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C$ 259 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 30/11. 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
0 bags

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Best Caribbean Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Punta Cana
Punta Cana1 stopC$ 570
Montego Bay
Montego Bay2 stopsC$ 602
Oranjestad
Oranjestad1 stopC$ 760
Nassau
Nassau2 stopsC$ 657
Kingston
Kingston2 stopsC$ 818
Bridgetown
Bridgetown1 stopC$ 625
Puerto Plata
Puerto Plata2 stopsC$ 591
Simpson Bay
Simpson Bay2 stopsC$ 689
Port of Spain
Port of Spain2 stopsC$ 1,543
Providenciales
Providenciales1 stopC$ 704
St. John's
St. John's1 stopC$ 1,255
Kingstown
Kingstown2 stopsC$ 2,514

Good to know

Low season

June

High season

January

Cheapest flight

C$ 259
Best time to beat the crowds (6% less expensive on average)
Most popular time to fly and prices are also 2% lower 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 to Caribbean from Winnipeg is likely to change within 7 days, so travelers 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 to Caribbean with an airline and back to Winnipeg 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 to Caribbean from Winnipeg up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Caribbean

  • Morning departure is around 16% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 4 airlines serving 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
DeltaOverall score based on 8835 reviews
7.9Comfort
7.9Entertainment
7.3Food
8.5Crew
8.2Boarding
Airline reviews

Very dissatisfied with the fact that I had upgraded to first class for the second part of my trip only to find out that the lounge was still not available to me, as well as not having any food or drink service on the flight due to weather, so I lost out more than what I paid for.

8.0 ExcellentEric, Oct 2024YYZ - SLC
Read more Delta reviews

Very dissatisfied with the fact that I had upgraded to first class for the second part of my trip only to find out that the lounge was still not available to me, as well as not having any food or drink service on the flight due to weather, so I lost out more than what I paid for.

Delta cancelled my flight less than 24 hours before departure and provided no alternative options. Left me to fend for myself basically. Scrambled to book flight on another airline and paid a fortune to do so last minute.. Can’t wait to see how Delta deals with my refund.

Overall Delta was amazing from automatically booking us on the next flight once we missed our connection due to a delay to the constant communication throughout the entire process. We will continue to fly Delta going forward more and pay a little more if needed.

Unfortunately I was stuck next to someone who should have purchased 2 seats instead of taking up their space and mine. I couldn’t move the entire 3+ hour flight. Very uncomfortable flight.

This was a code share Latam Airlines flight - everything very good except there was no seatback entertainment

Overall it was not that bad! The delay on the second leg to Indianapolis , was really unexpected!!

7 hour delay for mechanical reasons Handled badly by crew and delta personnel

It was very good. Our flight was delayed and we as a result missed our connecting flight but rescheduled to the next day. The Need Help staff was so great and offered us compensation that was beyond satisfactory.

the fight attendants were great and i appreciated that they had season 1 of The Wire from HBO as a viewing option

5 hour delay. They blamed the weather but it was the computer issues they had been dealing with for days.

Excellent and a surprise as I had never heard of it before.

Agent checking me in was great. Plane was nice. Problem was with the handling of my fragile check in. They damaged my steel drum, waiting to hear back from them to see if they will take any responsibility. Think twice about travelling with something fragile, they don't seem to treat it any different than normal luggage

The flight was on time and shorter time arrival than planned. I was an ultra basic passenger and understood one personal item on the plane. The announcements of one personal item and zone 9 boarding certainly felt like we were separated from the rest. Actually zone 9 passengers should be boarded second; we are not blocking aisles and can be seated much faster and deboarded faster too.

Was a short flight, not good or bad. Extremely cramped and I'm only 6feet 1inches. 295lbs.

I had a problem checking in as I didn’t have the correct code. I had to phone BudgetAir.com. They charged me an additional 174US for some tax or something in order to provide me with my booking number. I will never use a third party seller again. Absolutely criminal activity. But I did get to where I wanted to go

Still sitting in a hotel when I'm due for work

My trip was two parts flying from Canada to ATL then to PNS I had confirmed seats with tickets at boarding in Canada and bags tagged for said flight. Got to ATL got help to plane before boarding ended and was told at the gate that I had no seats on this flight even though I had tickets that said so I was told by a supervisor with Delta that I was booked on flight 5 hours later not the one on my ticket had to sit in ATL not knowing if my bags were on flight I was booked on or the one I was told at the gate for 5 hours later or even if I would have seat on that flight as seats were to be assigned at gate. Will never recommend West Jet product and am not sure about Delta any longer and had never booked thru Kayak for flight before and will probably never again and will be sharing my experience with who ever will listen to me about it to warn them to avoid the problems I went thru.

Delays happen but communication and care were very low on what ended up being a long day.

they forgot to load our luggage onto the plane and we were without it for half of our trip to Paris. Didn’t seem to have much interest in getting it to us expeditiously.

Terrible experience at the gate. Charged for carry on luggage despite them meeting the requirements for sizing.

Had to buy headphones. Which is sad. I did not so I listened to podcasts and slept. Free beer is excellent a d those pretzels are great too. Overall I feel Air Canada slightly exceeds Westjet for overall experience. But still more can be done. Like allowing guests to view a movie for free.

There was a terrible delay upon arrival in Barcelona. The plane had to park a great distance from the terminal, and only one bus was available to make the ~15 minutes each way trip, meaning it was ~ 45 minutes after we landed that I finally entered the terminal.

On the way to Vancouver from Toronto I was in AC 111. What an amazing aircraft. I was in economy but there was plenty of leg room and it was comfortable and also the entertainment system was good. On the way back from Vancouver to Toronto I was in Ac 120. It was not as good as the one before but it was okay. The entertainment unit was small and the seats were pretty tight but not the worst I have been in. Over all both flights were good but ac 111 was far better than ac 120. But I had a good experience. No delays, bags came on time. In fact both the times it was on time departure and early arrival which I appreciate

Crew were friendly and efficient. Love the hot towel service!

Our checked in luggage was not put on same plane as us in the trip to Quebec and on our return 4 days later to Toronto. At Toronto airport we were told it was at the airport and it would be 10 mins. This was not true as the i-tag in my luggage showed initially it was still in Quebec. We were made to wait 1 1/2 hours to get our luggage which it seems evident to me came on a later flight. This was despite being at airport in Quebec 2 hours before flight was due to fly out so our luggage was there very early. We were both wheelchair assisted so the wait in Toronto was especially difficult . As well as luggage issues our flight from Quebec to Toronto was cancelled and a new flight sent in the evening. We had to check out of our hotel and sit in a cafe for 3 hours until we came to airport still two hours earlier than required. This was by far the worst service I have used throughout my trips around the world

I book my air canada flight and i am an aeroplan card holder however I was required to pay for my first check-in bag. Terrible experience

Cold frozen fruit for breakfast was unexpected and a waste in my opinion. How about a warm bun would have been better. Otherwise great on time flight.

Everything was good on our two flights with Air Canada. Departed on time and smooth in the air. The short transfer window from domestic to international, although a little tight considering the distance one has to navigate is doable but some people freaked out tried to push off the domestic saying they would miss the international flight. They as disappointed t get a frozen breakfast something warm would have been much nicer. Glad for the vegan meals we ordered but a cold breakfast was unpleasant.

I used to enjoy the travelling experience, but no more. We pay more and get much less. No air travel for me on the near future.

On time, boarding was quick. Leg room plenty, entertainment choice great. Friendly hosts too

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).

Due to the onboard check on system malfunction, we were getting conflicting messages about the flight status. Found it very interesting that kayak gave us updates before the Sunwing app or representatives did.

Was not allowed to board because my KAYAK purchased ticket was declined / invalidated. DO NOT USE KAYAK.

