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 63% of people opting to fly with this airline when travelling to Caribbean. Keep in mind that there are 4 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?

United Airlines, WestJet, and Air Canada 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 September 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$ 273 Cheap Flights from Calgary to Caribbean in 2026/27

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.

12:05 a.m. - 8:55 a.m.YYC Calgary-PUJ Punta Cana

5h 50mdirect

9:55 a.m. - 3:55 p.m.PUJ Punta Cana-YYC Calgary

9h 00mdirect

C$ 510WestJet

Sun, 15 Nov - Mon, 23 Nov

12:05 a.m. - 8:55 a.m.YYC Calgary-PUJ Punta Cana

5h 50mdirect

9:55 a.m. - 3:55 p.m.PUJ Punta Cana-YYC Calgary

9h 00mdirect

C$ 512WestJet

Sun, 15 Nov - Mon, 23 Nov

8:10 a.m. - 5:49 p.m.YYC Calgary-NAS Nassau Intl

7h 39m1 stop Ottawa

12:25 p.m. - 11:25 p.m.NAS Nassau Intl-YYC Calgary

13h 00m1 stop Toronto Pearson Intl

C$ 518Porter Airlines

Sat, 28 Nov - Wed, 9 Dec

10:10 p.m. - 11:35 p.m.YYC Calgary-PUJ Punta Cana

22h 25m2 stops Edmonton Montreal Pierre Elliott Trudeau Intl

9:55 a.m. - 3:55 p.m.PUJ Punta Cana-YYC Calgary

9h 00mdirect

C$ 546Multiple Airlines

Mon, 16 Nov - Mon, 23 Nov

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

9h 25m1 stop Denver Intl

1:05 a.m. - 2:21 p.m.SJU San Juan Luis Munoz Marin Intl-YYC Calgary

15h 16m2 stops Newark Denver Intl

C$ 556United Airlines

Sun, 25 Oct - Wed, 28 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$ 556United Airlines

Sun, 25 Oct - Thu, 29 Oct

1:45 a.m. - 11:35 p.m.YYC Calgary-PUJ Punta Cana

18h 50m1 stop Montreal Pierre Elliott Trudeau Intl

7:45 p.m. - 12:25 p.m.PUJ Punta Cana-YYC Calgary

19h 40m1 stop Montreal Pierre Elliott Trudeau Intl

C$ 563Air Canada

Sun, 22 Nov - Fri, 27 Nov

5:10 p.m. - 10:35 p.m.YYC Calgary-PUJ Punta Cana

27h 25m1 stop Montreal Pierre Elliott Trudeau Intl

3:15 p.m. - 12:08 p.m.PUJ Punta Cana-YYC Calgary

23h 53m1 stop Montreal Pierre Elliott Trudeau Intl

C$ 563Air Canada

Wed, 28 Oct - Wed, 4 Nov

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

6:30 a.m. - 9:45 p.m.SJU San Juan Luis Munoz Marin Intl-YYC Calgary

17h 15m2 stops Miami Dallas/Fort Worth

C$ 595American Airlines

Fri, 23 Oct - Fri, 30 Oct

1:59 p.m. - 1:39 p.m.YYC Calgary-SJU San Juan Luis Munoz Marin Intl

21h 40m2 stops Chicago O'Hare Intl Charlotte Douglas

4:45 p.m. - 1:11 p.m.SJU San Juan Luis Munoz Marin Intl-YYC Calgary

23h 26m2 stops Charlotte Douglas Dallas/Fort Worth

C$ 595American Airlines

Sat, 31 Oct - Fri, 6 Nov

Cheap last-minute flights

Enter your travel dates to find the best prices.

1:56 p.m. - 1:47 p.m.YYC Calgary-NAS Nassau Intl

21h 51m1 stop Houston George Bush Intcntl

2:53 p.m. - 9:48 p.m.NAS Nassau Intl-YYC Calgary

32h 55m2 stops Houston George Bush Intcntl Denver Intl

C$ 594United Airlines

Fri, 2 Oct - Fri, 9 Oct

1:56 p.m. - 1:47 p.m.YYC Calgary-NAS Nassau Intl

21h 51m1 stop Houston George Bush Intcntl

2:53 p.m. - 11:28 a.m.NAS Nassau Intl-YYC Calgary

22h 35m2 stops Houston George Bush Intcntl Chicago O'Hare Intl

C$ 594United Airlines

Fri, 2 Oct - Sun, 4 Oct

1:00 p.m. - 11:10 a.m.YYC Calgary-NAS Nassau Intl

20h 10m1 stop Toronto Pearson Intl

12:00 p.m. - 8:20 a.m.NAS Nassau Intl-YYC Calgary

22h 20m1 stop Toronto Pearson Intl

C$ 602WestJet

Fri, 2 Oct - Sun, 4 Oct

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

14h 00m1 stop Toronto Pearson Intl

12:00 p.m. - 12:44 a.m.NAS Nassau Intl-YYC Calgary

14h 44m1 stop Toronto Pearson Intl

C$ 608WestJet

Fri, 2 Oct - Fri, 9 Oct

8:30 p.m. - 4:05 p.m.YYC Calgary-PUJ Punta Cana

41h 35m2 stops Edmonton Montreal Pierre Elliott Trudeau Intl

6:45 p.m. - 10:55 a.m.PUJ Punta Cana-YYC Calgary

42h 10m2 stops Montreal Pierre Elliott Trudeau Intl Edmonton

C$ 837Air Canada

Sat, 3 Oct - Sun, 25 Oct

1:00 a.m. - 11:10 a.m.YYC Calgary-NAS Nassau Intl

8h 10m1 stop Toronto Pearson Intl

6:30 p.m. - 11:00 a.m.NAS Nassau Intl-YYC Calgary

18h 30m2 stops Toronto Pearson Intl MET - Montreal Metropolitan

C$ 867Multiple Airlines

Sat, 3 Oct - Mon, 5 Oct

1:00 a.m. - 11:10 a.m.YYC Calgary-NAS Nassau Intl

8h 10m1 stop Toronto Pearson Intl

6:30 p.m. - 4:30 p.m.NAS Nassau Intl-YYC Calgary

24h 00m3 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl Ottawa

C$ 911Multiple Airlines

Sat, 3 Oct - Mon, 5 Oct

1:00 a.m. - 4:05 p.m.YYC Calgary-PUJ Punta Cana

13h 05m1 stop Montreal Pierre Elliott Trudeau Intl

5:05 p.m. - 8:30 p.m.PUJ Punta Cana-YYC Calgary

29h 25m2 stops Montreal Pierre Elliott Trudeau Intl Ottawa

C$ 959Air Canada

Tue, 29 Sep - Tue, 20 Oct

6:45 a.m. - 4:16 p.m.YYC Calgary-MBJ Montego Bay Sangster Intl

8h 31m1 stop Dallas/Fort Worth

12:18 p.m. - 9:44 p.m.MBJ Montego Bay Sangster Intl-YYC Calgary

10h 26m1 stop Dallas/Fort Worth

C$ 1,178American Airlines

Sun, 4 Oct - Sun, 11 Oct

12:50 p.m. - 3:02 p.m.YYC Calgary-BGI Bridgetown Grantley Adams Intl

24h 12m2 stops Dallas/Fort Worth Miami

3:52 p.m. - 12:51 p.m.BGI Bridgetown Grantley Adams Intl-YYC Calgary

22h 59m2 stops Miami Chicago O'Hare Intl

C$ 1,249American Airlines

Thu, 1 Oct - Wed, 21 Oct

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United Airlines flights from Calgary to Caribbean

Our best United Airlines deals on Calgary to Caribbean flight tickets

United Airlines

25 Oct

YYC6:00 a.m.Calgary

9h 25m

1 stop

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

29 Oct

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

10h 32m

1 stop

YYC9:53 p.m.Calgary

C$ 556

United Airlines

31 Oct

YYC6:00 a.m.Calgary

9h 25m

1 stop

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

6 Nov

SJU2:21 p.m.San Juan Luis Munoz Marin Intl

11h 32m

1 stop

YYC10:53 p.m.Calgary

C$ 557

United Airlines

25 Oct

YYC6:00 a.m.Calgary

29h 33m

2 stops

NAS1:33 p.m.Nassau Intl

29 Oct

NAS2:40 p.m.Nassau Intl

25h 41m

2 stops

YYC2:21 p.m.Calgary

C$ 594

American Airlines flights from Calgary to Caribbean

Our best American Airlines deals on Calgary to Caribbean flight tickets

American Airlines

31 Oct

YYC1:59 p.m.Calgary

21h 40m

2 stops

SJU1:39 p.m.San Juan Luis Munoz Marin Intl

6 Nov

SJU4:45 p.m.San Juan Luis Munoz Marin Intl

23h 26m

2 stops

YYC1:11 p.m.Calgary

C$ 598

American Airlines

9 Jan

YYC2:52 p.m.Calgary

19h 34m

2 stops

MBJ12:26 p.m.Montego Bay Sangster Intl

29 Jan

MBJ4:18 p.m.Montego Bay Sangster Intl

23h 36m

1 stop

YYC1:54 p.m.Calgary

C$ 658

American Airlines

9 Jan

YYC2:52 p.m.Calgary

19h 11m

2 stops

MBJ12:03 p.m.Montego Bay Sangster Intl

29 Jan

MBJ6:05 p.m.Montego Bay Sangster Intl

21h 49m

2 stops

YYC1:54 p.m.Calgary

C$ 662

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

CalgaryPunta Cana

YYC Calgary - PUJ Punta Cana

YYCPUJ

Calgary

Sun 15/11

12:05 a.m.-8:55 a.m.

Nonstop5h 50m

Punta Cana

Mon 23/11

9:55 a.m.-3:55 p.m.

Nonstop9h 00m

C$ 510

CalgaryPunta Cana

YYC Calgary - PUJ Punta Cana

YYCPUJ

Calgary

Sun 15/11

12:05 a.m.-8:55 a.m.

Nonstop5h 50m

Punta Cana

Mon 23/11

9:55 a.m.-3:55 p.m.

Nonstop9h 00m

C$ 512

CalgaryNassau

YYC Calgary - NAS Nassau Intl

YYCNAS

Calgary

Sat 28/11

8:10 a.m.-5:49 p.m.

1 stop7h 39m

Nassau Intl

Wed 9/12

12:25 p.m.-11:25 p.m.

1 stop13h 00m

C$ 518

CalgaryPunta Cana

YYC Calgary - PUJ Punta Cana

YYCPUJ

Calgary

Mon 16/11

10:10 p.m.-11:35 p.m.

2 stops22h 25m

Punta Cana

Mon 23/11

9:55 a.m.-3:55 p.m.

Nonstop9h 00m

C$ 546

CalgarySan Juan

YYC Calgary - SJU San Juan Luis Munoz Marin Intl

YYCSJU

Calgary

Sun 25/10

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

1 stop9h 25m

San Juan Luis Munoz Marin Intl

Wed 28/10

1:05 a.m.-2:21 p.m.

2 stops15h 16m

C$ 556

CalgarySan Juan

YYC Calgary - SJU San Juan Luis Munoz Marin Intl

YYCSJU

Calgary

Sun 25/10

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

1 stop9h 25m

San Juan Luis Munoz Marin Intl

Thu 29/10

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

1 stop10h 32m

C$ 556

CalgaryPunta Cana

YYC Calgary - PUJ Punta Cana

YYCPUJ

Calgary

Sun 22/11

1:45 a.m.-11:35 p.m.

1 stop18h 50m

Punta Cana

Fri 27/11

7:45 p.m.-12:25 p.m.

1 stop19h 40m

C$ 563

CalgaryPunta Cana

YYC Calgary - PUJ Punta Cana

YYCPUJ

Calgary

Wed 28/10

5:10 p.m.-10:35 p.m.

1 stop27h 25m

Punta Cana

Wed 4/11

3:15 p.m.-12:08 p.m.

1 stop23h 53m

C$ 563

CalgarySan Juan

YYC Calgary - SJU San Juan Luis Munoz Marin Intl

YYCSJU

Calgary

Fri 23/10

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

2 stops17h 55m

San Juan Luis Munoz Marin Intl

Fri 30/10

6:30 a.m.-9:45 p.m.

2 stops17h 15m

C$ 595

CalgarySan Juan

YYC Calgary - SJU San Juan Luis Munoz Marin Intl

YYCSJU

Calgary

Sat 31/10

1:59 p.m.-1:39 p.m.

2 stops21h 40m

San Juan Luis Munoz Marin Intl

Fri 6/11

4:45 p.m.-1:11 p.m.

2 stops23h 26m

C$ 595

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$ 764. If you don’t want to visit Caribbean in January, then you should wait until June to fly from Calgary, when ticket prices are also cheap, with an average price of C$ 782.

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$ 591. 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$ 1,070.

What is the cheapest Calgary to Caribbean flight route?

Fly from Calgary to Punta Cana 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$ 797 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$ 687 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$ 273
Fastest flight time	4h 45m
Direct flights	Mon, Tue, Wed, Fri and Sun
Airports in Caribbean	196 airports

The best one-way flight to Caribbean from Calgary in the past 72 hours is C$ 273. The best round-trip flight deal from Calgary to Caribbean found on momondo in the last 72 hours is C$ 510.

The fastest flight from Calgary to Caribbean takes 4h 45m

Direct flights go from Calgary to Caribbean on Monday, Tuesday, Wednesday, Friday 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 September 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 (95.65% of total bookings). The next most popular plane models are Boeing 737 (1.45%), Boeing 737-700 Passenger/BBJ1 (winglets) (1.45%), and Boeing 737-800 Passenger/BBJ2 (winglets) (1.45%).

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$ 330	Free Cancellation	Rating 7.4 10,245 reviews	Search United Airlines flights
Air Canada	PriceFrom C$ 451	Free Cancellation	Rating 7.1 11,701 reviews	Search Air Canada flights
WestJet	PriceFrom C$ 468	Free Cancellation	Rating 7.2 3,449 reviews	Search WestJet flights
Air Transat	PriceFrom C$ 914	Free Cancellation	Rating 7.7 582 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.