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 75% 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.

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

WestJet, United Airlines, and Air Canada 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 February 2026, 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$ 244 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

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Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:55 p.m. - 10:33 a.m.

YWG

NAS

14h 38m

2 stops

8:30 p.m. - 6:05 p.m.

NAS

YWG

22h 35m

2 stops

C$ 492WestJet

Sat, 11 Apr - Thu, 16 Apr

6:15 a.m. - 3:40 p.m.

YWG

NAS

32h 25m

2 stops

4:50 p.m. - 12:07 p.m.

NAS

YWG

44h 17m

2 stops

C$ 493WestJet

Tue, 24 Mar - Tue, 31 Mar

8:20 p.m. - 11:25 a.m.

YWG

PUJ

14h 05m

1 stop

3:32 p.m. - 3:09 p.m.

PUJ

YWG

24h 37m

1 stop

C$ 556Multiple Airlines

Thu, 19 Mar - Thu, 26 Mar

6:00 a.m. - 3:00 p.m.

YWG

AUA

31h 00m

2 stops

3:05 p.m. - 4:35 p.m.

AUA

YWG

26h 30m

2 stops

C$ 568Air Canada

Tue, 3 Mar - Tue, 10 Mar

7:20 p.m. - 3:00 p.m.

YWG

AUA

17h 40m

1 stop

3:05 p.m. - 9:44 a.m.

AUA

YWG

19h 39m

1 stop

C$ 590Air Canada

Tue, 3 Mar - Tue, 10 Mar

8:00 a.m. - 2:31 p.m.

YWG

SJU

29h 31m

1 stop

7:54 p.m. - 11:32 a.m.

SJU

YWG

40h 38m

2 stops

C$ 604Multiple Airlines

Mon, 9 Mar - Tue, 17 Mar

2:00 p.m. - 12:50 p.m.

YWG

MBJ

22h 50m

1 stop

2:40 p.m. - 11:52 a.m.

MBJ

YWG

21h 12m

2 stops

C$ 632United Airlines

Sun, 19 Apr - Sun, 10 May

7:20 p.m. - 3:22 p.m.

YWG

NAS

19h 02m

2 stops

4:05 p.m. - 11:57 a.m.

NAS

YWG

20h 52m

1 stop

C$ 664United Airlines

Mon, 23 Feb - Sat, 28 Feb

12:10 p.m. - 4:00 p.m.

YWG

POP

25h 50m

3 stops

3:53 p.m. - 11:35 p.m.

POP

YWG

32h 42m

2 stops

C$ 4,617American Airlines

Wed, 4 Mar - Sun, 15 Mar

12:10 p.m. - 4:00 p.m.

YWG

POP

25h 50m

3 stops

3:53 p.m. - 11:35 p.m.

POP

YWG

32h 42m

2 stops

C$ 4,619American Airlines

Wed, 4 Mar - Sun, 15 Mar

WestJet flights from Winnipeg to Caribbean

Our best WestJet deals on Winnipeg to Caribbean flight tickets

WestJet

11 Apr

YWG6:55 p.m.Winnipeg

14h 38m

2 stops

NAS10:33 a.m.Nassau Intl

16 Apr

NAS8:30 p.m.Nassau Intl

22h 35m

2 stops

YWG6:05 p.m.Winnipeg

C$ 492

WestJet

24 Mar

YWG6:15 a.m.Winnipeg

32h 25m

2 stops

NAS3:40 p.m.Nassau Intl

31 Mar

NAS4:50 p.m.Nassau Intl

44h 17m

2 stops

YWG12:07 p.m.Winnipeg

C$ 493

WestJet

24 Mar

YWG8:05 p.m.Winnipeg

18h 35m

1 stop

NAS3:40 p.m.Nassau Intl

31 Mar

NAS4:50 p.m.Nassau Intl

31h 57m

2 stops

YWG11:47 p.m.Winnipeg

C$ 497

Flair Airlines flights from Winnipeg to Caribbean

Our best Flair Airlines deals on Winnipeg to Caribbean flight tickets

Flair Airlines

1 Mar

YWG8:20 p.m.Winnipeg

15h 00m

1 stop

PUJ1:20 p.m.Punta Cana

15 Mar

PUJ3:35 p.m.Punta Cana

29h 00m

1 stop

YWG7:35 p.m.Winnipeg

C$ 785

Flair Airlines

20 Feb

YWG8:20 p.m.Winnipeg

14h 10m

1 stop

MBJ11:30 a.m.Montego Bay Sangster Intl

28 Feb

MBJ12:30 p.m.Montego Bay Sangster Intl

32h 05m

1 stop

YWG7:35 p.m.Winnipeg

C$ 863

Fly from

Fly to

Route

Depart

Return

Price

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Sat 11/4

6:55 p.m.-10:33 a.m.

2 stops14h 38m

Nassau Intl

Thu 16/4

8:30 p.m.-6:05 p.m.

2 stops22h 35m

C$ 492

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Tue 24/3

6:15 a.m.-3:40 p.m.

2 stops32h 25m

Nassau Intl

Tue 31/3

4:50 p.m.-12:07 p.m.

2 stops44h 17m

C$ 493

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Thu 19/3

8:20 p.m.-11:25 a.m.

1 stop14h 05m

Punta Cana

Thu 26/3

3:32 p.m.-3:09 p.m.

1 stop24h 37m

C$ 556

WinnipegOranjestad

YWG - AUA

YWGAUA

Winnipeg

Tue 3/3

6:00 a.m.-3:00 p.m.

2 stops31h 00m

Oranjestad Reina Beatrix

Tue 10/3

3:05 p.m.-4:35 p.m.

2 stops26h 30m

C$ 568

WinnipegOranjestad

YWG - AUA

YWGAUA

Winnipeg

Tue 3/3

7:20 p.m.-3:00 p.m.

1 stop17h 40m

Oranjestad Reina Beatrix

Tue 10/3

3:05 p.m.-9:44 a.m.

1 stop19h 39m

C$ 590

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Mon 9/3

8:00 a.m.-2:31 p.m.

1 stop29h 31m

San Juan Luis Munoz Marin Intl

Tue 17/3

7:54 p.m.-11:32 a.m.

2 stops40h 38m

C$ 604

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sun 19/4

2:00 p.m.-12:50 p.m.

1 stop22h 50m

Montego Bay Sangster Intl

Sun 10/5

2:40 p.m.-11:52 a.m.

2 stops21h 12m

C$ 632

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Mon 23/2

7:20 p.m.-3:22 p.m.

2 stops19h 02m

Nassau Intl

Sat 28/2

4:05 p.m.-11:57 a.m.

1 stop20h 52m

C$ 664

WinnipegPuerto Plata

YWG - POP

YWGPOP

Winnipeg

Wed 4/3

12:10 p.m.-4:00 p.m.

3 stops25h 50m

Puerto Plata La Union

Sun 15/3

3:53 p.m.-11:35 p.m.

2 stops32h 42m

C$ 4,617

WinnipegPuerto Plata

YWG - POP

YWGPOP

Winnipeg

Wed 4/3

12:10 p.m.-4:00 p.m.

3 stops25h 50m

Puerto Plata La Union

Sun 15/3

3:53 p.m.-11:35 p.m.

2 stops32h 42m

C$ 4,619

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$ 666. 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$ 720.

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 Wednesday. momondo users have found tickets for Wednesday departures for as low as C$ 943. 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$ 2,071.

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$ 779 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$ 553 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 67% 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$ 943
Fastest flight time	7h 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$ 943

The fastest flight from Winnipeg to Caribbean takes 7h 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 February 2026, 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 MAX 8 (63.27% of total bookings). The next most popular plane models are Boeing 737-800 Passenger/BBJ2 (winglets) (18.37%), Boeing 737-800 (Scimitar Winglets) (12.24%), and Boeing 737-700 Passenger/BBJ1 (winglets) (6.12%).

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$ 435	Free Cancellation	Rating 7.1 10,687 reviews	Search Air Canada flights
WestJet	PriceFrom C$ 472	Free Cancellation	Rating 7.2 3,255 reviews	Search WestJet flights
Porter Airlines	PriceFrom C$ 492	Free Cancellation	Rating 7.9 412 reviews	Search Porter Airlines flights
United Airlines	PriceFrom C$ 548	Free Cancellation	Rating 7.4 9,235 reviews	Search United Airlines flights
Delta	PriceFrom C$ 692	Free Cancellation	Rating 7.9 8,141 reviews	Search Delta flights
Air Transat	PriceFrom C$ 823	Free Cancellation	Rating 7.7 502 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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Find better results for your trip to Caribbean

Popular cities

Other flights from Winnipeg

Other flights to Caribbean

Airlines

Complete your trip

Feeling lucky

Popular Cities in Caribbean

Flights to Punta Canafrom C$ 186

Flights to Montego Bayfrom C$ 417

Flights to Oranjestadfrom C$ 351

Flights to Fort-de-Francefrom C$ 686

Flights to Kingstonfrom C$ 414

Flights to San Juanfrom C$ 347

Flights to Simpson Bayfrom C$ 369

Flights to Nassaufrom C$ 376

Flights to Pointe-à-Pitrefrom C$ 642

Flights to Bridgetownfrom C$ 391

Flights to Willemstadfrom C$ 397

Flights to Puerto Platafrom C$ 399

Cheap flights from Winnipeg to Caribbean from C$ 244

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 8/4. 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

WestJet flights from Winnipeg to Caribbean

Our best WestJet deals on Winnipeg to Caribbean flight tickets

Flair Airlines flights from Winnipeg to Caribbean

Our best Flair Airlines 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

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 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 67% 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, United Airlines, and Air Canada 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

Winnipeg flight routes

According to popular flight searches on momondo this year

Caribbean flight routes

According to popular flight searches on momondo this year

Fly your favourite airline to Caribbean

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Complete your trip to Caribbean

Explore popular destinations other users love

According to popular flight searches on momondo this year