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

WestJet, Air Canada, and Porter 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 September 2026, there are 3 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$ 271 Cheap Flights from Winnipeg to Caribbean in 2026/27

Discover deals from 900+ travel sites with momondo.

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.

7:00 a.m. - 2:25 p.m.YWG Winnipeg-SXM Simpson Bay Princess Juliana

30h 25m2 stops Edmonton Toronto Pearson Intl

4:20 p.m. - 11:59 p.m.SXM Simpson Bay Princess Juliana-YWG Winnipeg

33h 39m2 stops Toronto Pearson Intl Edmonton

C$ 492WestJet

Sun, 25 Oct - Sun, 1 Nov

8:05 p.m. - 2:25 p.m.YWG Winnipeg-SXM Simpson Bay Princess Juliana

17h 20m1 stop Toronto Pearson Intl

4:20 p.m. - 11:59 p.m.SXM Simpson Bay Princess Juliana-YWG Winnipeg

33h 39m2 stops Toronto Pearson Intl Edmonton

C$ 501WestJet

Sun, 25 Oct - Sun, 1 Nov

12:10 p.m. - 8:55 a.m.YWG Winnipeg-PUJ Punta Cana

18h 45m2 stops Edmonton Calgary

7:35 p.m. - 4:25 p.m.PUJ Punta Cana-YWG Winnipeg

22h 50m2 stops Regina Calgary

C$ 512WestJet

Wed, 9 Dec - Wed, 16 Dec

8:00 a.m. - 2:35 p.m.YWG Winnipeg-MBJ Montego Bay Sangster Intl

5h 35mdirect

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

6h 00mdirect

C$ 513WestJet

Sat, 28 Nov - Sat, 12 Dec

2:05 p.m. - 11:30 a.m.YWG Winnipeg-NAS Nassau Intl

44h 25m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl

12:30 p.m. - 10:24 a.m.NAS Nassau Intl-YWG Winnipeg

22h 54m1 stop Toronto Pearson Intl

C$ 516Air Canada

Sun, 25 Oct - Thu, 29 Oct

2:05 p.m. - 11:30 a.m.YWG Winnipeg-NAS Nassau Intl

44h 25m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl

12:30 p.m. - 6:25 p.m.NAS Nassau Intl-YWG Winnipeg

30h 55m2 stops Toronto Pearson Intl Ottawa

C$ 516Air Canada

Sun, 25 Oct - Thu, 29 Oct

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$ 525Air Canada

Wed, 16 Dec - Thu, 17 Dec

7:00 a.m. - 1:48 p.m.YWG Winnipeg-MBJ Montego Bay Sangster Intl

29h 48m1 stop Chicago O'Hare Intl

5:21 p.m. - 10:33 p.m.MBJ Montego Bay Sangster Intl-YWG Winnipeg

30h 12m2 stops Washington, D.C. Dulles Intl Chicago O'Hare Intl

C$ 577United Airlines

Sat, 23 Jan - Sat, 30 Jan

7:00 a.m. - 2:14 p.m.YWG Winnipeg-MBJ Montego Bay Sangster Intl

30h 14m2 stops Chicago O'Hare Intl Newark

6:00 p.m. - 10:33 p.m.MBJ Montego Bay Sangster Intl-YWG Winnipeg

29h 33m2 stops Newark Chicago O'Hare Intl

C$ 577United Airlines

Sat, 23 Jan - Sat, 30 Jan

8:35 p.m. - 4:35 p.m.YWG Winnipeg-MBJ Montego Bay Sangster Intl

19h 00m2 stops Calgary Toronto Pearson Intl

1:45 p.m. - 6:45 p.m.MBJ Montego Bay Sangster Intl-YWG Winnipeg

6h 00mdirect

C$ 601Multiple Airlines

Fri, 27 Nov - Sun, 13 Dec

Cheap last-minute flights

Enter your travel dates to find the best prices.

