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 73% 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?

Porter Airlines, Air Canada, and WestJet 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 December 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$ 222 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

Enter your travel dates to find the best prices.

7:30 a.m. - 12:31 a.m.

YWG

SJU

15h 01m1 stop

6:00 a.m. - 11:35 a.m.

SJU

YWG

31h 35m2 stops

C$ 451Multiple Airlines

Sun, 11 Jan - Fri, 16 Jan

7:30 a.m. - 12:31 a.m.

YWG

SJU

15h 01m1 stop

8:00 a.m. - 3:07 p.m.

SJU

YWG

33h 07m2 stops

C$ 456Multiple Airlines

Sun, 11 Jan - Sat, 17 Jan

6:55 p.m. - 3:40 p.m.

YWG

NAS

43h 45m2 stops

4:50 p.m. - 10:07 a.m.

NAS

YWG

42h 17m2 stops

C$ 488WestJet

Sun, 29 Mar - Fri, 3 Apr

9:00 p.m. - 1:44 p.m.

YWG

GCM

15h 44m2 stops

2:50 p.m. - 11:35 a.m.

GCM

YWG

21h 45m1 stop

C$ 490WestJet

Sat, 17 Jan - Thu, 22 Jan

6:00 a.m. - 12:55 p.m.

YWG

NAS

29h 55m2 stops

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

NAS

YWG

22h 00m1 stop

C$ 507Air Canada

Mon, 2 Mar - Wed, 4 Mar

6:00 a.m. - 12:25 p.m.

YWG

GCM

53h 25m2 stops

1:30 p.m. - 8:28 p.m.

GCM

YWG

31h 58m2 stops

C$ 510Air Canada

Sat, 17 Jan - Thu, 22 Jan

2:20 p.m. - 2:32 p.m.

YWG

NAS

23h 12m2 stops

3:35 p.m. - 11:57 a.m.

NAS

YWG

21h 22m1 stop

C$ 635United Airlines

Mon, 2 Mar - Wed, 4 Mar

8:45 a.m. - 11:43 a.m.

YWG

MBJ

26h 58m2 stops

2:40 p.m. - 8:52 p.m.

MBJ

YWG

30h 12m2 stops

C$ 705United Airlines

Mon, 30 Mar - Sat, 4 Apr

11:53 a.m. - 1:10 p.m.

YWG

SDQ

23h 17m2 stops

8:45 p.m. - 4:29 p.m.

SDQ

YWG

21h 44m2 stops

C$ 1,544Delta

Mon, 2 Feb - Thu, 5 Feb

11:53 a.m. - 1:10 p.m.

YWG

SDQ

23h 17m2 stops

8:45 p.m. - 4:29 p.m.

SDQ

YWG

21h 44m2 stops

C$ 1,579Delta

Mon, 2 Feb - Mon, 9 Feb

American Airlines flights from Winnipeg to Caribbean

Our best American Airlines deals on Winnipeg to Caribbean flight tickets

American Airlines

27 Dec

YWG6:00 a.m.Winnipeg

15h 59m

2 stops

SJU11:59 p.m.San Juan Luis Munoz Marin Intl

3 Jan

SJU5:24 a.m.San Juan Luis Munoz Marin Intl

20h 11m

3 stops

YWG11:35 p.m.Winnipeg

C$ 3,122

Find similar

American Airlines

27 Dec

YWG6:00 a.m.Winnipeg

14h 05m

3 stops

SJU10:05 p.m.San Juan Luis Munoz Marin Intl

3 Jan

SJU5:24 a.m.San Juan Luis Munoz Marin Intl

20h 11m

3 stops

YWG11:35 p.m.Winnipeg

C$ 3,253

Find similar

Air Transat flights from Winnipeg to Caribbean

Our best Air Transat deals on Winnipeg to Caribbean flight tickets

Air Transat

10 Jan

YWG6:00 a.m.Winnipeg

14h 30m

1 stop

PUJ10:30 p.m.Punta Cana

11 Jan

PUJ11:55 p.m.Punta Cana

13h 18m

1 stop

YWG11:13 a.m.Winnipeg

C$ 714

Find similar

Air Transat

7 Jan

YWG4:25 p.m.Winnipeg

28h 25m

1 stop

PUJ10:50 p.m.Punta Cana

11 Jan

PUJ11:55 p.m.Punta Cana

13h 18m

1 stop

YWG11:13 a.m.Winnipeg

C$ 734

Find similar

Fly from

Fly to

Route

Depart

Return

Price

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sun 11/1

7:30 a.m.-12:31 a.m.

1 stop15h 01m

San Juan Luis Munoz Marin Intl

Fri 16/1

6:00 a.m.-11:35 a.m.

2 stops31h 35m

C$ 451

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sun 11/1

7:30 a.m.-12:31 a.m.

