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C$ 271 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 8/11. 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
Sat 24/8
Sat 31/8

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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$ 623
Montego Bay
Montego BaydirectC$ 427
Nassau
Nassau2 stopsC$ 760
Kingston
Kingston1 stopC$ 661
Bridgetown
Bridgetown2 stopsC$ 634
Puerto Plata
Puerto Plata2 stopsC$ 983
Santo Domingo
Santo Domingo2 stopsC$ 593
Willemstad
Willemstad2 stopsC$ 1,067
Providenciales
Providenciales2 stopsC$ 677
George Town
George Town2 stopsC$ 708

Good to know

Low season

June

High season

January

Cheapest flight

C$ 271
Best time to beat the crowds (7% less expensive on average)
Most popular time to fly and prices are also 3% lower on average.
Flight from Winnipeg to Montego Bay

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 27% 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 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 9630 reviews
8.6Crew
7.4Food
8.0Entertainment
8.2Boarding
7.9Comfort
Airline reviews

Excellent. No issue and it was on time and arrived early, the best!

10.0 ExcellentAnonymous, Jul. 2024YYZ - ATL
Read more about Delta reviews

Excellent. No issue and it was on time and arrived early, the best!

The flight was oversold and they kept on announcing they were looking for a volunteer to give away their seat, but the announcement has to be louder and clear @ gate 88 and also must precise. Additionally, the departure time kept on changing. But overall it was fine since it was a short flight.

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

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.

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

Had a broken tray in business class. Crew just shrugged it off.

I didn’t not like that I could not select my seat and ended up with the worse seat.

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

I was never able to depart because of an IT outage, I could not get help through Delta’s website, app, or on the concourse. I eventually (after more than three hours in the airport) got rebooked with another airline the following day and Delta didn’t offer vouchers or any assistance with finding a hotel or getting to the hotel. I need to file a claim. Just an awful experience.

Delayed by 4 hours. Missed connection back to UK. Ended up 24 hours late with an overnight delay. Westjet offered hotel accommodation but when we got to the hotel they said it was fully booked. Terrible experience

Over an hour late. Lousy flight attendant who was just going through the motions in every aspect of her job. The Dash 8 aircraft is super basic (no entertainment system, small seats, limited storage). Carry on luggage doesn’t fit in overhead bins.

I always worry about flying budget airlines but I was impressed by Westjet. The checkin agent was terrific. Seated my husband & me together w/o us asking. TSA checkin was smooth & easy. Plane was clean & comfortable. Drink & snack was unexpected. I will fly with them again.

Slow boarding process, tickets downgraded to Ultra Basic with no carry-on luggage, not enough space in overhead compartments

All was good except that the option to purchase wifi for texting throughout the flight didn't work. My partner and I both tried via the app, Chrome and Safari, we tried all payment options. Nothing worked. He was able to get ok blonde with he full coverage option, but it's nice to what we wanted or needed.

WiFi was not working. Zero entertainment. Did not receive a discount etc to make up for this.

Calgary WJET supervisor was the most professional, and diligent official who I have experienced personally to resolve our flight issues.

The agent denied our cat from boarding just because the carrier has to be slightly shorter to go under the seat. It is a soft sided carrier and WestJet had mentioned that soft sided carriers can be squished to go under the seat. So we had to transport the cat via road to YYC. In Yyc the connection flight terminal supervisor of WestJet was surprised about the edmonton agent decision as she said the size of bag should be 11in indeed so that cat can move freely even if the bag has to be slightly adjusted to go under the seat. Avoid WestJet - they are a dying organization with incompetent staff!!!... No guarantee the flight is maintained since the crew went on strike. Very unsafe and unpredictable business, a cancerous corn in the hands of Canadian business !!

Horrible. I couldn’t add bags or pick seats through the app or website. I called and they told me to wait until checkin. They changed my itinerary to include an overnight layover. Still couldn’t add bags. When it came time to check in, I couldn’t check in or add bags and the error message in the app said “don’t call us, just do it at the airport “. Woke up the day of the flight and they changed the itinerary again to not include any WestJet flights but didn’t give me the new reservation code so it took me a long time to figure out how to check In on the other airline. And I wasted $200 on a hotel in a city I never went to. And our seats in the new flight weren’t together even though I was traveling with my kid and they could have paired her with either adult. Instead they put the 2 adults together and the kid by herself

Everything got delayed we were supposed to land at 1pm and landes at 8-9 pm … was horrible

Calgary desperately needs a star alliance lounge in the transborder area for United.

