C$ 229 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 25/10. 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
1 adult, Economy

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Flight Deals

Best Caribbean Flight Deals from Winnipeg

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stopC$ 544
Montego Bay
Montego Bay1 stopC$ 579
Kingston
Kingston2 stopsC$ 852
Nassau
Nassau2 stopsC$ 632
Bridgetown
Bridgetown2 stopsC$ 650
Puerto Plata
Puerto Plata2 stopsC$ 740
Willemstad
Willemstad2 stopsC$ 719
George Town
George Town1 stopC$ 924
Punta Cana
Punta Cana1 stopC$ 544
Montego Bay
Montego Bay1 stopC$ 579
Kingston
Kingston2 stopsC$ 852
Nassau
Nassau2 stopsC$ 632
Bridgetown
Bridgetown2 stopsC$ 650
Puerto Plata
Puerto Plata2 stopsC$ 740
Willemstad
Willemstad2 stopsC$ 719
George Town
George Town1 stopC$ 924

Cheap Flights from Winnipeg to Caribbean

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Winnipeg to Caribbean that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Winnipeg to Caribbean

Mon, 22 Sep - Mon, 6 Oct
Air Canada Logo
5:00 a.m. - 3:20 p.m.YWG-PUJ
9h 20m1 stop
Air Canada Logo
4:25 p.m. - 10:10 a.m.PUJ-YWG
18h 45m2 stops
C$ 544Air Canada
Find Deal
Mon, 22 Sep - Mon, 6 Oct
Air Canada Logo
8:10 p.m. - 1:25 p.m.YWG-PUJ
40h 15m2 stops
Air Canada Logo
4:25 p.m. - 10:10 a.m.PUJ-YWG
42h 45m2 stops
C$ 549Air Canada
Find Deal
Wed, 29 Oct - Sun, 2 Nov
WestJet Logo
8:05 p.m. - 12:54 p.m.YWG-MBJ
16h 49m1 stop
WestJet Logo
1:25 p.m. - 11:35 a.m.MBJ-YWG
23h 10m1 stop
C$ 579WestJet
Find Deal
Fri, 14 Nov - Sat, 29 Nov
 Logo
7:30 a.m. - 3:15 p.m.YWG-MBJ
30h 45m1 stop
 Logo
2:50 p.m. - 12:41 a.m.MBJ-YWG
10h 51m1 stop
C$ 583
Find Deal
Thu, 13 Nov - Thu, 20 Nov
 Logo
8:20 p.m. - 10:30 p.m.YWG-PUJ
24h 10m1 stop
 Logo
9:30 a.m. - 7:35 p.m.PUJ-YWG
12h 05m1 stop
C$ 583
Find Deal
Wed, 29 Oct - Sun, 2 Nov
WestJet Logo
6:55 p.m. - 12:54 p.m.YWG-MBJ
17h 59m2 stops
WestJet Logo
8:25 p.m. - 3:21 p.m.MBJ-YWG
19h 56m2 stops
C$ 600WestJet
Find Deal
Thu, 30 Oct - Tue, 4 Nov
United Airlines Logo
2:20 p.m. - 3:12 p.m.YWG-MBJ
48h 52m2 stops
United Airlines Logo
1:25 p.m. - 11:57 a.m.MBJ-YWG
23h 32m2 stops
C$ 621United Airlines
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Sat, 25 Oct - Sat, 1 Nov
United Airlines Logo
2:20 p.m. - 3:14 p.m.YWG-PUJ
23h 54m2 stops
United Airlines Logo
4:20 p.m. - 12:57 p.m.PUJ-YWG
21h 37m2 stops
C$ 683United Airlines
Find Deal
Sun, 28 Dec - Tue, 6 Jan
Delta Logo
5:56 p.m. - 2:50 p.m.YWG-SXM
18h 54m2 stops
Delta Logo
4:26 p.m. - 5:00 p.m.SXM-YWG
26h 34m2 stops
C$ 1,230Delta
Find Deal
Fri, 6 Feb - Thu, 19 Feb
Delta Logo
7:30 a.m. - 2:45 p.m.YWG-CUR
29h 15m1 stop
Delta Logo
4:10 p.m. - 3:09 p.m.CUR-YWG
24h 59m1 stop
C$ 1,940Delta
Find Deal
Booking Insights

KAYAK's insights & trends for Winnipeg to Caribbean flights

Get data-powered insights and trends into flights from Winnipeg to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Winnipeg to Caribbean flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean from Winnipeg found in the last 72 hours was to Montego Bay, at C$ 860 round-trip. The most popular route is from Winnipeg (YWG) to Montego Bay (MBJ), and the cheapest round-trip airline ticket found on this route in the last 72 hours was C$ 860.

Can I save money by flying with a layover from Winnipeg to Caribbean?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of C$ 906, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Winnipeg to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Winnipeg to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Winnipeg to Caribbean is June, when tickets cost C$ 676 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is C$ 988 and C$ 845 respectively.

How far in advance should I book a flight from Winnipeg to Caribbean?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Winnipeg to Caribbean, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below-average price on a flight from Winnipeg to Caribbean, you should book around 2 weeks before departure, which saves you about 14% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 3 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flightC$ 229
Best time to beat the crowds (16% less expensive on average)
Most popular time to fly and prices are also 8% lower on average.
Flight from Winnipeg to George Town

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 from Winnipeg to Caribbean is likely to change within 7 days, so travellers 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 from Winnipeg to Caribbean with an airline and back 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 from Winnipeg to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Caribbean?

