What is the cheapest airline that flies from Winnipeg to Caribbean Islands?

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

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

Prices for flights from Winnipeg Airport to Caribbean Islands refresh daily.

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

There are 3 operators available for flights from Winnipeg Airport to Caribbean Islands as of September 2026.

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

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Winnipeg Airport to Caribbean Islands.

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

The necessary travel and health documents for your Caribbean Islands 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$ 221 Cheap Flights from Winnipeg to Caribbean Islands in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Winnipeg to Caribbean Islands

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:00 a.m. - 7:35 p.m.YWG Winnipeg-MBJ Montego Bay Sangster Intl

12h 35m2 stops Edmonton Toronto Pearson Intl

3:35 p.m. - 8:35 p.m.MBJ Montego Bay Sangster Intl-YWG Winnipeg

6h 00mdirect

C$ 444WestJet

Sat, 21 Nov - Sat, 28 Nov

6:00 a.m. - 7:35 p.m.YWG Winnipeg-MBJ Montego Bay Sangster Intl

12h 35m2 stops Edmonton Toronto Pearson Intl

3:35 p.m. - 8:35 p.m.MBJ Montego Bay Sangster Intl-YWG Winnipeg

6h 00mdirect

C$ 445WestJet

Sat, 21 Nov - Sat, 28 Nov

5:00 a.m. - 7:35 p.m.YWG Winnipeg-MBJ Montego Bay Sangster Intl

13h 35m1 stop Toronto Pearson Intl

3:35 p.m. - 8:35 p.m.MBJ Montego Bay Sangster Intl-YWG Winnipeg

6h 00mdirect

C$ 449WestJet

Sat, 21 Nov - Sat, 28 Nov

8:05 a.m. - 11:35 p.m.YWG Winnipeg-PUJ Punta Cana

13h 30m1 stop Montreal Pierre Elliott Trudeau Intl

5:30 p.m. - 10:00 p.m.PUJ Punta Cana-YWG Winnipeg

6h 30mdirect

C$ 465Air Canada

Thu, 3 Dec - Thu, 17 Dec

2:05 p.m. - 1:45 p.m.YWG Winnipeg-PUJ Punta Cana

21h 40m1 stop Montreal Pierre Elliott Trudeau Intl

5:30 p.m. - 10:00 p.m.PUJ Punta Cana-YWG Winnipeg

6h 30mdirect

C$ 480Air Canada

Wed, 16 Dec - Thu, 17 Dec

8:05 a.m. - 11:35 p.m.YWG Winnipeg-PUJ Punta Cana

13h 30m1 stop Montreal Pierre Elliott Trudeau Intl

5:30 p.m. - 10:00 p.m.PUJ Punta Cana-YWG Winnipeg

6h 30mdirect

C$ 480Air Canada

Mon, 14 Dec - Thu, 17 Dec

7:15 a.m. - 5:20 p.m.YWG Winnipeg-MBJ Montego Bay Sangster Intl

9h 05m1 stop Toronto Pearson Intl

3:35 p.m. - 8:35 p.m.MBJ Montego Bay Sangster Intl-YWG Winnipeg

6h 00mdirect

C$ 532Multiple Airlines

Sat, 28 Nov - Sat, 5 Dec

12:10 p.m. - 3:25 p.m.YWG Winnipeg-SXM Simpson Bay Princess Juliana

25h 15m2 stops Edmonton Toronto Pearson Intl

1:05 p.m. - 7:45 p.m.SXM Simpson Bay Princess Juliana-YWG Winnipeg

32h 40m3 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl Calgary

C$ 568Multiple Airlines

Mon, 23 Nov - Wed, 25 Nov

5:15 a.m. - 8:25 p.m.YWG Winnipeg-NAS Nassau Intl

14h 10m1 stop Toronto Pearson Intl

5:05 p.m. - 11:45 a.m.NAS Nassau Intl-YWG Winnipeg

19h 40m2 stops Toronto Pearson Intl Edmonton

C$ 578Multiple Airlines

Thu, 17 Dec - Fri, 18 Dec

7:00 a.m. - 4:45 p.m.YWG Winnipeg-MBJ Montego Bay Sangster Intl

8h 45m1 stop Toronto Pearson Intl

2:25 p.m. - 9:57 p.m.MBJ Montego Bay Sangster Intl-YWG Winnipeg

8h 32m1 stop Toronto Pearson Intl

C$ 582Porter Airlines

Mon, 7 Dec - Wed, 16 Dec

Cheap last-minute flights

Enter your travel dates to find the best prices.

