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 76% 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, Air Canada, and Delta 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 June 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$ 259 Cheap Flights from Winnipeg to Caribbean in 2026

Discover deals from 900+ travel sites with momondo.

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.

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

YWG

NAS

27h 05m

2 stops

6:30 p.m. - 8:00 p.m.

NAS

YWG

26h 30m

2 stops

C$ 563Air Canada

Mon, 19 Oct - Fri, 23 Oct

1:25 p.m. - 1:35 p.m.

YWG

NAS

47h 10m

2 stops

6:30 p.m. - 2:22 p.m.

NAS

YWG

20h 52m

1 stop

C$ 577Air Canada

Mon, 19 Oct - Fri, 23 Oct

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

YWG

MBJ

27h 45m

2 stops

7:30 p.m. - 9:40 p.m.

MBJ

YWG

26h 10m

2 stops

C$ 644WestJet

Sun, 12 Jul - Sun, 19 Jul

6:15 a.m. - 5:24 p.m.

YWG

MBJ

10h 09m

1 stop

8:25 p.m. - 11:35 a.m.

MBJ

YWG

16h 10m

1 stop

C$ 650WestJet

Tue, 8 Dec - Fri, 18 Dec

7:00 a.m. - 12:34 p.m.

YWG

SJU

28h 34m

2 stops

4:55 p.m. - 11:52 a.m.

SJU

YWG

19h 57m

2 stops

C$ 874United Airlines

Fri, 28 Aug - Mon, 31 Aug

7:00 a.m. - 12:34 p.m.

YWG

SJU

28h 34m

2 stops

4:55 p.m. - 11:52 a.m.

SJU

YWG

19h 57m

2 stops

C$ 876United Airlines

Fri, 28 Aug - Mon, 31 Aug

6:55 p.m. - 4:30 p.m.

YWG

SDQ

20h 35m

2 stops

6:10 a.m. - 8:40 a.m.

SDQ

YWG

27h 30m

3 stops

C$ 1,160Multiple Airlines

Thu, 15 Oct - Sat, 17 Oct

7:10 p.m. - 4:30 p.m.

YWG

SDQ

20h 20m

3 stops

6:10 a.m. - 8:40 a.m.

SDQ

YWG

27h 30m

3 stops

C$ 1,180Multiple Airlines

Thu, 15 Oct - Sat, 17 Oct

6:35 a.m. - 1:35 a.m.

YWG

SDQ

17h 00m

2 stops

6:45 a.m. - 11:34 p.m.

SDQ

YWG

18h 49m

2 stops

C$ 1,439Delta

Wed, 18 Nov - Fri, 27 Nov

6:35 a.m. - 1:35 a.m.

YWG

SDQ

17h 00m

2 stops

6:45 a.m. - 11:34 p.m.

SDQ

YWG

18h 49m

2 stops

C$ 1,448Delta

Wed, 18 Nov - Fri, 27 Nov

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United Airlines flights from Winnipeg to Caribbean

