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Cheap flights from Caribbean to Calgary from C$ 400

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 15/7. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — YYC
17 Jun — 24 Jun1
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 18 May 2026.

Thu 4/65:15 p.m.
SJU
-
YYC
1 stop19h 45m
Multiple Airlines
Sat 6/67:00 a.m.
YYC
-
SJU
2 stops29h 33m
Multiple Airlines
Deal found 13/5C$ 834
Thu 11/63:35 p.m.
SJU
-
YYC
1 stop32h 25m
Multiple Airlines
Thu 18/68:45 a.m.
YYC
-
SJU
2 stops37h 52m
Multiple Airlines
Deal found 13/5C$ 863
Sat 30/51:50 p.m.
AUA
-
YYC
1 stop10h 47m
United Airlines
Wed 3/612:28 p.m.
YYC
-
AUA
1 stop25h 07m
United Airlines
Deal found 14/5C$ 872
Thu 23/75:15 p.m.
SJU
-
YYC
1 stop30h 35m
Multiple Airlines
Mon 27/710:15 a.m.
YYC
-
SJU
2 stops28h 27m
Multiple Airlines
Deal found 13/5C$ 876
Wed 3/67:00 a.m.
SJU
-
YYC
2 stops36h 10m
Multiple Airlines
Fri 5/612:30 a.m.
YYC
-
SJU
1 stop11h 37m
Multiple Airlines
Deal found 13/5C$ 887
Sun 31/53:20 p.m.
SXM
-
YYC
2 stops20h 30m
WestJet
Wed 3/61:00 a.m.
YYC
-
SXM
1 stop11h 10m
WestJet
Deal found 16/5C$ 900
Sun 28/64:00 p.m.
SJU
-
YYC
2 stops34h 07m
Multiple Airlines
Fri 10/710:15 a.m.
YYC
-
SJU
1 stop27h 03m
Multiple Airlines
Deal found 13/5C$ 910
Tue 21/75:15 p.m.
SJU
-
YYC
1 stop30h 35m
Multiple Airlines
Tue 28/78:45 a.m.
YYC
-
SJU
2 stops36h 44m
Multiple Airlines
Deal found 12/5C$ 911
Thu 11/63:35 p.m.
SJU
-
YYC
1 stop32h 25m
Multiple Airlines
Tue 16/612:30 a.m.
YYC
-
SJU
2 stops21h 45m
Multiple Airlines
Deal found 13/5C$ 914
Tue 2/67:00 a.m.
SJU
-
YYC
2 stops30h 00m
Multiple Airlines
Fri 5/612:30 a.m.
YYC
-
SJU
1 stop11h 37m
Multiple Airlines
Deal found 13/5C$ 922
Fri 18/94:55 p.m.
SJU
-
YYC
1 stop21h 03m
Air Canada
Mon 21/98:30 a.m.
YYC
-
SJU
1 stop28h 14m
Air Canada
Deal found 16/5C$ 929
Sat 30/56:00 a.m.
SJU
-
YYC
2 stops18h 20m
Multiple Airlines
Fri 5/612:30 a.m.
YYC
-
SJU
1 stop11h 37m
Multiple Airlines
Deal found 13/5C$ 938

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 18 May 2026.

Round-trip from

C$ 834

One-way from

C$ 400

Popular in

July

Cheapest in

May

Average price

C$ 615

Good one-way deal

C$ 414 or less
4/6-6/6
  • 4/6-6/6
  • 3 total stops
  • 49h 18m total
  • Caribbean to Calgary
Search Deals
15/7
  • 15/7
  • 3 total stops
  • 54h 45m total
  • Caribbean to Calgary
Search Deals
Highest demand for flights based on searches. 13% potential increase in price (C$ 160 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 18 May 2026.
Use the filters below to find and compare flights from Caribbean to Calgary that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

OranjestadCalgary

AUA - YYC

AUAYYC

Oranjestad Reina Beatrix

Sat 30/5

1:50 p.m.-10:37 p.m.

1 stop10h 47m

Calgary

Wed 3/6

12:28 p.m.-3:35 p.m.

