C$ 299 Find Cheap Flights from Winnipeg to Caribbean

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Winnipeg to Caribbean departing on 11/9. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

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Best Caribbean Flight Deals from Winnipeg

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stopsC$ 534
Montego Bay
Montego Bay2 stopsC$ 631
Kingston
Kingston3 stopsC$ 938
Oranjestad
Oranjestad1 stopC$ 680
Nassau
Nassau2 stopsC$ 633
Simpson Bay
Simpson Bay1 stopC$ 740
Bridgetown
Bridgetown1 stopC$ 842
Puerto Plata
Puerto Plata1 stopC$ 601
Port of Spain
Port of Spain1 stopC$ 795
Providenciales
Providenciales2 stopsC$ 878
George Town
George Town1 stopC$ 651
Santo Domingo
Santo Domingo2 stopsC$ 970
Punta Cana
Punta Cana2 stopsC$ 534
Montego Bay
Montego Bay2 stopsC$ 631
Kingston
Kingston3 stopsC$ 938
Oranjestad
Oranjestad1 stopC$ 680
Nassau
Nassau2 stopsC$ 633
Simpson Bay
Simpson Bay1 stopC$ 740
Bridgetown
Bridgetown1 stopC$ 842
Puerto Plata
Puerto Plata1 stopC$ 601
Port of Spain
Port of Spain1 stopC$ 795
Providenciales
Providenciales2 stopsC$ 878
George Town
George Town1 stopC$ 651
Santo Domingo
Santo Domingo2 stopsC$ 970

Cheap Flights from Winnipeg to Caribbean

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Winnipeg to Caribbean that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Winnipeg to Caribbean

Tue, 25 Nov - Tue, 2 Dec
WestJet Logo
6:55 p.m. - 1:35 p.m.YWG-PUJ
16h 40m2 stops
WestJet Logo
4:30 p.m. - 10:08 a.m.PUJ-YWG
19h 38m2 stops
C$ 534WestJet
Find Deal
Wed, 3 Dec - Wed, 10 Dec
WestJet Logo
4:10 p.m. - 3:35 p.m.YWG-PUJ
21h 25m2 stops
WestJet Logo
2:30 p.m. - 11:53 a.m.PUJ-YWG
23h 23m2 stops
C$ 535WestJet
Find Deal
Mon, 22 Sep - Mon, 6 Oct
Air Canada Logo
7:00 p.m. - 3:20 p.m.YWG-PUJ
19h 20m1 stop
Air Canada Logo
4:25 p.m. - 10:10 a.m.PUJ-YWG
18h 45m2 stops
C$ 605Air Canada
Find Deal
Tue, 2 Sep - Tue, 9 Sep
Air Canada Logo
11:50 a.m. - 1:25 p.m.YWG-PUJ
24h 35m2 stops
Air Canada Logo
4:25 p.m. - 10:40 a.m.PUJ-YWG
19h 15m2 stops
C$ 609Air Canada
Find Deal
Sat, 18 Oct - Fri, 24 Oct
United Airlines Logo
4:25 p.m. - 12:40 p.m.YWG-PUJ
19h 15m2 stops
United Airlines Logo
4:35 p.m. - 3:31 p.m.PUJ-YWG
23h 56m2 stops
C$ 611United Airlines
Find Deal
Sun, 7 Sep - Thu, 11 Sep
United Airlines Logo
2:20 p.m. - 12:40 p.m.YWG-PUJ
45h 20m2 stops
United Airlines Logo
3:15 p.m. - 1:09 p.m.PUJ-YWG
22h 54m2 stops
C$ 625United Airlines
Find Deal
Mon, 10 Nov - Thu, 20 Nov
 Logo
5:00 a.m. - 3:40 p.m.YWG-AUA
8h 40m1 stop
 Logo
2:50 p.m. - 4:35 p.m.AUA-YWG
27h 45m2 stops
C$ 680
Find Deal
Mon, 10 Nov - Thu, 20 Nov
 Logo
9:00 p.m. - 3:40 p.m.YWG-AUA
40h 40m2 stops
 Logo
4:10 p.m. - 4:35 p.m.AUA-YWG
26h 25m2 stops
C$ 682
Find Deal
Sun, 18 Jan - Wed, 28 Jan
Air Transat Logo
6:00 a.m. - 2:20 p.m.YWG-PUJ
30h 20m1 stop
Air Transat Logo
9:30 a.m. - 11:35 p.m.PUJ-YWG
16h 05m1 stop
C$ 830Air Transat
Find Deal
Mon, 26 Jan - Wed, 1 Apr
Air Transat Logo
6:00 a.m. - 10:30 p.m.YWG-PUJ
14h 30m1 stop
Air Transat Logo
8:30 a.m. - 11:35 p.m.PUJ-YWG
16h 05m1 stop
C$ 831Air Transat
Find Deal
Booking Insights

KAYAK's insights & trends for Winnipeg to Caribbean flights

Get data-powered insights and trends into flights from Winnipeg to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Winnipeg to Caribbean flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Winnipeg to Caribbean.

The cheapest ticket to Caribbean from Winnipeg found in the last 72 hours was to Montego Bay, at C$ 364 round-trip. The most popular route is from Winnipeg (YWG) to Montego Bay (MBJ), and the cheapest round-trip airline ticket found on this route in the last 72 hours was C$ 364.

Can I save money by flying with a layover from Winnipeg to Caribbean?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at C$ 1,221 on average.

What is the cheapest month to fly from Winnipeg to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Winnipeg to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Winnipeg to Caribbean is October, when tickets cost C$ 641 (return) on average. On the other hand, the most expensive months are December and April, when the average cost of round-trip tickets is C$ 997 and C$ 831 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Winnipeg to Caribbean, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below-average price on the flight from Winnipeg to Caribbean, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.


Good to know

Low seasonSeptember
Cheapest flightC$ 299
Best time to beat the crowds (18% less expensive on average)
Most popular time to fly and prices are also 6% lower on average.
Flight from Winnipeg to Punta Cana

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Winnipeg to Caribbean?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Winnipeg to Caribbean.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Winnipeg to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Winnipeg to Caribbean is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Winnipeg to Caribbean?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Winnipeg to Caribbean with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Winnipeg to Caribbean?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Winnipeg to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Caribbean?

    The cheapest time of day to fly to Caribbean is generally in the evening, when round-trip flights cost C$ 572 on average. Morning departures are around 45% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the morning, which is peak travel time and where the average cost of a ticket is C$ 828.

Reviews of the top 5 airlines flying from Winnipeg to Caribbean

 
Need help choosing which airline to fly with from Winnipeg to Caribbean? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.7
Air TransatOverall score based on 424 reviews
6.7Food
7.3Comfort
7.1Entertainment
7.9Boarding
8.4Crew
Airline reviews

Check in slow even though completed online check in, there was no bag drop available so had to query for 90mins as only 2 staff on desks.

8.0 ExcellentSuzanne, Jul 2025MAN - YYZ
Read more Air Transat reviews

Check in slow even though completed online check in, there was no bag drop available so had to query for 90mins as only 2 staff on desks.

Flying to a far away destination is a miracle in itself, so please take these with a grain of salt. The seats are a bit tired, and need a freshen up. The entertainment could be a bit newer, especially with all services available now. The food really is where we need help. But again, flying is a privilege, so all is good.

Not so much porter it's your site! Not good

They are a sister company with Air Transat and the two companies do not work well together. If you have any issues the two companies will blame each other and you will miss your flights. The help line does not help

Never book through a third party. Book through Air transats website. Terrible process to get help and many issues happen with them and sister companies because half the flights you book with them aren’t even through air transat.

The plane was pretty full, and we dis not have any includes meal for our 4h30 flight? And on-board entertainment wasn't available, there was no TV or plugging to charger your device on the plane. They told us to download an app if we wanted to watch movies but it never connected, that was a disappointment, the r we st was very good though and the crew were really nice!

Seats were very tight especially for first leg of trip.

Not necessarily a Transat issue but it took 2 hours to go through immigration. Tried to reach out to Transat for resolution but was unable to reach an agent.

The flight was excellent, once it started, however we were delayed two hours when the first plane’s engines wouldn’t start. They found another identical plane and transferred us and our luggage in under two hours and made up almost an hour in the air.

Really low cost trip for the huge amount I paid…o paid 550 dollars just for the trip, one way trip, plus 95 for 1 luggage’s and the second 135 dollars…no blanket, not headphones for entertainment, food was served after 3 hours and 2 hours after, breakfast was served Bad, low cost company for high prices

It was all good flight was on time, service was good I enjoyed a few movies and everything was smooth

Efficient, calm when things were delayed and kept us regularly informed of what was happening.

Airbus plane, nice and polite staff, entertainment even as it was a short flight.

Very nice and clean plane. Transit time between flights was tight though

Our flights got changed from United to Air Canada and our purchased seats did not get transferred so we had to pay for seats twice. I brought it up with Air Canada and they stated I had to go back and chase it with United. The united seats were $21 Canadian each and Air Canada were $56 each so we have paid $77 for each seat. Very unhappy

So far so good but food and entertainment are not available for this flight

Plane temperature was comfortable (not to hot) when boarding and waiting for takeoff.

Michael, our FA was very attentive, even finding me a chocolate brownie from economy class when the dessert selections were all dairy based. ( intolerant, not allergic so don’t usually need to order dairy free)

We tried to upgrade to economy premium but were told this was not possible as we had booked through United Airlines (and Air Canada was operating the flight). This seemed silly given there was ample space in economy premium. Additionally, we had to wait almost 1.5 hours upon arrival to taxi to the gate. Otherwise, the crew were very pleasant and passengers were friendly.

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

7 hour layover was a drag. Free internet on the long leg was great.

Staff were courteous and helpful. The only negative was the flight delays (which are usually unavoidable) and the high baggage price.