Our best United Airlines deals on Winnipeg to Caribbean flight tickets

United Airlines

28 Aug

YWG7:00 a.m.Winnipeg

28h 34m

2 stops

SJU12:34 p.m.San Juan Luis Munoz Marin Intl

31 Aug

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

19h 57m

2 stops

YWG11:52 a.m.Winnipeg

C$ 874

United Airlines

28 Aug

YWG7:00 a.m.Winnipeg

28h 34m

2 stops

SJU12:34 p.m.San Juan Luis Munoz Marin Intl

31 Aug

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

19h 57m

2 stops

YWG11:52 a.m.Winnipeg

C$ 876

United Airlines

28 Aug

YWG2:00 p.m.Winnipeg

22h 45m

2 stops

SJU1:45 p.m.San Juan Luis Munoz Marin Intl

31 Aug

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

19h 57m

2 stops

YWG11:52 a.m.Winnipeg

C$ 882

WestJet flights from Winnipeg to Caribbean

Our best WestJet deals on Winnipeg to Caribbean flight tickets

WestJet

17 Oct

YWG4:15 p.m.Winnipeg

19h 30m

2 stops

MBJ11:45 a.m.Montego Bay Sangster Intl

31 Oct

MBJ1:50 p.m.Montego Bay Sangster Intl

34h 00m

2 stops

YWG11:50 p.m.Winnipeg

C$ 624

WestJet

17 Oct

YWG4:15 p.m.Winnipeg

43h 30m

2 stops

MBJ11:45 a.m.Montego Bay Sangster Intl

31 Oct

MBJ1:50 p.m.Montego Bay Sangster Intl

11h 05m

1 stop

YWG12:55 a.m.Winnipeg

C$ 631

WestJet

17 Oct

YWG4:25 p.m.Winnipeg

19h 20m

1 stop

MBJ11:45 a.m.Montego Bay Sangster Intl

31 Oct

MBJ1:50 p.m.Montego Bay Sangster Intl

25h 30m

1 stop

YWG3:20 p.m.Winnipeg

C$ 637

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Mon 19/10

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

2 stops27h 05m

Nassau Intl

Fri 23/10

6:30 p.m.-8:00 p.m.

2 stops26h 30m

C$ 563

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Mon 19/10

1:25 p.m.-1:35 p.m.

2 stops47h 10m

Nassau Intl

Fri 23/10

6:30 p.m.-2:22 p.m.

1 stop20h 52m

C$ 577

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sun 12/7

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

2 stops27h 45m

Montego Bay Sangster Intl

Sun 19/7

7:30 p.m.-9:40 p.m.

2 stops26h 10m

C$ 644

Quickest round-trip

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 8/12

6:15 a.m.-5:24 p.m.

1 stop10h 09m

Montego Bay Sangster Intl

Fri 18/12

8:25 p.m.-11:35 a.m.

1 stop16h 10m

C$ 650

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Fri 28/8

7:00 a.m.-12:34 p.m.

2 stops28h 34m

San Juan Luis Munoz Marin Intl

Mon 31/8

4:55 p.m.-11:52 a.m.

2 stops19h 57m

C$ 874

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Fri 28/8

7:00 a.m.-12:34 p.m.

2 stops28h 34m

San Juan Luis Munoz Marin Intl

Mon 31/8

4:55 p.m.-11:52 a.m.

2 stops19h 57m

C$ 876

WinnipegSanto Domingo

YWG - SDQ

YWGSDQ

Winnipeg

Thu 15/10

6:55 p.m.-4:30 p.m.

2 stops20h 35m

Santo Domingo Las Americas

Sat 17/10

6:10 a.m.-8:40 a.m.

3 stops27h 30m

C$ 1,160

WinnipegSanto Domingo

YWG - SDQ

YWGSDQ

Winnipeg

Thu 15/10

7:10 p.m.-4:30 p.m.

3 stops20h 20m

Santo Domingo Las Americas

Sat 17/10

6:10 a.m.-8:40 a.m.

3 stops27h 30m

C$ 1,180

WinnipegSanto Domingo

YWG - SDQ

YWGSDQ

Winnipeg

Wed 18/11

6:35 a.m.-1:35 a.m.

2 stops17h 00m

Santo Domingo Las Americas

Fri 27/11

6:45 a.m.-11:34 p.m.

2 stops18h 49m

C$ 1,439

WinnipegSanto Domingo

YWG - SDQ

YWGSDQ

Winnipeg

Wed 18/11

6:35 a.m.-1:35 a.m.

2 stops17h 00m

Santo Domingo Las Americas

Fri 27/11

6:45 a.m.-11:34 p.m.

2 stops18h 49m

C$ 1,448

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$ 195. 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$ 215.

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$ 934. 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 Punta Cana 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$ 836 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$ 671 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 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$ 783
Fastest flight time	8h 35m
Direct flights	Fri
Airports in Caribbean	195 airports

The best flight deal from Winnipeg to Caribbean found on momondo in the last 72 hours is C$ 783

The fastest flight from Winnipeg to Caribbean takes 8h 35m

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

There are 195 airports in Caribbean. From Winnipeg there are direct flights to 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 June 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) (61.67% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (31.67%), Boeing 737-800 (Scimitar Winglets) (5.00%), and Boeing 737-700 Passenger/BBJ1 (winglets) (1.67%).

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$ 398	Free Cancellation	Rating 7.1 11,229 reviews	Search Air Canada flights
WestJet	PriceFrom C$ 500	Free Cancellation	Rating 7.2 3,375 reviews	Search WestJet flights
Porter Airlines	PriceFrom C$ 510	Free Cancellation	Rating 8.0 438 reviews	Search Porter Airlines flights
Air Transat	PriceFrom C$ 814	Free Cancellation	Rating 7.8 556 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.