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Find cheap flights from Winnipeg to Caribbean from C$ 308

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 10/6. 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
0 bags
Thu 16/5
Thu 23/5

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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$ 593
Montego Bay
Montego Bay2 stopsC$ 750
Nassau
Nassau2 stopsC$ 557
Bridgetown
Bridgetown1 stopC$ 753
Puerto Plata
Puerto Plata2 stopsC$ 769
Kingston
Kingston2 stopsC$ 819
Port of Spain
Port of Spain2 stopsC$ 1,248
Santo Domingo
Santo Domingo2 stopsC$ 732
Providenciales
Providenciales1 stopC$ 683
George Town
George Town2 stopsC$ 663
St. John's
St. John's2 stopsC$ 1,486

Good to know

Low season

June

High season

December

Cheapest flight

C$ 308
Best time to beat the crowds (13% less expensive on average)
Most popular time to fly (23% more expensive 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 14% 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 11123 reviews
7.9comfort
7.5food
8.6crew
8.0entertainment
8.2boarding
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

I have to say that Delta has improved their service radically since I flew with them last. I purposely have avoided flying with them for years owing to absolutely terrible service. This is no longer the case, I am glad to say.

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

For some reason there was a change in the cockpit which delayed us by an hour

flight changed by airline. then could not check imto mew flight because kiwi had messed up the reservation. still waiting to depart…

Crew was rude.didn’t even say hi or welcome to board

Menu selection was limited and not appropriate for a flight of this length

I like WJ but I don’t like traveling anymore

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

There was no lounge for passengers waiting before boarding the aircraft at F65, so passengers are just sitting on the floor or just spread everywhere the premises before boarding.

Great crew, friendly. Found the trip long just sitting with no onboard entertainment

Flight was delayed, jeopardizing the following connections. Food was terrible. Crew was great.

Headphones for the movies have too much bass and can't be adjusted. Almost impossible to hear. Great movie selections but can't really watch them because you can't hear them. Also the system is very slow.

This was the first AC flight in a long time that we experienced no delays or frustrations. The gate attendant was extremely polite and accommodating to my husband who has Parkinson’s disease which made boarding extremely stress free. Flight departed ON TIME and was a smooth ride. If only all my AC experiences could be like this.

I liked that I paid for the bulkhead. That was the only saving grace those seats suck. Why do they pack you in so tight pack you so tight

Great experience on this Air Canada flight. Everyone was polite and respectful, even the passengers are very polite.

My wife and I especially liked the fact that the Toronto agent went beyond expectation to allow my wife and I to sit together. There was no option for us when we booked our seats. Very thankful!

The flight attendant bumped into me repeatedly time and time again, throughout the entire flight, preventing me from getting any rest. He seemed unaware of his actions and I was very close to saying something, but I didn't because I don't believe he would have understood or altered his behaviour. It was very irritating

I didn’t like the fact that all the customs officers went to lunch so I was in line for 90 minutes due to where the staff directed me. We were told three very different reasons for why the plane was delayed. It was a crowded plane with difficult storage situations for the Carry On bags. The Air Canada airline staff were all very good and professional. I was so disappointed in my cheese and fruit box as the cheese had molded and the fruit wasn’t fresh so I couldn’t eat the majority of the food. This was the last meal I could find as the restaurants had closed when I got in to my destination. I think you could work on improving the food quality.

There was no entertainment at our seats. The flight was comfortable and we had leg room. The snack we had was really good.

Economy seats were surprisingly comfortable, and snacks not too bad. Checked luggage arrived at destination without problems. It was annoying to wait until last to board as lowest-tier seats but understand it’s difficult to gauge when loading a full plane At least checked carryon luggage seemed to come off first. Annoying to have to use app to order food/drink when wifi availability didn’t allow time for it. Advance communication would have helped Food on menu seemed highly processed and unpalatable, overpriced and over packaged. So maybe a good thing to have missed chance to order

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

7/5Tue
2 stopsWestJet
39h 15mYWG-NAS
11/5Sat
2 stopsWestJet
32h 53mNAS-YWG
C$ 557
23/5Thu
2 stopsWestJet
17h 34mYWG-PUJ
1/6Sat
2 stopsWestJet
27h 31mPUJ-YWG
C$ 593
14/5Tue
2 stopsAir Canada
28h 20mYWG-GCM
21/5Tue
2 stopsAir Canada
45h 24mGCM-YWG
C$ 663
14/5Tue
2 stopsAir Canada
52h 20mYWG-GCM
21/5Tue
2 stopsAir Canada
45h 24mGCM-YWG
C$ 694
26/4Fri
2 stopsDelta
27h 56mYWG-NAS
3/5Fri
2 stopsDelta
23h 59mNAS-YWG
C$ 695
15/5Wed
1 stop
11h 31mYWG-SJU
22/5Wed
2 stops
24h 45mSJU-YWG
C$ 703
25/5Sat
1 stopUnited Airlines
22h 37mYWG-GCM
29/5Wed
2 stopsUnited Airlines
23h 31mGCM-YWG
C$ 731
1/5Wed
2 stopsDelta
28h 25mYWG-SDQ
8/5Wed
2 stopsDelta
17h 36mSDQ-YWG
C$ 732
18/6Tue
2 stops
18h 06mYWG-POP
25/6Tue
1 stop
30h 05mPOP-YWG
C$ 769
25/5Sat
1 stopUnited Airlines
22h 37mYWG-GCM
29/5Wed
2 stopsUnited Airlines
20h 56mGCM-YWG
C$ 801

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Recent one-way flight deals

10/6Mon
2 stopsWestJet
45h 34mYWG-POP
C$ 308
7/7Sun
1 stop
22h 57mYWG-MBJ
C$ 315
7/7Sun
2 stopsAir Canada
19h 50mYWG-MBJ
C$ 370
10/6Mon
1 stop
20h 13mYWG-POP
C$ 413
21/4Sun
2 stopsDelta
16h 19mYWG-SDQ
C$ 453
10/6Mon
3 stops
41h 20mYWG-POP
C$ 506
7/7Sun
3 stops
21h 06mYWG-MBJ
C$ 615

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Last minute flights from Winnipeg to Caribbean

Last minute flight, train and bus deals

21/4Sun
multi-stopDelta
16h 19mYWG-SDQ
1/5Wed
multi-stopDelta
17h 47mSDQ-YWG
C$ 787
21/4Sun
multi-stopDelta
16h 19mYWG-SDQ
1/5Wed
multi-stopDelta
21h 48mSDQ-YWG
C$ 790
20/4Sat
multi-stopDelta
47h 55mYWG-SDQ
1/5Wed
multi-stopDelta
28h 38mSDQ-YWG
C$ 797
20/4Sat
multi-stopDelta
29h 25mYWG-SDQ
1/5Wed
multi-stopDelta
28h 38mSDQ-YWG
C$ 800
21/4Sun
multi-stopDelta
29h 25mYWG-SDQ
2/5Thu
multi-stopDelta
38h 12mSDQ-YWG
C$ 826
20/4Sat
multi-stop
21h 45mYWG-MBJ
27/4Sat
multi-stop
27h 28mMBJ-YWG
C$ 1,241
20/4Sat
multi-stopAir Transat
29h 10mYWG-MBJ
24/4Wed
multi-stopAir Transat
30h 50mMBJ-YWG
C$ 1,313
20/4Sat
multi-stop
27h 20mYWG-MBJ
24/4Wed
multi-stop
30h 50mMBJ-YWG
C$ 1,430
20/4Sat
multi-stopAir Canada
21h 00mYWG-MBJ
24/4Wed
multi-stopAir Canada
22h 50mMBJ-YWG
C$ 1,639
20/4Sat
multi-stopAir Canada
16h 40mYWG-MBJ
27/4Sat
multi-stopAir Canada
27h 04mMBJ-YWG
C$ 1,750

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Winnipeg - Caribbean Flights