1 stop15h 01m

San Juan Luis Munoz Marin Intl

Sat 17/1

8:00 a.m.-3:07 p.m.

2 stops33h 07m

C$ 456

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Sun 29/3

6:55 p.m.-3:40 p.m.

2 stops43h 45m

Nassau Intl

Fri 3/4

4:50 p.m.-10:07 a.m.

2 stops42h 17m

C$ 488

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 17/1

9:00 p.m.-1:44 p.m.

2 stops15h 44m

George Town Owen Roberts Intl

Thu 22/1

2:50 p.m.-11:35 a.m.

1 stop21h 45m

C$ 490

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Mon 2/3

6:00 a.m.-12:55 p.m.

2 stops29h 55m

Nassau Intl

Wed 4/3

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

1 stop22h 00m

C$ 507

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 17/1

6:00 a.m.-12:25 p.m.

2 stops53h 25m

George Town Owen Roberts Intl

Thu 22/1

1:30 p.m.-8:28 p.m.

2 stops31h 58m

C$ 510

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Mon 2/3

2:20 p.m.-2:32 p.m.

2 stops23h 12m

Nassau Intl

Wed 4/3

3:35 p.m.-11:57 a.m.

1 stop21h 22m

C$ 635

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 30/3

8:45 a.m.-11:43 a.m.

2 stops26h 58m

Montego Bay Sangster Intl

Sat 4/4

2:40 p.m.-8:52 p.m.

2 stops30h 12m

C$ 705

WinnipegSanto Domingo

YWG - SDQ

YWGSDQ

Winnipeg

Mon 2/2

11:53 a.m.-1:10 p.m.

2 stops23h 17m

Santo Domingo Las Americas

Thu 5/2

8:45 p.m.-4:29 p.m.

2 stops21h 44m

C$ 1,544

WinnipegSanto Domingo

YWG - SDQ

YWGSDQ

Winnipeg

Mon 2/2

11:53 a.m.-1:10 p.m.

2 stops23h 17m

Santo Domingo Las Americas

Mon 9/2

8:45 p.m.-4:29 p.m.

2 stops21h 44m

C$ 1,579

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$ 672. 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$ 727.

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$ 786. 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$ 1,971.

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$ 789. In the morning is when there is more demand to fly to Caribbean, so prices are often more expensive at around C$ 1,114 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$ 786 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$ 550 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 15% 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$ 335
Fastest flight time	5h 25m
Direct flights	Sun
Airports in Caribbean	195 airports

The best one-way flight to Caribbean from Winnipeg in the past 72 hours is C$ 335. The best round-trip flight deal from Winnipeg to Caribbean found on momondo in the last 72 hours is C$ 682.

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

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

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 December 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 MAX 8 (53.85% of total bookings). The next most popular plane models are Boeing 737-800 Passenger/BBJ2 (winglets) (34.62%), Boeing 737-800 (Scimitar Winglets) (7.69%), and Boeing 737-700 Passenger/BBJ1 (winglets) (3.85%).

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$ 485	Free Cancellation	Rating 7.1 10,533 reviews	Search Air Canada flights
WestJet	PriceFrom C$ 503	Free Cancellation	Rating 7.2 3,203 reviews	Search WestJet flights
United Airlines	PriceFrom C$ 544	Free Cancellation	Rating 7.4 9,091 reviews	Search United Airlines flights
Delta	PriceFrom C$ 698	Free Cancellation	Rating 7.9 8,005 reviews	Search Delta flights
Sunwing Airlines	PriceFrom C$ 733	Free Cancellation	Rating 6.7 36 reviews	Search Sunwing Airlines flights
Air Transat	PriceFrom C$ 801	Free Cancellation	Rating 7.8 483 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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Sat 17/1

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Find better results for your trip to Caribbean

Popular Cities in Caribbean

Flights to Punta Canafrom C$ 322

Flights to Montego Bayfrom C$ 406

Flights to Oranjestadfrom C$ 373

Flights to Kingstonfrom C$ 463

Flights to Fort-de-Francefrom C$ 619

Flights to San Juanfrom C$ 324

Flights to Pointe-à-Pitrefrom C$ 620

Flights to Simpson Bayfrom C$ 386

Flights to Bridgetownfrom C$ 455

Flights to Nassaufrom C$ 325

Flights to Puerto Platafrom C$ 398

Flights to Willemstadfrom C$ 384

Cheap flights from Winnipeg to Caribbean from C$ 222

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 28/2. 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

American Airlines flights from Winnipeg to Caribbean

Our best American Airlines deals on Winnipeg to Caribbean flight tickets

Air Transat flights from Winnipeg to Caribbean

Our best Air Transat 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 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 15% on your flight if you consider stops on a Winnipeg to Caribbean flight.

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

Porter Airlines, Air Canada, and WestJet 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