Brutal as can be … delayed by 24 hours then delayed and hour on the tarmac then delayed three hours in Chicago, screaming child behind me kicking the seat for the better part of 10 hours… couldn’t be worse

My flight was delayed by a whole day, so I lost a day of my vacation.

The check-in and passport submission was complicated and repetitive, due to the poor communication between Air Canada and United. There should have been a single set of instructions and a single questionnaire that provided the data for both airlines.

-The cabin was ice cold - When we arrived in Houston there was no gate available -We had to wait 90 minutes for our luggage to arrive.. In the future I will avoid flying with Air Canada at at costs

How would you rate my experience when I was stuck in YOW without being offered a cup of water by the airline?

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

Flight was delayed and still they didn't manage to transfer my bag to the flight. The onboard staff was quick to show desperation and frustration with the not-so-easy passengers.

Do not book a flight thru Toronto Pearson to the US with less than 2 hrs between connecting flights. With 90 minutes (which I had) if your first plane is 25-30 minutes late by the time you debark, walk to go through security again, go through US customs and find your new gate with at least 15 minutes before your departure. If you stop to go the the bathroom you will be lucky to catch your flight, in my case I wasn’t lucky. The airline should not offer flights that do not allow you time to get to your second plane, bad customer service!

It was swiss air flight and they were very helpful and kind

My flight was delayed in Calgary and I missed my connecting flight to Cincinnati. I was rebooked on a flight the following day. I did not receive a food or lodging voucher.

I didn't actually get to take this flight. It was canceled and the automated system rerouted my party of four (including a minor and a person in a wheelchair) to three different airports. Since we had a three hour drive from Newark this was clearly unacceptable. For all of us to end up in Newark would have required waiting at least one day, probably longer.

Constant delays worked out in our favor but definitely extended our travel day

Flight was excellent in all aspects, - comfort , food, drinks, service, entertainment. Inspite of the computer glitch, the flight was on schedule and flawlessly. Thank you, air Canada.

There was no entertainment on board and wi-fi did not work for me. Food consisted of beverage and pretzels. Flight was over 2 hours delayed due to unscheduled maintenance. We missed our Toronto connection. Air Canada rebooked us for the next day. We had purchased premium seats but our rebooked flight was nearly full and we did not sit together. Seats were way in the back of the plane. Air Canada did provide us with a hotel stay. Agent upon deplaning told us luggage would be sent through to our final destination. Customer service person told us our luggage would be at the carousel. It never showed up, so we lost an hour waiting for it, already well past my bedtime by now. My husband has limited mobility. Baggage agent advised us the luggage did, indeed, get placed somewhere for our next day flight and provided us with an overnight kit (shaving kit, oral hygiene kit, sleep shirt, etc.) and it was very much appreciated and needed. Husband has mobility issues and we found that wheelchair assistance is not provided during layover stops, which made it difficult (and slow) for us to get from gate to customer service to baggage claim to hotel shuttle. We were given food vouchers but were too exhausted to use them before going to hotel. For the most part, all agents we dealt with were respectful and pleasant, although only a few were as warm, friendly and helpful as most of the Canadians we had interacted with during our visit.

There was no entertainment on board and wi-fi did not work for me. Food consisted of beverage and pretzels. Flight was over 2 hours delayed due to unscheduled maintenance. We missed our Toronto connection. Air Canada rebooked us for the next day. We had purchased premium seats but our rebooked flight was nearly full and we did not sit together. Seats were way in the back of the plane. Air Canada did provide us with a hotel stay. Agent upon deplaning told us luggage would be sent through to our final destination. Customer service person told us our luggage would be at the carousel. It never showed up, so we lost an hour waiting for it, already well past my bedtime by now. My husband has limited mobility. Baggage agent advised us the luggage did, indeed, get placed somewhere for our next day flight and provided us with an overnight kit (shaving kit, oral hygiene kit, sleep shirt, etc.) and it was very much appreciated and needed. Husband has mobility issues and we found that wheelchair assistance is not provided during layover stops, which made it difficult (and slow) for us to get from gate to customer service to baggage claim to hotel shuttle. For the most part, all agents we dealt with were respectful and pleasant, although only a few were as warm, friendly and helpful as most of the Canadians we had interacted with during our visit.

We paid $110 for more leg room. My traveling companion’s knees were right up against the seat in front. Where was more leg room. We feel ripped off. Food,,,there wasn’t any not even a bag of pretzels. As a result, there was very little service.

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

7/12Sat
directWestJet
5h 31mYWG-MBJ
14/12Sat
directWestJet
5h 48mMBJ-YWG
C$ 427
4/12Wed
1 stopWestJet
24h 33mYWG-MBJ
14/12Sat
directWestJet
5h 48mMBJ-YWG
C$ 433
8/12Sun
2 stopsAir Canada
30h 00mYWG-MBJ
11/12Wed
1 stopAir Canada
25h 53mMBJ-YWG
C$ 507
8/12Sun
2 stopsAir Canada
30h 00mYWG-MBJ
13/12Fri
1 stopAir Canada
25h 53mMBJ-YWG
C$ 509
20/11Wed
2 stopsDelta
22h 27mYWG-SDQ
27/11Wed
2 stopsDelta
41h 55mSDQ-YWG
C$ 593
25/10Fri
2 stopsDelta
42h 10mYWG-MBJ
5/11Tue
2 stopsDelta
34h 25mMBJ-YWG
C$ 612
18/10Fri
2 stopsUnited Airlines
21h 00mYWG-MBJ
29/10Tue
2 stopsUnited Airlines
22h 39mMBJ-YWG
C$ 652
13/9Fri
1 stop
22h 30mYWG-KIN
30/9Mon
1 stop
18h 40mKIN-YWG
C$ 661
16/9Mon
1 stop
8h 30mYWG-KIN
27/9Fri
1 stop
18h 40mKIN-YWG
C$ 665
5/10Sat
2 stopsUnited Airlines
19h 07mYWG-MBJ
11/10Fri
2 stopsUnited Airlines
24h 33mMBJ-YWG
C$ 681

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Recent one-way flight deals

8/11Fri
2 stopsWestJet
26h 01mYWG-MBJ
C$ 271
14/9Sat
3 stops
21h 31mYWG-MBJ
C$ 285
8/11Fri
1 stopWestJet
22h 26mYWG-MBJ
C$ 290
14/9Sat
2 stops
19h 31mYWG-MBJ
C$ 293
28/12Sat
directWestJet
5h 31mYWG-MBJ
C$ 321
4/9Wed
2 stopsDelta
48h 17mYWG-PUJ
C$ 343
4/9Wed
1 stopAir Canada
17h 15mYWG-PUJ
C$ 370
4/9Wed
1 stopAir Canada
17h 15mYWG-PUJ
C$ 372
13/8Tue
2 stopsDelta
26h 20mYWG-MBJ
C$ 459
3/8Sat
2 stopsUnited Airlines
20h 52mYWG-MBJ
C$ 493

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Last minute flights from Winnipeg to Caribbean

Last minute flight, train and bus deals

28/7Sun
multi-stopUnited Airlines
24h 41mYWG-PLS
3/8Sat
multi-stopUnited Airlines
23h 26mPLS-YWG
C$ 832
30/7Tue
multi-stop
23h 00mYWG-KIN
27/8Tue
multi-stop
27h 11mKIN-YWG
C$ 896
28/7Sun
multi-stopUnited Airlines
24h 41mYWG-PLS
3/8Sat
multi-stopUnited Airlines
26h 11mPLS-YWG
C$ 903
29/7Mon
multi-stop
10h 30mYWG-KIN
27/8Tue
multi-stop
27h 11mKIN-YWG
C$ 919
29/7Mon
multi-stop
41h 15mYWG-KIN
27/8Tue
multi-stop
22h 31mKIN-YWG
C$ 1,079
26/7Fri
multi-stop
17h 25mYWG-KIN
27/8Tue
multi-stop
27h 11mKIN-YWG
C$ 1,244
28/7Sun
multi-stop
9h 05mYWG-KIN
27/8Tue
multi-stop
27h 11mKIN-YWG
C$ 1,254
30/7Tue
multi-stopAir Canada
16h 45mYWG-KIN
27/8Tue
multi-stopAir Canada
20h 22mKIN-YWG
C$ 1,343
29/7Mon
multi-stopAir Canada
16h 45mYWG-KIN
27/8Tue
multi-stopAir Canada
20h 22mKIN-YWG
C$ 1,464
26/7Fri
multi-stopDelta
12h 02mYWG-KIN
27/8Tue
multi-stopDelta
30h 12mKIN-YWG
C$ 4,242

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