h 03m

Calgary

Tue 3/2

6:30 p.m.-3:17 p.m.

1 stop17h 47m

C$ 735

OranjestadCalgary

AUA - YYC

AUAYYC

Oranjestad Reina Beatrix

Thu 2/4

4:05 p.m.-10:23 p.m.

2 stops32h 18m

Calgary

Fri 10/4

8:45 p.m.-3:10 p.m.

2 stops40h 25m

C$ 764

OranjestadCalgary

AUA - YYC

AUAYYC

Oranjestad Reina Beatrix

Thu 2/4

3:30 p.m.-6:53 a.m.

2 stops17h 23m

Calgary

Fri 10/4

11:40 p.m.-1:10 p.m.

2 stops35h 30m

C$ 873

Port of SpainCalgary

POS - YYC

POSYYC

Port of Spain Piarco Intl

Mon 13/7

1:25 a.m.-12:46 p.m.

1 stop13h 21m

Calgary

Tue 21/7

3:50 p.m.-12:15 a.m.

2 stops30h 25m

C$ 919

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

6:30 a.m.-11:31 p.m.

1 stop14h 01m

C$ 1,035

Port of SpainCalgary

POS - YYC

POSYYC

Port of Spain Piarco Intl

Fri 26/6

1:25 a.m.-8:31 a.m.

2 stops33h 06m

Calgary

Sat 8/8

9:20 a.m.-12:15 a.m.

2 stops36h 55m

C$ 1,065

San JuanCalgary

SJU - YYC

SJUYYC

San Juan Luis Munoz Marin Intl

Tue 7/7

10:23 a.m.-11:42 p.m.

2 stops15h 19m

Calgary

Fri 17/7

6:15 a.m.-10:51 p.m.

1 stop14h 36m

C$ 1,084

Simpson BayCalgary

SXM - YYC

SXMYYC

Simpson Bay Princess Juliana

Fri 30/1

2:52 p.m.-9:53 p.m.

2 stops34h 01m

Calgary

Tue 3/2

6:15 a.m.-2:09 p.m.

2 stops28h 54m

C$ 1,113

Port of SpainCalgary

POS - YYC

POSYYC

Port of Spain Piarco Intl

Mon 13/7

1:25 a.m.-3:02 p.m.

2 stops15h 37m

Calgary

Mon 20/7

12:55 a.m.-8:15 p.m.

3 stops17h 20m

C$ 1,187

Port of SpainCalgary

POS - YYC

POSYYC

Port of Spain Piarco Intl

Fri 27/2

2:20 a.m.-6:54 p.m.

1 stop19h 34m

Calgary

Sat 7/3

11:40 p.m.-12:20 a.m.

1 stop21h 40m

C$ 1,191

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/1

Showing 1-10 of 21 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, June is the cheapest month in which you can book a flight from Caribbean Islands to Calgary (average of C$ 334). Flying from Caribbean Islands to Calgary in November is currently the most expensive (average of C$ 639). 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 15 January 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 15 January 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
9,163 reviews
Check prices

Comfort

7.3

Overall

7.4

Entertainment

7.1

Food

6.6

Boarding

7.7

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
9,163 reviews
United Airlines
7.4
Good
9,163 reviews
Check prices

Comfort

7.3

Overall

7.4

Entertainment

7.1

Food

6.6

Boarding

7.7

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
3,242 reviews
United Airlines
7.4
Good
9,163 reviews
Check prices

Comfort

7.3

Overall

7.4

Entertainment

7.1

Food

6.6

Boarding

7.7

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
10,622 reviews
United Airlines
7.4
Good
9,163 reviews
Check prices

Comfort

7.3

Overall

7.4

Entertainment

7.1

Food

6.6

Boarding

7.7

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 16h 38m. 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$ 230), WestJet (C$ 254), and Air Canada (C$ 289).

  • 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, June is the cheapest month in which you can book a flight from Caribbean Islands to Calgary (average of C$ 334). Flying from Caribbean Islands to Calgary in November is currently the most expensive (average of C$ 639). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Caribbean Islands to Calgary

See prices for flight routes from nearby airports that may be better suited for you.
Pearson Intl to Calgary flights
Vancouver Intl to Edmonton flights
Vancouver Intl to Calgary flights
Pierre Elliott Trudeau Intl to Calgary flights
Toronto Island to Calgary flights
Hamilton to Calgary flights
Abbotsford to Calgary flights
Region of Waterloo Intl to Calgary flights
Newark to Calgary flights
Ottawa to Calgary flights
O'Hare Intl to Calgary flights
John F Kennedy Intl to Calgary flights
Pearson Intl to Edmonton flights
Abbotsford to Edmonton flights
Winnipeg to Calgary flights
Los Angeles to Calgary flights
LaGuardia to Calgary flights
San Francisco to Calgary flights
Atlanta to Calgary flights
Hamilton to Edmonton flights
Toronto Island to Edmonton flights
Pierre Elliott Trudeau Intl to Edmonton flights
Boston to Calgary flights
Hobby to Calgary flights
Winnipeg to Edmonton flights
George Bush Intcntl to Calgary flights
Dulles Intl to Calgary flights
Denver to Calgary flights
Ottawa to Edmonton flights
Victoria to Calgary flights
Orlando to Calgary flights
Minneapolis to Calgary flights
Seattle to Calgary flights
Calgary to Edmonton flights
Halifax to Calgary flights
Québec City to Calgary flights
Kelowna to Calgary flights
Dallas/Fort Worth to Calgary flights
Baltimore to Calgary flights
Kelowna to Edmonton flights
Reagan-National to Calgary flights
Detroit to Calgary flights
Fort Lauderdale to Calgary flights
Saskatoon to Calgary flights
Halifax to Edmonton flights
Mexico City to Calgary flights
Victoria to Edmonton flights
Ontario to Calgary flights
Saskatoon to Edmonton flights

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 15 January 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 333AverageC$ 815FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 334AverageC$ 794FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 482AverageC$ 966FlexibilityNo 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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.