C$ 267 Find Cheap Flights from Winnipeg to Caribbean – Compare and Save

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 10/9. 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.
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Flight Deals

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$ 537
Montego Bay
Montego Bay1 stopC$ 536
Kingston
Kingston2 stopsC$ 617
Nassau
Nassau2 stopsC$ 498
Bridgetown
Bridgetown1 stopC$ 526
Willemstad
Willemstad1 stopC$ 422
Puerto Plata
Puerto Plata1 stopC$ 710
George Town
George Town1 stopC$ 502
Santo Domingo
Santo Domingo2 stopsC$ 1,167
Punta Cana
Punta Cana2 stopsC$ 537
Montego Bay
Montego Bay1 stopC$ 536
Kingston
Kingston2 stopsC$ 617
Nassau
Nassau2 stopsC$ 498
Bridgetown
Bridgetown1 stopC$ 526
Willemstad
Willemstad1 stopC$ 422
Puerto Plata
Puerto Plata1 stopC$ 710
George Town
George Town1 stopC$ 502
Santo Domingo
Santo Domingo2 stopsC$ 1,167

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

Sun, 25 Oct - Wed, 4 Nov
Air Canada Logo
6:55 p.m. - 2:45 p.m.
YWG
-
CUR
18h 50m
1 stop
Air Canada Logo
4:45 p.m. - 10:24 a.m.
CUR
-
YWG
19h 39m
1 stop
C$ 422Air Canada
Sun, 25 Oct - Wed, 4 Nov
Air Canada Logo
6:55 p.m. - 2:45 p.m.
YWG
-
CUR
18h 50m
1 stop
Air Canada Logo
4:45 p.m. - 4:38 p.m.
CUR
-
YWG
25h 53m
2 stops
C$ 427Air Canada
Thu, 29 Oct - Fri, 6 Nov
WestJet Logo
6:45 a.m. - 2:17 p.m.
YWG
-
CUR
30h 32m
2 stops
WestJet Logo
4:10 p.m. - 9:05 p.m.
CUR
-
YWG
30h 55m
2 stops
C$ 448WestJet
Thu, 29 Oct - Fri, 6 Nov
WestJet Logo
6:45 a.m. - 2:17 p.m.
YWG
-
CUR
30h 32m
2 stops
WestJet Logo
4:10 p.m. - 12:45 a.m.
CUR
-
YWG
10h 35m
1 stop
C$ 450WestJet
Sun, 29 Nov - Thu, 10 Dec
Air Canada Logo
6:55 p.m. - 3:45 p.m.
YWG
-
CUR
18h 50m
1 stop
Air Canada Logo
4:45 p.m. - 2:34 p.m.
CUR
-
YWG
23h 49m
1 stop
C$ 456Air Canada
Sun, 29 Nov - Thu, 10 Dec
Air Canada Logo
6:55 p.m. - 3:45 p.m.
YWG
-
CUR
18h 50m
1 stop
Air Canada Logo
4:45 p.m. - 6:25 p.m.
CUR
-
YWG
27h 40m
2 stops
C$ 456Air Canada
Thu, 29 Oct - Fri, 6 Nov
WestJet Logo
12:20 p.m. - 2:17 p.m.
YWG
-
CUR
24h 57m
1 stop
WestJet Logo
4:10 p.m. - 11:35 a.m.
CUR
-
YWG
21h 25m
1 stop
C$ 457WestJet
Wed, 2 Dec - Wed, 9 Dec
Multiple Airlines Logo
8:05 p.m. - 3:17 p.m.
YWG
-
CUR
17h 12m
1 stop
Multiple Airlines Logo
4:45 p.m. - 2:09 p.m.
CUR
-
YWG
23h 24m
1 stop
C$ 550Multiple Airlines
Wed, 2 Dec - Tue, 8 Dec
Multiple Airlines Logo
12:55 p.m. - 3:17 p.m.
YWG
-
CUR
24h 22m
2 stops
Multiple Airlines Logo
4:45 p.m. - 10:09 a.m.
CUR
-
YWG
19h 24m
1 stop
C$ 571Multiple Airlines
Sat, 28 Nov - Sun, 6 Dec
Multiple Airlines Logo
11:55 a.m. - 7:45 p.m.
YWG
-
PUJ
5h 50mdirect
Multiple Airlines Logo
12:35 p.m. - 10:00 a.m.
PUJ
-
YWG
23h 25m
1 stop
C$ 615Multiple Airlines
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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean from Winnipeg found in the last 5 days was to Montego Bay, at C$ 633 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 5 days was C$ 633.

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

The average price for all round-trip flights from Winnipeg to Caribbean depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Caribbean is generally in the morning, when round-trip flights cost C$ 969 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$ 969.

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.

No, with an average price for the route of C$ 857, prices are generally cheapest when you fly direct.

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 April, when tickets cost C$ 742 (return) on average. On the other hand, the most expensive months are December and February, when the average cost of round-trip tickets is C$ 1,010 and C$ 979 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 a flight from Winnipeg to Caribbean, you should book around 2 weeks before departure, which saves you about 15% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Good to know

Low season

June
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly (31% more expensive on average)

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.

Reviews of the top 4 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.
8.0
Porter AirlinesOverall score based on 449 reviews
7.5Food
8.6Crew
6.9Entertainment
8.0Comfort
8.2Boarding
Airline reviews

Boarding pass counter did not open until 2 hrs before flight. We were there 3 hrs before as we like to be early ( eat, relax etc). Due to this the line up was large , thus never got through security till 15 min before boarding. Other than that, everything was great

8.0 ExcellentDarren, Jul 2026
YYT - YHM
Read more Porter Airlines reviews

Boarding pass counter did not open until 2 hrs before flight. We were there 3 hrs before as we like to be early ( eat, relax etc). Due to this the line up was large , thus never got through security till 15 min before boarding. Other than that, everything was great

The agent at check in was very cordial and gave me seat 4a with nobody beside me as I asked if possible

Seats not as comfortable but understand as it was a smaller plane/ short flight. All in all, I’ve never had any issues with Porter. Great company to fly with

Look, I understand that Kayak doesn't know I cancelled my flight on Porter. So I didn't actually fly yesterday. My main disappointment is with Porter ticket fare policies, and maybe you can pass this on to them: At my employer's request, I had booked a full fare ticket with no change fees since my trip to Toronto would likely be extended. Indeed, when I went to change my flight home to a later date, I was told the Fare Difference would cost an additional $550. So much for no change fees lol! While I had the agent on the line, I hopped over to Kayak, searched for new flights on the date in question, and saw a one-way ticket that got me home for only $355. So I got reimbursed about $450for the unused half of my roundtrip and bought a new ticket for $355. What good is a full fare / no change fee ticket if they screw you with "fare difference" BS. I'm still flying home on Porter Airlines but they just lost a hundred bucks with their stupid shenanigans.

I flew with Porter yesterday and overall had a positive experience. The flight was delayed, but the airline did a good job keeping passengers informed with frequent updates throughout the process. My biggest challenge was actually in Terminal 3, where the speaker system wasn’t very clear. It was often difficult to hear the announcements, which made it harder to follow updates at the gate. On board, the experience improved significantly. The aircraft felt very new and well maintained, and the seats were surprisingly comfortable for a short-haul flight. One of the flight attendants seemed a little disengaged, but the other was excellent—friendly, professional, and a pleasure to interact with. Despite the delay, the comfortable aircraft, clear communication from Porter, and positive onboard service made for a good overall experience.

We were very offended Reserva check in agent in Calgary. Erroneously profiled and reprimanded for using Reserve line . Hadn't even looked at tickets. We were in fact Reserve passengers

The staff was amazing. Best service I’ve had on an aircraft in a long time. Was not particularly happy with the food. Flight was at 10:50 and left home too early for breakfast and wasn’t able to purchase food at airport and felt for sure I could get some breakfast to buy on airplane. Nope as food was served around 11:30 and only one choice left (I was at 22C) so ordered the chicken dish thinking I’m getting a hot meal but cold chicken with rice and carrots etc. I was looking forward to a croissant sandwich and a hot cup of tea. The FA was kind to explain they were serving dinner at that time. She was lovely Other than the disappointment with the food the staff was amazing. On my return flight I will make sure to eat and take some food with me so I’m not hungry or disappointed. This was my second time ever flying Porter and will consider checking them when I next come to visit my daughter. Have to say it again best crew I’ve ever experienced on a flight and I travel quite a bit. Thanks.

