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

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

Which airlines fly to Caribbean Islands?

WestJet, Air Canada and Air Transat are the top three most popular airlines that fly to Caribbean Islands from Winnipeg according to our data. WestJet is the first choice among our users, with 78% of people opting to fly with this airline when travelling to Caribbean Islands. Keep in mind that there are 4 different airlines that fly to Caribbean Islands 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 Islands?

Prices for flights from Winnipeg Airport to Caribbean Islands refresh daily.

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

There are 4 operators available for flights from Winnipeg Airport to Caribbean Islands as of April 2026.

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

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Winnipeg Airport to Caribbean Islands.

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

The necessary travel and health documents for your Caribbean Islands 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$ 235 Cheap Flights from Winnipeg to Caribbean Islands in 2026

1 adult

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Winnipeg to Caribbean Islands

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

9:05 p.m. - 11:45 a.m.

YWG

MBJ

14h 40m

2 stops

12:45 p.m. - 12:55 a.m.

MBJ

YWG

12h 10m

1 stop

C$ 487WestJet

Mon, 18 May - Thu, 11 Jun

6:05 p.m. - 11:45 a.m.

YWG

MBJ

17h 40m

1 stop

12:45 p.m. - 12:55 a.m.

MBJ

YWG

12h 10m

1 stop

C$ 493WestJet

Sun, 17 May - Thu, 11 Jun

2:00 p.m. - 5:30 p.m.

YWG

NAS

26h 30m

1 stop

6:30 p.m. - 10:00 a.m.

NAS

YWG

16h 30m

1 stop

C$ 549Air Canada

Tue, 16 Jun - Sat, 20 Jun

2:00 p.m. - 5:30 p.m.

YWG

NAS

26h 30m

1 stop

6:30 p.m. - 11:15 a.m.

NAS

YWG

17h 45m

1 stop

C$ 550Air Canada

Tue, 16 Jun - Sat, 20 Jun

7:20 p.m. - 2:43 p.m.

YWG

SXM

18h 23m

2 stops

3:20 p.m. - 11:10 a.m.

SXM

YWG

20h 50m

2 stops

C$ 630Multiple Airlines

Mon, 8 Jun - Mon, 22 Jun

7:20 p.m. - 11:25 a.m.

YWG

GCM

16h 05m

1 stop

1:45 p.m. - 12:55 a.m.

GCM

YWG

11h 10m

1 stop

C$ 631Multiple Airlines

Sun, 10 May - Sat, 16 May

2:00 p.m. - 12:40 p.m.

YWG

AUA

21h 40m

2 stops

1:50 p.m. - 11:52 a.m.

AUA

YWG

23h 02m

1 stop

C$ 754United Airlines

Tue, 12 May - Sat, 16 May

2:00 p.m. - 12:40 p.m.

YWG

AUA

21h 40m

2 stops

4:30 p.m. - 11:52 a.m.

AUA

YWG

20h 22m

2 stops

C$ 775United Airlines

Mon, 11 May - Sat, 16 May

5:38 p.m. - 12:20 p.m.

YWG

SDQ

17h 42m

2 stops

7:40 p.m. - 8:09 p.m.

SDQ

YWG

25h 29m

2 stops

C$ 1,417Delta

Tue, 22 Sep - Thu, 24 Sep

5:38 p.m. - 12:20 p.m.

YWG

SDQ

17h 42m

2 stops

7:40 p.m. - 11:27 p.m.

