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.

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

WestJet, United Airlines, and Flair 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 October 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$ 285 Cheap Flights from Winnipeg to Caribbean in 2025/26

1 adult

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Find the cheapest flights from Winnipeg to Caribbean

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

6:55 p.m. - 1:35 p.m.YWG-PUJ

16h 40m2 stops

2:30 p.m. - 10:41 p.m.PUJ-YWG

34h 11m2 stops

C$ 486WestJet

Find Deal

qua, 7 jan - qua, 14 jan

12:20 p.m. - 3:35 p.m.YWG-PUJ

25h 15m1 stop

2:30 p.m. - 11:35 a.m.PUJ-YWG

23h 05m1 stop

C$ 489WestJet

Find Deal

qua, 7 jan - qua, 14 jan

2:20 p.m. - 4:14 p.m.YWG-PUJ

23h 54m2 stops

5:20 p.m. - 11:57 a.m.PUJ-YWG

20h 37m2 stops

C$ 533United Airlines

Find Deal

sex, 9 jan - sex, 16 jan

6:00 a.m. - 9:45 p.m.YWG-PUJ

13h 45m1 stop

1:05 p.m. - 11:54 p.m.PUJ-YWG

12h 49m1 stop

C$ 543Air Canada

Find Deal

ter, 3 fev - qua, 4 mar

7:05 p.m. - 9:45 p.m.YWG-PUJ

24h 40m2 stops

10:25 p.m. - 9:44 p.m.PUJ-YWG

25h 19m1 stop

C$ 553Air Canada

Find Deal

seg, 2 fev - ter, 3 mar

9:00 p.m. - 3:06 p.m.YWG-SJU

16h 06m2 stops

4:11 p.m. - 3:09 p.m.SJU-YWG

24h 58m1 stop

C$ 585Multiple Airlines

Find Deal

sáb, 24 jan - sáb, 31 jan

8:40 a.m. - 6:18 p.m.YWG-PUJ

31h 38m1 stop

5:20 p.m. - 11:57 a.m.PUJ-YWG

44h 37m2 stops

C$ 612United Airlines

Find Deal

sex, 28 nov - sex, 5 dez

8:05 p.m. - 3:40 p.m.YWG-AUA

17h 35m1 stop

4:05 p.m. - 11:54 p.m.AUA-YWG

9h 49m1 stop

C$ 673Multiple Airlines

Find Deal

dom, 16 nov - qui, 20 nov

12:10 p.m. - 1:15 p.m.YWG-MBJ

24h 05m1 stop

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

26h 05m1 stop

C$ 753Air Transat

Find Deal

ter, 3 mar - ter, 17 mar

12:10 p.m. - 1:15 p.m.YWG-MBJ

24h 05m1 stop

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

10h 10m1 stop

C$ 754Air Transat

Find Deal

ter, 3 mar - ter, 17 mar

United Airlines flights from Winnipeg to Caribbean

Our best United Airlines deals on Winnipeg to Caribbean flight tickets

United Airlines

9 Jan

YWG2:20 p.m.Winnipeg

23h 54m

2 stops

PUJ4:14 p.m.Punta Cana

16 Jan

PUJ5:20 p.m.Punta Cana

20h 37m

2 stops

YWG11:57 a.m.Winnipeg

C$ 533

Find similar

United Airlines

28 Nov

YWG8:40 a.m.Winnipeg

31h 38m

1 stop

PUJ6:18 p.m.Punta Cana

5 Dec

PUJ5:20 p.m.Punta Cana

44h 37m

2 stops

YWG11:57 a.m.Winnipeg

C$ 612

Find similar

United Airlines

31 Jan

YWG2:20 p.m.Winnipeg

20h 39m

2 stops

PUJ12:59 p.m.Punta Cana

5 Mar

PUJ2:55 p.m.Punta Cana

22h 44m

1 stop

YWG11:39 a.m.Winnipeg

C$ 614

Find similar

Air Canada flights from Winnipeg to Caribbean

Our best Air Canada deals on Winnipeg to Caribbean flight tickets

Air Canada

3 Feb

YWG6:00 a.m.Winnipeg

13h 45m

1 stop

PUJ9:45 p.m.Punta Cana

4 Mar

PUJ1:05 p.m.Punta Cana

12h 49m

1 stop

YWG11:54 p.m.Winnipeg

C$ 543

Find similar

Air Canada

2 Feb

YWG7:05 p.m.Winnipeg

24h 40m

2 stops

PUJ9:45 p.m.Punta Cana

3 Mar

PUJ10:25 p.m.Punta Cana

25h 19m

1 stop

YWG9:44 p.m.Winnipeg

C$ 553

Find similar

Air Canada

11 Jan

YWG7:05 p.m.Winnipeg

24h 30m

1 stop

PUJ9:35 p.m.Punta Cana

25 Jan

PUJ10:25 p.m.Punta Cana

20h 10m

2 stops

YWG4:35 p.m.Winnipeg

C$ 559

Find similar

Fly from

Fly to

Route

Depart

Return

Price

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

qua 7/1

6:55 p.m.-1:35 p.m.

