Which airlines fly to Caribbean?

WestJet, Air Canada and Air Transat are the top three most popular airlines that fly to Caribbean from Winnipeg according to our data. WestJet is the first choice among our users, with 79% 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 Winnipeg to Caribbean?

Air Canada, WestJet, and United Airlines are the most popular carriers operating from Winnipeg to Caribbean

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

Prices for flights from Winnipeg Airport to Caribbean were last updated today.

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

As of May 2026, there are 4 operators available to choose from for flights from Winnipeg Airport to Caribbean.

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

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Winnipeg Airport to Caribbean.

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

The necessary travel and health documents for your Caribbean trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

C$ 248 Cheap Flights from Winnipeg to Caribbean in 2026

1 adult

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Find the cheapest flights from Winnipeg to Caribbean

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:00 a.m. - 12:45 p.m.

YWG

GCM

30h 45m

2 stops

1:45 p.m. - 2:15 p.m.

GCM

YWG

24h 30m

2 stops

C$ 512WestJet

Mon, 22 Jun - Tue, 11 Aug

4:55 p.m. - 12:45 p.m.

YWG

GCM

19h 50m

2 stops

1:45 p.m. - 12:55 a.m.

GCM

YWG

11h 10m

1 stop

C$ 521WestJet

Mon, 22 Jun - Tue, 11 Aug

7:20 p.m. - 11:20 a.m.

YWG

MBJ

16h 00m

1 stop

12:30 p.m. - 11:08 a.m.

MBJ

YWG

22h 38m

1 stop

C$ 524Air Canada

Mon, 1 Jun - Mon, 8 Jun

1:25 p.m. - 11:20 a.m.

YWG

MBJ

21h 55m

2 stops

12:30 p.m. - 11:08 a.m.

MBJ

YWG

22h 38m

1 stop

C$ 531Air Canada

Mon, 1 Jun - Mon, 8 Jun

1:25 p.m. - 11:25 a.m.

YWG

GCM

46h 00m

2 stops

1:45 p.m. - 3:25 p.m.

GCM

YWG

25h 40m

2 stops

C$ 567Multiple Airlines

Sat, 6 Jun - Sat, 13 Jun

5:10 p.m. - 7:30 p.m.

YWG

SJU

25h 20m

2 stops

4:30 p.m. - 7:25 p.m.

SJU

YWG

27h 55m

2 stops

C$ 797Multiple Airlines

Fri, 16 Oct - Tue, 20 Oct

8:30 a.m. - 11:50 p.m.

YWG

SJU

14h 20m

2 stops

2:00 p.m. - 8:48 p.m.

SJU

YWG

31h 48m

1 stop

C$ 826United Airlines

Wed, 23 Sep - Fri, 25 Sep

8:30 a.m. - 11:50 p.m.

YWG

SJU

14h 20m

2 stops

4:55 p.m. - 11:39 a.m.

SJU

YWG

19h 44m

2 stops

C$ 830United Airlines

Wed, 23 Sep - Fri, 25 Sep

12:40 p.m. - 12:20 p.m.

YWG

SDQ

22h 40m

2 stops

7:40 p.m. - 11:27 p.m.

SDQ

YWG

28h 47m

2 stops

C$ 1,412Delta

Mon, 21 Sep - Wed, 23 Sep

12:40 p.m. - 12:20 p.m.

YWG

SDQ

22h 40m

2 stops

7:40 p.m. - 8:09 p.m.

SDQ

YWG

25h 29m

2 stops

C$ 1,418Delta

Mon, 21 Sep - Wed, 23 Sep

United Airlines flights from Winnipeg to Caribbean

Our best United Airlines deals on Winnipeg to Caribbean flight tickets

United Airlines

23 Sep

YWG8:30 a.m.Winnipeg

14h 20m

2 stops

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

25 Sep

SJU4:55 p.m.San Juan Luis Munoz Marin Intl

19h 44m

2 stops

YWG11:39 a.m.Winnipeg

C$ 826

United Airlines

23 Sep

YWG8:30 a.m.Winnipeg

14h 20m

2 stops

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

25 Sep

SJU4:55 p.m.San Juan Luis Munoz Marin Intl

19h 44m

2 stops

YWG11:39 a.m.Winnipeg

C$ 830

United Airlines

23 Sep

YWG8:30 a.m.Winnipeg

14h 20m

2 stops

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

25 Sep

SJU4:55 p.m.San Juan Luis Munoz Marin Intl

19h 44m

2 stops

YWG11:39 a.m.Winnipeg

C$ 831

Air Canada flights from Winnipeg to Caribbean

Our best Air Canada deals on Winnipeg to Caribbean flight tickets

Air Canada

1 Jun

YWG7:20 p.m.Winnipeg

16h 00m

1 stop

MBJ11:20 a.m.Montego Bay Sangster Intl

8 Jun

MBJ12:30 p.m.Montego Bay Sangster Intl

22h 38m

1 stop

YWG11:08 a.m.Winnipeg

C$ 524

Air Canada

1 Jun

YWG1:25 p.m.Winnipeg

21h 55m

2 stops

MBJ11:20 a.m.Montego Bay Sangster Intl

8 Jun

MBJ12:30 p.m.Montego Bay Sangster Intl

22h 38m

1 stop

YWG11:08 a.m.Winnipeg

C$ 531

Air Canada

9 Jun

YWG7:20 p.m.Winnipeg

16h 00m

1 stop

MBJ11:20 a.m.Montego Bay Sangster Intl

17 Jun

MBJ12:30 p.m.Montego Bay Sangster Intl

10h 48m

1 stop

YWG11:18 p.m.Winnipeg

C$ 554

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Mon 22/6

6:00 a.m.-12:45 p.m.

2 stops30h 45m

George Town Owen Roberts Intl

Tue 11/8

1:45 p.m.-2:15 p.m.

2 stops24h 30m

C$ 512

Quickest round-trip

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Mon 22/6

4:55 p.m.-12:45 p.m.

2 stops19h 50m

George Town Owen Roberts Intl

Tue 11/8

1:45 p.m.-12:55 a.m.

1 stop11h 10m

C$ 521

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 1/6

7:20 p.m.-11:20 a.m.

1 stop16h 00m

Montego Bay Sangster Intl

Mon 8/6

12:30 p.m.-11:08 a.m.

1 stop22h 38m

C$ 524

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 1/6

1:25 p.m.-11:20 a.m.

2 stops21h 55m

Montego Bay Sangster Intl

Mon 8/6

12:30 p.m.-11:08 a.m.

1 stop22h 38m

C$ 531

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 6/6

1:25 p.m.-11:25 a.m.

2 stops46h 00m

George Town Owen Roberts Intl

Sat 13/6

1:45 p.m.-3:25 p.m.

2 stops25h 40m

C$ 567

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Fri 16/10

5:10 p.m.-7:30 p.m.

2 stops25h 20m

San Juan Luis Munoz Marin Intl

Tue 20/10

4:30 p.m.-7:25 p.m.

2 stops27h 55m

C$ 797

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Wed 23/9

8:30 a.m.-11:50 p.m.

2 stops14h 20m

San Juan Luis Munoz Marin Intl

Fri 25/9

2:00 p.m.-8:48 p.m.

1 stop31h 48m

C$ 826

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Wed 23/9

8:30 a.m.-11:50 p.m.

2 stops14h 20m

San Juan Luis Munoz Marin Intl

Fri 25/9

4:55 p.m.-11:39 a.m.

2 stops19h 44m

C$ 830

WinnipegSanto Domingo

YWG - SDQ

YWGSDQ

Winnipeg

Mon 21/9

12:40 p.m.-12:20 p.m.

2 stops22h 40m

Santo Domingo Las Americas

Wed 23/9

7:40 p.m.-11:27 p.m.

2 stops28h 47m

C$ 1,412

WinnipegSanto Domingo

YWG - SDQ

YWGSDQ

Winnipeg

Mon 21/9

12:40 p.m.-12:20 p.m.

2 stops22h 40m

Santo Domingo Las Americas

Wed 23/9

7:40 p.m.-8:09 p.m.

2 stops25h 29m

C$ 1,418

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 Winnipeg 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, March is the cheapest month to fly from Winnipeg to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 188. If you don’t want to visit Caribbean in March, then you should wait until October to fly from Winnipeg, when ticket prices are also cheap, with an average price of C$ 207.

What is the cheapest Winnipeg to Caribbean flight route?

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

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

You are more likely to see cheaper flights to Caribbean from Winnipeg when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean for around C$ 791 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean from Winnipeg for as low as C$ 589 on momondo.

Can stopping save me money on Winnipeg to Caribbean flights?

You could potentially save up to 68% on your flight if you consider stops on a Winnipeg to Caribbean flight.

Cheap Winnipeg to Caribbean flight deals and tips

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

Best price found	C$ 1,251
Fastest flight time	6h 57m
Direct flights	None

The best flight deal from Winnipeg to Caribbean found on momondo in the last 72 hours is C$ 1,251

The fastest flight from Winnipeg to Caribbean takes 6h 57m

There are no direct flights from Winnipeg to Caribbean. There are no popular flight routes from Winnipeg to Caribbean.

Search flight deals

Frequently asked questions about flying from Winnipeg to Caribbean

When did momondo last update prices for flights from Winnipeg Airport to Caribbean?
Prices for flights from Winnipeg Airport to Caribbean were last updated today.
How many operators does momondo search for flights from Winnipeg Airport to Caribbean?
As of May 2026, there are 4 operators available to choose from for flights from Winnipeg Airport to Caribbean.
How old do you have to be to fly from Winnipeg Airport to Caribbean?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Winnipeg Airport to Caribbean.
What documentation or ID do you need to fly to Caribbean?
The necessary travel and health documents for your Caribbean trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Winnipeg to Caribbean?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Winnipeg to Caribbean is Boeing 737-800 Passenger/BBJ2 (winglets) (50.91% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (32.73%), Boeing 737-800 (Scimitar Winglets) (14.55%), and Boeing 737-700 Passenger/BBJ1 (winglets) (1.82%).

Best airlines flying from Winnipeg to Caribbean

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

Airline	Rating	Free Cancellation	Price
Air Canada	PriceFrom C$ 382	Free Cancellation	Rating 7.1 10,999 reviews	Search Air Canada flights
WestJet	PriceFrom C$ 470	Free Cancellation	Rating 7.2 3,331 reviews	Search WestJet flights
Porter Airlines	PriceFrom C$ 490	Free Cancellation	Rating 8.0 436 reviews	Search Porter Airlines flights
Air Transat	PriceFrom C$ 783	Free Cancellation	Rating 7.8 548 reviews	Search Air Transat flights

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Caribbean from Winnipeg.

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

Flights from Winnipeg to Caribbean with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Caribbean from Winnipeg.

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

If you are simply researching potential flights to Caribbean, momondo offers a useful price alert feature which will track prices for flights to Caribbean from Winnipeg and alert you when they change.