5:00 a.m. - 3:25 p.m.YWG Winnipeg-PUJ Punta Cana

9h 25m1 stop Toronto Pearson Intl

4:20 p.m. - 8:00 p.m.PUJ Punta Cana-YWG Winnipeg

28h 40m2 stops Toronto Pearson Intl Ottawa

C$ 706Air Canada

Tue, 15 Sep - Tue, 29 Sep

5:00 a.m. - 3:25 p.m.YWG Winnipeg-PUJ Punta Cana

9h 25m1 stop Toronto Pearson Intl

5:05 p.m. - 8:00 p.m.PUJ Punta Cana-YWG Winnipeg

27h 55m2 stops Montreal Pierre Elliott Trudeau Intl Ottawa

C$ 758Air Canada

Sun, 13 Sep - Sun, 20 Sep

1:30 p.m. - 3:25 p.m.YWG Winnipeg-PUJ Punta Cana

24h 55m2 stops Ottawa Toronto Pearson Intl

4:20 p.m. - 2:17 p.m.PUJ Punta Cana-YWG Winnipeg

22h 57m1 stop Toronto Pearson Intl

C$ 784Air Canada

Tue, 15 Sep - Tue, 29 Sep

7:10 p.m. - 3:25 p.m.YWG Winnipeg-PUJ Punta Cana

19h 15m1 stop Toronto Pearson Intl

4:20 p.m. - 9:57 a.m.PUJ Punta Cana-YWG Winnipeg

18h 37m1 stop Toronto Pearson Intl

C$ 784Air Canada

Tue, 15 Sep - Tue, 29 Sep

1:30 p.m. - 3:25 p.m.YWG Winnipeg-PUJ Punta Cana

24h 55m2 stops Ottawa Toronto Pearson Intl

4:20 p.m. - 8:00 p.m.PUJ Punta Cana-YWG Winnipeg

28h 40m2 stops Toronto Pearson Intl Ottawa

C$ 784Air Canada

Tue, 15 Sep - Tue, 29 Sep

5:00 a.m. - 3:25 p.m.YWG Winnipeg-PUJ Punta Cana

9h 25m1 stop Toronto Pearson Intl

5:05 p.m. - 9:59 a.m.PUJ Punta Cana-YWG Winnipeg

17h 54m1 stop Montreal Pierre Elliott Trudeau Intl

C$ 805Air Canada

Sun, 13 Sep - Sun, 20 Sep

1:30 p.m. - 3:25 p.m.YWG Winnipeg-PUJ Punta Cana

24h 55m2 stops Ottawa Toronto Pearson Intl

4:20 p.m. - 8:00 p.m.PUJ Punta Cana-YWG Winnipeg

28h 40m2 stops Toronto Pearson Intl Ottawa

C$ 824Air Canada

Tue, 15 Sep - Tue, 29 Sep

5:00 a.m. - 3:25 p.m.YWG Winnipeg-PUJ Punta Cana

9h 25m1 stop Toronto Pearson Intl

4:20 p.m. - 8:00 p.m.PUJ Punta Cana-YWG Winnipeg

28h 40m2 stops Toronto Pearson Intl Ottawa

C$ 844Air Canada

Tue, 15 Sep - Tue, 29 Sep

4:15 p.m. - 1:25 p.m.YWG Winnipeg-PUJ Punta Cana

20h 10m2 stops Ottawa Toronto Pearson Intl

5:05 p.m. - 11:17 p.m.PUJ Punta Cana-YWG Winnipeg

31h 12m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl

C$ 1,015Multiple Airlines

Sun, 13 Sep - Sun, 20 Sep

11:40 a.m. - 1:45 p.m.YWG Winnipeg-PUJ Punta Cana

25h 05m3 stops Ottawa Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

5:05 p.m. - 9:27 p.m.PUJ Punta Cana-YWG Winnipeg

29h 22m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl

C$ 1,108Multiple Airlines

Sun, 13 Sep - Sun, 20 Sep

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United Airlines flights from Winnipeg to Caribbean Islands

Our best United Airlines deals on Winnipeg to Caribbean Islands flight tickets

United Airlines

16 Jan

YWG7:00 a.m.Winnipeg

54h 14m

2 stops

MBJ2:14 p.m.Montego Bay Sangster Intl

22 Jan

MBJ3:20 p.m.Montego Bay Sangster Intl

56h 13m

2 stops

YWG10:33 p.m.Winnipeg

C$ 609

United Airlines

6 Feb

YWG7:00 a.m.Winnipeg

15h 36m

2 stops

SJU12:36 a.m.San Juan Luis Munoz Marin Intl

13 Feb

SJU8:10 a.m.San Juan Luis Munoz Marin Intl

12h 31m

2 stops

YWG6:41 p.m.Winnipeg

C$ 629

United Airlines

23 Sep

YWG8:45 a.m.Winnipeg

14h 05m

2 stops

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

26 Sep

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

12h 37m

2 stops

YWG12:37 p.m.Winnipeg

C$ 677

WestJet flights from Winnipeg to Caribbean Islands

Our best WestJet deals on Winnipeg to Caribbean Islands flight tickets

WestJet

21 Nov

YWG6:00 a.m.Winnipeg

12h 35m

2 stops

MBJ7:35 p.m.Montego Bay Sangster Intl

28 Nov

MBJ3:35 p.m.Montego Bay Sangster Intl

6h 00m

YWG8:35 p.m.Winnipeg

C$ 444

WestJet

21 Nov

YWG6:00 a.m.Winnipeg

12h 35m

2 stops

MBJ7:35 p.m.Montego Bay Sangster Intl

28 Nov

MBJ3:35 p.m.Montego Bay Sangster Intl

6h 00m

YWG8:35 p.m.Winnipeg

C$ 445

WestJet

21 Nov

YWG5:00 a.m.Winnipeg

13h 35m

1 stop

MBJ7:35 p.m.Montego Bay Sangster Intl

28 Nov

MBJ3:35 p.m.Montego Bay Sangster Intl

6h 00m

YWG8:35 p.m.Winnipeg

C$ 449

momondo Fare Finder

Use the filters below to find and compare flights from Winnipeg to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegMontego Bay

YWG Winnipeg - MBJ Montego Bay Sangster Intl

YWGMBJ

Winnipeg

Sat 21/11

6:00 a.m.-7:35 p.m.

2 stops12h 35m

Montego Bay Sangster Intl

Sat 28/11

3:35 p.m.-8:35 p.m.

Nonstop6h 00m

C$ 444

WinnipegMontego Bay

YWG Winnipeg - MBJ Montego Bay Sangster Intl

YWGMBJ

Winnipeg

Sat 21/11

6:00 a.m.-7:35 p.m.

2 stops12h 35m

Montego Bay Sangster Intl

Sat 28/11

3:35 p.m.-8:35 p.m.

Nonstop6h 00m

C$ 445

WinnipegMontego Bay

YWG Winnipeg - MBJ Montego Bay Sangster Intl

YWGMBJ

Winnipeg

Sat 21/11

5:00 a.m.-7:35 p.m.

1 stop13h 35m

Montego Bay Sangster Intl

Sat 28/11

3:35 p.m.-8:35 p.m.

Nonstop6h 00m

C$ 449

WinnipegPunta Cana

YWG Winnipeg - PUJ Punta Cana

YWGPUJ

Winnipeg

Thu 3/12

8:05 a.m.-11:35 p.m.

1 stop13h 30m

Punta Cana

Thu 17/12

5:30 p.m.-10:00 p.m.

Nonstop6h 30m

C$ 465

WinnipegPunta Cana

YWG Winnipeg - PUJ Punta Cana

YWGPUJ

Winnipeg

Wed 16/12

2:05 p.m.-1:45 p.m.

1 stop21h 40m

Punta Cana

Thu 17/12

5:30 p.m.-10:00 p.m.

Nonstop6h 30m

C$ 480

WinnipegPunta Cana

YWG Winnipeg - PUJ Punta Cana

YWGPUJ

Winnipeg

Mon 14/12

8:05 a.m.-11:35 p.m.

1 stop13h 30m

Punta Cana

Thu 17/12

5:30 p.m.-10:00 p.m.

Nonstop6h 30m

C$ 480

Quickest round-trip

WinnipegMontego Bay

YWG Winnipeg - MBJ Montego Bay Sangster Intl

YWGMBJ

Winnipeg

Sat 28/11

7:15 a.m.-5:20 p.m.

1 stop9h 05m

Montego Bay Sangster Intl

Sat 5/12

3:35 p.m.-8:35 p.m.

Nonstop6h 00m

C$ 532

WinnipegSimpson Bay

YWG Winnipeg - SXM Simpson Bay Princess Juliana

YWGSXM

Winnipeg

Mon 23/11

12:10 p.m.-3:25 p.m.

