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Cheap flights from Caribbean to Calgary from C$ 258

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 18/3. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — YYC
10 Mar — 17 Mar1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Caribbean to Calgary

Enter your travel dates to find the best prices.

Cheapest flights from Caribbean to Calgary
Explore the most affordable flight options available from Caribbean to Calgary. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 8 February 2026.

Tue 24/23:40 p.m.
SXM
-
YYC
1 stop22h 54m
Multiple Airlines
Sat 28/211:40 p.m.
YYC
-
SXM
2 stops36h 37m
Multiple Airlines
Deal found 8/2C$ 763
Thu 21/57:00 a.m.
SJU
-
YYC
2 stops15h 05m
Multiple Airlines
Sun 24/512:00 p.m.
YYC
-
SJU
1 stop27h 54m
Multiple Airlines
Deal found 7/2C$ 805
Fri 18/912:05 p.m.
SJU
-
YYC
2 stops13h 15m
American Airlines
Sat 26/96:30 a.m.
YYC
-
SJU
2 stops15h 29m
American Airlines
Deal found 6/2C$ 817
Tue 24/26:00 a.m.
SJU
-
YYC
2 stops21h 05m
Multiple Airlines
Sat 28/28:45 p.m.
YYC
-
SJU
3 stops19h 04m
Multiple Airlines
Deal found 8/2C$ 864
Tue 24/26:00 a.m.
SJU
-
YYC
2 stops18h 45m
Multiple Airlines
Fri 27/27:30 a.m.
YYC
-
SJU
2 stops23h 47m
Multiple Airlines
Deal found 6/2C$ 875
Thu 1/107:30 a.m.
SJU
-
YYC
1 stop11h 40m
Delta
Sat 3/1012:30 a.m.
YYC
-
SJU
1 stop10h 46m
Delta
Deal found 7/2C$ 891
Wed 25/22:05 a.m.
SJU
-
YYC
2 stops25h 09m
Air Canada
Mon 2/36:15 p.m.
YYC
-
SJU
2 stops27h 21m
Air Canada
Deal found 8/2C$ 913
Thu 1/103:55 p.m.
SJU
-
YYC
2 stops22h 40m
American Airlines
Sun 4/101:20 p.m.
YYC
-
SJU
2 stops21h 20m
American Airlines
Deal found 7/2C$ 925
Fri 13/27:33 a.m.
SJU
-
YYC
1 stop17h 23m
American Airlines
Sat 21/26:30 a.m.
YYC
-
SJU
1 stop14h 01m
American Airlines
Deal found 8/2C$ 931
Mon 6/71:25 a.m.
POS
-
YYC
1 stop17h 46m
Air Canada
Tue 14/78:30 p.m.
YYC
-
POS
2 stops25h 45m
Air Canada
Deal found 7/2C$ 946
Fri 28/812:30 a.m.
POS
-
YYC
2 stops48h 24m
United Airlines
Sat 5/96:20 a.m.
YYC
-
POS
2 stops39h 03m
United Airlines
Deal found 7/2C$ 1,036
Tue 3/34:06 p.m.
POS
-
YYC
2 stops22h 38m
American Airlines
Tue 10/312:45 p.m.
YYC
-
POS
2 stops23h 25m
American Airlines
Deal found 7/2C$ 1,111

Find flight deals from Caribbean to Calgary

Keep the following information in mind while searching for Caribbean to Calgary flight deals. Data was last updated 8 February 2026.

Round-trip from

C$ 729

One-way from

C$ 258

Popular in

April

Cheapest in

November

Average price

C$ 719

Good one-way deal

C$ 357 or less
WestJet
  • WestJet
  • 12/3-18/3
  • 4 total stops
  • 40h 38m total
  • Caribbean to Calgary
Search Deals
18/3
  • 18/3
  • 1 total stop
  • 33h 04m total
  • Caribbean to Calgary
Search Deals
Highest demand for flights based on searches. 6% potential increase in price (C$ 72 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 27 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals
Price to beat on a one-way flight from Caribbean to Calgary.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean 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 8 February 2026.
Use the filters below to find and compare flights from Caribbean to Calgary that are best for you.

Fly from

Caribbean

Fly to

Calgary

Route

Depart

Return

Price

Simpson BayCalgary

SXM - YYC

SXMYYC

Simpson Bay Princess Juliana

Tue 24/2

3:40 p.m.-11:34 a.m.

1 stop22h 54m

Calgary

Sat 28/2

11:40 p.m.-3:17 p.m.

2 stops36h 37m

C$ 763

San JuanCalgary

SJU - YYC

SJUYYC

San Juan Luis Munoz Marin Intl

Thu 21/5

7:00 a.m.-8:05 p.m.

2 stops15h 05m

Calgary

Sun 24/5

12:00 p.m.-5:54 p.m.

1 stop27h 54m

C$ 805

San JuanCalgary

SJU - YYC

SJUYYC

San Juan Luis Munoz Marin Intl

Tue 24/2

6:00 a.m.-12:05 a.m.

2 stops21h 05m

Calgary

Sat 28/2

8:45 p.m.-6:49 p.m.

3 stops19h 04m

C$ 864

San JuanCalgary

SJU - YYC

SJUYYC

San Juan Luis Munoz Marin Intl

Tue 24/2

6:00 a.m.-9:45 p.m.

2 stops18h 45m

Calgary

Fri 27/2

7:00 p.m.-6:58 p.m.

3 stops20h 58m

C$ 906

San JuanCalgary

SJU - YYC

SJUYYC

San Juan Luis Munoz Marin Intl

Wed 25/2

2:05 a.m.-12:14 a.m.

2 stops25h 09m

Calgary

Mon 2/3

6:15 p.m.-12:36 a.m.

2 stops27h 21m

C$ 913

Port of SpainCalgary

POS - YYC

POSYYC

Port of Spain Piarco Intl

Mon 6/7

1:25 a.m.-5:11 p.m.

1 stop17h 46m

Calgary

Tue 14/7

8:30 p.m.-12:15 a.m.

2 stops25h 45m

C$ 946

San JuanCalgary

SJU - YYC

SJUYYC

San Juan Luis Munoz Marin Intl

Fri 15/5

1:00 a.m.-12:43 p.m.

2 stops13h 43m

Calgary

Sat 16/5

7:45 p.m.-1:45 p.m.

2 stops16h 00m

C$ 1,028

Port of SpainCalgary

POS - YYC

POSYYC

Port of Spain Piarco Intl

Sat 11/4

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

2 stops23h 18m

Calgary

Thu 23/4

12:34 p.m.-11:23 p.m.

2 stops32h 49m

C$ 1,039

San JuanCalgary

SJU - YYC

SJUYYC

San Juan Luis Munoz Marin Intl

Wed 25/2

7:33 a.m.-9:56 p.m.

1 stop17h 23m

Calgary

Sun 1/3

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

1 stop14h 01m

C$ 1,047

San JuanCalgary

SJU - YYC

SJUYYC

San Juan Luis Munoz Marin Intl

Sun 26/7

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

2 stops15h 19m

Calgary

Mon 27/7

6:45 a.m.-4:32 a.m.

1 stop19h 47m

C$ 1,052

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/2

Showing 1-10 of 32 results
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Best time to book a flight from Caribbean to Calgary

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

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

Currently, August is the cheapest month in which you can book a flight from Caribbean to Calgary (average of C$ 340). Flying from Caribbean to Calgary in January is currently the most expensive (average of C$ 698). 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 CB to YYC?

Find hourly flight availability from Caribbean 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 8 February 2026.

When flying from Caribbean 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 8 February 2026.
Get a feel of what it's like to fly with United Airlines,WestJet, andAir Canada from Caribbean to Calgary by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,259 reviews
Check prices

Entertainment

7.1

Overall

7.4

Food

6.6

Comfort

7.3

Crew

8.1

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
9,259 reviews
United Airlines
7.4
Good
9,259 reviews
Check prices

Entertainment

7.1

Overall

7.4

Food

6.6

Comfort

7.3

Crew

8.1

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
3,256 reviews
United Airlines
7.4
Good
9,259 reviews
Check prices

Entertainment

7.1

Overall

7.4

Food

6.6

Comfort

7.3

Crew

8.1

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
10,698 reviews
United Airlines
7.4
Good
9,259 reviews
Check prices

Entertainment

7.1

Overall

7.4

Food

6.6

Comfort

7.3

Crew

8.1

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 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?

    Most people fly into Calgary (YYC) if they book a flight to Calgary from Caribbean. Calgary is conveniently located just 9.3 km from Calgary’s city centre.

  • How long is the flight from Caribbean to Calgary?

    A quick flight from Caribbean to Calgary can take about 23h 18m. Air Canada provides one of the quickest options available for as low as C$ 1,039. There are 6540 km between Caribbean and Calgary. This flight may include one or multiple stops.

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

    For one-way options, check prices for United Airlines. According to our data, you can fly for as low as C$ 226. Users have also found prices from C$ 250 and C$ 284 on WestJet and Air Canada, respectively.

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

    While some choose either Port of Spain Piarco Intl - Calgary or Oranjestad Reina Beatrix - Calgary, San Juan Luis Munoz Marin Intl - Calgary is the most popular route from Caribbean to Calgary.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Caribbean 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 to Calgary?

    Currently, August is the cheapest month in which you can book a flight from Caribbean to Calgary (average of C$ 340). Flying from Caribbean to Calgary in January is currently the most expensive (average of C$ 698). 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

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Top 3 airlines flying from Caribbean to Calgary

Discover the top 3 airlines that operate flights from Caribbean 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 8 February 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 328AverageC$ 781FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 475AverageC$ 950FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 760AverageC$ 896FlexibilityNo 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 to Calgary?

When you search for this flight from Caribbean to Calgary, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

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

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Caribbean to Calgary for you. Better yet — we are completely free to use.

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

Need flexible booking options for your flight to Calgary from Caribbean? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

Can Cheapflights notify me if prices for flights from Caribbean to Calgary become cheaper?

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Calgary from Caribbean today and book when prices fit your budget.

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