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 70% of people opting to fly with this airline when travelling to Caribbean. Keep in mind that there are 5 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 Air Canada 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 August 2025, there are 5 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$ 253 Cheap Flights from Winnipeg to Caribbean in 2025

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

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

16h 40m2 stops

2:30 p.m. - 7:12 p.m.PUJ-YWG

30h 42m1 stop

C$ 531WestJet

Find Deal

Mon, 17 Nov - Mon, 24 Nov

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

16h 40m2 stops

4:30 p.m. - 10:08 a.m.PUJ-YWG

19h 38m2 stops

C$ 537WestJet

Find Deal

Tue, 25 Nov - Tue, 2 Dec

2:20 p.m. - 12:59 p.m.YWG-PUJ

44h 39m2 stops

2:55 p.m. - 11:57 a.m.PUJ-YWG

23h 02m1 stop

C$ 557United Airlines

Find Deal

Fri, 14 Nov - Sun, 23 Nov

2:20 p.m. - 4:02 p.m.YWG-PUJ

23h 42m1 stop

3:28 p.m. - 11:57 a.m.PUJ-YWG

22h 29m2 stops

C$ 559United Airlines

Find Deal

Thu, 13 Nov - Sat, 22 Nov

7:05 p.m. - 2:00 p.m.YWG-PUJ

40h 55m2 stops

1:05 p.m. - 11:44 p.m.PUJ-YWG

12h 39m1 stop

C$ 567Air Canada

Find Deal

Sat, 8 Nov - Wed, 12 Nov

7:05 p.m. - 12:45 a.m.YWG-PUJ

51h 40m2 stops

1:05 p.m. - 10:16 a.m.PUJ-YWG

23h 11m2 stops

C$ 571Air Canada

Find Deal

Sat, 8 Nov - Wed, 12 Nov

8:20 p.m. - 5:47 p.m.YWG-PUJ

19h 27m1 stop

9:30 a.m. - 7:12 p.m.PUJ-YWG

11h 42m1 stop

C$ 628

Find Deal

Fri, 14 Nov - Sun, 23 Nov

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

16h 40m2 stops

1:50 p.m. - 11:13 a.m.PUJ-YWG

23h 23m3 stops

C$ 683

Find Deal

Mon, 17 Nov - Mon, 24 Nov

5:38 p.m. - 12:41 p.m.YWG-MBJ

18h 03m2 stops

4:05 p.m. - 11:32 p.m.MBJ-YWG

8h 27m1 stop

C$ 1,004Delta

Find Deal

Mon, 1 Dec - Wed, 31 Dec

5:40 p.m. - 12:40 p.m.YWG-AUA

18h 00m2 stops

1:55 p.m. - 11:54 a.m.AUA-YWG

22h 59m2 stops

C$ 1,069Delta

Find Deal

Sun, 14 Sep - Tue, 30 Sep

United Airlines flights from Winnipeg to Caribbean

Our best United Airlines deals on Winnipeg to Caribbean flight tickets

United Airlines

14 Nov

YWG2:20 p.m.Winnipeg

44h 39m

2 stops

PUJ12:59 p.m.Punta Cana

23 Nov

PUJ2:55 p.m.Punta Cana

23h 02m

1 stop

YWG11:57 a.m.Winnipeg

C$ 557

Find similar

United Airlines

13 Nov

YWG2:20 p.m.Winnipeg

23h 42m

1 stop

PUJ4:02 p.m.Punta Cana

22 Nov

PUJ3:28 p.m.Punta Cana

22h 29m

2 stops

YWG11:57 a.m.Winnipeg

C$ 559

Find similar

United Airlines

13 Nov

YWG8:40 a.m.Winnipeg

26h 19m

2 stops

PUJ12:59 p.m.Punta Cana

22 Nov

PUJ2:55 p.m.Punta Cana

23h 02m

1 stop

YWG11:57 a.m.Winnipeg

C$ 698

Find similar

WestJet flights from Winnipeg to Caribbean

Our best WestJet deals on Winnipeg to Caribbean flight tickets

WestJet

17 Nov

YWG6:55 p.m.Winnipeg

16h 40m

2 stops

PUJ1:35 p.m.Punta Cana

24 Nov

PUJ2:30 p.m.Punta Cana

30h 42m

1 stop

YWG7:12 p.m.Winnipeg

C$ 531

Find similar

WestJet

25 Nov

YWG6:55 p.m.Winnipeg

16h 40m

2 stops

PUJ1:35 p.m.Punta Cana

2 Dec

PUJ4:30 p.m.Punta Cana

19h 38m

2 stops

YWG10:08 a.m.Winnipeg

C$ 536

Find similar

WestJet

25 Nov

YWG5:00 a.m.Winnipeg

8h 35m

1 stop

PUJ3:35 p.m.Punta Cana

2 Dec

PUJ4:30 p.m.Punta Cana

21h 05m

1 stop

YWG11:35 a.m.Winnipeg

C$ 541

Find similar

Fly from

Fly to

Route

Depart

Return

Price

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Mon 17/11

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

2 stops16h 40m

Punta Cana

Mon 24/11

2:30 p.m.-7:12 p.m.

1 stop30h 42m

C$ 531

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Tue 25/11

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

2 stops16h 40m

Punta Cana

Tue 2/12

4:30 p.m.-10:08 a.m.

2 stops19h 38m

C$ 536

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Fri 14/11

2:20 p.m.-12:59 p.m.

2 stops44h 39m

Punta Cana

Sun 23/11

2:55 p.m.-11:57 a.m.

1 stop23h 02m

C$ 557

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Thu 13/11

2:20 p.m.-4:02 p.m.

1 stop23h 42m

Punta Cana

Sat 22/11

3:28 p.m.-11:57 a.m.

2 stops22h 29m

C$ 559

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Sat 8/11

7:05 p.m.-2:00 p.m.

2 stops40h 55m

Punta Cana

Wed 12/11

1:05 p.m.-11:44 p.m.

1 stop12h 39m

C$ 567

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Sat 8/11

7:05 p.m.-12:45 a.m.

2 stops51h 40m

Punta Cana

Wed 12/11

1:05 p.m.-10:16 a.m.

2 stops23h 11m

C$ 571

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Fri 14/11

8:20 p.m.-5:47 p.m.

1 stop19h 27m

Punta Cana

Sun 23/11

9:30 a.m.-7:12 p.m.

1 stop11h 42m

C$ 628

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Mon 17/11

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

2 stops16h 40m

Punta Cana

Mon 24/11

1:50 p.m.-11:13 a.m.

3 stops23h 23m

C$ 683

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Mon 1/12

5:38 p.m.-12:41 p.m.

2 stops18h 03m

Montego Bay Sangster Intl

Wed 31/12

4:05 p.m.-11:32 p.m.

1 stop8h 27m

C$ 1,004

WinnipegOranjestad

YWG - AUA

YWGAUA

Winnipeg

Sun 14/9

5:40 p.m.-12:40 p.m.

2 stops18h 00m

Oranjestad Reina Beatrix

Tue 30/9

1:55 p.m.-11:54 a.m.

2 stops22h 59m

C$ 1,069

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, October 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$ 644. If you don’t want to visit Caribbean in October, then you should wait until June to fly from Winnipeg, when ticket prices are also cheap, with an average price of C$ 675.

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$ 789. 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$ 1,191.

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$ 792. In the morning is when there is more demand to fly to Caribbean, so prices are often more expensive at around C$ 1,145 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$ 785 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$ 716 on momondo.

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

There are 1 cabin classes 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?

No. A direct flight is the cheapest option for a flight between Winnipeg 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	C$ 253
Fastest flight time	5h 30m
Direct flights	Sun
Airports in Caribbean	8 airports

The best one-way flight to Caribbean from Winnipeg in the past 72 hours is C$ 253. The best round-trip flight deal from Winnipeg to Caribbean found on momondo in the last 72 hours is C$ 531.

The fastest flight from Winnipeg to Caribbean takes 5h 30m

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

There are 8 airports near Caribbean: George Town Owen Roberts Intl (GCM), Puerto Plata La Union (POP), Willemstad Hato Int. (CUR), Kingston Norman Manley (KIN), Punta Cana (PUJ), Montego Bay Sangster Intl (MBJ), Oranjestad Reina Beatrix (AUA), San Juan Luis Munoz Marin Intl (SJU)

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 August 2025, there are 5 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 737-700 Passenger/BBJ1 (winglets) (60.71% of total bookings). The next most popular plane models are Boeing 737-800 Passenger/BBJ2 (winglets) (17.86%), Boeing 737-800 (Scimitar Winglets) (17.86%), and Boeing 737 MAX 8 (3.57%).

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
United Airlines	PriceFrom C$ 470	Free Cancellation	Rating 7.4 8,904 reviews	Search United Airlines flights
WestJet	PriceFrom C$ 476	Free Cancellation	Rating 7.2 2,980 reviews	Search WestJet flights
Air Canada	PriceFrom C$ 487	Free Cancellation	Rating 7.1 9,855 reviews	Search Air Canada flights
Sunwing Airlines	PriceFrom C$ 708	Free Cancellation	Rating 6.7 36 reviews	Search Sunwing Airlines flights
Air Transat	PriceFrom C$ 811	Free Cancellation	Rating 7.7 424 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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Find better results for your trip to Caribbean

Popular Cities in Caribbean

Flights to Punta Canafrom C$ 268

Flights to Montego Bayfrom C$ 430

Flights to Oranjestadfrom C$ 380

Flights to Kingstonfrom C$ 384

Flights to San Juanfrom C$ 383

Flights to Fort-de-Francefrom C$ 510

Flights to Simpson Bayfrom C$ 383

Flights to Nassaufrom C$ 409

Flights to Bridgetownfrom C$ 424

Flights to Pointe-à-Pitrefrom C$ 669

Flights to Puerto Platafrom C$ 460

Flights to Port of Spainfrom C$ 608

Cheap flights from Winnipeg to Caribbean from C$ 253

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 15/12. 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

WestJet flights from Winnipeg to Caribbean

Our best WestJet 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 are 1 cabin classes 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?

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

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

WestJet, United Airlines, and Air Canada 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