    The cheapest time of day to fly to Caribbean is generally in the evening, when round-trip flights cost C$ 572 on average. Morning departures are around 45% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the morning, which is peak travel time and where the average cost of a ticket is C$ 828.

Reviews of the top 5 airlines flying 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.
7.7
Air TransatOverall score based on 438 reviews
7.3Comfort
8.4Crew
7.0Entertainment
6.7Food
7.9Boarding
Airline reviews

This has been the worst experience I’ve ever had. Basically, I lost my round-trip tickets because one of my last names was missing, and you didn’t allow me to correct it. I had to purchase a full ticket again. Once I get home, I will start legal proceedings against you.

2.0 MediocreAnonymous, Sep 2025YYZ - ZAG
Read more Air Transat reviews

This has been the worst experience I’ve ever had. Basically, I lost my round-trip tickets because one of my last names was missing, and you didn’t allow me to correct it. I had to purchase a full ticket again. Once I get home, I will start legal proceedings against you.

The crew were polite and courteous. The Pilot did an excellent landing. It was very smooth and gentle. My only regret is that I was charged twice for my luggage . The attendant gave me no receipt . I didn't realize until I was about to board. How can this be resolved? Thank you.

Very smooth flights Toronto to Rome and return. Crews were great, food was fine but very narrow seats and limited leg room. Aisle seats on our return helped with a bit more space.

YUL AIRPORT is the worst. 1 Hr to Get out of the plane, 1 Hr To Cross the Border. 1Hr waiting to be pick up curbside. Trafic is ubeliveble.

It’s ok just the boarding point is far too far

Check in slow even though completed online check in, there was no bag drop available so had to query for 90mins as only 2 staff on desks.

Flying to a far away destination is a miracle in itself, so please take these with a grain of salt. The seats are a bit tired, and need a freshen up. The entertainment could be a bit newer, especially with all services available now. The food really is where we need help. But again, flying is a privilege, so all is good.

Not so much porter it's your site! Not good

They are a sister company with Air Transat and the two companies do not work well together. If you have any issues the two companies will blame each other and you will miss your flights. The help line does not help

Never book through a third party. Book through Air transats website. Terrible process to get help and many issues happen with them and sister companies because half the flights you book with them aren’t even through air transat.

Overall, it was good. I was seating next to a wonderful lady and did not notice how time flew. Thanks

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

The experience was great, the crew was very polite and hospitable. I will definitely make if my go to airlines.

It was all good flight was on time, service was good I enjoyed a few movies and everything was smooth

Efficient, calm when things were delayed and kept us regularly informed of what was happening.

Airbus plane, nice and polite staff, entertainment even as it was a short flight.

Very nice and clean plane. Transit time between flights was tight though

Our flights got changed from United to Air Canada and our purchased seats did not get transferred so we had to pay for seats twice. I brought it up with Air Canada and they stated I had to go back and chase it with United. The united seats were $21 Canadian each and Air Canada were $56 each so we have paid $77 for each seat. Very unhappy

So far so good but food and entertainment are not available for this flight

Plane temperature was comfortable (not to hot) when boarding and waiting for takeoff.

The experience was good just the upcharge of over a hundred dollars was not cool.

No internet, not even westjet connect makes for a boring flight

Our first flight from LAX to Winnipeg was changed but you never informed us at all. It went from a nonstop flight to a stay at Calgary. This impacted our trip negatively as we arrived much later than we planned to. Our returning flight was horrible. The flight was delayed 6 hours!! And we were NOT going to wait that long. The only way we got on our original flight was running there. However all of our suitcases were now coming on the delayed flight. It was the worst experience we ever had flying. I want my money back.

Typical Canadian airline experience. Charger and tray were broken, food was poor quality, and yet you're still paying more than flights with equal to better service than elsewhere globally.

Good, a bit cramped in the seat as my neighbour was a bit large

There was a man who was very rude at boarding. On the other hand personal bag measuring box is too small compared to USA airlines,

While I appreciated the food (it was unexpected), it was interruptive for sleeping. We paid extra for reserved seats, but when we checked in they gave us different seats. I had to call WestJet arounf 11:30pm the night before our flight to get this fixed. We were give seats in the emengency row to resolve the issue.

Not enough food option. And not enough advices or information about what we are gonna eat.

Please make more option. And be more precise on the type of food you giving. Diner and breakfast can be different

I like how spacious the plane was but I did not like the fact that there was no entertainment

Had to cancel flight due to strike. Hope things will be better next August when we will rebook. Very disappointing as it was our 50th wedding anniversary celebration l!

I’ve wasted 7 hours of my time because of the delayed. ;(

The crew were fabulous. The flight was bumpy and I always like the captain to tell me what that is about or my imagination gets carries away.

Overall great. The crews were lovely. The seats are awful. I always emerge with a back ache.

I liked the behaviour of the crew members.The flight was good.

Would like whole can of pop for 2. Treats were not great . The garlic pretzels were terrible for someone who can't eat garlic. Passenger was 84.

I had boarding pass on my phone. Husband and I were seated together. Agent printed out boarding passes and we were separated for the flight

1 hour late No hot drinks No restroom in the back of the plane

You was on strike and I had to get another r flight and you did not give me my money back

Food can be better. Taste and option, the pasta wasn't the greatest.

Confortable plane. Clean modern No frills. Competent crew. On time

Not good. The planes are old, no food for a 5 hour + flight (unless you pay), paid for a carry-on, had to take a bus to board the plane - so far from the actual airport, waited 60 minutes after the flight landed to receive our luggage, no entertainment in the plane, no charging available, boarding passes error message for everyone trying to add to Apple Wallet. Probably my worst experience on a flight.

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).

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

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