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Find cheap flights from Winnipeg to Caribbean from C$ 296

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 24/10. 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
Fri 14/6
Fri 21/6

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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 Cana2 stopsC$ 546
Montego Bay
Montego Bay1 stopC$ 647
Oranjestad
Oranjestad2 stopsC$ 707
Nassau
Nassau1 stopC$ 533
Bridgetown
Bridgetown2 stopsC$ 584
Kingston
Kingston2 stopsC$ 752
Port of Spain
Port of Spain2 stopsC$ 1,208
Santo Domingo
Santo Domingo2 stopsC$ 584
Providenciales
Providenciales1 stopC$ 572
George Town
George Town2 stopsC$ 657

Good to know

Low season

June

High season

January

Cheapest flight

C$ 296
Best time to beat the crowds (3% less expensive on average)
Most popular time to fly and prices are also 6% lower on average.
Flight from Winnipeg to Puerto Plata

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 2% cheaper 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 5 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 10691 reviews
7.9Comfort
8.6Crew
8.2Boarding
7.4Food
8.0Entertainment
Airline reviews

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.

6.0 GoodEric, May 2024CUN - BOS
Read more about Delta reviews

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!

I guess they don’t serve drinks on planes anymore

Gate agent was a terrible person out to make people miserable

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.

Boarding, staff and flight great. A bit disappointed with no in flight online entertainment but I'll live. Landing was a bit of a jolt (more than usual) but hey everything else was smooth. LoL

I’ve been delayed for two days and I’m still stuck in Honolulu tired spending money

1.5 hours late departing YVR for a 14-minute flight. Packed waiting area. Full plane. Families with tired, screaming kids. 40-minute wait for baggage at YYJ. For a Dash-8. Obviously there was some kind of breakdown but there was no communication from anyone. Most of this was not WestJet's fault but it was an unpleasant night overall. I fell asleep in a chair waiting for the luggage carousel to start.

Nothing to like about flying in the Dash 8s. With very small seats, little legroom, and a very noisy plane, nothing about such trips is enjoyable.

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.

The flight I was connecting with waited for me even though my 1st flight was late. I really appreciated that.

Air Canada cancelled my prepaid/prebooked seat selection and changed my seats without any options.

Pretty good service and US Migratory officers providing services in Canada was awesome, because the arrival was quick and smooth

It was late leaving but made up time in the air.

Rude Customer Service at checkin, 90 minute limit in flight check in is too strict. I was in line for 30 minutes because of slow/insufficient workers. Somewhere I got to the the counter of course the employee warned me about the 90 minutes. People were cutting the lines. No one did anything.

Squeeze like sardines. ANA has much better leg room. The food on air canada was disgusting. Worse that left over microwave dinner. Like you heated up microwave dinner then saved it overnight, then microwaved it again and added nasty garnish to try to elevate but instead made it as edible as cat food.

Rouge needs to offer seats with better pitch in economy. Many sick people on a full flight.

Overall, I would have to say my experience with Air Canada was mediocre their DC tens. Need to be updated not comfortable at all. Only one out of my four flights was decent. The staffing was very nice. Going through customs in Montreal was quick and easy. Air Canada has room for improvement with their facilities.

The first flight Seattle to Toronto was very poor. My seat was changed. The aircraft was changed. They were having issues with the meals. My second flight from Toronto to Quebec was fine. Short flight still no entertainment. My third flight Quebec to Montreal was very short seats are very uncomfortable, too old and way worn out almost like sitting on a bench. My last flight Montreal to Seattle was fine. Finally, they had some entertainment. Proper food was offered as advertised flight staff was accommodating and friendly, but once again, the aircraft seats are hard like benches.

Crew was terrific. In flight entertainment system is very slow and the touch screen can be not sensitive enough or too sensitive. It was such a pain to pause a movie in case when I unpaused it accidentally thought I presses stop. This happened 3 times. I gave up and went back to my phone for entertainment.

Everything was great. I really like how they had their safety film set up showing you the beauty of the country.

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

16/6Sun
1 stopWestJet
28h 22mYWG-NAS
20/6Thu
2 stopsWestJet
31h 06mNAS-YWG
C$ 533
30/5Thu
2 stopsAir Canada
24h 50mYWG-PUJ
5/6Wed
1 stopAir Canada
21h 59mPUJ-YWG
C$ 546
30/5Thu
2 stopsAir Canada
24h 50mYWG-PUJ
5/6Wed
2 stopsAir Canada
19h 50mPUJ-YWG
C$ 554
31/8Sat
1 stopWestJet
23h 48mYWG-NAS
7/9Sat
1 stopWestJet
13h 47mNAS-YWG
C$ 560
27/10Sun
2 stopsDelta
38h 45mYWG-SDQ
31/10Thu
2 stopsDelta
29h 41mSDQ-YWG
C$ 584
22/9Sun
2 stopsDelta
28h 35mYWG-GCM
26/9Thu
2 stopsDelta
34h 31mGCM-YWG
C$ 657
1/6Sat
2 stopsUnited Airlines
22h 56mYWG-PLS
4/6Tue
2 stopsUnited Airlines
25h 06mPLS-YWG
C$ 717
16/6Sun
1 stopAir Transat
10h 00mYWG-MBJ
20/6Thu
1 stopAir Transat
28h 55mMBJ-YWG
C$ 873
29/5Wed
1 stopUnited Airlines
24h 10mYWG-SJU
5/6Wed
1 stopUnited Airlines
24h 31mSJU-YWG
C$ 895
27/5Mon
1 stopAir Transat
17h 40mYWG-PUJ
30/5Thu
1 stopAir Transat
21h 45mPUJ-YWG
C$ 1,142

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Recent one-way flight deals

24/10Thu
2 stopsWestJet
47h 33mYWG-POP
C$ 296
8/6Sat
3 stops
39h 03mYWG-KIN
C$ 384
19/7Fri
1 stopAir Canada
17h 20mYWG-MBJ
C$ 416
8/6Sat
2 stopsDelta
37h 15mYWG-KIN
C$ 425
24/9Tue
2 stopsAeromexico
40h 01mYWG-SDQ
C$ 436
19/7Fri
2 stopsWestJet
17h 37mYWG-MBJ
C$ 465
8/6Sat
1 stop
24h 00mYWG-KIN
C$ 470
24/9Tue
3 stops
37h 14mYWG-SDQ
C$ 488
23/10Wed
1 stop
9h 53mYWG-POP
C$ 557
24/10Thu
1 stopAir Transat
28h 45mYWG-POP
C$ 569

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Last minute flights from Winnipeg to Caribbean

Last minute flight, train and bus deals

17/5Fri
multi-stopUnited Airlines
33h 20mYWG-AUA
24/5Fri
multi-stopUnited Airlines
24h 09mAUA-YWG
C$ 808
17/5Fri
multi-stop
22h 23mYWG-AUA
24/5Fri
multi-stop
46h 29mAUA-YWG
C$ 1,064
17/5Fri
multi-stop
40h 10mYWG-AUA
24/5Fri
multi-stop
22h 44mAUA-YWG
C$ 1,578
17/5Fri
multi-stop
23h 15mYWG-AUA
24/5Fri
multi-stop
24h 19mAUA-YWG
C$ 1,699

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Winnipeg - Caribbean Flights