2 stops25h 15m

Simpson Bay Princess Juliana

Wed 25/11

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

3 stops32h 40m

C$ 568

WinnipegNassau

YWG Winnipeg - NAS Nassau Intl

YWGNAS

Winnipeg

Thu 17/12

5:15 a.m.-8:25 p.m.

1 stop14h 10m

Nassau Intl

Fri 18/12

5:05 p.m.-11:45 a.m.

2 stops19h 40m

C$ 578

WinnipegMontego Bay

YWG Winnipeg - MBJ Montego Bay Sangster Intl

YWGMBJ

Winnipeg

Mon 7/12

7:00 a.m.-4:45 p.m.

1 stop8h 45m

Montego Bay Sangster Intl

Wed 16/12

2:25 p.m.-9:57 p.m.

1 stop8h 32m

C$ 582

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 Islands

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 Islands?

In general, April is the cheapest month to fly from Winnipeg to Caribbean Islands. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 735. If you aren’t able to travel to Caribbean Islands during the month of April, then flying in June is also cheap. Prices for this month can be found on momondo for an average of C$ 760.

What is the cheapest day to depart on your flight to Caribbean Islands?

The cheapest day to depart from Winnipeg to Caribbean Islands is on a Thursday when prices can be found for as low as C$ 904. Be sure to avoid booking your departure on a Wednesday as prices are generally higher than usual. According to our data, the average ticket price to Caribbean Islands on Wednesday is C$ 952.

What is the cheapest Winnipeg to Caribbean Islands flight route?

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

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

You are more likely to see cheaper flights to Caribbean Islands from Winnipeg when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around C$ 798 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Winnipeg for as low as C$ 590 on momondo.

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

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

No. A direct flight is the cheapest option for a flight between Winnipeg to Caribbean Islands.

Cheap Winnipeg to Caribbean Islands flight deals and tips

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

Best price found	C$ 221
Fastest flight time	5h 20m
Direct flights	Mon, Fri and Sun
Airports in Caribbean Islands	100 airports

The best one-way flight to Caribbean Islands from Winnipeg in the past 72 hours is C$ 221. The best round-trip flight deal from Winnipeg to Caribbean Islands found on momondo in the last 72 hours is C$ 444.

The fastest flight from Winnipeg to Caribbean Islands takes 5h 20m

Direct flights go from Winnipeg to Caribbean Islands on Monday, Friday and Sunday. There are no airlines offering direct flights.

There are 100 airports in Caribbean Islands. From Winnipeg there are direct flights to Montego Bay Sangster Intl (MBJ), Punta Cana (PUJ).

Search flight deals

Frequently asked questions about flying from Winnipeg to Caribbean Islands

When did momondo last update prices for flights from Winnipeg Airport to Caribbean Islands?
Prices for flights from Winnipeg Airport to Caribbean Islands refresh daily.
How many operators does momondo search for flights from Winnipeg Airport to Caribbean Islands?
There are 3 operators available for flights from Winnipeg Airport to Caribbean Islands as of September 2026.
How old do you have to be to fly from Winnipeg Airport to Caribbean Islands?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Winnipeg Airport to Caribbean Islands.
What documentation or ID do you need to fly to Caribbean Islands?
The necessary travel and health documents for your Caribbean Islands 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 Islands?
momondo data reveals that the most frequently booked plane model on the route from Winnipeg to Caribbean Islands is Boeing 737 MAX 8, representing 39.49% of all bookings. The subsequent popular models are Embraer 195 E2 at 23.27%, Boeing 737-800 Passenger/BBJ2 (winglets) at 10.69%, and Boeing 737-700 Passenger/BBJ1 (winglets) at 9.68%.

Best airlines flying from Winnipeg to Caribbean Islands

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

Airline	Rating	Free Cancellation	Price
WestJet	PriceFrom C$ 374	Free Cancellation	Rating 7.2 3,445 reviews		Search WestJet flights
Air Canada	PriceFrom C$ 456	Free Cancellation	Rating 7.1 11,609 reviews		Search Air Canada flights

Why use momondo?

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

Finding the right flight to Caribbean Islands from Winnipeg is quick and easy when you have a range of options in front of you, from reputable agents and recognizable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Caribbean Islands quick and easy, saving you time and money.

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

Flights from Winnipeg to Caribbean Islands 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 Islands?

Once you have performed a search for Winnipeg to Caribbean Islands flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Yes momondo offers price alerts on flights to Caribbean Islands from Winnipeg. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.