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

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

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 69% 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.

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 July 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$ 269 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.

10:00 a.m. - 4:24 p.m.

YYC

MBJ

5h 24mdirect

2:50 p.m. - 9:58 p.m.

MBJ

YYC

8h 08mdirect

C$ 541WestJet

Tue, 17 Nov - Tue, 1 Dec

6:00 a.m. - 5:38 p.m.

YYC

SJU

9h 38m

1 stop

1:00 a.m. - 11:28 a.m.

SJU

YYC

12h 28m

2 stops

C$ 547United Airlines

Tue, 20 Oct - Wed, 21 Oct

6:00 a.m. - 11:50 p.m.

YYC

SJU

15h 50m

2 stops

1:00 a.m. - 11:28 a.m.

SJU

YYC

12h 28m

2 stops

C$ 548United Airlines

Tue, 20 Oct - Wed, 21 Oct

10:00 a.m. - 4:24 p.m.

YYC

MBJ

5h 24mdirect

2:50 p.m. - 9:58 p.m.

MBJ

YYC

8h 08mdirect

C$ 552WestJet

Tue, 17 Nov - Tue, 1 Dec

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

YYC

SJU

9h 25m

1 stop

1:05 a.m. - 1:56 p.m.

SJU

YYC

14h 51m

2 stops

C$ 555United Airlines

Mon, 26 Oct - Wed, 28 Oct

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

YYC

SJU

9h 25m

1 stop

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

SJU

YYC

10h 32m

1 stop

C$ 559United Airlines

Mon, 26 Oct - Thu, 29 Oct

1:51 p.m. - 12:09 p.m.

YYC

SJU

20h 18m

2 stops

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

SJU

YYC

22h 08m

2 stops

C$ 591American Airlines

Mon, 26 Oct - Thu, 29 Oct

7:00 a.m. - 11:15 p.m.

YYC

SJU

14h 15m

1 stop

7:00 a.m. - 11:29 p.m.

SJU

YYC

18h 29m

2 stops

C$ 595American Airlines

Wed, 2 Sep - Wed, 9 Sep

8:15 a.m. - 11:36 p.m.

YYC

SJU

13h 21m

1 stop

2:05 a.m. - 9:17 p.m.

SJU

YYC

21h 12m

1 stop

C$ 600Air Canada

Sat, 31 Oct - Fri, 13 Nov

1:25 p.m. - 1:30 p.m.

YYC

SJU

22h 05m

2 stops

2:05 a.m. - 9:17 p.m.

SJU

YYC

21h 12m

1 stop

C$ 603Air Canada

Sat, 31 Oct - Fri, 13 Nov

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Air Canada flights from Calgary to Caribbean

Our best Air Canada deals on Calgary to Caribbean flight tickets

Air Canada

31 Oct

YYC8:15 a.m.Calgary

13h 21m

1 stop

SJU11:36 p.m.San Juan Luis Munoz Marin Intl

13 Nov

SJU2:05 a.m.San Juan Luis Munoz Marin Intl

21h 12m

1 stop

YYC9:17 p.m.Calgary

C$ 600

Air Canada

31 Oct

YYC1:25 p.m.Calgary

22h 05m

2 stops

SJU1:30 p.m.San Juan Luis Munoz Marin Intl

13 Nov

SJU2:05 a.m.San Juan Luis Munoz Marin Intl

21h 12m

1 stop

YYC9:17 p.m.Calgary

C$ 603

Air Canada

2 Nov

YYC1:20 a.m.Calgary

9h 30m

1 stop

MBJ11:50 a.m.Montego Bay Sangster Intl

8 Nov

MBJ2:20 p.m.Montego Bay Sangster Intl

23h 15m

2 stops

YYC12:35 p.m.Calgary

C$ 605

United Airlines flights from Calgary to Caribbean

Our best United Airlines deals on Calgary to Caribbean flight tickets

United Airlines

20 Oct

YYC6:00 a.m.Calgary

9h 38m

1 stop

SJU5:38 p.m.San Juan Luis Munoz Marin Intl

21 Oct

SJU1:00 a.m.San Juan Luis Munoz Marin Intl

12h 28m

2 stops

YYC11:28 a.m.Calgary

C$ 547

United Airlines

20 Oct

YYC6:00 a.m.Calgary

15h 50m

2 stops

SJU11:50 p.m.San Juan Luis Munoz Marin Intl

21 Oct

SJU1:00 a.m.San Juan Luis Munoz Marin Intl

12h 28m

2 stops

YYC11:28 a.m.Calgary

C$ 548

United Airlines

26 Oct

YYC6:00 a.m.Calgary

9h 25m

1 stop

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

28 Oct

SJU1:05 a.m.San Juan Luis Munoz Marin Intl

14h 51m

2 stops

YYC1:56 p.m.Calgary

C$ 555

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

CalgaryMontego Bay

YYC - MBJ

YYCMBJ

Calgary

Tue 17/11

10:00 a.m.-4:24 p.m.

Nonstop5h 24m

Montego Bay Sangster Intl

Tue 1/12

2:50 p.m.-9:58 p.m.

Nonstop8h 08m

C$ 541

CalgarySan Juan

YYC - SJU

YYCSJU

Calgary

Tue 20/10

6:00 a.m.-5:38 p.m.

1 stop9h 38m

San Juan Luis Munoz Marin Intl

Wed 21/10

1:00 a.m.-11:28 a.m.

2 stops12h 28m

C$ 547

CalgarySan Juan

YYC - SJU

YYCSJU

Calgary

Tue 20/10

6:00 a.m.-11:50 p.m.

2 stops15h 50m

San Juan Luis Munoz Marin Intl

Wed 21/10

1:00 a.m.-11:28 a.m.

2 stops12h 28m

C$ 548

CalgaryMontego Bay

YYC - MBJ

YYCMBJ

Calgary

Tue 17/11

10:00 a.m.-4:24 p.m.

Nonstop5h 24m

Montego Bay Sangster Intl

Tue 1/12

2:50 p.m.-9:58 p.m.

Nonstop8h 08m

C$ 552

CalgarySan Juan

YYC - SJU

YYCSJU

Calgary

Mon 26/10

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

1 stop9h 25m

San Juan Luis Munoz Marin Intl

Wed 28/10

1:05 a.m.-1:56 p.m.

2 stops14h 51m

C$ 555

CalgarySan Juan

YYC - SJU

YYCSJU

Calgary

Mon 26/10

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$ 559

CalgarySan Juan

YYC - SJU

YYCSJU

Calgary

Mon 26/10

1:51 p.m.-12:09 p.m.

2 stops20h 18m

San Juan Luis Munoz Marin Intl

Thu 29/10

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

2 stops22h 08m

C$ 590

CalgarySan Juan

YYC - SJU

YYCSJU

Calgary

Wed 2/9

7:00 a.m.-11:15 p.m.

1 stop14h 15m

San Juan Luis Munoz Marin Intl

Wed 9/9

7:00 a.m.-11:29 p.m.

2 stops18h 29m

C$ 595

CalgarySan Juan

YYC - SJU

YYCSJU

Calgary

Sat 31/10

8:15 a.m.-11:36 p.m.

1 stop13h 21m

San Juan Luis Munoz Marin Intl

Fri 13/11

2:05 a.m.-9:17 p.m.

1 stop21h 12m

C$ 600

CalgarySan Juan

YYC - SJU

YYCSJU

Calgary

Sat 31/10

1:25 p.m.-1:30 p.m.

2 stops22h 05m

San Juan Luis Munoz Marin Intl

Fri 13/11

2:05 a.m.-9:17 p.m.

1 stop21h 12m

C$ 603

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, September 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$ 710. If you don’t want to visit Caribbean in September, then you should wait until January to fly from Calgary, when ticket prices are also cheap, with an average price of C$ 753.

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$ 630. 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$ 906.

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$ 766 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$ 661 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$ 542
Fastest flight time	4h 42m
Direct flights	Mon, Tue, Wed, Fri, Sat and Sun
Airports in Caribbean	195 airports

The best flight deal from Calgary to Caribbean found on momondo in the last 72 hours is C$ 542

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

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

There are 195 airports in Caribbean. From Calgary there are direct flights to Puerto Plata La Union (POP), 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 July 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 (89.55% of total bookings). The next most popular plane models are Boeing 737-700 Passenger/BBJ1 (winglets) (5.97%), Boeing 737-800 Passenger/BBJ2 (winglets) (2.99%), and Boeing 737 (1.49%).

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$ 304	Free Cancellation	Rating 7.4 10,024 reviews	Search United Airlines flights
WestJet	PriceFrom C$ 439	Free Cancellation	Rating 7.2 3,411 reviews	Search WestJet flights
Air Canada	PriceFrom C$ 439	Free Cancellation	Rating 7.1 11,371 reviews	Search Air Canada flights
Air Transat	PriceFrom C$ 576	Free Cancellation	Rating 7.8 566 reviews	Search Air Transat flights
American Airlines	PriceFrom C$ 630	Free Cancellation	Rating 7.1 11,832 reviews	Search American Airlines 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.