8:45 a.m. - 11:50 p.m.YWG Winnipeg-SJU San Juan Luis Munoz Marin Intl

14h 05m2 stops Denver Intl Newark

1:00 a.m. - 12:37 p.m.SJU San Juan Luis Munoz Marin Intl-YWG Winnipeg

12h 37m2 stops Newark Chicago O'Hare Intl

C$ 906United Airlines

Sat, 3 Oct - Sat, 10 Oct

5:10 p.m. - 11:00 a.m.YWG Winnipeg-PUJ Punta Cana

16h 50m1 stop Toronto Pearson Intl

7:25 p.m. - 4:25 p.m.PUJ Punta Cana-YWG Winnipeg

22h 00m1 stop Toronto Pearson Intl

C$ 969Multiple Airlines

Tue, 29 Sep - Tue, 6 Oct

1:30 p.m. - 4:05 p.m.YWG Winnipeg-PUJ Punta Cana

25h 35m2 stops Ottawa Montreal Pierre Elliott Trudeau Intl

4:20 p.m. - 3:09 p.m.PUJ Punta Cana-YWG Winnipeg

23h 49m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

C$ 994Air Canada

Tue, 29 Sep - Tue, 6 Oct

1:30 p.m. - 4:05 p.m.YWG Winnipeg-PUJ Punta Cana

25h 35m2 stops Ottawa Montreal Pierre Elliott Trudeau Intl

4:20 p.m. - 11:12 a.m.PUJ Punta Cana-YWG Winnipeg

19h 52m1 stop Toronto Pearson Intl

C$ 995Air Canada

Tue, 29 Sep - Tue, 6 Oct

8:45 p.m. - 1:25 p.m.YWG Winnipeg-PUJ Punta Cana

15h 40m1 stop Toronto Pearson Intl

9:55 a.m. - 1:10 a.m.PUJ Punta Cana-YWG Winnipeg

16h 15m1 stop Calgary

C$ 1,039Multiple Airlines

Thu, 1 Oct - Sat, 31 Oct

8:45 a.m. - 11:50 p.m.YWG Winnipeg-SJU San Juan Luis Munoz Marin Intl

14h 05m2 stops Denver Intl Newark

3:56 p.m. - 10:33 p.m.SJU San Juan Luis Munoz Marin Intl-YWG Winnipeg

31h 37m1 stop Chicago O'Hare Intl

C$ 1,046United Airlines

Sat, 3 Oct - Sun, 11 Oct

8:45 p.m. - 1:25 p.m.YWG Winnipeg-PUJ Punta Cana

15h 40m1 stop Toronto Pearson Intl

9:55 a.m. - 12:45 p.m.PUJ Punta Cana-YWG Winnipeg

27h 50m2 stops Calgary Edmonton

C$ 1,051Multiple Airlines

Thu, 1 Oct - Sat, 31 Oct

5:10 p.m. - 11:00 a.m.YWG Winnipeg-PUJ Punta Cana

16h 50m1 stop Toronto Pearson Intl

7:25 p.m. - 8:40 a.m.PUJ Punta Cana-YWG Winnipeg

14h 15m1 stop Toronto Pearson Intl

C$ 1,073Multiple Airlines

Thu, 1 Oct - Thu, 8 Oct

2:55 p.m. - 11:40 a.m.YWG Winnipeg-PUJ Punta Cana

19h 45m2 stops Calgary Montreal Pierre Elliott Trudeau Intl

9:55 a.m. - 12:45 p.m.PUJ Punta Cana-YWG Winnipeg

27h 50m2 stops Calgary Edmonton

C$ 1,076Multiple Airlines

Thu, 1 Oct - Sat, 31 Oct

11:40 a.m. - 11:00 a.m.YWG Winnipeg-PUJ Punta Cana

22h 20m2 stops Ottawa Toronto Island

7:25 p.m. - 8:40 a.m.PUJ Punta Cana-YWG Winnipeg

14h 15m1 stop Toronto Pearson Intl

C$ 1,172Multiple Airlines

Thu, 1 Oct - Thu, 8 Oct

Cheap direct flights

Enter your travel dates to find the best prices.

