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 72% 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?

WestJet, United Airlines, 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 June 2026, there are 4 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$ 254 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.

1:00 a.m. - 11:10 a.m.

YYC

NAS

8h 10m

1 stop

12:00 p.m. - 10:30 p.m.

NAS

YYC

12h 30m

2 stops

C$ 565WestJet

Sat, 26 Sep - Sat, 3 Oct

1:00 a.m. - 11:10 a.m.

YYC

NAS

8h 10m

1 stop

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

NAS

YYC

26h 20m

1 stop

C$ 572WestJet

Sat, 26 Sep - Sat, 3 Oct

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

YYC

SJU

9h 25m

1 stop

8:05 a.m. - 9:53 p.m.

SJU

YYC

16h 48m

2 stops

C$ 620United Airlines

Tue, 27 Oct - Sat, 7 Nov

6:00 a.m. - 1:30 p.m.

YYC

MBJ

30h 30m

2 stops

4:33 p.m. - 9:48 p.m.

MBJ

YYC

30h 15m

2 stops

C$ 643United Airlines

Sat, 25 Jul - Sat, 1 Aug

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

YYC

SJU

9h 25m

1 stop

2:25 p.m. - 8:44 a.m.

SJU

YYC

21h 19m

1 stop

C$ 703Multiple Airlines

Tue, 27 Oct - Sat, 7 Nov

1:35 p.m. - 9:24 p.m.

YYC

SJU

28h 49m

1 stop

7:35 p.m. - 7:17 p.m.

SJU

YYC

26h 42m

1 stop

C$ 707Air Canada

Fri, 13 Nov - Wed, 25 Nov

6:45 a.m. - 11:57 a.m.

YYC

SJU

27h 12m

1 stop

1:25 p.m. - 5:30 p.m.

SJU

YYC

30h 05m

1 stop

C$ 710Air Canada

Sat, 10 Oct - Sat, 17 Oct

1:51 p.m. - 10:39 a.m.

YYC

PUJ

18h 48m

2 stops

3:03 p.m. - 12:51 p.m.

PUJ

YYC

23h 48m

1 stop

C$ 732American Airlines

Wed, 21 Oct - Wed, 28 Oct

1:51 p.m. - 10:39 a.m.

YYC

PUJ

18h 48m

2 stops

3:03 p.m. - 11:59 a.m.

PUJ

YYC

22h 56m

2 stops

C$ 738American Airlines

Wed, 21 Oct - Wed, 28 Oct

2:25 p.m. - 2:30 p.m.

YYC

KIN

47h 05m

2 stops

6:25 p.m. - 8:25 p.m.

KIN

YYC

27h 00m

2 stops

C$ 955Multiple Airlines

Mon, 10 Aug - Mon, 17 Aug

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Air Canada flights from Calgary to Caribbean

Our best Air Canada deals on Calgary to Caribbean flight tickets

Air Canada

11 Sep

YYC12:55 a.m.Calgary

9h 25m

1 stop

MBJ11:20 a.m.Montego Bay Sangster Intl

14 Sep

MBJ12:30 p.m.Montego Bay Sangster Intl

27h 32m

2 stops

YYC3:02 p.m.Calgary

C$ 684

Air Canada

12 Sep

YYC3:50 p.m.Calgary

18h 30m

2 stops

MBJ11:20 a.m.Montego Bay Sangster Intl

14 Sep

MBJ12:30 p.m.Montego Bay Sangster Intl

24h 17m

2 stops

YYC11:47 a.m.Calgary

C$ 685

Air Canada

11 Sep

YYC12:55 a.m.Calgary

9h 25m

1 stop

MBJ11:20 a.m.Montego Bay Sangster Intl

14 Sep

MBJ12:30 p.m.Montego Bay Sangster Intl

32h 02m

1 stop

YYC7:32 p.m.Calgary

C$ 687

United Airlines flights from Calgary to Caribbean

Our best United Airlines deals on Calgary to Caribbean flight tickets

United Airlines

27 Oct

YYC6:00 a.m.Calgary

9h 25m

1 stop

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

7 Nov

SJU8:05 a.m.San Juan Luis Munoz Marin Intl

16h 48m

2 stops

YYC9:53 p.m.Calgary

C$ 620

United Airlines

25 Jul

YYC6:00 a.m.Calgary

30h 30m

2 stops

MBJ1:30 p.m.Montego Bay Sangster Intl

1 Aug

MBJ4:33 p.m.Montego Bay Sangster Intl

30h 15m

2 stops

YYC9:48 p.m.Calgary

C$ 643

United Airlines

16 Nov

YYC12:37 p.m.Calgary

23h 37m

2 stops

MBJ2:14 p.m.Montego Bay Sangster Intl

23 Nov

MBJ3:20 p.m.Montego Bay Sangster Intl

32h 33m

2 stops

YYC9:53 p.m.Calgary

C$ 644

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

CalgaryNassau

YYC - NAS

YYCNAS

Calgary

Sat 26/9

1:00 a.m.-11:10 a.m.

1 stop8h 10m

Nassau Intl

Sat 3/10

12:00 p.m.-10:30 p.m.

2 stops12h 30m

C$ 565

CalgaryNassau

YYC - NAS

YYCNAS

Calgary

Sat 26/9

1:00 a.m.-11:10 a.m.

1 stop8h 10m

Nassau Intl

Sat 3/10

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

1 stop26h 20m

C$ 572

CalgarySan Juan

YYC - SJU

YYCSJU

Calgary

Tue 27/10

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

1 stop9h 25m

San Juan Luis Munoz Marin Intl

Sat 7/11

8:05 a.m.-9:53 p.m.

2 stops16h 48m

C$ 620

CalgaryMontego Bay

YYC - MBJ

YYCMBJ

Calgary

Sat 25/7

6:00 a.m.-1:30 p.m.

2 stops30h 30m

Montego Bay Sangster Intl

Sat 1/8

4:33 p.m.-9:48 p.m.

2 stops30h 15m

C$ 643

CalgarySan Juan

YYC - SJU

YYCSJU

Calgary

Tue 27/10

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

1 stop9h 25m

San Juan Luis Munoz Marin Intl

Sat 7/11

2:25 p.m.-8:44 a.m.

1 stop21h 19m

C$ 702

CalgarySan Juan

YYC - SJU

YYCSJU

Calgary

Fri 13/11

1:35 p.m.-9:24 p.m.

1 stop28h 49m

San Juan Luis Munoz Marin Intl

Wed 25/11

7:35 p.m.-7:17 p.m.

1 stop26h 42m

C$ 707

CalgarySan Juan

YYC - SJU

YYCSJU

Calgary

Sat 10/10

6:45 a.m.-11:57 a.m.

1 stop27h 12m

San Juan Luis Munoz Marin Intl

Sat 17/10

1:25 p.m.-5:30 p.m.

1 stop30h 05m

C$ 710

CalgaryPunta Cana

YYC - PUJ

YYCPUJ

Calgary

Wed 21/10

1:51 p.m.-10:39 a.m.

2 stops18h 48m

Punta Cana

Wed 28/10

3:03 p.m.-12:51 p.m.

1 stop23h 48m

C$ 732

CalgaryPunta Cana

YYC - PUJ

YYCPUJ

Calgary

Wed 21/10

1:51 p.m.-10:39 a.m.

2 stops18h 48m

Punta Cana

Wed 28/10

3:03 p.m.-11:59 a.m.

2 stops22h 56m

C$ 738

CalgaryKingston

YYC - KIN

YYCKIN

Calgary

Mon 10/8

2:25 p.m.-2:30 p.m.

2 stops47h 05m

Kingston Norman Manley

Mon 17/8

6:25 p.m.-8:25 p.m.

2 stops27h 00m

C$ 955

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, October 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$ 217. If you don’t want to visit Caribbean in October, then you should wait until April to fly from Calgary, when ticket prices are also cheap, with an average price of C$ 226.

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$ 635. 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$ 913.

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$ 780 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$ 644 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$ 643
Fastest flight time	4h 42m
Direct flights	Every day
Airports in Caribbean	195 airports

The best flight deal from Calgary to Caribbean found on momondo in the last 72 hours is C$ 643

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

Direct flights go from Calgary to Caribbean every day.

There are 195 airports in Caribbean. From Calgary there are direct flights to Nassau Intl (NAS), Punta Cana (PUJ), Montego Bay Sangster Intl (MBJ).

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 June 2026, there are 4 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 (92.55% of total bookings). The next most popular plane models are Boeing 737-700 Passenger/BBJ1 (winglets) (4.26%), Boeing 737-800 Passenger/BBJ2 (winglets) (2.13%), and Boeing 737 (1.06%).

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$ 306	Free Cancellation	Rating 7.4 9,899 reviews	Search United Airlines flights
WestJet	PriceFrom C$ 442	Free Cancellation	Rating 7.2 3,385 reviews	Search WestJet flights
Air Canada	PriceFrom C$ 442	Free Cancellation	Rating 7.1 11,269 reviews	Search Air Canada flights
American Airlines	PriceFrom C$ 635	Free Cancellation	Rating 7.1 11,774 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.