2 stops16h 40m

Punta Cana

qua 14/1

2:30 p.m.-10:41 p.m.

2 stops34h 11m

C$ 486

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

qua 7/1

12:20 p.m.-3:35 p.m.

1 stop25h 15m

Punta Cana

qua 14/1

2:30 p.m.-11:35 a.m.

1 stop23h 05m

C$ 489

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

sex 9/1

2:20 p.m.-4:14 p.m.

2 stops23h 54m

Punta Cana

sex 16/1

5:20 p.m.-11:57 a.m.

2 stops20h 37m

C$ 533

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

ter 3/2

6:00 a.m.-9:45 p.m.

1 stop13h 45m

Punta Cana

qua 4/3

1:05 p.m.-11:54 p.m.

1 stop12h 49m

C$ 543

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

seg 2/2

7:05 p.m.-9:45 p.m.

2 stops24h 40m

Punta Cana

ter 3/3

10:25 p.m.-9:44 p.m.

1 stop25h 19m

C$ 553

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

sáb 24/1

9:00 p.m.-3:06 p.m.

2 stops16h 06m

San Juan Luis Munoz Marin Intl

sáb 31/1

4:11 p.m.-3:09 p.m.

1 stop24h 58m

C$ 585

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

sex 28/11

8:40 a.m.-6:18 p.m.

1 stop31h 38m

Punta Cana

sex 5/12

5:20 p.m.-11:57 a.m.

2 stops44h 37m

C$ 612

WinnipegOranjestad

YWG - AUA

YWGAUA

Winnipeg

dom 16/11

8:05 p.m.-3:40 p.m.

1 stop17h 35m

Oranjestad Reina Beatrix

qui 20/11

4:05 p.m.-11:54 p.m.

1 stop9h 49m

C$ 673

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

ter 3/3

12:10 p.m.-1:15 p.m.

1 stop24h 05m

Montego Bay Sangster Intl

ter 17/3

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

1 stop26h 05m

C$ 753

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

ter 3/3

12:10 p.m.-1:15 p.m.

1 stop24h 05m

Montego Bay Sangster Intl

ter 17/3

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

1 stop10h 10m

C$ 754

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$ 681. 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$ 740.

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$ 797. 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$ 1,318.

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$ 799. In the morning is when there is more demand to fly to Caribbean, so prices are often more expensive at around C$ 1,156 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$ 812 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$ 730 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 29% 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$ 542
Fastest flight time	5h 25m
Direct flights	Mon and Sun
Airports in Caribbean	1 airport

The best one-way flight to Caribbean from Winnipeg in the past 72 hours is C$ 542. The best round-trip flight deal from Winnipeg to Caribbean found on momondo in the last 72 hours is C$ 798.

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

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

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 October 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) (60.32% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (25.40%), Boeing 737-800 (Scimitar Winglets) (9.52%), and Boeing 737-700 Passenger/BBJ1 (winglets) (4.76%).

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$ 492	Free Cancellation	Rating 7.1 10,383 reviews	Search Air Canada flights
United Airlines	PriceFrom C$ 508	Free Cancellation	Rating 7.4 8,996 reviews	Search United Airlines flights
WestJet	PriceFrom C$ 516	Free Cancellation	Rating 7.2 3,152 reviews	Search WestJet flights
Delta	PriceFrom C$ 707	Free Cancellation	Rating 7.9 7,998 reviews	Search Delta flights
Sunwing Airlines	PriceFrom C$ 715	Free Cancellation	Rating 6.7 36 reviews	Search Sunwing Airlines flights
Air Transat	PriceFrom C$ 812	Free Cancellation	Rating 7.8 469 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

Find my bookings

Get notified when prices go down

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

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sáb 29/11

sáb 6/12

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Find better results for your trip to Caribbean

Popular Cities in Caribbean

Flights to Punta Canafrom C$ 328

Flights to Montego Bayfrom C$ 401

Flights to Oranjestadfrom C$ 408

Flights to Kingstonfrom C$ 480

Flights to Fort-de-Francefrom C$ 533

Flights to Simpson Bayfrom C$ 380

Flights to Pointe-à-Pitrefrom C$ 568

Flights to San Juanfrom C$ 334

Flights to Bridgetownfrom C$ 426

Flights to Nassaufrom C$ 366

Flights to Puerto Platafrom C$ 423

Flights to Willemstadfrom C$ 339

Cheap flights from Winnipeg to Caribbean from C$ 285

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 12/12. 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

Air Canada flights from Winnipeg to Caribbean

Our best Air Canada 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 29% 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 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