From vancouver go calgary nd vice vetsa fligjt was delayed

Absolutely terrible, from the customer service to boarding the plane. On the phone, there was some mishaps with getting in my correct date and they did not help me retrieve a refund or any assistance. I’m gonna be reporting to all my followers and family around the region of Los Angeles to New York.

It was good! Short flight and it was on time!

Could not fly out of Canada. Called airlines on Monday, July 14th. Tried to cancel the flight 7 days away, but they said I could not cancel and there would be no refund.

A little disorganized but overall good. The Delta flights were great though

Price was good. Entertainment and food could have been better

My flight was delayed three times then eventually cancelled the next flight was the following day scheduled for 1030 it was delayed I had to cancel reservations I had to put people up in hotels on the other end as they came out of town to pick me up all at my expense because WestJet couldn’t get it together I’m very disappointed in WestJet’s performance and how they handled the situation Get your customers to where they need to be in a timely fashion, even if that means putting them on your competitors jets Customer service should be number one I will think twice now with booking with WestJet

Staff was nice, helpful, and did all they could. I understand economy seats are bottom of the barrel, but we're crammed in there with others in our row.

Flying in the Dreamliner is always comfortable. Though the food options for Air Canada aren't great.

I did not noticed baggage was separate - I had assumed international flights included luggage, so it surprised me I had to pay to check a bag.

Everything could have been better from the planes not being delayed to the rudeness of staff to it was just horrible will not use kayak again or Air Canada I can't see what would ever change my mind now

Business class was not worth the extra charge. Overpriced for slightly larger seat. Nothing special. Small older plane.

Flight got delayed for no reason. And Air Canada was doing 3 boardings via the same gate. It was chaotic!

Bad experience flying with air Canada . Seats not comfortable . Checked bag was delayed and was bought home next day by airport employee. Had to buy toiletries since bag was delayed . No compensation was even suggested . Will not fly air canada again

I n the Toronto airport I had trouble finding my zone. It was 47. I went from Zone 1 to the end of the line.didn't find it. Then saw my zone somewhat by accident over by where you first come in. Signs could be more helpful or more personnel directing people like me.

When I came in the front door in Montreal airport I didn't know where to go, first time traveling. Signs were not directing me.

The AC could have been better . Other than that , all was good

No room when you sit. Fell very cramped. Food was only ok. Service was acceptable. Entertainment system was very buggy.

Confortable plane. Clean modern No frills. Competent crew. On time

Not good. The planes are old, no food for a 5 hour + flight (unless you pay), paid for a carry-on, had to take a bus to board the plane - so far from the actual airport, waited 60 minutes after the flight landed to receive our luggage, no entertainment in the plane, no charging available, boarding passes error message for everyone trying to add to Apple Wallet. Probably my worst experience on a flight.

It's good value for the price. Snacks are available for a price but there is no meal. The flight was aboutr 40 mn late leaving, and the gate was not ready for the plaine in Ottawa. That took an extra 15 mn once landed. You can use the express NEXUS line at Customs in Ottawa if you have a NEXUS card. I thought it was worth paying an extra $50 for extra leg room on the flight.

Good flight and all but airlines are now moving away from providing anything as part of the flight which was previously included, ie in flight entertainment service or snacks.

The real problem with Sunwing is that they are totally undependable. Plane was supposed to heave at 8:20 pm from Varadero to Toronto. Instead because of delays on their part, finally left at 2:30 AM Same thing happened a few days back to my family whereby they were delayed one full day. Throughout the process, no one told them anything. They found out by accident from another passenger after waiting a few hours in the hotel all for nothing Same thing happened with my daughter and husband last year with delays which caused them to miss two days of s much needed 7 days break to Aruba No matter what the cost, I will nit fly Sunwing again and also encourage friends and values to never fly this hihh highly problematic airline

Edreams did not pay the airline and I had to buy another ticket to be able to travel and they still have not refunded my money

Why do I have to pay $20 to leave the airport? Why do I have to pay $25 for the carry on? This was my worst travelling experiences ever. This was my second time and my last time

Minimal service (no entertainment or snack) as advertised, so be prepared. Very friendly flight crew and staff. Excellent service all around

Most standard features are now to be paid as extra

I bought a 1-way ticket from Punta Cana home to Canada, surprise, when I got to the lineup at the airport Sunwing charges a 20 USD airport tax separately. I was told I should have known, though it is the only airline in the terminal that charges it (separately, USD only, no cards or local currency accepted). ATMs at the airport out of service, nowhere to purchase USD on-site. Local banks do not sell you USD if you don't have an account with them... Eventually I found a taxi driver to buy the currency from. Luckily I speak Spanish and am comfortable in the country on my own. I was able to find a solution as the Nexus greeter for Sunwing offered no help. Other Sunwing team members and flight crew I met later were much more helpful when I could not complete self-check-in (flying with carry-on only) as all the seats were locked and apparently could only be assigned at the desk (despite the greeter telling me to use the self-check-in).

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

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