1 stop25h 07m

C$ 872
Quickest round-trip

Simpson BayCalgary

SXM - YYC

SXMYYC

Simpson Bay Princess Juliana

Sun 31/5

3:20 p.m.-9:50 a.m.

2 stops20h 30m

Calgary

Wed 3/6

1:00 a.m.-2:10 p.m.

1 stop11h 10m

C$ 900

San JuanCalgary

SJU - YYC

SJUYYC

San Juan Luis Munoz Marin Intl

Thu 17/9

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

1 stop18h 30m

Calgary

Mon 21/9

2:25 p.m.-1:53 p.m.

2 stops21h 28m

C$ 933

Port of SpainCalgary

POS - YYC

POSYYC

Port of Spain Piarco Intl

Tue 23/6

12:30 a.m.-6:10 p.m.

2 stops43h 40m

Calgary

Sun 28/6

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

2 stops27h 35m

C$ 980

Port of SpainCalgary

POS - YYC

POSYYC

Port of Spain Piarco Intl

Wed 24/6

12:30 a.m.-6:10 p.m.

2 stops19h 40m

Calgary

Mon 29/6

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

2 stops39h 23m

C$ 982

Port of SpainCalgary

POS - YYC

POSYYC

Port of Spain Piarco Intl

Fri 3/7

12:30 a.m.-6:10 p.m.

2 stops19h 40m

Calgary

Fri 7/8

6:00 a.m.-12:50 a.m.

2 stops16h 50m

C$ 1,010

Port of SpainCalgary

POS - YYC

POSYYC

Port of Spain Piarco Intl

Mon 31/8

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

2 stops23h 18m

Calgary

Wed 16/9

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

2 stops15h 23m

C$ 1,010

Port of SpainCalgary

POS - YYC

POSYYC

Port of Spain Piarco Intl

Sun 1/11

1:30 a.m.-9:38 p.m.

2 stops23h 08m

Calgary

Sat 14/11

1:55 p.m.-12:23 a.m.

1 stop31h 28m

C$ 1,037

Simpson BayCalgary

SXM - YYC

SXMYYC

Simpson Bay Princess Juliana

Sat 12/9

6:00 p.m.-11:32 a.m.

1 stop19h 32m

Calgary

Fri 2/10

12:55 a.m.-5:00 p.m.

1 stop14h 05m

C$ 1,038

Simpson BayCalgary

SXM - YYC

SXMYYC

Simpson Bay Princess Juliana

Sun 31/5

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

3 stops33h 00m

Calgary

Thu 4/6

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

2 stops57h 00m

C$ 1,059

Flights are sorted by cheapest round-trip flights first.

Deals found on 16/5

Showing 1-10 of 49 resultsSorted by cheapest first
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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, February is the cheapest month in which you can book a flight from Caribbean to Calgary (average of C$ 318). Flying from Caribbean to Calgary in April is currently the most expensive (average of C$ 648). 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 18 May 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 18 May 2026.
Get a feel of what it's like to fly with United Airlines and WestJet 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
9,737 reviews
Check prices

Comfort

7.3

Overall

7.4

Boarding

7.7

Entertainment

7.1

Crew

8.1

Food

6.6

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
9,737 reviews
United Airlines
7.4
Good
9,737 reviews
Check prices

Comfort

7.3

Overall

7.4

Boarding

7.7

Entertainment

7.1

Crew

8.1

Food

6.6

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
3,339 reviews
United Airlines
7.4
Good
9,737 reviews
Check prices

Comfort

7.3

Overall

7.4

Boarding

7.7

Entertainment

7.1

Crew

8.1

Food

6.6

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 10h 47m. United Airlines provides one of the quickest options available for as low as C$ 872. There are 5829 km between Caribbean and Calgary. This flight may include one or multiple stops.

  • 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, February is the cheapest month in which you can book a flight from Caribbean to Calgary (average of C$ 318). Flying from Caribbean to Calgary in April is currently the most expensive (average of C$ 648). 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
Kananaskis
Airdrie
Drumheller

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Top airline flying from Caribbean to Calgary

Discover the top airline 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 18 May 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 476AverageC$ 895FlexibilityNo 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 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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