8:00 a.m. - 2:35 p.m.YWG Winnipeg-MBJ Montego Bay Sangster Intl

5h 35mdirect

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

6h 00mdirect

C$ 513WestJet

Sat, 28 Nov - Sat, 12 Dec

8:20 a.m. - 2:40 p.m.YWG Winnipeg-MBJ Montego Bay Sangster Intl

5h 20mdirect

3:40 p.m. - 8:20 p.m.MBJ Montego Bay Sangster Intl-YWG Winnipeg

5h 40mdirect

C$ 684Air Canada

Sun, 10 Jan - Sun, 17 Jan

9:15 a.m. - 3:50 p.m.YWG Winnipeg-MBJ Montego Bay Sangster Intl

5h 35mdirect

12:45 p.m. - 6:45 p.m.MBJ Montego Bay Sangster Intl-YWG Winnipeg

6h 00mdirect

C$ 739WestJet

Sat, 13 Mar - Sun, 4 Apr

8:20 a.m. - 2:40 p.m.YWG Winnipeg-MBJ Montego Bay Sangster Intl

5h 20mdirect

3:40 p.m. - 8:20 p.m.MBJ Montego Bay Sangster Intl-YWG Winnipeg

5h 40mdirect

C$ 751Air Canada

Sun, 13 Dec - Sun, 10 Jan

8:00 a.m. - 3:50 p.m.YWG Winnipeg-PUJ Punta Cana

5h 50mdirect

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

6h 30mdirect

C$ 764Air Canada

Thu, 10 Dec - Thu, 17 Dec

9:15 a.m. - 3:50 p.m.YWG Winnipeg-MBJ Montego Bay Sangster Intl

5h 35mdirect

1:45 p.m. - 6:45 p.m.MBJ Montego Bay Sangster Intl-YWG Winnipeg

6h 00mdirect

C$ 769WestJet

Sat, 13 Feb - Sun, 21 Feb

6:10 a.m. - 12:45 p.m.YWG Winnipeg-MBJ Montego Bay Sangster Intl

5h 35mdirect

3:40 p.m. - 8:20 p.m.MBJ Montego Bay Sangster Intl-YWG Winnipeg

5h 40mdirect

C$ 789Multiple Airlines

Sun, 14 Feb - Sun, 21 Feb

7:00 a.m. - 2:30 p.m.YWG Winnipeg-POP Puerto Plata La Union

5h 30mdirect

3:30 p.m. - 7:45 p.m.POP Puerto Plata La Union-YWG Winnipeg

6h 15mdirect

C$ 819WestJet

Tue, 19 Jan - Tue, 26 Jan

6:10 a.m. - 12:45 p.m.YWG Winnipeg-MBJ Montego Bay Sangster Intl

5h 35mdirect

3:40 p.m. - 8:20 p.m.MBJ Montego Bay Sangster Intl-YWG Winnipeg

5h 40mdirect

C$ 877Multiple Airlines

Sun, 14 Feb - Sun, 21 Feb

8:00 a.m. - 3:50 p.m.YWG Winnipeg-PUJ Punta Cana

5h 50mdirect

8:45 p.m. - 1:25 a.m.PUJ Punta Cana-YWG Winnipeg

6h 40mdirect

C$ 1,215Multiple Airlines

Thu, 14 Jan - Sat, 23 Jan

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United Airlines flights from Winnipeg to Caribbean

Our best United Airlines deals on Winnipeg to Caribbean flight tickets

United Airlines

23 Jan

YWG7:00 a.m.Winnipeg

30h 14m

2 stops

MBJ2:14 p.m.Montego Bay Sangster Intl

30 Jan

MBJ6:00 p.m.Montego Bay Sangster Intl

29h 33m

2 stops

YWG10:33 p.m.Winnipeg

C$ 577

United Airlines

26 Jan

YWG7:00 a.m.Winnipeg

28h 13m

2 stops

MBJ12:13 p.m.Montego Bay Sangster Intl

10 Feb

MBJ2:54 p.m.Montego Bay Sangster Intl

8h 39m

1 stop

YWG10:33 p.m.Winnipeg

C$ 614

United Airlines

28 Jan

YWG7:00 a.m.Winnipeg

28h 13m

2 stops

MBJ12:13 p.m.Montego Bay Sangster Intl

5 Feb

MBJ3:20 p.m.Montego Bay Sangster Intl

32h 13m

2 stops

YWG10:33 p.m.Winnipeg

C$ 717

Air Canada flights from Winnipeg to Caribbean

Our best Air Canada deals on Winnipeg to Caribbean flight tickets

Air Canada

25 Oct

YWG2:05 p.m.Winnipeg

44h 25m

2 stops

NAS11:30 a.m.Nassau Intl

29 Oct

NAS12:30 p.m.Nassau Intl

30h 55m

2 stops

YWG6:25 p.m.Winnipeg

C$ 516

Air Canada

16 Dec

YWG6:00 a.m.Winnipeg

10h 45m

2 stops

PUJ6:45 p.m.Punta Cana

17 Dec

PUJ5:30 p.m.Punta Cana

6h 30m

YWG10:00 p.m.Winnipeg

C$ 525

Air Canada

25 Oct

YWG1:30 p.m.Winnipeg

27h 15m

1 stop

PUJ5:45 p.m.Punta Cana

29 Oct

PUJ2:15 p.m.Punta Cana

29h 10m

2 stops

YWG6:25 p.m.Winnipeg

C$ 557

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegSimpson Bay

YWG Winnipeg - SXM Simpson Bay Princess Juliana

YWGSXM

Winnipeg

Sun 25/10

7:00 a.m.-2:25 p.m.

