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

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

Which airlines fly to Caribbean?

WestJet, Air Canada and United Airlines 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 71% of people opting to fly with this airline when travelling to Caribbean. Keep in mind that there are 6 different airlines that fly to Caribbean on a routine basis, so you have a few additional options to choose from.

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 2025, there are 6 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$ 209 Cheap Flights from Winnipeg to Caribbean in 2025/26

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

7:05 p.m. - 3:20 p.m.YWG-CUR

19h 15m1 stop

5:20 p.m. - 9:49 a.m.CUR-YWG

18h 29m1 stop

C$ 495Air Canada

Find Deal

Fri, 31 Oct - Thu, 6 Nov

4:10 p.m. - 4:40 p.m.YWG-AUA

22h 30m2 stops

4:30 p.m. - 6:06 p.m.AUA-YWG

27h 36m2 stops

C$ 501WestJet

Find Deal

Thu, 13 Nov - Wed, 19 Nov

5:00 a.m. - 3:50 p.m.YWG-NAS

9h 50m1 stop

6:15 p.m. - 11:35 a.m.NAS-YWG

18h 20m1 stop

C$ 502WestJet

Find Deal

Sat, 29 Nov - Sat, 6 Dec

7:05 p.m. - 3:20 p.m.YWG-CUR

19h 15m1 stop

5:20 p.m. - 4:35 p.m.CUR-YWG

25h 15m2 stops

C$ 552Air Canada

Find Deal

Fri, 31 Oct - Thu, 6 Nov

8:40 a.m. - 12:36 a.m.YWG-SJU

13h 56m2 stops

7:45 a.m. - 8:56 p.m.SJU-YWG

15h 11m2 stops

C$ 692United Airlines

Find Deal

Wed, 12 Nov - Wed, 19 Nov

6:00 a.m. - 11:15 a.m.YWG-MBJ

28h 15m1 stop

1:25 p.m. - 11:35 p.m.MBJ-YWG

10h 10m1 stop

C$ 713Air Transat

Find Deal

Mon, 23 Feb - Wed, 11 Mar

8:40 a.m. - 11:50 a.m.YWG-PUJ

25h 10m2 stops

3:28 p.m. - 8:55 p.m.PUJ-YWG

31h 27m2 stops

C$ 717United Airlines

Find Deal

Sun, 7 Dec - Sun, 14 Dec

12:10 p.m. - 11:15 a.m.YWG-MBJ

22h 05m1 stop

1:25 p.m. - 3:30 p.m.MBJ-YWG

26h 05m1 stop

C$ 733Air Transat

Find Deal

Mon, 23 Feb - Tue, 10 Mar

12:20 p.m. - 1:24 p.m.YWG-PUJ

24h 04m2 stops

3:56 p.m. - 4:50 p.m.PUJ-YWG

25h 54m2 stops

C$ 984Delta

Find Deal

Fri, 24 Oct - Fri, 31 Oct

5:56 p.m. - 12:50 p.m.YWG-PLS

17h 54m2 stops

3:50 p.m. - 11:54 a.m.PLS-YWG

21h 04m2 stops

C$ 1,033Delta

Find Deal

Tue, 23 Dec - Wed, 31 Dec

United Airlines flights from Winnipeg to Caribbean

Our best United Airlines deals on Winnipeg to Caribbean flight tickets

United Airlines

12 Nov

YWG8:40 a.m.Winnipeg

13h 56m

2 stops

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

19 Nov

SJU7:45 a.m.San Juan Luis Munoz Marin Intl

15h 11m

2 stops

YWG8:56 p.m.Winnipeg

C$ 692

Find similar

United Airlines

7 Dec

YWG8:40 a.m.Winnipeg

25h 10m

2 stops

PUJ11:50 a.m.Punta Cana

14 Dec

PUJ3:28 p.m.Punta Cana

31h 27m

2 stops

YWG8:55 p.m.Winnipeg

C$ 717

