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Find cheap flights from Winnipeg to Caribbean from C$ 266

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 14/5. 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 7/6
Fri 14/6

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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 Cana1 stopC$ 518
Montego Bay
Montego Bay1 stopC$ 660
Oranjestad
Oranjestad2 stopsC$ 745
Nassau
Nassau1 stopC$ 530
Bridgetown
Bridgetown1 stopC$ 756
Kingston
Kingston2 stopsC$ 755
Puerto Plata
Puerto Plata1 stopC$ 794
Port of Spain
Port of Spain3 stopsC$ 1,264
Simpson Bay
Simpson Bay2 stopsC$ 537
Santo Domingo
Santo Domingo2 stopsC$ 586
Providenciales
Providenciales2 stopsC$ 719
George Town
George Town2 stopsC$ 661

Good to know

Low season

June

High season

January

Cheapest flight

C$ 266
Best time to beat the crowds (6% less expensive on average)
Most popular time to fly and prices are also 6% 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 3% 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 10789 reviews
8.6Crew
7.9Comfort
8.0Entertainment
8.2Boarding
7.4Food
Airline reviews

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

2.0 MediocreGregg, Mar. 2024PWM - DTW
Read more about Delta reviews

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

long flights are never truly comfortable but the airline did their best. crew was great and the flight was safe.

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.

I wish that seats closer to the front of the plan were available, but when I booked the flight the seats were VERY expensive so I did not book seats at that time. The day before flying only seats at the back of the plane were available. It takes so long to board the plane and empty the plane on arrival due to SO many roller bags.

Difficult to say. Over crowded but that is the fault of the airplane not WestJet

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.

The seat is too hard and my back and bottom are having servers pain

Crew was very respectful and ready to serve. Much better than before.

This time my experience was superior! Much better and improved from after the COVID-19. I hope they maintain the same. Earlier, service (specially crew attitude) was awful and sometime rude, but this time, crew was very welcoming, respectful and ready to serve. I will definitely repeat :-)

Inexperienced crew. Food was so so. They lost my luggage on a direct flight. Was flying business so my luggage was priority. Not impressed.

I liked the early check in. Flight was a bit bumpy due yo weather. Overall, everything went well.

I couldn't rate food or entertainment as neither were a factor in my short flight. I was impressed with with respect of time and schedule. Also, this was an incredibly smooth flight from terminal to terminal. My only minor complaint was being woken up for refreshment service. This was the end of a very long day, and I was happy to miss a juice box and pretzels for a little rest.

It was awful. For a 37 minute flight time,we had 1:30 hours delay. If someone had a connection flight he or she couldn’t reach for sure. The only positive point was online check in.

Limited snack options cause the snack vendor was on strike

Not full, so lots of room, which is really the only thing that can make flying economy more comfortable. Direct to Toronto is great! I didn't eat or use the entertainment.

The experience was generally above average. The only downside was the absence of WiFi during my flight from Vancouver to San Francisco.

It was overall above average experience. If there is only one thing i could complain about was the lack of wifi availability on my flight from Vancouver to San Francisco

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

27/5Mon
1 stop
27h 41mYWG-SJU
4/6Tue
1 stop
26h 53mSJU-YWG
C$ 507
27/5Mon
1 stop
27h 41mYWG-SJU
4/6Tue
1 stop
26h 53mSJU-YWG
C$ 508
6/6Thu
1 stopWestJet
22h 07mYWG-PUJ
11/6Tue
1 stopWestJet
10h 12mPUJ-YWG
C$ 518
12/8Mon
1 stopWestJet
16h 52mYWG-NAS
22/8Thu
1 stopWestJet
13h 02mNAS-YWG
C$ 530
8/6Sat
2 stopsAir Canada
43h 00mYWG-PUJ
13/6Thu
1 stopAir Canada
21h 59mPUJ-YWG
C$ 544
1/6Sat
1 stopAir Canada
17h 35mYWG-NAS
2/7Tue
1 stopAir Canada
22h 17mNAS-YWG
C$ 559
27/10Sun
2 stopsDelta
22h 27mYWG-SDQ
31/10Thu
2 stopsDelta
33h 25mSDQ-YWG
C$ 586
27/10Sun
2 stopsDelta
28h 02mYWG-SDQ
31/10Thu
2 stopsDelta
29h 41mSDQ-YWG
C$ 588
1/6Sat
2 stopsUnited Airlines
22h 48mYWG-PLS
4/6Tue
2 stopsUnited Airlines
25h 06mPLS-YWG
C$ 719
1/6Sat
2 stopsUnited Airlines
22h 48mYWG-PLS
4/6Tue
2 stopsUnited Airlines
25h 06mPLS-YWG
C$ 740

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Recent one-way flight deals

14/5Tue
2 stopsDelta
21h 54mYWG-NAS
C$ 266
4/8Sun
1 stop
22h 57mYWG-MBJ
C$ 297
20/5Mon
1 stop
22h 57mYWG-MBJ
C$ 300
20/5Mon
2 stops
16h 38mYWG-MBJ
C$ 307
18/10Fri
1 stopWestJet
26h 17mYWG-MBJ
C$ 366
14/5Tue
3 stops
21h 00mYWG-NAS
C$ 370
4/8Sun
2 stopsWestJet
43h 27mYWG-MBJ
C$ 386
14/8Wed
2 stopsAir Canada
19h 00mYWG-PUJ
C$ 400
15/5Wed
2 stops
27h 41mYWG-MBJ
C$ 401
14/8Wed
1 stopAir Canada
24h 05mYWG-PUJ
C$ 466

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Last minute flights from Winnipeg to Caribbean

Last minute flight, train and bus deals

11/5Sat
multi-stop
28h 54mYWG-PUJ
18/5Sat
multi-stop
24h 28mPUJ-YWG
C$ 874
12/5Sun
multi-stopDelta
23h 43mYWG-SDQ
18/5Sat
multi-stopDelta
24h 51mSDQ-YWG
C$ 961
12/5Sun
multi-stopAir Canada
19h 45mYWG-PUJ
18/5Sat
multi-stopAir Canada
19h 55mPUJ-YWG
C$ 987
13/5Mon
multi-stop
21h 41mYWG-SDQ
19/5Sun
multi-stop
33h 58mSDQ-YWG
C$ 1,002
11/5Sat
multi-stopAir Canada
24h 05mYWG-PUJ
18/5Sat
multi-stopAir Canada
19h 55mPUJ-YWG
C$ 1,009
13/5Mon
multi-stop
33h 28mYWG-SDQ
19/5Sun
multi-stop
33h 58mSDQ-YWG
C$ 1,015
11/5Sat
multi-stopWestJet
31h 54mYWG-PUJ
18/5Sat
multi-stopWestJet
34h 03mPUJ-YWG
C$ 1,152
12/5Sun
multi-stopUnited Airlines
30h 09mYWG-PUJ
19/5Sun
multi-stopUnited Airlines
22h 35mPUJ-YWG
C$ 1,445
12/5Sun
multi-stopAir Transat
30h 25mYWG-PUJ
19/5Sun
multi-stopAir Transat
21h 45mPUJ-YWG
C$ 2,112
11/5Sat
multi-stopAir Transat
30h 25mYWG-PUJ
19/5Sun
multi-stopAir Transat
21h 45mPUJ-YWG
C$ 2,132

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Winnipeg - Caribbean Flights