2 stops30h 25m

Simpson Bay Princess Juliana

Sun 1/11

4:20 p.m.-11:59 p.m.

2 stops33h 39m

C$ 492

WinnipegSimpson Bay

YWG Winnipeg - SXM Simpson Bay Princess Juliana

YWGSXM

Winnipeg

Sun 25/10

8:05 p.m.-2:25 p.m.

1 stop17h 20m

Simpson Bay Princess Juliana

Sun 1/11

4:20 p.m.-11:59 p.m.

2 stops33h 39m

C$ 501

WinnipegPunta Cana

YWG Winnipeg - PUJ Punta Cana

YWGPUJ

Winnipeg

Wed 9/12

12:10 p.m.-8:55 a.m.

2 stops18h 45m

Punta Cana

Wed 16/12

7:35 p.m.-4:25 p.m.

2 stops22h 50m

C$ 512

Quickest round-trip

WinnipegMontego Bay

YWG Winnipeg - MBJ Montego Bay Sangster Intl

YWGMBJ

Winnipeg

Sat 28/11

8:00 a.m.-2:35 p.m.

Nonstop5h 35m

Montego Bay Sangster Intl

Sat 12/12

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

Nonstop6h 00m

C$ 513

WinnipegNassau

YWG Winnipeg - NAS Nassau Intl

YWGNAS

Winnipeg

Sun 25/10

2:05 p.m.-11:30 a.m.

2 stops44h 25m

Nassau Intl

Thu 29/10

12:30 p.m.-10:24 a.m.

1 stop22h 54m

C$ 516

WinnipegNassau

YWG Winnipeg - NAS Nassau Intl

YWGNAS

Winnipeg

Sun 25/10

2:05 p.m.-11:30 a.m.

2 stops44h 25m

Nassau Intl

Thu 29/10

12:30 p.m.-6:25 p.m.

2 stops30h 55m

C$ 516

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$ 525

WinnipegMontego Bay

YWG Winnipeg - MBJ Montego Bay Sangster Intl

YWGMBJ

Winnipeg

Sat 23/1

7:00 a.m.-1:48 p.m.

1 stop29h 48m

Montego Bay Sangster Intl

Sat 30/1

5:21 p.m.-10:33 p.m.

2 stops30h 12m

C$ 577

WinnipegMontego Bay

YWG Winnipeg - MBJ Montego Bay Sangster Intl

YWGMBJ

Winnipeg

Sat 23/1

7:00 a.m.-2:14 p.m.

2 stops30h 14m

Montego Bay Sangster Intl

Sat 30/1

6:00 p.m.-10:33 p.m.

2 stops29h 33m

C$ 577

WinnipegMontego Bay

YWG Winnipeg - MBJ Montego Bay Sangster Intl

YWGMBJ

Winnipeg

Fri 27/11

8:35 p.m.-4:35 p.m.

2 stops19h 00m

Montego Bay Sangster Intl

Sun 13/12

1:45 p.m.-6:45 p.m.

Nonstop6h 00m

C$ 601

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, April 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$ 739. If you don’t want to visit Caribbean in April, then you should wait until March to fly from Winnipeg, when ticket prices are also cheap, with an average price of C$ 772.

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

On average, the least expensive day to fly to Caribbean from Winnipeg is on a Thursday. momondo users have found tickets for Thursday departures for as low as C$ 621. However, this price may fluctuate depending on the airline, the season, and holidays. 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 on Wednesday is C$ 977.

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$ 809 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$ 605 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 6% 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$ 271
Fastest flight time	5h 20m
Direct flights	Mon, Wed, Fri and Sun
Airports in Caribbean	196 airports

The best one-way flight to Caribbean from Winnipeg in the past 72 hours is C$ 271. The best round-trip flight deal from Winnipeg to Caribbean found on momondo in the last 72 hours is C$ 492.

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

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

There are 196 airports in Caribbean. From Winnipeg there are direct flights to Puerto Plata La Union (POP), Montego Bay Sangster Intl (MBJ), Punta Cana (PUJ).

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 September 2026, there are 3 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 (60.23% of total bookings). The next most popular plane models are Boeing 737-800 Passenger/BBJ2 (winglets) (32.95%), Boeing 737 (3.41%), and Boeing 737-800 (Scimitar Winglets) (2.27%).

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
WestJet	PriceFrom C$ 383	Free Cancellation	Rating 7.2 3,449 reviews		Search WestJet flights
Air Canada	PriceFrom C$ 467	Free Cancellation	Rating 7.1 11,695 reviews		Search Air Canada 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.