Find similar

United Airlines

12 Nov

YWG8:40 a.m.Winnipeg

13h 56m

2 stops

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

18 Nov

SJU2:05 a.m.San Juan Luis Munoz Marin Intl

12h 34m

2 stops

YWG12:39 p.m.Winnipeg

C$ 879

Find similar

Delta flights from Winnipeg to Caribbean

Our best Delta deals on Winnipeg to Caribbean flight tickets

Delta

24 Oct

YWG12:20 p.m.Winnipeg

24h 04m

2 stops

PUJ1:24 p.m.Punta Cana

31 Oct

PUJ3:56 p.m.Punta Cana

25h 54m

2 stops

YWG4:50 p.m.Winnipeg

C$ 984

Find similar

Delta

23 Dec

YWG5:56 p.m.Winnipeg

17h 54m

2 stops

PLS12:50 p.m.Providenciales

31 Dec

PLS3:50 p.m.Providenciales

21h 04m

2 stops

YWG11:54 a.m.Winnipeg

C$ 1,033

Find similar

Delta

22 Sep

YWG5:40 p.m.Winnipeg

17h 45m

2 stops

MBJ11:25 a.m.Montego Bay Sangster Intl

29 Sep

MBJ1:25 p.m.Montego Bay Sangster Intl

10h 02m

2 stops

YWG11:27 p.m.Winnipeg

C$ 1,198

Find similar

Fly from

Fly to

Route

Depart

Return

Price

WinnipegWillemstad

YWG - CUR

YWGCUR

Winnipeg

Fri 31/10

7:05 p.m.-3:20 p.m.

1 stop19h 15m

Willemstad Hato Int.

Thu 6/11

5:20 p.m.-9:49 a.m.

1 stop18h 29m

C$ 495

WinnipegOranjestad

YWG - AUA

YWGAUA

Winnipeg

Thu 13/11

4:10 p.m.-4:40 p.m.

2 stops22h 30m

Oranjestad Reina Beatrix

Wed 19/11

4:30 p.m.-6:06 p.m.

2 stops27h 36m

C$ 501

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Sat 29/11

5:00 a.m.-3:50 p.m.

1 stop9h 50m

Nassau Intl

Sat 6/12

6:15 p.m.-11:35 a.m.

1 stop18h 20m

C$ 502

WinnipegWillemstad

YWG - CUR

YWGCUR

Winnipeg

Fri 31/10

7:05 p.m.-3:20 p.m.

1 stop19h 15m

Willemstad Hato Int.

Thu 6/11

5:20 p.m.-4:35 p.m.

2 stops25h 15m

C$ 552

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Wed 12/11

8:40 a.m.-12:36 a.m.

2 stops13h 56m

San Juan Luis Munoz Marin Intl

Wed 19/11

7:45 a.m.-8:56 p.m.

2 stops15h 11m

C$ 692

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 23/2

6:00 a.m.-11:15 a.m.

1 stop28h 15m

Montego Bay Sangster Intl

Wed 11/3

1:25 p.m.-11:35 p.m.

1 stop10h 10m

C$ 713

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Sun 7/12

8:40 a.m.-11:50 a.m.

2 stops25h 10m

Punta Cana

Sun 14/12

3:28 p.m.-8:55 p.m.

2 stops31h 27m

C$ 717

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 23/2

12:10 p.m.-11:15 a.m.

1 stop22h 05m

Montego Bay Sangster Intl

Tue 10/3

1:25 p.m.-3:30 p.m.

1 stop26h 05m

C$ 733

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Fri 24/10

12:20 p.m.-1:24 p.m.

2 stops24h 04m

Punta Cana

Fri 31/10

3:56 p.m.-4:50 p.m.

2 stops25h 54m

C$ 984

WinnipegProvidenciales

YWG - PLS

YWGPLS

Winnipeg

Tue 23/12

5:56 p.m.-12:50 p.m.

2 stops17h 54m

Providenciales

Wed 31/12

3:50 p.m.-11:54 a.m.

2 stops21h 04m

C$ 1,033

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, 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$ 671. If you don’t want to visit Caribbean in June, then you should wait until July to fly from Winnipeg, when ticket prices are also cheap, with an average price of C$ 729.

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 Monday. momondo users have found tickets for Monday departures for as low as C$ 785. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Caribbean on Sunday is C$ 1,298.

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

Our data shows that the cheapest Winnipeg to Caribbean flights are usually those with departure times in the afternoon. Our users have found flights to Caribbean in the afternoon for as low as C$ 787. In the morning is when there is more demand to fly to Caribbean, so prices are often more expensive at around C$ 1,139 per ticket.

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$ 796 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$ 721 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 42% 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$ 731
Fastest flight time	5h 25m
Direct flights	Mon and Sun
Airports in Caribbean	1 airport

The best flight deal from Winnipeg to Caribbean found on momondo in the last 72 hours is C$ 731

The fastest flight from Winnipeg to Caribbean takes 5h 25m

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

There is 1 airport near Caribbean: 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 September 2025, there are 6 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) (45.83% of total bookings). The next most popular plane models are Boeing 737-700 Passenger/BBJ1 (winglets) (22.92%), Boeing 737 MAX 8 (18.75%), and Boeing 737-800 (Scimitar Winglets) (12.50%).

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$ 484	Free Cancellation	Rating 7.1 10,000 reviews	Search Air Canada flights
United Airlines	PriceFrom C$ 500	Free Cancellation	Rating 7.4 8,926 reviews	Search United Airlines flights
WestJet	PriceFrom C$ 508	Free Cancellation	Rating 7.2 3,095 reviews	Search WestJet flights
Delta	PriceFrom C$ 697	Free Cancellation	Rating 7.9 7,961 reviews	Search Delta flights
Sunwing Airlines	PriceFrom C$ 705	Free Cancellation	Rating 6.7 36 reviews	Search Sunwing Airlines flights
Air Transat	PriceFrom C$ 800	Free Cancellation	Rating 7.7 439 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.

An easier way to manage your Caribbean trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Start using Trips

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Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

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Fri 17/10

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Find better results for your trip to Caribbean

Popular Cities in Caribbean

Flights to Punta Canafrom C$ 281

Flights to Montego Bayfrom C$ 402

Flights to Oranjestadfrom C$ 395

Flights to Kingstonfrom C$ 426

Flights to Simpson Bayfrom C$ 358

Flights to Fort-de-Francefrom C$ 509

Flights to San Juanfrom C$ 344

Flights to Bridgetownfrom C$ 415

Flights to Pointe-à-Pitrefrom C$ 508

Flights to Nassaufrom C$ 338

Flights to Puerto Platafrom C$ 439

Flights to Port of Spainfrom C$ 585

Cheap flights from Winnipeg to Caribbean from C$ 209

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Winnipeg to Caribbean departing on 23/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names, great deals

Big names, great deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Winnipeg to Caribbean

Cheap round-trip flights

Cheap one-way flights

Cheap last-minute flights

Cheap direct flights

United Airlines flights from Winnipeg to Caribbean

Our best United Airlines deals on Winnipeg to Caribbean flight tickets

Delta flights from Winnipeg to Caribbean

Our best Delta deals on Winnipeg to Caribbean flight tickets

momondo Fare Finder

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

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

What is the cheapest month to fly to Caribbean?

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

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

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?

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 42% on your flight if you consider stops on a Winnipeg to Caribbean flight.

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

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

Which airlines fly to Caribbean?

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

Fastest flight time

Direct flights

Airports in Caribbean

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

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

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

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

What is the most popular plane model from Winnipeg to Caribbean?

Best airlines flying from Winnipeg to Caribbean

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

Why use momondo?

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

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

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

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

An easier way to manage your Caribbean trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Caribbean

Popular Cities in Caribbean

Popular flights according to clicks in the last 7 days on momondo