SDQ

YWG

28h 47m

2 stops

C$ 1,418Delta

Tue, 22 Sep - Thu, 24 Sep

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Air Canada flights from Winnipeg to Caribbean Islands

Our best Air Canada deals on Winnipeg to Caribbean Islands flight tickets

Air Canada

16 Jun

YWG2:00 p.m.Winnipeg

26h 30m

1 stop

NAS5:30 p.m.Nassau Intl

20 Jun

NAS6:30 p.m.Nassau Intl

16h 30m

1 stop

YWG10:00 a.m.Winnipeg

C$ 549

Air Canada

16 Jun

YWG2:00 p.m.Winnipeg

26h 30m

1 stop

NAS5:30 p.m.Nassau Intl

20 Jun

NAS6:30 p.m.Nassau Intl

17h 45m

1 stop

YWG11:15 a.m.Winnipeg

C$ 550

Air Canada

16 Jun

YWG11:00 a.m.Winnipeg

29h 30m

2 stops

NAS5:30 p.m.Nassau Intl

20 Jun

NAS6:30 p.m.Nassau Intl

17h 45m

1 stop

YWG11:15 a.m.Winnipeg

C$ 554

WestJet flights from Winnipeg to Caribbean Islands

Our best WestJet deals on Winnipeg to Caribbean Islands flight tickets

WestJet

18 May

YWG9:05 p.m.Winnipeg

14h 40m

2 stops

MBJ11:45 a.m.Montego Bay Sangster Intl

11 Jun

MBJ12:45 p.m.Montego Bay Sangster Intl

12h 10m

1 stop

YWG12:55 a.m.Winnipeg

C$ 487

WestJet

17 May

YWG6:05 p.m.Winnipeg

17h 40m

1 stop

MBJ11:45 a.m.Montego Bay Sangster Intl

11 Jun

MBJ12:45 p.m.Montego Bay Sangster Intl

12h 10m

1 stop

YWG12:55 a.m.Winnipeg

C$ 493

WestJet

19 May

YWG7:10 p.m.Winnipeg

16h 35m

2 stops

MBJ11:45 a.m.Montego Bay Sangster Intl

3 Jun

MBJ12:45 p.m.Montego Bay Sangster Intl

23h 30m

2 stops

YWG12:15 p.m.Winnipeg

C$ 498

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 18/5

9:05 p.m.-11:45 a.m.

2 stops14h 40m

Montego Bay Sangster Intl

Thu 11/6

12:45 p.m.-12:55 a.m.

1 stop12h 10m

C$ 487

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sun 17/5

6:05 p.m.-11:45 a.m.

1 stop17h 40m

Montego Bay Sangster Intl

Thu 11/6

12:45 p.m.-12:55 a.m.

1 stop12h 10m

C$ 493

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Tue 16/6

2:00 p.m.-5:30 p.m.

1 stop26h 30m

Nassau Intl

Sat 20/6

6:30 p.m.-10:00 a.m.

1 stop16h 30m

C$ 549

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Tue 16/6

2:00 p.m.-5:30 p.m.

1 stop26h 30m

Nassau Intl

Sat 20/6

6:30 p.m.-11:15 a.m.

1 stop17h 45m

C$ 550

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Mon 8/6

7:20 p.m.-2:43 p.m.

2 stops18h 23m

Simpson Bay Princess Juliana

Mon 22/6

3:20 p.m.-11:10 a.m.

2 stops20h 50m

C$ 630

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sun 10/5

7:20 p.m.-11:25 a.m.

1 stop16h 05m

George Town Owen Roberts Intl

Sat 16/5

1:45 p.m.-12:55 a.m.

1 stop11h 10m

C$ 631

WinnipegOranjestad

YWG - AUA

YWGAUA

Winnipeg

Tue 12/5

2:00 p.m.-12:40 p.m.

2 stops21h 40m

Oranjestad Reina Beatrix

Sat 16/5

1:50 p.m.-11:52 a.m.

1 stop23h 02m

C$ 754

WinnipegOranjestad

YWG - AUA

YWGAUA

Winnipeg

Mon 11/5

2:00 p.m.-12:40 p.m.

2 stops21h 40m

Oranjestad Reina Beatrix

Sat 16/5

4:30 p.m.-11:52 a.m.

2 stops20h 22m

C$ 775

WinnipegSanto Domingo

YWG - SDQ

YWGSDQ

Winnipeg

Tue 22/9

5:38 p.m.-12:20 p.m.

2 stops17h 42m

Santo Domingo Las Americas

Thu 24/9

7:40 p.m.-8:09 p.m.

2 stops25h 29m

C$ 1,416

WinnipegSanto Domingo

YWG - SDQ

YWGSDQ

Winnipeg

Tue 22/9

5:38 p.m.-12:20 p.m.

2 stops17h 42m

Santo Domingo Las Americas

Thu 24/9

7:40 p.m.-11:27 p.m.

2 stops28h 47m

C$ 1,418

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 Islands

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 Islands?

In general, June is the cheapest month to fly from Winnipeg to Caribbean Islands. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 668. If you aren’t able to travel to Caribbean Islands during the month of June, then flying in July is also cheap. Prices for this month can be found on momondo for an average of C$ 731.

What is the cheapest Winnipeg to Caribbean Islands flight route?

Fly from Winnipeg to Montego Bay Sangster Intl for the best Winnipeg - Caribbean Islands flight prices

How far in advance should I book a flight from Winnipeg to Caribbean Islands?

You are more likely to see cheaper flights to Caribbean Islands from Winnipeg when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands 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 Islands from Winnipeg for as low as C$ 593 on momondo.

What cabin class options are available on Winnipeg to Caribbean Islands flights?

There is only 1 cabin class available to choose from on Winnipeg to Caribbean Islands 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 Islands flights?

No. A direct flight is the cheapest option for a flight between Winnipeg to Caribbean Islands.

Cheap Winnipeg to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Winnipeg to Caribbean Islands

Fastest flight time	8h 05m
Direct flights	None

The fastest flight from Winnipeg to Caribbean Islands takes 8h 05m

There are no direct flights from Winnipeg to Caribbean Islands. There are no popular flight routes from Winnipeg to Caribbean Islands.

Search flight deals

Frequently asked questions about flying from Winnipeg to Caribbean Islands

When did momondo last update prices for flights from Winnipeg Airport to Caribbean Islands?
Prices for flights from Winnipeg Airport to Caribbean Islands refresh daily.
How many operators does momondo search for flights from Winnipeg Airport to Caribbean Islands?
There are 4 operators available for flights from Winnipeg Airport to Caribbean Islands as of April 2026.
How old do you have to be to fly from Winnipeg Airport to Caribbean Islands?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Winnipeg Airport to Caribbean Islands.
What documentation or ID do you need to fly to Caribbean Islands?
The necessary travel and health documents for your Caribbean Islands 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 Islands?
momondo data reveals that the most frequently booked plane model on the route from Winnipeg to Caribbean Islands is Boeing 737 MAX 8, representing 29.56% of all bookings. The subsequent popular models are Embraer 195 E2 at 22.80%, Airbus A320-100/200 at 11.28%, and Boeing 737-700 Passenger/BBJ1 (winglets) at 10.95%.

Best airlines flying from Winnipeg to Caribbean Islands

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

Airline	Rating	Free Cancellation	Price
Air Canada	PriceFrom C$ 385	Free Cancellation	Rating 7.1 10,966 reviews	Search Air Canada flights
WestJet	PriceFrom C$ 473	Free Cancellation	Rating 7.2 3,325 reviews	Search WestJet flights
Porter Airlines	PriceFrom C$ 493	Free Cancellation	Rating 8.0 435 reviews	Search Porter Airlines flights
Air Transat	PriceFrom C$ 787	Free Cancellation	Rating 7.8 541 reviews	Search Air Transat flights

Why use momondo?

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

Finding the right flight to Caribbean Islands from Winnipeg is quick and easy when you have a range of options in front of you, from reputable agents and recognizable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Caribbean Islands quick and easy, saving you time and money.

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

Flights from Winnipeg to Caribbean Islands 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 Islands?

Once you have performed a search for Winnipeg to Caribbean Islands flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Yes momondo offers price alerts on flights to Caribbean Islands from Winnipeg. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.