Which airlines fly to Caribbean?

WestJet, Air Canada and United Airlines are the top three most popular airlines that fly to Caribbean from Calgary according to our data. WestJet is the first choice among our users, with 66% of people opting to fly with this airline when travelling to Caribbean. Keep in mind that there are 5 different airlines that fly to Caribbean on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Calgary to Caribbean?

Air Canada, WestJet, and American Airlines are the most popular carriers operating from Calgary to Caribbean

When did momondo last update prices for flights from Calgary Airport to Caribbean?

Prices for flights from Calgary Airport to Caribbean refresh daily.

How many operators does momondo search for flights from Calgary Airport to Caribbean?

As of August 2026, there are 5 operators available to choose from for flights from Calgary Airport to Caribbean.

How old do you have to be to fly from Calgary Airport to Caribbean?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Calgary Airport to Caribbean.

What documentation or ID do you need to fly to Caribbean?

The travel and health documents you'll need for your trip to Caribbean may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Caribbean. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

C$ 205 Cheap Flights from Calgary to Caribbean in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Calgary to Caribbean

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

9:50 p.m. - 1:30 p.m.YYC Calgary-MBJ Montego Bay Sangster Intl

14h 40m1 stop Winnipeg

3:25 p.m. - 4:00 p.m.MBJ Montego Bay Sangster Intl-YYC Calgary

25h 35m1 stop Winnipeg

C$ 471WestJet

Fri, 11 Dec - Sat, 19 Dec

12:10 a.m. - 12:30 p.m.YYC Calgary-SJU San Juan Luis Munoz Marin Intl

10h 20m1 stop Toronto Pearson Intl

1:25 p.m. - 10:44 a.m.SJU San Juan Luis Munoz Marin Intl-YYC Calgary

23h 19m1 stop Toronto Pearson Intl

C$ 502Air Canada

Sat, 24 Oct - Sat, 31 Oct

11:00 a.m. - 1:30 p.m.YYC Calgary-MBJ Montego Bay Sangster Intl

25h 30m2 stops Regina Winnipeg

3:25 p.m. - 8:20 p.m.MBJ Montego Bay Sangster Intl-YYC Calgary

29h 55m2 stops Winnipeg Edmonton

C$ 503WestJet

Fri, 11 Dec - Sat, 19 Dec

12:10 a.m. - 12:30 p.m.YYC Calgary-SJU San Juan Luis Munoz Marin Intl

10h 20m1 stop Toronto Pearson Intl

1:25 p.m. - 10:44 a.m.SJU San Juan Luis Munoz Marin Intl-YYC Calgary

23h 19m1 stop Toronto Pearson Intl

C$ 506Air Canada

Sat, 24 Oct - Sat, 31 Oct

6:00 a.m. - 5:25 p.m.YYC Calgary-SJU San Juan Luis Munoz Marin Intl

9h 25m1 stop Denver Intl

1:21 p.m. - 9:53 p.m.SJU San Juan Luis Munoz Marin Intl-YYC Calgary

10h 32m1 stop Denver Intl

C$ 530United Airlines

Mon, 26 Oct - Fri, 30 Oct

6:00 a.m. - 5:25 p.m.YYC Calgary-SJU San Juan Luis Munoz Marin Intl

9h 25m1 stop Denver Intl

7:25 a.m. - 9:53 p.m.SJU San Juan Luis Munoz Marin Intl-YYC Calgary

16h 28m2 stops Chicago O'Hare Intl Denver Intl

C$ 530United Airlines

Mon, 26 Oct - Fri, 30 Oct

1:51 p.m. - 11:20 a.m.YYC Calgary-SJU San Juan Luis Munoz Marin Intl

19h 29m2 stops Chicago O'Hare Intl Charlotte Douglas

3:51 p.m. - 11:59 a.m.SJU San Juan Luis Munoz Marin Intl-YYC Calgary

22h 08m2 stops Charlotte Douglas Dallas/Fort Worth

C$ 566American Airlines

Tue, 13 Oct - Fri, 23 Oct

11:05 a.m. - 11:45 a.m.YYC Calgary-MBJ Montego Bay Sangster Intl

23h 40m2 stops Winnipeg Toronto Pearson Intl

12:30 p.m. - 8:40 p.m.MBJ Montego Bay Sangster Intl-YYC Calgary

33h 10m2 stops Toronto Pearson Intl Ottawa

C$ 623Multiple Airlines

Wed, 14 Oct - Sat, 17 Oct

7:10 p.m. - 4:15 p.m.YYC Calgary-NAS Nassau Intl

19h 05m1 stop Toronto Pearson Intl

12:00 p.m. - 10:20 a.m.NAS Nassau Intl-YYC Calgary

24h 20m1 stop Toronto Pearson Intl

C$ 641Multiple Airlines

Tue, 15 Sep - Sun, 20 Sep

1:51 p.m. - 9:46 a.m.YYC Calgary-SJU San Juan Luis Munoz Marin Intl

17h 55m2 stops Chicago O'Hare Intl Miami

12:41 p.m. - 11:59 a.m.SJU San Juan Luis Munoz Marin Intl-YYC Calgary

25h 18m2 stops Charlotte Douglas Dallas/Fort Worth

C$ 656American Airlines

Wed, 14 Oct - Fri, 23 Oct

Cheap last-minute flights

Enter your travel dates to find the best prices.

12:34 p.m. - 1:47 p.m.YYC Calgary-NAS Nassau Intl

47h 13m2 stops Chicago O'Hare Intl Houston George Bush Intcntl

2:53 p.m. - 10:37 p.m.NAS Nassau Intl-YYC Calgary

33h 44m2 stops Houston George Bush Intcntl Chicago O'Hare Intl

C$ 705United Airlines

Thu, 13 Aug - Sat, 22 Aug

6:00 a.m. - 1:47 p.m.YYC Calgary-NAS Nassau Intl

53h 47m2 stops Denver Intl Houston George Bush Intcntl

2:35 p.m. - 9:48 p.m.NAS Nassau Intl-YYC Calgary

33h 13m2 stops Newark Denver Intl

C$ 838United Airlines

Thu, 13 Aug - Thu, 20 Aug

12:28 p.m. - 12:40 p.m.YYC Calgary-PUJ Punta Cana

22h 12m2 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl

3:35 p.m. - 6:30 p.m.PUJ Punta Cana-YYC Calgary

28h 55m2 stops Washington, D.C. Dulles Intl Denver Intl

C$ 842United Airlines

Mon, 10 Aug - Thu, 20 Aug

6:15 p.m. - 11:10 a.m.YYC Calgary-NAS Nassau Intl

14h 55m1 stop Toronto Pearson Intl

6:30 p.m. - 5:11 p.m.NAS Nassau Intl-YYC Calgary

24h 41m1 stop Toronto Pearson Intl

C$ 955Multiple Airlines

Thu, 13 Aug - Thu, 20 Aug

7:00 a.m. - 11:10 a.m.YYC Calgary-NAS Nassau Intl

26h 10m1 stop Toronto Pearson Intl

6:30 p.m. - 10:45 p.m.NAS Nassau Intl-YYC Calgary

30h 15m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

C$ 977Multiple Airlines

Thu, 13 Aug - Thu, 20 Aug

12:45 p.m. - 9:30 a.m.YYC Calgary-NAS Nassau Intl

18h 45m2 stops Dallas/Fort Worth Miami

3:34 p.m. - 11:50 a.m.NAS Nassau Intl-YYC Calgary

22h 16m2 stops Charlotte Douglas Dallas/Fort Worth

C$ 992American Airlines

Thu, 13 Aug - Sat, 22 Aug

9:55 p.m. - 2:30 p.m.YYC Calgary-KIN Kingston Norman Manley

39h 35m2 stops Edmonton Toronto Pearson Intl

3:30 p.m. - 8:30 a.m.KIN Kingston Norman Manley-YYC Calgary

18h 00m2 stops Toronto Pearson Intl Ottawa

C$ 1,580WestJet

Wed, 12 Aug - Mon, 17 Aug

6:50 p.m. - 2:30 p.m.YYC Calgary-KIN Kingston Norman Manley

42h 40m2 stops Ottawa Toronto Pearson Intl

3:30 p.m. - 12:44 a.m.KIN Kingston Norman Manley-YYC Calgary

10h 14m1 stop Toronto Pearson Intl

C$ 1,586WestJet

Wed, 12 Aug - Mon, 17 Aug

1:52 p.m. - 6:26 p.m.YYC Calgary-KIN Kingston Norman Manley

27h 34m2 stops Chicago O'Hare Intl Miami

5:16 p.m. - 11:50 a.m.KIN Kingston Norman Manley-YYC Calgary

19h 34m2 stops Miami Dallas/Fort Worth

C$ 2,199American Airlines

Tue, 11 Aug - Tue, 18 Aug

2:25 p.m. - 10:25 a.m.YYC Calgary-KIN Kingston Norman Manley

43h 00m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl

3:05 p.m. - 1:56 a.m.KIN Kingston Norman Manley-YYC Calgary

11h 51m1 stop Toronto Pearson Intl

C$ 2,284Air Canada

Tue, 11 Aug - Tue, 18 Aug

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United Airlines flights from Calgary to Caribbean

Our best United Airlines deals on Calgary to Caribbean flight tickets

United Airlines

26 Oct

YYC6:00 a.m.Calgary

9h 25m

1 stop

SJU5:25 p.m.San Juan Luis Munoz Marin Intl

30 Oct

SJU1:21 p.m.San Juan Luis Munoz Marin Intl

10h 32m

1 stop

YYC9:53 p.m.Calgary

C$ 530

United Airlines

26 Oct

YYC6:00 a.m.Calgary

9h 25m

1 stop

SJU5:25 p.m.San Juan Luis Munoz Marin Intl

30 Oct

SJU1:21 p.m.San Juan Luis Munoz Marin Intl

10h 32m

1 stop

YYC9:53 p.m.Calgary

C$ 531

United Airlines

26 Oct

YYC6:00 a.m.Calgary

9h 25m

1 stop

SJU5:25 p.m.San Juan Luis Munoz Marin Intl

30 Oct

SJU7:25 a.m.San Juan Luis Munoz Marin Intl

16h 28m

2 stops

YYC9:53 p.m.Calgary

C$ 532

Air Canada flights from Calgary to Caribbean

Our best Air Canada deals on Calgary to Caribbean flight tickets

Air Canada

24 Oct

YYC12:10 a.m.Calgary

10h 20m

1 stop

SJU12:30 p.m.San Juan Luis Munoz Marin Intl

31 Oct

SJU1:25 p.m.San Juan Luis Munoz Marin Intl

23h 19m

1 stop

YYC10:44 a.m.Calgary

C$ 502

Air Canada

24 Oct

YYC12:10 a.m.Calgary

10h 20m

1 stop

SJU12:30 p.m.San Juan Luis Munoz Marin Intl

31 Oct

SJU1:25 p.m.San Juan Luis Munoz Marin Intl

23h 19m

1 stop

YYC10:44 a.m.Calgary

C$ 506

Air Canada

24 Oct

YYC12:10 a.m.Calgary

10h 20m

1 stop

SJU12:30 p.m.San Juan Luis Munoz Marin Intl

31 Oct

SJU1:25 p.m.San Juan Luis Munoz Marin Intl

25h 43m

2 stops

YYC1:08 p.m.Calgary

C$ 507

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

CalgaryMontego Bay

YYC Calgary - MBJ Montego Bay Sangster Intl

YYCMBJ

Calgary

Fri 11/12

9:50 p.m.-1:30 p.m.

1 stop14h 40m

Montego Bay Sangster Intl

Sat 19/12

3:25 p.m.-4:00 p.m.

1 stop25h 35m

C$ 471

CalgarySan Juan

YYC Calgary - SJU San Juan Luis Munoz Marin Intl

YYCSJU

Calgary

Sat 24/10

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

1 stop10h 20m

San Juan Luis Munoz Marin Intl

Sat 31/10

1:25 p.m.-10:44 a.m.

1 stop23h 19m

C$ 502

CalgaryMontego Bay

YYC Calgary - MBJ Montego Bay Sangster Intl

YYCMBJ

Calgary

Fri 11/12

11:00 a.m.-1:30 p.m.

2 stops25h 30m

Montego Bay Sangster Intl

Sat 19/12

3:25 p.m.-8:20 p.m.

2 stops29h 55m

C$ 503

CalgarySan Juan

YYC Calgary - SJU San Juan Luis Munoz Marin Intl

YYCSJU

Calgary

Sat 24/10

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

1 stop10h 20m

San Juan Luis Munoz Marin Intl

Sat 31/10

1:25 p.m.-10:44 a.m.

1 stop23h 19m

C$ 506

Quickest round-trip

CalgarySan Juan

YYC Calgary - SJU San Juan Luis Munoz Marin Intl

YYCSJU

Calgary

Mon 26/10

6:00 a.m.-5:25 p.m.

1 stop9h 25m

San Juan Luis Munoz Marin Intl

Fri 30/10

1:21 p.m.-9:53 p.m.

1 stop10h 32m

C$ 530

CalgarySan Juan

YYC Calgary - SJU San Juan Luis Munoz Marin Intl

YYCSJU

Calgary

Mon 26/10

6:00 a.m.-5:25 p.m.

1 stop9h 25m

San Juan Luis Munoz Marin Intl

Fri 30/10

7:25 a.m.-9:53 p.m.

2 stops16h 28m

C$ 530

CalgarySan Juan

YYC Calgary - SJU San Juan Luis Munoz Marin Intl

YYCSJU

Calgary

Tue 13/10

1:51 p.m.-11:20 a.m.

2 stops19h 29m

San Juan Luis Munoz Marin Intl

Fri 23/10

3:51 p.m.-11:59 a.m.

2 stops22h 08m

C$ 566

CalgaryMontego Bay

YYC Calgary - MBJ Montego Bay Sangster Intl

YYCMBJ

Calgary

Wed 14/10

11:05 a.m.-11:45 a.m.

2 stops23h 40m

Montego Bay Sangster Intl

Sat 17/10

12:30 p.m.-8:40 p.m.

2 stops33h 10m

C$ 623

CalgaryNassau

YYC Calgary - NAS Nassau Intl

YYCNAS

Calgary

Tue 15/9

7:10 p.m.-4:15 p.m.

1 stop19h 05m

Nassau Intl

Sun 20/9

12:00 p.m.-10:20 a.m.

1 stop24h 20m

C$ 641

CalgarySan Juan

YYC Calgary - SJU San Juan Luis Munoz Marin Intl

YYCSJU

Calgary

Wed 14/10

1:51 p.m.-9:46 a.m.

2 stops17h 55m

San Juan Luis Munoz Marin Intl

Fri 23/10

12:41 p.m.-11:59 a.m.

2 stops25h 18m

C$ 656

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Calgary to Caribbean

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

What is the cheapest month to fly to Caribbean?

In general, January is the cheapest month to fly from Calgary to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 743. If you don’t want to visit Caribbean in January, then you should wait until September to fly from Calgary, when ticket prices are also cheap, with an average price of C$ 757.

What is the cheapest day to depart on your flight to Caribbean?

On average, the least expensive day to fly to Caribbean from Calgary is on a Monday. momondo users have found tickets for Monday departures for as low as C$ 706. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Tuesday as prices are generally higher than usual. According to our data, the average ticket price to Caribbean on Tuesday is C$ 908.

What is the cheapest Calgary to Caribbean flight route?

Fly from Calgary to Montego Bay Sangster Intl for the best Calgary - Caribbean flight prices

How far in advance should I book a flight from Calgary to Caribbean?

You are more likely to see cheaper flights to Caribbean from Calgary when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean for around C$ 776 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean from Calgary for as low as C$ 640 on momondo.

What cabin class options are available on Calgary to Caribbean flights?

There are 2 cabin classes available to choose from on Calgary to Caribbean flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Calgary to Caribbean flights?

You could potentially save up to 17% on your flight if you consider stops on a Calgary to Caribbean flight.

Cheap Calgary to Caribbean flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Calgary to Caribbean

Best price found	C$ 590
Fastest flight time	4h 42m
Direct flights	Mon, Wed, Thu, Fri, Sat and Sun
Airports in Caribbean	196 airports

The best flight deal from Calgary to Caribbean found on momondo in the last 72 hours is C$ 590

The fastest flight from Calgary to Caribbean takes 4h 42m

Direct flights go from Calgary to Caribbean on Monday, Wednesday, Thursday, Friday, Saturday and Sunday. The only airline offering direct flights is WestJet.

There are 196 airports in Caribbean. From Calgary there are direct flights to Nassau Intl (NAS), Montego Bay Sangster Intl (MBJ), Punta Cana (PUJ).

Search flight deals

Frequently asked questions about flying from Calgary to Caribbean

When did momondo last update prices for flights from Calgary Airport to Caribbean?
Prices for flights from Calgary Airport to Caribbean refresh daily.
How many operators does momondo search for flights from Calgary Airport to Caribbean?
As of August 2026, there are 5 operators available to choose from for flights from Calgary Airport to Caribbean.
How old do you have to be to fly from Calgary Airport to Caribbean?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Calgary Airport to Caribbean.
What documentation or ID do you need to fly to Caribbean?
The travel and health documents you'll need for your trip to Caribbean may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Caribbean. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Calgary to Caribbean?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Calgary to Caribbean is Boeing 737 MAX 8 (93.33% of total bookings). The next most popular plane models are Boeing 737-700 Passenger/BBJ1 (winglets) (2.67%), Boeing 737-800 Passenger/BBJ2 (winglets) (2.67%), and Boeing 737 (1.33%).

Best airlines flying from Calgary to Caribbean

Compare and see reviews for airlines that fly from Calgary to Caribbean with momondo

Airline	Rating	Free Cancellation	Price
United Airlines	PriceFrom C$ 329	Free Cancellation	Rating 7.4 10,088 reviews	Search United Airlines flights
WestJet	PriceFrom C$ 429	Free Cancellation	Rating 7.2 3,428 reviews	Search WestJet flights
Air Canada	PriceFrom C$ 512	Free Cancellation	Rating 7.1 11,455 reviews	Search Air Canada flights
American Airlines	PriceFrom C$ 739	Free Cancellation	Rating 7.1 11,893 reviews	Search American Airlines flights
Air Transat	PriceFrom C$ 901	Free Cancellation	Rating 7.8 572 reviews	Search Air Transat flights

Why use momondo?

Why should I use momondo to find a flight deal from Calgary to Caribbean?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Calgary to Caribbean for you.

Can I find flights from Calgary to Caribbean with flexible booking policies on momondo?

momondo does allow users to show only those flights to Caribbean from Calgary which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Calgary to Caribbean?

Once all potential Calgary to Caribbean flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Calgary to Caribbean right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Calgary to Caribbean now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Caribbean and let you know when they change.