C$ 268 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 23/6. 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, 0 bags

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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$ 704
Montego Bay
Montego Bay2 stopsC$ 626
Kingston
Kingston1 stopC$ 803
Nassau
Nassau1 stopC$ 649
Bridgetown
Bridgetown2 stopsC$ 662
Willemstad
Willemstad2 stopsC$ 757
Puerto Plata
Puerto Plata1 stopC$ 741
George Town
George Town1 stopC$ 665
Santo Domingo
Santo Domingo2 stopsC$ 1,226
Punta Cana
Punta Cana2 stopsC$ 704
Montego Bay
Montego Bay2 stopsC$ 626
Kingston
Kingston1 stopC$ 803
Nassau
Nassau1 stopC$ 649
Bridgetown
Bridgetown2 stopsC$ 662
Willemstad
Willemstad2 stopsC$ 757
Puerto Plata
Puerto Plata1 stopC$ 741
George Town
George Town1 stopC$ 665
Santo Domingo
Santo Domingo2 stopsC$ 1,226

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

Fri, 16 Oct - Mon, 26 Oct
WestJet Logo
10:30 p.m. - 6:30 p.m.
YWG
-
MBJ
20h 00m
2 stops
WestJet Logo
1:55 p.m. - 12:05 p.m.
MBJ
-
YWG
22h 10m
2 stops
C$ 626WestJet
Sun, 8 Nov - Sun, 8 Nov
WestJet Logo
5:00 a.m. - 3:40 p.m.
YWG
-
NAS
9h 40m
1 stop
WestJet Logo
8:30 p.m. - 9:05 p.m.
NAS
-
YWG
49h 35m
2 stops
C$ 649WestJet
Sun, 8 Nov - Sun, 8 Nov
WestJet Logo
5:00 a.m. - 3:40 p.m.
YWG
-
NAS
9h 40m
1 stop
WestJet Logo
8:30 p.m. - 12:45 a.m.
NAS
-
YWG
29h 15m
1 stop
C$ 655WestJet
Mon, 7 Dec - Wed, 9 Dec
Air Canada Logo
1:45 p.m. - 1:15 p.m.
YWG
-
NAS
22h 30m
1 stop
Air Canada Logo
2:05 p.m. - 10:16 a.m.
NAS
-
YWG
21h 11m
1 stop
C$ 680Air Canada
Thu, 3 Sep - Sat, 5 Sep
Air Canada Logo
5:15 p.m. - 11:20 a.m.
YWG
-
MBJ
18h 05m
1 stop
Air Canada Logo
12:30 p.m. - 8:01 p.m.
MBJ
-
YWG
31h 31m
2 stops
C$ 690Air Canada
Tue, 22 Sep - Sat, 26 Sep
United Airlines Logo
8:45 a.m. - 11:43 a.m.
YWG
-
MBJ
26h 58m
2 stops
United Airlines Logo
2:40 p.m. - 12:37 p.m.
MBJ
-
YWG
21h 57m
2 stops
C$ 767United Airlines
Sun, 8 Nov - Sat, 14 Nov
Multiple Airlines Logo
8:15 a.m. - 1:00 p.m.
YWG
-
PLS
27h 45m
1 stop
Multiple Airlines Logo
2:30 p.m. - 11:35 a.m.
PLS
-
YWG
22h 05m
1 stop
C$ 778Multiple Airlines
Sun, 8 Nov - Sat, 14 Nov
Multiple Airlines Logo
8:15 a.m. - 1:00 p.m.
YWG
-
PLS
27h 45m
1 stop
Multiple Airlines Logo
2:30 p.m. - 9:05 p.m.
PLS
-
YWG
31h 35m
2 stops
C$ 779Multiple Airlines
Sat, 12 Sep - Tue, 15 Sep
United Airlines Logo
7:00 a.m. - 12:18 p.m.
YWG
-
CUR
52h 18m
2 stops
United Airlines Logo
1:23 p.m. - 10:33 p.m.
CUR
-
YWG
34h 10m
2 stops
C$ 1,178United Airlines
Mon, 7 Dec - Thu, 10 Dec
Delta Logo
6:35 a.m. - 2:40 p.m.
YWG
-
SDQ
30h 05m
2 stops
Delta Logo
8:35 p.m. - 11:50 a.m.
SDQ
-
YWG
17h 15m
2 stops
C$ 1,420Delta
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$ 771 round-trip. The most popular route is from Winnipeg (YWG) to Punta Cana (PUJ), and the cheapest round-trip airline ticket found on this route in the last 5 days was C$ 778.

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$ 963 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$ 963.

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$ 661, 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 March, when tickets cost C$ 192 (return) on average. On the other hand, the most expensive months are June and January, when the average cost of round-trip tickets is C$ 486 and C$ 463 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 6 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flightC$ 268
Best time to beat the crowds but there is an average 8% increase in price.
Most popular time to fly (41% more expensive on average)
Flight from Winnipeg to Nassau

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 438 reviews
7.6Food
8.0Comfort
8.2Boarding
6.9Entertainment
8.6Crew
Airline reviews

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.

10.0 ExcellentAngela, May 2026
YYZ - YVR
Read more Porter Airlines reviews

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.

The Flight took off 2hrs late because there was no pilot showing up when the flight was ready to board.. Though the cabin crew was present and had prepared the plane, the FO turned around after 15 min and went away. A crew to fly the plane finally arrived over an hour later and we were able to board 1h30 min later than planned time... until everything was loaded, we left 2h late from the gate. This was a small plane, so don't expect any Entertainment... Wi-Fi access on board would work, but took an awful amount of time to figure out and get it work (I'm an IT person). Flying as VIPorter customer, I was expecting at least some warm meal, but everything served was just cold.. except the coffee maybe. Even in so-called VIPorter seats, space is cramped and trays are so tiny, you can barely setup your food. Flight caught up during the coast-to-coast crossing and was able to recoup about 45 min from the delay.. still arrived very late in Vancouver and had to wait a long time to get our registered bags. Let's see how the return flight will be in a few days..

It was okay. Had a thing with the front desk, she had me repack my suitcases to have them be under the weight restrictions, but then the other one was overweight, she argued with me about it when there were tons of people in line. Wasn’t great.

Due to a known technical error that Porter has not fixed in over a year, I was unable to check in the children on my reservation online and had to do it at the airport. Upon check in, there were no seats together, which was an issue as we had young children. The gate agent did manage to seat us together by moving other passengers, which was appreciated, but the other passengers were never informed, leading to confusion and delay upon boarding. The flight was over an hour late; no explanation or apology was ever issued. The bags on Porter take a long time to arrive--over half an hour at Hamilton on my inbound flight, and not much better on my return to Edmonton.

On my e-boarding pass it shows free wifi, yet the plane I was on didn’t have wifi. Please remove false advertising from your website and boarding passes

3.5 hr delay for a 1 hr work flight. No information as to why the delay until 20 mins before boarding.

Organization and the adjusted times but the snacks could be of a bigger portion

Smaller plane. Food and bar service for free is amazing. Drinks were in glass not plastic cups.

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

Arm rests are too small and too close. No screens, movie selection was very limited and poor. Food is pretty much overpriced cheap convenience store food.

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.

Crew was good, helpful. Flight ran on time.would have liked to take airtransat home to MTL. But the price back from San Jose Costa Rica was MUCH more expensive than the flight from MTL to San Jose c.r.

i was not able to take my flight because the information i needed to book my dog correctly was not provided

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.

They never sent me a confirmation to say my flight time had changed so I cut my holiday short by 6 hours Had to pay over 50 American for my luggage to be checked on the way home and that’s more that it cost on the way there. Arbitrarily charging more for the same thing when the passenger has no options is shady The cabin was an icebox going there and back, if all the passengers have their gloves on and their hoods up that should be an obvious sign to turn up the heat

I was very nice to arrive earlier than scheduled. Very much appreciated. No issues with flight. All was good.

The on-board crew were professional and friendly and made the trip feel like we were taken care of well. The gate for the flight departure changed three times...not great but not terrible. Considering it was the day of the New Jalisco Cartel mayhem, we can't really complain.

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.

Despite travelling ultra basic for the first time due to such increased rates we both managed with one bag each. Even boarding last wasn’t SO bad.

There was no food but a singular cookie for a flight that was over 5hours??? Yeah not fun I was starving and again super cramped plane and you guys need to get planes with screens too, WiFi is nice but common we need more

I loved the fact it was on time and it was a smooth flight to my destination.

I like that we landed safely and that my dog was safe underneath as well. Outside of that, we were 45 mins late for a direct flight that is 1.5 hours long. And 2 of my 3 bags did not make the flight. Only my dog was onboard.

Service was okay except attendant over served alcohol to passenger and passenger got tipsy and made me uncomfortable

Food was not inspired but was satisfying. Same for infotainment selection. You’d think business class would come with complimentary WiFi. Crew was uniformly attentive and excellent.

Could not make the flight. No one would help us at all

Decent entertainment although my wife was not offered any ear buds so couldn’t enjoy. Real issue was the appalling food. Presentation was unacceptable with cheap hard to open packaged bread, plastic cheese again in hard to open shrink wrap, main course in small cardboard box again hard to open, wooden utensils which lack substance making the whole experience poor. Surprised I didn’t cover myself or neighbour as the food moved all over the place. Breakfast calzone was dry and unappealing with the staff basically throwing them around. Very disappointed

Better movie options. More diligence on the size and amount of bags people bring on board. Lady across aisle from me had a bucket style bag that would only go so far under the seat in front of her. She was not told once that the whole bag is supposed to be under the seat. Crew is very hardworking however.

I didn’t have any food but my Prosecco hit the spot. We left on time and the crew was friendly.

Screens not working; flight delay due to mechanical issues I tried to get information about food on flight — no information available

Flight was delayed twice which made our arrival extremely late (actually into next day). Not an easy travel. But when we requested assistance for boarding we were really impressed with how they helped us! Strongly praise their assistance.

Food abd wine was good and for the price this was a true bargain, relative to other transatlantic options. But it is still significantly behind my experiences with Air France long haul in both hard and soft product. But for the price air Canada to Europe from Vancouver is currently the best value of quality for the dollar cost.

I liked the fact that we arrived on time. What I did not like, I paid for a seat. Unfortunately a very large women sat beside me (required a belt extension). Her body spilled to my side. Not her fault but I had to lean to the left because her body was literally on my side of the seat. This caused a back ache. I was unable to sit straight the entire flight. There should be some form allowance (wider seat) for morbidly obese passengers. These seats are not designed for extremely obese people. I feel compassionate towards these obese passengers but I got off the plane with a substantial lower back ache. I myself have a degenerative disk disease and this did not help me

Air Canada doesn't have the jl most comfortable seats. It wasn't bad it just want what you expect for business class and there are adjusters for that but, they weren't that great.

It was out first time flying Air Canada and it was ok, comfort-wise. I hope airlines are able to get a quiet room installed for young children flying. Screaming and crying the whole time in business class is quite unfortunate. That was the only thing that really messed up the experience.

gave me complimentary food as the flight was not full and was attentive to my needs

Received an email a few hours before boarding that wifi and seatback entertainment would not be available. There was no explanation for this. We were served 1 x 20 gram granola bar as a snack (not even a full granola bar) which was really embarrassing. The crew was lovely (none of this was their fault) and the flight was successful, but the aircraft itself was falling apart on the inside. Overhead comfort control panels were worn and some were hanging out and non functional, This aircraft needs to be upgraded.

Didnt make it on flight. Flight was delayed. Then had to get rebooked for a flight that was 8 hours later. Guess who had to wait for 8 hours at the airport?

It was a nice and smooth trip. Gave a friendly environment throughout the journey.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports