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 76% 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 June 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$ 268 Cheap Flights from Winnipeg to Caribbean Islands in 2026

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.

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

YWG

MBJ

20h 00m

2 stops

1:55 p.m. - 12:05 p.m.

MBJ

YWG

22h 10m

2 stops

C$ 628WestJet

Fri, 16 Oct - Mon, 26 Oct

1:45 p.m. - 12:50 p.m.

YWG

MBJ

22h 05m

1 stop

1:50 p.m. - 8:28 p.m.

MBJ

YWG

31h 38m

2 stops

C$ 675Air Canada

Tue, 8 Dec - Fri, 18 Dec

1:45 p.m. - 1:15 p.m.

YWG

NAS

22h 30m

1 stop

2:05 p.m. - 10:16 a.m.

NAS

YWG

21h 11m

1 stop

C$ 681Air Canada

Mon, 7 Dec - Wed, 9 Dec

1:45 p.m. - 1:15 p.m.

YWG

NAS

22h 30m

1 stop

2:05 p.m. - 10:16 a.m.

NAS

YWG

21h 11m

1 stop

C$ 682Air Canada

Mon, 7 Dec - Wed, 9 Dec

2:00 p.m. - 2:44 p.m.

YWG

SJU

23h 44m

1 stop

3:56 p.m. - 12:37 p.m.

SJU

YWG

21h 41m

1 stop

C$ 688Air Canada

Mon, 21 Sep - Fri, 25 Sep

5:15 p.m. - 11:20 a.m.

YWG

MBJ

18h 05m

1 stop

12:30 p.m. - 8:01 p.m.

MBJ

YWG

31h 31m

2 stops

C$ 692Air Canada

Thu, 3 Sep - Sat, 5 Sep

12:00 p.m. - 7:29 p.m.

YWG

MBJ

30h 29m

2 stops

2:55 p.m. - 9:05 p.m.

MBJ

YWG

31h 10m

2 stops

C$ 693WestJet

Tue, 8 Dec - Fri, 18 Dec

2:00 p.m. - 2:44 p.m.

YWG

SJU

23h 44m

1 stop

3:56 p.m. - 10:33 p.m.

SJU

YWG

31h 37m

1 stop

C$ 888United Airlines

Mon, 21 Sep - Fri, 25 Sep

12:56 p.m. - 8:34 p.m.

YWG

SJU

30h 38m

1 stop

1:25 p.m. - 11:15 a.m.

SJU

YWG

22h 50m

2 stops

C$ 1,001United Airlines

Mon, 6 Jul - Mon, 13 Jul

6:35 a.m. - 2:40 p.m.

YWG

SDQ

30h 05m

2 stops

8:35 p.m. - 11:50 a.m.

SDQ

YWG

17h 15m

2 stops

C$ 1,424Delta

Mon, 7 Dec - Thu, 10 Dec

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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

YWG7:20 p.m.Winnipeg

21h 10m

1 stop

NAS5:30 p.m.Nassau Intl

23 Jun

NAS6:30 p.m.Nassau Intl

40h 35m

2 stops

YWG10:05 a.m.Winnipeg

C$ 644

Air Canada

8 Dec

YWG1:45 p.m.Winnipeg

22h 05m

1 stop

MBJ12:50 p.m.Montego Bay Sangster Intl

18 Dec

MBJ1:50 p.m.Montego Bay Sangster Intl

31h 38m

2 stops

YWG8:28 p.m.Winnipeg

C$ 675

Air Canada

7 Dec

YWG6:00 a.m.Winnipeg

30h 15m

2 stops

NAS1:15 p.m.Nassau Intl

9 Dec

NAS2:05 p.m.Nassau Intl

27h 31m

1 stop

YWG4:36 p.m.Winnipeg

C$ 681

United Airlines flights from Winnipeg to Caribbean Islands

Our best United Airlines deals on Winnipeg to Caribbean Islands flight tickets

United Airlines

22 Sep

YWG8:45 a.m.Winnipeg

26h 58m

2 stops

MBJ11:43 a.m.Montego Bay Sangster Intl

26 Sep

MBJ2:40 p.m.Montego Bay Sangster Intl

31h 53m

2 stops

YWG10:33 p.m.Winnipeg

C$ 769

United Airlines

21 Sep

YWG2:00 p.m.Winnipeg

23h 44m

1 stop

SJU2:44 p.m.San Juan Luis Munoz Marin Intl

25 Sep

SJU3:56 p.m.San Juan Luis Munoz Marin Intl

31h 37m

1 stop

YWG10:33 p.m.Winnipeg

C$ 888

United Airlines

7 Nov

YWG12:35 p.m.Winnipeg

24h 54m

2 stops

MBJ2:29 p.m.Montego Bay Sangster Intl

13 Nov

MBJ3:36 p.m.Montego Bay Sangster Intl

27h 53m

3 stops

YWG6:29 p.m.Winnipeg

C$ 934

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Fri 16/10

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

2 stops20h 00m

Montego Bay Sangster Intl

Mon 26/10

1:55 p.m.-12:05 p.m.

2 stops22h 10m

C$ 628

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 8/12

1:45 p.m.-12:50 p.m.

1 stop22h 05m

Montego Bay Sangster Intl

Fri 18/12

1:50 p.m.-8:28 p.m.

2 stops31h 38m

C$ 675

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Mon 7/12

1:45 p.m.-1:15 p.m.

1 stop22h 30m

Nassau Intl

Wed 9/12

2:05 p.m.-10:16 a.m.

1 stop21h 11m

C$ 681

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Mon 7/12

1:45 p.m.-1:15 p.m.

1 stop22h 30m

Nassau Intl

Wed 9/12

2:05 p.m.-10:16 a.m.

1 stop21h 11m

C$ 682

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Mon 21/9

2:00 p.m.-2:44 p.m.

1 stop23h 44m

San Juan Luis Munoz Marin Intl

Fri 25/9

3:56 p.m.-12:37 p.m.

1 stop21h 41m

C$ 688

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Thu 3/9

5:15 p.m.-11:20 a.m.

1 stop18h 05m

Montego Bay Sangster Intl

Sat 5/9

12:30 p.m.-8:01 p.m.

2 stops31h 31m

C$ 692

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 8/12

12:00 p.m.-7:29 p.m.

2 stops30h 29m

Montego Bay Sangster Intl

Fri 18/12

2:55 p.m.-9:05 p.m.

2 stops31h 10m

C$ 693

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Mon 21/9

2:00 p.m.-2:44 p.m.

1 stop23h 44m

San Juan Luis Munoz Marin Intl

Fri 25/9

3:56 p.m.-10:33 p.m.

1 stop31h 37m

C$ 888

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Mon 6/7

12:56 p.m.-8:34 p.m.

1 stop30h 38m

San Juan Luis Munoz Marin Intl

Mon 13/7

1:25 p.m.-11:15 a.m.

2 stops22h 50m

C$ 1,001

WinnipegSanto Domingo

YWG - SDQ

YWGSDQ

Winnipeg

Mon 7/12

6:35 a.m.-2:40 p.m.

2 stops30h 05m

Santo Domingo Las Americas

Thu 10/12

8:35 p.m.-11:50 a.m.

2 stops17h 15m

C$ 1,424

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, March 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$ 193. If you aren’t able to travel to Caribbean Islands during the month of March, then flying in October is also cheap. Prices for this month can be found on momondo for an average of C$ 212.

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

The cheapest day to depart from Winnipeg to Caribbean Islands is on a Thursday when prices can be found for as low as C$ 923. Be sure to avoid booking your departure on a Wednesday as prices are generally higher than usual. According to our data, the average ticket price to Caribbean Islands on Wednesday is C$ 966.

What is the cheapest Winnipeg to Caribbean Islands flight route?

Fly from Winnipeg to Punta Cana 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$ 831 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$ 623 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	11h 30m
Direct flights	None

The fastest flight from Winnipeg to Caribbean Islands takes 11h 30m

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 June 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 38.55% of all bookings. The subsequent popular models are Embraer 195 E2 at 22.59%, Boeing 737-800 Passenger/BBJ2 (winglets) at 9.84%, and Airbus A320-100/200 at 7.82%.

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$ 393	Free Cancellation	Rating 7.1 11,172 reviews	Search Air Canada flights
WestJet	PriceFrom C$ 494	Free Cancellation	Rating 7.2 3,357 reviews	Search WestJet flights
Porter Airlines	PriceFrom C$ 504	Free Cancellation	Rating 8.0 438 reviews	Search Porter Airlines flights
Air Transat	PriceFrom C$ 804	Free Cancellation	Rating 7.8 555 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.