Book cheap flights from Winnipeg to Caribbean

Recent round-trip flight deals

2/2dom
2 stopsAir Canada
20h 27mYWG-SJU
14/2sex
2 stopsAir Canada
16h 23mSJU-YWG
C$ 498
27/11qua
2 stops
40h 46mYWG-SJU
4/12qua
1 stop
10h 50mSJU-YWG
C$ 501
8/1qua
2 stopsWestJet
21h 20mYWG-POP
22/1qua
2 stopsWestJet
24h 55mPOP-YWG
C$ 591
8/1qua
1 stopWestJet
17h 45mYWG-POP
22/1qua
2 stopsWestJet
21h 28mPOP-YWG
C$ 593
13/1seg
2 stopsUnited Airlines
17h 24mYWG-PUJ
2/2dom
2 stopsUnited Airlines
46h 02mPUJ-YWG
C$ 779
13/11qua
2 stopsUnited Airlines
46h 18mYWG-NAS
17/11dom
2 stopsUnited Airlines
47h 52mNAS-YWG
C$ 846
22/1qua
directSunwing Airlines
5h 45mYWG-PUJ
29/1qua
directSunwing Airlines
6h 25mPUJ-YWG
C$ 1,287
12/2qua
directSunwing Airlines
5h 45mYWG-PUJ
19/2qua
directSunwing Airlines
6h 25mPUJ-YWG
C$ 1,298
10/1sex
2 stopsDelta
25h 00mYWG-POP
24/1sex
2 stopsDelta
21h 02mPOP-YWG
C$ 1,695
10/1sex
1 stopDelta
29h 50mYWG-POP
24/1sex
2 stopsDelta
21h 02mPOP-YWG
C$ 1,749

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Recent one-way flight deals

30/11sáb
2 stopsWestJet
41h 32mYWG-NAS
C$ 259
30/11sáb
1 stopAir Canada
19h 05mYWG-NAS
C$ 288
11/12qua
1 stop
16h 50mYWG-PUJ
C$ 288
30/11sáb
1 stop
27h 30mYWG-PUJ
C$ 310
5/11ter
2 stops
21h 17mYWG-KIN
C$ 330
11/12qua
2 stopsWestJet
29h 09mYWG-PUJ
C$ 353
30/11sáb
2 stopsAir Canada
14h 15mYWG-PUJ
C$ 360
15/12dom
3 stops
26h 10mYWG-PUJ
C$ 370
5/11ter
1 stopFlair Airlines
17h 15mYWG-KIN
C$ 373
28/12sáb
1 stopFlair Airlines
17h 15mYWG-PUJ
C$ 742

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Last minute flights from Winnipeg to Caribbean

Last minute flight, train and bus deals

5/11ter
multi-stopAir Canada
39h 00mYWG-PUJ
12/11ter
multi-stopAir Canada
25h 07mPUJ-YWG
C$ 607
5/11ter
multi-stopAir Canada
14h 00mYWG-PUJ
12/11ter
multi-stopAir Canada
25h 07mPUJ-YWG
C$ 682
5/11ter
multi-stopAir Canada
13h 05mYWG-PUJ
12/11ter
multi-stopAir Canada
23h 18mPUJ-YWG
C$ 704
5/11ter
multi-stop
21h 17mYWG-KIN
12/11ter
multi-stop
27h 55mKIN-YWG
C$ 739
1/11sex
multi-stopWestJet
27h 17mYWG-SJU
8/11sex
multi-stopWestJet
9h 10mSJU-YWG
C$ 757
5/11ter
multi-stop
17h 30mYWG-KIN
12/11ter
multi-stop
27h 55mKIN-YWG
C$ 794
1/11sex
multi-stopWestJet
27h 17mYWG-SJU
8/11sex
multi-stopWestJet
32h 59mSJU-YWG
C$ 826
5/11ter
multi-stopAir Canada
53h 50mYWG-KIN
12/11ter
multi-stopAir Canada
30h 13mKIN-YWG
C$ 828
1/11sex
multi-stopUnited Airlines
22h 06mYWG-SJU
8/11sex
multi-stopUnited Airlines
21h 37mSJU-YWG
C$ 1,178
1/11sex
multi-stopUnited Airlines
18h 17mYWG-SJU
7/11qui
multi-stopUnited Airlines
13h 22mSJU-YWG
C$ 1,363

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Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports