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 5 different airlines that fly to Caribbean Islands 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 Islands?

WestJet, Air Canada, and United Airlines are the most popular carriers operating 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 5 operators available for flights from Winnipeg Airport to Caribbean Islands as of March 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$ 191 Cheap Flights from Winnipeg to Caribbean Islands in 2026

1 adult

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Winnipeg to Caribbean Islands

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:10 p.m. - 11:45 a.m.

YWG

MBJ

16h 35m

2 stops

12:45 p.m. - 8:15 p.m.

MBJ

YWG

31h 30m

2 stops

C$ 482WestJet

Sat, 25 Jul - Tue, 4 Aug

2:55 p.m. - 6:30 p.m.

YWG

MBJ

27h 35m

2 stops

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

MBJ

YWG

12h 10m

1 stop

C$ 483WestJet

Fri, 12 Jun - Sun, 21 Jun

4:55 p.m. - 11:10 a.m.

YWG

NAS

17h 15m

2 stops

12:00 p.m. - 11:10 a.m.

NAS

YWG

24h 10m

2 stops

C$ 487WestJet

Fri, 5 Jun - Wed, 17 Jun

7:10 p.m. - 11:45 a.m.

YWG

MBJ

16h 35m

2 stops

7:30 p.m. - 2:25 p.m.

MBJ

YWG

18h 55m

1 stop

C$ 488WestJet

Sat, 13 Jun - Sun, 21 Jun

7:30 a.m. - 7:14 p.m.

YWG

SJU

10h 44m

1 stop

11:30 a.m. - 3:09 p.m.

SJU

YWG

28h 39m

2 stops

C$ 517Multiple Airlines

Fri, 17 Apr - Tue, 21 Apr

12:15 p.m. - 5:30 p.m.

YWG

NAS

28h 15m

1 stop

6:30 p.m. - 10:09 a.m.

NAS

YWG

40h 39m

2 stops

C$ 518Air Canada

Mon, 25 May - Mon, 1 Jun

7:05 p.m. - 11:10 a.m.

YWG

GCM

16h 05m

1 stop

11:55 a.m. - 8:17 p.m.

GCM

YWG

32h 22m

2 stops

C$ 545Air Canada

Mon, 13 Apr - Thu, 16 Apr

8:00 a.m. - 11:49 a.m.

YWG

SJU

26h 49m

1 stop

7:54 p.m. - 7:25 p.m.

SJU

YWG

48h 31m

2 stops

C$ 627Multiple Airlines

Mon, 6 Apr - Mon, 13 Apr

2:00 p.m. - 4:05 p.m.

YWG

PLS

25h 05m

2 stops

5:15 p.m. - 11:52 a.m.

PLS

YWG

43h 37m

2 stops

C$ 652United Airlines

Sun, 12 Apr - Thu, 16 Apr

2:00 p.m. - 4:05 p.m.

YWG

PLS

25h 05m

2 stops

5:15 p.m. - 11:52 a.m.

PLS

YWG

43h 37m

2 stops

C$ 657United Airlines

Sun, 12 Apr - Thu, 16 Apr

American Airlines flights from Winnipeg to Caribbean Islands

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

American Airlines

17 Apr

YWG6:00 a.m.Winnipeg

26h 11m

3 stops

SJU9:11 a.m.San Juan Luis Munoz Marin Intl

21 Apr

SJU7:00 p.m.San Juan Luis Munoz Marin Intl

53h 35m

3 stops

YWG11:35 p.m.Winnipeg

C$ 1,287

American Airlines

10 Mar

YWG12:10 p.m.Winnipeg

25h 33m

3 stops

NAS2:43 p.m.Nassau Intl

17 Mar

NAS8:06 a.m.Nassau Intl

16h 29m

3 stops

YWG11:35 p.m.Winnipeg

C$ 3,316

WestJet flights from Winnipeg to Caribbean Islands

Our best WestJet deals on Winnipeg to Caribbean Islands flight tickets

WestJet

25 Jul

YWG7:10 p.m.Winnipeg

16h 35m

2 stops

MBJ11:45 a.m.Montego Bay Sangster Intl

4 Aug

MBJ12:45 p.m.Montego Bay Sangster Intl

31h 30m

2 stops

YWG8:15 p.m.Winnipeg

C$ 482

WestJet

12 Jun

YWG2:55 p.m.Winnipeg

27h 35m

2 stops

MBJ6:30 p.m.Montego Bay Sangster Intl

21 Jun

MBJ12:45 p.m.Montego Bay Sangster Intl

12h 10m

1 stop

YWG12:55 a.m.Winnipeg

C$ 483

WestJet

5 Jun

YWG4:55 p.m.Winnipeg

17h 15m

2 stops

NAS11:10 a.m.Nassau Intl

17 Jun

NAS12:00 p.m.Nassau Intl

24h 10m

2 stops

YWG11:10 a.m.Winnipeg

C$ 487

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 25/7

7:10 p.m.-11:45 a.m.

2 stops16h 35m

Montego Bay Sangster Intl

Tue 4/8

12:45 p.m.-8:15 p.m.

2 stops31h 30m

C$ 482

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Fri 12/6

2:55 p.m.-6:30 p.m.

2 stops27h 35m

Montego Bay Sangster Intl

Sun 21/6

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

1 stop12h 10m

C$ 483

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Fri 5/6

4:55 p.m.-11:10 a.m.

2 stops17h 15m

Nassau Intl

Wed 17/6

12:00 p.m.-11:10 a.m.

2 stops24h 10m

C$ 487

Quickest round-trip

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Sat 13/6

7:10 p.m.-11:45 a.m.

2 stops16h 35m

Montego Bay Sangster Intl

Sun 21/6

7:30 p.m.-2:25 p.m.

1 stop18h 55m

C$ 488

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Fri 17/4

7:30 a.m.-7:14 p.m.

1 stop10h 44m

San Juan Luis Munoz Marin Intl

Tue 21/4

11:30 a.m.-3:09 p.m.

2 stops28h 39m

C$ 517

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Mon 25/5

12:15 p.m.-5:30 p.m.

1 stop28h 15m

Nassau Intl

Mon 1/6

6:30 p.m.-10:09 a.m.

2 stops40h 39m

C$ 518

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Mon 13/4

7:05 p.m.-11:10 a.m.

1 stop16h 05m

George Town Owen Roberts Intl

Thu 16/4

11:55 a.m.-8:17 p.m.

2 stops32h 22m

C$ 545

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Mon 6/4

8:00 a.m.-11:49 a.m.

1 stop26h 49m

San Juan Luis Munoz Marin Intl

Mon 13/4

7:54 p.m.-7:25 p.m.

2 stops48h 31m

C$ 627

WinnipegProvidenciales

YWG - PLS

YWGPLS

Winnipeg

Sun 12/4

2:00 p.m.-4:05 p.m.

2 stops25h 05m

Providenciales

Thu 16/4

5:15 p.m.-11:52 a.m.

2 stops43h 37m

C$ 652

WinnipegProvidenciales

YWG - PLS

YWGPLS

Winnipeg

Sun 12/4

2:00 p.m.-4:05 p.m.

2 stops25h 05m

Providenciales

Thu 16/4

5:15 p.m.-11:52 a.m.

2 stops43h 37m

C$ 656

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$ 662. If you aren’t able to travel to Caribbean Islands during the month of June, then flying in March is also cheap. Prices for this month can be found on momondo for an average of C$ 694.

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 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$ 777 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$ 549 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?

You could potentially save up to 3% on your flight if you consider stops on a Winnipeg to Caribbean Islands flight.

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	5h 25m
Direct flights	Sun
Airports in Caribbean Islands	99 airports

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

Direct flights go from Winnipeg to Caribbean Islands on Sunday. There are no airlines offering direct flights.

There are 99 airports in Caribbean Islands. 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 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 5 operators available for flights from Winnipeg Airport to Caribbean Islands as of March 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 27.38% of all bookings. The subsequent popular models are Embraer 195 E2 at 23.63%, Airbus A320-100/200 at 14.51%, and Airbus A321-100/200 at 9.90%.

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$ 381	Free Cancellation	Rating 7.1 10,799 reviews	Search Air Canada flights
WestJet	PriceFrom C$ 469	Free Cancellation	Rating 7.2 3,283 reviews	Search WestJet flights
Porter Airlines	PriceFrom C$ 489	Free Cancellation	Rating 8.0 423 reviews	Search Porter Airlines flights
United Airlines	PriceFrom C$ 544	Free Cancellation	Rating 7.4 9,408 reviews	Search United Airlines flights
Air Transat	PriceFrom C$ 818	Free Cancellation	Rating 7.7 519 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.