I didn’t receive any help when they messed up and wasn’t honest and the supervisor did absolutely nothing to help me so I had to buy another ticket at $537

Even tho the flight was a bit delayed the team was apologetic. Everyone was friendly and efficient.

Everything was good except the fact you charge more for a carry on bag vs a check in bag and to top it off in US$ that was not impressive

The flight was terrible based off the temperature in the plane and the air smelled so stale and gross. I have never wanted to hosed lore in my life after I got off. The food was disgusting and seemingly low quality. The staff was friendly. The bathrooms were so gross after a couple of hours. I will definitely never book with them again.

The crew was great. There was no entertainment and the internet wasn't working. We sat in the run way for a LONG time which is always so upsetting. The seats are very close together and the flights are completely full which makes for a tough flight. Flying is just an uncomfortable experience.

Very kind crew. Vegetarian food better than usual. Prompt take off. Entertainment worked well. Could always do with more room!

I liked the reliability. I liked less the chair comfort...

The dinner was bland and boring, but the economy seats were surprisingly comfortable. The flight was very packed.

I didn't have any problems during my flight. My main issue is with airlines in general, they keep offering less and less every year, AirTransat is no different.

We are a senior couple (70+) and chose emergency exit seats so we would have 2 seats together and neither of us had to sit in a middle seat. My husband is type 1 diabetic on an insulin pump and I monitor his blood sugar levels. I am 5'9" and 250 lbs and found the seats extremely uncomfortable. Toward the end of the flight I developed diarrhea which lasted a full 24 hours.

We were treated well by the staff at the airport and on board aircraft. Delay was uncontrollable due to the weather. Had to wait for another gate as we were late landing in Fort Lauderdale.

I was supose to have a carrey on incluided for each passenger and they made me paid 75$ each at the gate.

Great crew and entertaining Captain. Seats were not what we had expected based on my booking but things worked out in the end. Of course, like all airlines these days not enough leg or elbow room.

My flight was cancelled due to weather but Westjet got me on a new flight in a timely and efficient manor.

No internet, not even westjet connect makes for a boring flight

Our first flight from LAX to Winnipeg was changed but you never informed us at all. It went from a nonstop flight to a stay at Calgary. This impacted our trip negatively as we arrived much later than we planned to. Our returning flight was horrible. The flight was delayed 6 hours!! And we were NOT going to wait that long. The only way we got on our original flight was running there. However all of our suitcases were now coming on the delayed flight. It was the worst experience we ever had flying. I want my money back.

Lots of overhead storage and a good crew and service.

On time. Friendly and efficient staff at check in and flight crew.

Very good over all , would have been nice to have entertainment on the flight

It was an awesome experience flying with Westjet. This was my first domestic flight experience in Canada.

The flight itself was fine, but two of the ladies at the gate were extremely rude to a few of us in line. Their customer service really needs some help. I’ve always had good experiences with WestJet until these two ladies. They had the worst attitudes and really left a bad taste in my mouth after a good trip

Smooth process, on time. Everything ran perfectly. It would be nice to have in flight entertainment and better food choices but these were short flights so not a big deal

Flight got cancelled. I had to spend many hours on phone to have it rescheduled at my convenience

I like the fact air Canada is on time The food you guys serve is not good

Upgraded to sit at the exit door so good leg room.

Very tight leg room and not a fan of the new policy on no free carry on luggage. Besides that, it was fine.

Flight delay, cancellation rescheduling and misdirected luggage which created some stress. It all worked out in the end.

The flight was delayed several times, however , they kept me well informed with enough advance warning that I had not left home yet

Sat on the tarmac with no ventilation for almost an hour, without a single word from the crew. Appalling. When Air Canada goes bankrupt, again, almost everyone in Canada will be cheering.

If you have checked the status of my booking you would have seen that it was cancelled. And the travelers insurance we purchased only covered $100 per ticket. So my overall experience with kayak and air canada is poor

The plane for my second flight was reassigned. We had to wait for them to get a different plane out of the hangar and call in a crew

Send me 20 dollars and i will do the survey. You survey people think we do things in life to do surveys.

It was swiss air flight and they were very helpful and kind

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports