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Cheap flights from Caribbean to Calgary from C$ 254

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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — YYC
11 Oct — 18 Oct1
1 adult
1 adult, Economy

Cheap flight deals from Caribbean to Calgary

Keep the following information in mind while searching for Caribbean to Calgary flight deals. Data was last updated 11 September 2025.

Round-trip from

C$ 607

One-way from

C$ 254

Popular in

March

Cheapest in

September

Average price

C$ 718

Good round-trip deal

C$ 914 or less

Good one-way deal

C$ 647 or less
14/10-22/10
  • 14/10-22/10
  • 3 total stops
  • 47h 40m total
  • Caribbean to Calgary
Search Deals
1/11
  • 1/11
  • 1 total stop
  • 21h 45m total
  • Caribbean to Calgary
Search Deals
Highest demand for flights based on searches. 14% potential increase in price (C$ 211 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 40 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Caribbean to Calgary.
Search Deals
Price to beat on a one-way flight from Caribbean to Calgary.
Search Deals

Find flight deals from Caribbean to Calgary

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 11 September 2025.

Wed 15/106:22 a.m.SJU - YYC
1 stop16h 41mMultiple Airlines
Wed 22/109:45 a.m.YYC - SJU
1 stop27h 39mMultiple Airlines
Deal found 9/9C$ 597
Wed 15/107:00 a.m.SJU - YYC
2 stops16h 54mAmerican Airlines
Wed 22/101:29 p.m.YYC - SJU
2 stops19h 37mAmerican Airlines
Deal found 11/9C$ 966
Sat 20/125:20 p.m.SXM - YYC
2 stops23h 46mDelta
Sun 28/1212:45 p.m.YYC - SXM
2 stops23h 05mDelta
Deal found 10/9C$ 1,021
Tue 14/101:05 a.m.SJU - YYC
2 stops22h 43mUnited Airlines
Wed 22/106:15 a.m.YYC - SJU
2 stops27h 45mUnited Airlines
Deal found 11/9C$ 1,161
Wed 15/107:15 a.m.SJU - YYC
2 stops15h 37mWestJet
Tue 21/1012:20 a.m.YYC - SJU
2 stops19h 39mWestJet
Deal found 11/9C$ 1,183
Sun 21/124:20 p.m.SXM - YYC
1 stop19h 46mWestJet
Sun 28/125:15 p.m.YYC - SXM
1 stop19h 06mWestJet
Deal found 10/9C$ 1,556
Sat 20/125:00 p.m.SXM - YYC
1 stop20h 34mAir Canada
Sun 28/126:15 p.m.YYC - SXM
1 stop18h 45mAir Canada
Deal found 10/9C$ 2,153

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 11 September 2025.
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

San JuanCalgary

SJU - YYC

SJUYYC

San Juan Luis Munoz Marin Intl

Tue 14/10

1:59 a.m.-8:00 p.m.

2 stops20h 01m

Calgary

Wed 22/10

9:45 a.m.-3:24 p.m.

1 stop27h 39m

C$ 607

San JuanCalgary

SJU - YYC

SJUYYC

San Juan Luis Munoz Marin Intl

Tue 10/2

4:40 p.m.-11:23 a.m.

2 stops21h 43m

Calgary

Mon 16/2

6:14 a.m.-4:55 a.m.

1 stop19h 41m

C$ 801

Simpson BayCalgary

SXM - YYC

SXMYYC

Simpson Bay Princess Juliana

Fri 6/3

4:20 p.m.-6:53 a.m.

2 stops17h 33m

Calgary

Mon 9/3

9:35 p.m.-2:17 p.m.

2 stops14h 42m

C$ 829

San JuanCalgary

SJU - YYC

SJUYYC

San Juan Luis Munoz Marin Intl

Fri 6/3

7:00 a.m.-9:09 p.m.

1 stop17h 09m

Calgary

Tue 10/3

6:35 a.m.-2:20 p.m.

1 stop29h 45m

C$ 938

San JuanCalgary

SJU - YYC

SJUYYC

San Juan Luis Munoz Marin Intl

Wed 15/10

7:00 a.m.-9:54 p.m.

2 stops16h 54m

Calgary

Wed 22/10

1:29 p.m.-11:06 a.m.

2 stops19h 37m

C$ 966

Simpson BayCalgary

SXM - YYC

SXMYYC

Simpson Bay Princess Juliana

Fri 6/3

4:55 p.m.-9:38 p.m.

2 stops31h 43m

Calgary

Mon 9/3

12:30 p.m.-2:51 p.m.

2 stops24h 21m

C$ 994

Simpson BayCalgary

SXM - YYC

SXMYYC

Simpson Bay Princess Juliana

Sun 21/12

4:15 p.m.-2:06 p.m.

2 stops24h 51m

Calgary

Sun 28/12

12:45 p.m.-2:50 p.m.

2 stops23h 05m

C$ 1,021

Simpson BayCalgary

SXM - YYC

SXMYYC

Simpson Bay Princess Juliana

Sat 20/12

5:20 p.m.-2:06 p.m.

2 stops23h 46m

Calgary

Sun 28/12

12:45 p.m.-2:50 p.m.

2 stops23h 05m

C$ 1,021

Port of SpainCalgary

POS - YYC

POSYYC

Port of Spain Piarco Intl

Thu 5/2

1:30 a.m.-9:53 p.m.

2 stops23h 23m

Calgary

Mon 9/2

12:37 p.m.-1:05 a.m.

2 stops33h 28m

C$ 1,814

Port of SpainCalgary

POS - YYC

POSYYC

Port of Spain Piarco Intl

Thu 5/2

2:15 a.m.-2:24 p.m.

1 stop15h 09m

Calgary

Mon 9/2

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

1 stop22h 30m

C$ 1,819

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 28 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, January is the cheapest month in which you can book a flight from Caribbean to Calgary (average of C$ 138). Flying from Caribbean to Calgary in July is currently the most expensive (average of C$ 263). 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 11 September 2025.

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 11 September 2025.
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
8,937 reviews
Check prices

Comfort

7.3

Entertainment

7.1

Overall

7.4

Food

6.6

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
8,937 reviews
United Airlines
7.4
Good
8,937 reviews
Check prices

Comfort

7.3

Entertainment

7.1

Overall

7.4

Food

6.6

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
3,091 reviews
United Airlines
7.4
Good
8,937 reviews
Check prices

Comfort

7.3

Entertainment

7.1

Overall

7.4

Food

6.6

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
10,000 reviews
United Airlines
7.4
Good
8,937 reviews
Check prices

Comfort

7.3

Entertainment

7.1

Overall

7.4

Food

6.6

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 17h 09m. American Airlines provides one of the quickest options available for as low as C$ 938. There are 5541 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 Air Canada. According to our data, you can fly for as low as C$ 269. Users have also found prices from C$ 303 and C$ 388 on United Airlines and American Airlines, respectively.

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

    While some choose either Simpson Bay Princess Juliana - Calgary or Providenciales - 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, January is the cheapest month in which you can book a flight from Caribbean to Calgary (average of C$ 138). Flying from Caribbean to Calgary in July is currently the most expensive (average of C$ 263). 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
Airdrie
Radium Hot Springs
Drumheller
Kananaskis

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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 11 September 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 332AverageC$ 748FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 333AverageC$ 792FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 481AverageC$ 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 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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