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Find cheap flights from Winnipeg to Caribbean Islands from C$ 359

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 Islands departing on 5/9. 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
0 bags
Mon 24/6
Mon 1/7

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Best Caribbean Islands Flight Deals

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

Punta Cana
Punta Cana1 stopC$ 697
Montego Bay
Montego Bay1 stopC$ 599
Nassau
Nassau1 stopC$ 401
Kingston
Kingston1 stopC$ 1,288
Bridgetown
Bridgetown2 stopsC$ 785
Port of Spain
Port of Spain2 stopsC$ 1,175
George Town
George Town2 stopsC$ 569

Good to know

Low season

August

High season

January

Cheapest flight

C$ 359
Best time to beat the crowds but there is an average 14% increase in price.
Most popular time to fly and prices are also 5% lower on average.
Flight from Winnipeg to Punta Cana

FAQs - booking Caribbean Islands flights

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

    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 Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Caribbean Islands 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 Islands?

    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 Islands 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 Islands?

    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 Islands 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 5 airlines serving from Winnipeg to Caribbean Islands

 
Need help choosing which airline to fly with from Winnipeg to Caribbean Islands? 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 10550 reviews
8.6Crew
7.9Comfort
7.4Food
8.0Entertainment
8.2Boarding
Airline reviews

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

2.0 MediocreRick, May 2024HNL - LAX
Read more about Delta reviews

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

The boarding was horrible. You couldn’t hear the announcements at all. Probably because there is so much in the area for businesses. They need a louder PA system. Other than that it was a good Delta experience.

Delta did an awful job w logistics at DTW. Missed connection. We were there an hour early. SUCKED

It was a Red-Eye flight so was not comfortable enough to sleep, but seat was as expected. Crew was great and in-flight entertainment was excellent. Flight was smooth

The helpful attitude of the staff, and being a wheelchair passenger everyone was helpful and understanding. The trip was made comfortable by the upgraded seat which was given without my request, that was a great surprise. Thank you Delta.

Crew was great. Friendly, calm, interesting, happy to be there. That makes a huge difference. Plane was very quiet. Also quite empty so I had three seats to sleep across

Standard economy seats on Deltas 767 were better than Alaska premium seats on their 737 MAX9; more legroom, wider seats. Entertainment was great, no ipad or phone required. Could have included a meal service.

Everything was smooth and easy to fly. No complains and a lot of thanks!

I received the two differed meals: chicken and pasta. I asked and I received. I am anti-wasting food!

My wife and I had an uncomfortable experience with your WestJet ticket counter rep at the WestJet Priority Member ticket counter at YYC (Calgary) on May 15, 2024. I not knowing this individual’s exact name, however, in order to easily identify her, she was one (of only two at the time) ticket counter reps at your Priority members ticket counter check-in, upon our arrival around 12:15 p.m. She was a Caucasian woman with blonde hair, and wore spectacles, approximate age being probably somewhere in her 30’s or 40’s. Background: After arriving in to the West Jet terminal in Calgary (YYC), I asked a terminal employee where the West Jet check-in ticket counter was. He told me, “Column 16”. My wife and I continuing to walk through the terminal, we finally arrived at the Column 16 area, i.e. this woman’s ticket counter area, which we discovered later was the Priority Member ticket counter. However, I was simply going by the directions given to me by the previous employee, i.e. “Walk to column 16.” Standing in her line (my wife and I being the only people in her line at the time), I tried to get her attention, and I then gestured to her, motioning to her as if to ask her if I should then possibly leave the waiting line in order to then proceed to walk up to her ticket counter. She never really motioned me to come forward. I sort of had to figure this out on my own, as my wife and I then finally decided to walk forward to her station. From this point on, after I arrived at her ticket counter, never once did she ever look me in the eye. She was always looking at her computer screen, or down at the ground, as she and I occasionally exchanged conversation with one another in order for me to be able to acquire my boarding passes from her. Shortly after she began servicing us, she commented that her work section is for Priority members only. Fair enough. I did not realize this at the time. Wishing to be polite, I then mentioned to her that, if I should, I could then walk over to the regular West Jet check-in ticket counter in order to complete the check-in process. She remained quiet, never responding to this goodwill gesture of mine. She continued to work in order to print out my boarding passes, and then finally handed them to me, never at all the entire time looking at me. I told her, “Thank you.” Never once did she respond. My wife and I then walked away. Even my wife commented to me afterward that this woman absolutely never looked at us. I cannot say that this attendant was outright rude. However, she certainly was not at all warm, congenial, nor friendly. Additionally, … After getting on the plane, we then discovered that she had needlessly assigned us seats in the very last row of the plane, these being the seats adjacent to the restroom back wall, thus, unfortunately not at all reclinable. I think that the row number of this last row of seats was 30. [However, I am not sure.] How strangely awkward that we were assigned these uncomfortable row of seats when in fact the row immediately ahead of us, i.e. I think that was row 29, had two vacancies, which could have otherwise easily seated my wife and me. That is, my wife and I could have easily been assigned these more comfortable seats, which would be reclinable, and then row 30 could have otherwise had instead our two vacancies. After our flight departed, and the fasten seatbelt sign was turned off, my wife and I had hoped to “jump seats”, that is, to leave row 30 and instead sit in row 29 to utilize the reclinable seats. However, another couple apparently had the same idea as us. That is, these other two people, for whatever reason, decided to leave their previously assigned seats, and instead, seat themselves in row 29. Thus, my wife and I were stuck with these miserably cramped row 30 seats for the entire 3.5 hour flight. To reiterate, the WestJet rep we originally encountered, knowledgeable of the plane lay-out as it appeared on her computer screen, could have easily assigned us the more comfortable row 29 seats, instead of the non-reclinable row 30 seats.

Keep better track of bags. Not sure how they got lost. Also not sure why it took two weeks for us to get them back. Had to buy a bunch of necessities because they were packed.

It was very, very cold extremely uncomfortable almost unbearable I was sitting at the front of the cabin

Our trip was booked to be 2 hours after arriving in Calgary but it was changed until the next morning forcing us to stay overnight in Calgary with no compensation

Was the longest flight I have ever taken to Orlando. Not Westjet’s fault necessarily. There was a traffic issue in Orlando. We sat in the airplane for about 2 hrs before leaving Calgary on a 5 hour flight was just a little long to be stuck in the plane. Once we arrived in Orlando we were stuck in traffic on the ground for another 30min. I guess maybe the flight could be delayed so boarding would have been later so we wouldn’t have to have the discomfort of being on the plane so long.

Great Experience! Flight was ahead of schedule and very smooth! Wonderful flight

Too many oversized carryon baggage. If carrier reduced checked luggage fee this could be avoided. The staff were friendly and helpful, very professional.

Airport monitors did not give the gate for our flight returning Detroit to Vancouver Juice served from glass storage containers are a far more healthy alternative for people. And would also minimize the need for recycling plastic or aluminum containers

Nice smooth flight with pleasant stewards. Slept most of the flight, they could have slowly turned on the lights to make it more pleasant. Otherwise a good trip.

Great! No food was available during the flight due to the catering service strike but snacks were given throughout the flight which was nice.

Marked by flight delays on all segments of the trip. Food in first class cabin was mediocre and overhead cabin storage was not adequate. Overall, the premium charge for first class cabin was poor and over hyped. This will be our last flight with UA.

We enjoyed that we boarded and took off on time. We didn’t like that our connection flight was a twenty minute walk through the airport with only one hour in between flights.

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

Two flights,both poor. No entertainment. Cramped and uncomfortable seats, little space, the rest was OK. Staff were acceptable good.

The crew was doing their best on an old plane needing updating. Chairs that creaked and wouldn’t stay in position. My tray table was unusable as was on-board entertainment due the audio needing usb earphones (that were not provided). Prior to boarding in Toronto and despite being scheduled for a wheelchair and assistance, we were dropped off by clubcar without a wheelchair which I found myself by a gate. Due to no boarding gate assigned at that time we waited and when it was, it subsequently was moved from 64 to 95. No help could be found so I pushed my husband’s chair to that furthest gate in the airport at the highest speed possible for a 73 year old. And by that I mean I ran. It was a very stressful experience.

Wifi wasn't working on one of the UA flights after boarding.

Leg room was lacking. Legs crammed into seat in front.

T hey did a great job. Flight was on time .

the plane was old. the wifi didn’t work. the entertainment was boring and dated. the charging ports were impossible to find. i was mostly ignored by flight attendants that had no problem speaking to the man beside me. i got two drinks the entire time i was on the plane.

Crew was not very helpful. They forgot to serve me coffee and had to wait for a long time.It looked as if they were not very happy with what they were doing.

Prepaid for my seat selection over a month in advance only to be told when I arrive at the airport that the plane has changed and no pre-selected seats would be honored and refunds would not be issued immediately. Was forced to separate from my traveling companion Air Canada. Unsurprisingly was no assistance in this whatsoever. Plane. We got switched on to also has no entertainment options available

The flight was excellent the problem was that my luggage was damaged (zipper pulls ripped out) and it is difficult to contact the number to claim the damage while in another country and going back to the airport is not an option and no matter what I tried I got the same response to just call the number that is not possible for me to call in the first place. So very disappointed that I can’t claim such damage and that now I have to take part of my trip looking for a new luggage.

The flight itself was ok the staff was great and so was the inflight food. The biggest problem was that my luggage was damaged (the zipper pull from both sides of the zipper where completely ripped out) and I didn’t notice at the airport but at the hotel and when I tried to make a claim it was not possible for me because I have to either call (which is difficult because I’m in another country) I tried to call every nombre given to me but the one that I need I was never able to contact and going back to the airport was not an option. So it’s basically impossible to make a claim if you are abroad. Very disappointed that there are no other ways to claim a damaged bag and now I need to buy a new luggage while on my trip.

Too many notifications. Non of which were useful. 4 hours before traveling we discovered that we needed a transit visa. That's useful information. Air Canada should flag and keep flagging that up. Then the useless too much information had us go to Paris not Brussels. Chaos involving the customer. We will try never to use AC again.

The terminal this flight boarded from was so far away, poorly temperature controlled, and generally uncomfortable. The plane was small but the flight was short, so it wasn't so bad.

My flight was canceled and next one was 1 hour later. The gate was changed 3 times.

They changed my flight twice. The 2nd time they changed it they did so the day before the scheduled departure and replaced the lie flat seat in a 777 to a 737. I paid extra to be in the 777 only for them to change it. Then the departure was delayed twice. The connecting flight was also delayed.

We did not have seat assigned until almost the very end of boarding and my husband and I did not sit together I don’t know why even though we bought tickets 3 months in advance and checked in very early. We were not standby and we were treated as we had stand by tickets. I will never fly Air Canada again.

The last minute change of planes, then putting us right beside the bathroom was a poor choice.

Terrible 3-4-3 seat configuration, I thankfully was able to choose a seat at the back where it narrowed to 2-4-2 for some relief though seats were still narrow. Staff did not manage the boarding lines at all either, was total chaos.

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 Islands

Recent round-trip flight deals

15/10Tue
1 stopWestJet
18h 44mYWG-NAS
21/10Mon
1 stopWestJet
10h 57mNAS-YWG
C$ 401
15/10Tue
2 stopsWestJet
17h 59mYWG-NAS
21/10Mon
2 stopsWestJet
25h 29mNAS-YWG
C$ 419
9/7Tue
2 stopsDelta
28h 35mYWG-GCM
16/7Tue
2 stopsDelta
10h 38mGCM-YWG
C$ 569
21/7Sun
2 stopsDelta
29h 59mYWG-NAS
25/7Thu
2 stopsDelta
45h 12mNAS-YWG
C$ 595
25/7Thu
2 stops
13h 15mYWG-SJU
3/8Sat
1 stop
26h 46mSJU-YWG
C$ 664
25/7Thu
1 stop
30h 25mYWG-SJU
3/8Sat
1 stop
26h 46mSJU-YWG
C$ 670
20/6Thu
2 stopsUnited Airlines
22h 42mYWG-GCM
27/6Thu
2 stopsUnited Airlines
23h 41mGCM-YWG
C$ 696
20/6Thu
2 stopsUnited Airlines
22h 42mYWG-GCM
27/6Thu
2 stopsUnited Airlines
23h 41mGCM-YWG
C$ 716
9/7Tue
2 stopsAir Canada
17h 15mYWG-PUJ
16/7Tue
1 stopAir Canada
19h 52mPUJ-YWG
C$ 718
9/7Tue
2 stopsAir Canada
19h 00mYWG-PUJ
16/7Tue
2 stopsAir Canada
19h 47mPUJ-YWG
C$ 747

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Recent one-way flight deals

5/9Thu
2 stopsWestJet
29h 58mYWG-PUJ
C$ 359
24/6Mon
2 stops
27h 41mYWG-MBJ
C$ 427
24/6Mon
1 stop
29h 26mYWG-MBJ
C$ 441
24/6Mon
3 stops
27h 41mYWG-MBJ
C$ 471

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Last minute flights from Winnipeg to Caribbean Islands

Last minute flight, train and bus deals

30/5Thu
multi-stopAir Canada
19h 45mYWG-PUJ
5/6Wed
multi-stopAir Canada
21h 59mPUJ-YWG
C$ 655
30/5Thu
multi-stopAir Canada
19h 45mYWG-PUJ
5/6Wed
multi-stopAir Canada
19h 50mPUJ-YWG
C$ 662
30/5Thu
multi-stopAir Canada
19h 00mYWG-PUJ
5/6Wed
multi-stopAir Canada
19h 50mPUJ-YWG
C$ 670

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