How many flights depart from Winnipeg to Caribbean on average per week?

As of March 2026, 1 flights take off from Winnipeg and land in Caribbean each week. The most common flight departure day for this route is Sat, with 100% of weekly flights taking off on this day.

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 78% 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?

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 March 2026, there are 5 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$ 226 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

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:00 a.m. - 11:45 a.m.

YWG

MBJ

27h 45m

2 stops

7:30 p.m. - 9:45 a.m.

MBJ

YWG

14h 15m

1 stop

C$ 494WestJet

Sat, 13 Jun - Sun, 21 Jun

7:10 p.m. - 11:45 a.m.

YWG

MBJ

16h 35m

2 stops

7:30 p.m. - 12:15 p.m.

MBJ

YWG

16h 45m

2 stops

C$ 499WestJet

Sat, 13 Jun - Sun, 21 Jun

9:05 p.m. - 6:30 p.m.

YWG

MBJ

21h 25m

2 stops

7:30 p.m. - 12:00 p.m.

MBJ

YWG

16h 30m

2 stops

C$ 501WestJet

Sat, 13 Jun - Sun, 21 Jun

6:00 a.m. - 12:25 p.m.

YWG

NAS

29h 25m

2 stops

1:15 p.m. - 3:14 p.m.

NAS

YWG

26h 59m

1 stop

C$ 539Air Canada

Sun, 26 Apr - Thu, 30 Apr

7:05 p.m. - 9:00 p.m.

YWG

NAS

24h 55m

1 stop

1:15 p.m. - 10:09 a.m.

NAS

YWG

21h 54m

1 stop

C$ 546Air Canada

Sun, 26 Apr - Thu, 30 Apr

6:00 a.m. - 6:40 p.m.

YWG

NAS

35h 40m

2 stops

3:15 p.m. - 11:35 p.m.

NAS

YWG

9h 20m

1 stop

C$ 584Porter Airlines

Fri, 17 Apr - Fri, 24 Apr

2:00 p.m. - 2:57 p.m.

YWG

NAS

23h 57m

1 stop

1:15 p.m. - 11:52 a.m.

NAS

YWG

47h 37m

2 stops

C$ 634United Airlines

Fri, 24 Apr - Sat, 2 May

8:45 a.m. - 11:50 p.m.

YWG

SJU

14h 05m

2 stops

1:00 a.m. - 11:52 a.m.

SJU

YWG

11h 52m

2 stops

C$ 731United Airlines

Tue, 14 Apr - Tue, 28 Apr

8:20 p.m. - 1:00 p.m.

YWG

SJU

15h 40m

1 stop

12:57 p.m. - 3:19 p.m.

SJU

YWG

27h 22m

2 stops

C$ 771Multiple Airlines

Sat, 11 Apr - Thu, 30 Apr

7:05 p.m. - 1:45 p.m.

YWG

CUR

41h 40m

2 stops

9:50 p.m. - 11:35 p.m.

CUR

YWG

26h 45m

3 stops

C$ 842Multiple Airlines

Wed, 8 Apr - Wed, 22 Apr

Air Canada flights from Winnipeg to Caribbean

Our best Air Canada deals on Winnipeg to Caribbean flight tickets

Air Canada

26 Apr

YWG6:00 a.m.Winnipeg

29h 25m

2 stops

NAS12:25 p.m.Nassau Intl

30 Apr

NAS1:15 p.m.Nassau Intl

26h 59m

1 stop

YWG3:14 p.m.Winnipeg

C$ 539

Air Canada

26 Apr

YWG7:05 p.m.Winnipeg

24h 55m

1 stop

NAS9:00 p.m.Nassau Intl

30 Apr

NAS1:15 p.m.Nassau Intl

21h 54m

1 stop

YWG10:09 a.m.Winnipeg

C$ 546

Air Canada

26 Apr

YWG6:00 a.m.Winnipeg

29h 25m

2 stops

NAS12:25 p.m.Nassau Intl

30 Apr

NAS9:10 p.m.Nassau Intl

19h 04m

2 stops

YWG3:14 p.m.Winnipeg

C$ 550

WestJet flights from Winnipeg to Caribbean

Our best WestJet deals on Winnipeg to Caribbean flight tickets

WestJet

13 Jun

YWG8:00 a.m.Winnipeg

27h 45m

2 stops

MBJ11:45 a.m.Montego Bay Sangster Intl

21 Jun

MBJ7:30 p.m.Montego Bay Sangster Intl

14h 15m

1 stop

YWG9:45 a.m.Winnipeg

C$ 494

WestJet

13 Jun

YWG7:10 p.m.Winnipeg

16h 35m

2 stops

MBJ11:45 a.m.Montego Bay Sangster Intl

21 Jun

MBJ7:30 p.m.Montego Bay Sangster Intl

16h 45m

2 stops

YWG12:15 p.m.Winnipeg

C$ 499

WestJet

13 Jun

YWG9:05 p.m.Winnipeg

21h 25m

2 stops

MBJ6:30 p.m.Montego Bay Sangster Intl

21 Jun

MBJ7:30 p.m.Montego Bay Sangster Intl

16h 30m

2 stops

YWG12:00 p.m.Winnipeg

C$ 501

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 13/6

8:00 a.m.-11:45 a.m.

2 stops27h 45m

Montego Bay Sangster Intl

Sun 21/6

7:30 p.m.-9:45 a.m.

1 stop14h 15m

C$ 494

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 13/6

7:10 p.m.-11:45 a.m.

2 stops16h 35m

Montego Bay Sangster Intl

Sun 21/6

7:30 p.m.-12:15 p.m.

2 stops16h 45m

C$ 499

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 13/6

9:05 p.m.-6:30 p.m.

2 stops21h 25m

Montego Bay Sangster Intl

Sun 21/6

7:30 p.m.-12:00 p.m.

2 stops16h 30m

C$ 501

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Sun 26/4

6:00 a.m.-12:25 p.m.

2 stops29h 25m

Nassau Intl

Thu 30/4

1:15 p.m.-3:14 p.m.

1 stop26h 59m

C$ 539

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Sun 26/4

7:05 p.m.-9:00 p.m.

1 stop24h 55m

Nassau Intl

Thu 30/4

1:15 p.m.-10:09 a.m.

1 stop21h 54m

C$ 546

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Fri 17/4

6:00 a.m.-6:40 p.m.

2 stops35h 40m

Nassau Intl

Fri 24/4

3:15 p.m.-11:35 p.m.

1 stop9h 20m

C$ 584

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Fri 24/4

2:00 p.m.-2:57 p.m.

1 stop23h 57m

Nassau Intl

Sat 2/5

1:15 p.m.-11:52 a.m.

2 stops47h 37m

C$ 634

Quickest round-trip

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Tue 14/4

8:45 a.m.-11:50 p.m.

2 stops14h 05m

San Juan Luis Munoz Marin Intl

Tue 28/4

1:00 a.m.-11:52 a.m.

2 stops11h 52m

C$ 731

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sat 11/4

8:20 p.m.-1:00 p.m.

1 stop15h 40m

San Juan Luis Munoz Marin Intl

Thu 30/4

12:57 p.m.-3:19 p.m.

2 stops27h 22m

C$ 771

WinnipegWillemstad

YWG - CUR

YWGCUR

Winnipeg

Wed 8/4

7:05 p.m.-1:45 p.m.

2 stops41h 40m

Willemstad Hato Int.

Wed 22/4

9:50 p.m.-11:35 p.m.

3 stops26h 45m

C$ 842

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

Other information

What is the cheapest month to fly to Caribbean?

In general, June 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$ 669. If you don’t want to visit Caribbean in June, then you should wait until March to fly from Winnipeg, when ticket prices are also cheap, with an average price of C$ 683.

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 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$ 783 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$ 556 on momondo.

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

There is only 1 cabin class available to choose from on Winnipeg 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 Winnipeg to Caribbean flights?

You could potentially save up to 74% 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$ 651
Fastest flight time	8h 15m
Direct flights	Sun
Airports in Caribbean	195 airports

The best flight deal from Winnipeg to Caribbean found on momondo in the last 72 hours is C$ 651

The fastest flight from Winnipeg to Caribbean takes 8h 15m

Direct flights go from Winnipeg to Caribbean on Sunday. There are no airlines offering direct flights.

There are 195 airports in Caribbean. From Winnipeg there are direct flights to Montego Bay Sangster Intl (MBJ).

Search flight deals

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 March 2026, there are 5 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 MAX 8 (41.46% of total bookings). The next most popular plane models are Boeing 737-800 Passenger/BBJ2 (winglets) (41.46%), Boeing 737-800 (Scimitar Winglets) (14.63%), and Boeing 737-700 Passenger/BBJ1 (winglets) (2.44%).

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$ 386	Free Cancellation	Rating 7.1 10,835 reviews	Search Air Canada flights
WestJet	PriceFrom C$ 474	Free Cancellation	Rating 7.2 3,300 reviews	Search WestJet flights
Porter Airlines	PriceFrom C$ 494	Free Cancellation	Rating 8.0 427 reviews	Search Porter Airlines flights
Air Transat	PriceFrom C$ 789	Free Cancellation	Rating 7.7 521 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.