C$ 248 Find Cheap Flights from Winnipeg to Caribbean – Compare and Save

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Best Caribbean Flight Deals from Winnipeg

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
Simpson Bay, St. Maarten
18h 45m5 stops
from C$ 449per person
Montego Bay, Jamaica
5h 20mNonstop
from C$ 460per person
Punta Cana, Dominican Republic
5h 50mNonstop
from C$ 467per person
George Town, Cayman Islands
9h 52m2 stops
from C$ 472per person
Oranjestad, Aruba
9h 15m2 stops
from C$ 476per person
Nassau, The Bahamas
10h 00m2 stops
from C$ 509per person
Providenciales, Turks and Caicos Islands
16h 15m2 stops
from C$ 516per person
San Juan, Puerto Rico
11h 31m4 stops
from C$ 632per person
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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?

The cheapest ticket to Caribbean from Winnipeg found in the last 5 days was to Punta Cana, at C$ 581 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 5 days was C$ 622.

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

The cheapest time of day to fly to Caribbean is generally in the morning, when round-trip flights cost C$ 958 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$ 958.

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

No, with an average price for the route of C$ 634, prices are generally cheapest when you fly direct.

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

The cheapest month for flights from Winnipeg to Caribbean is April, when tickets cost C$ 717 (return) on average. On the other hand, the most expensive months are December and February, when the average cost of round-trip tickets is C$ 972 and C$ 960 respectively.

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

To get a below-average price on the flight from Winnipeg to Caribbean, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Good to know

Low season

June

Cheapest flight

C$ 248
Best time to beat the crowds (5% less expensive on average)
Most popular time to fly (33% more expensive 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 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.

Reviews of the top 3 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.
8.0
Porter AirlinesOverall score based on 460 reviews
8.6Crew
6.9Entertainment
8.2Boarding
8.0Comfort
7.6Food
Airline reviews

A very comfortable flight, an additional wash room could have made it almost perfect.

10.0 ExcellentAnonymous, Aug 2026
Read more Porter Airlines reviews

A very comfortable flight, an additional wash room could have made it almost perfect.

Boarding pass counter did not open until 2 hrs before flight. We were there 3 hrs before as we like to be early ( eat, relax etc). Due to this the line up was large , thus never got through security till 15 min before boarding. Other than that, everything was great

The agent at check in was very cordial and gave me seat 4a with nobody beside me as I asked if possible

Seats not as comfortable but understand as it was a smaller plane/ short flight. All in all, I’ve never had any issues with Porter. Great company to fly with

Look, I understand that Kayak doesn't know I cancelled my flight on Porter. So I didn't actually fly yesterday. My main disappointment is with Porter ticket fare policies, and maybe you can pass this on to them: At my employer's request, I had booked a full fare ticket with no change fees since my trip to Toronto would likely be extended. Indeed, when I went to change my flight home to a later date, I was told the Fare Difference would cost an additional $550. So much for no change fees lol! While I had the agent on the line, I hopped over to Kayak, searched for new flights on the date in question, and saw a one-way ticket that got me home for only $355. So I got reimbursed about $450for the unused half of my roundtrip and bought a new ticket for $355. What good is a full fare / no change fee ticket if they screw you with "fare difference" BS. I'm still flying home on Porter Airlines but they just lost a hundred bucks with their stupid shenanigans.

I flew with Porter yesterday and overall had a positive experience. The flight was delayed, but the airline did a good job keeping passengers informed with frequent updates throughout the process. My biggest challenge was actually in Terminal 3, where the speaker system wasn’t very clear. It was often difficult to hear the announcements, which made it harder to follow updates at the gate. On board, the experience improved significantly. The aircraft felt very new and well maintained, and the seats were surprisingly comfortable for a short-haul flight. One of the flight attendants seemed a little disengaged, but the other was excellent—friendly, professional, and a pleasure to interact with. Despite the delay, the comfortable aircraft, clear communication from Porter, and positive onboard service made for a good overall experience.

We were very offended Reserva check in agent in Calgary. Erroneously profiled and reprimanded for using Reserve line . Hadn't even looked at tickets. We were in fact Reserve passengers

The staff was amazing. Best service I’ve had on an aircraft in a long time. Was not particularly happy with the food. Flight was at 10:50 and left home too early for breakfast and wasn’t able to purchase food at airport and felt for sure I could get some breakfast to buy on airplane. Nope as food was served around 11:30 and only one choice left (I was at 22C) so ordered the chicken dish thinking I’m getting a hot meal but cold chicken with rice and carrots etc. I was looking forward to a croissant sandwich and a hot cup of tea. The FA was kind to explain they were serving dinner at that time. She was lovely Other than the disappointment with the food the staff was amazing. On my return flight I will make sure to eat and take some food with me so I’m not hungry or disappointed. This was my second time ever flying Porter and will consider checking them when I next come to visit my daughter. Have to say it again best crew I’ve ever experienced on a flight and I travel quite a bit. Thanks.

Even tho the flight was a bit delayed the team was apologetic. Everyone was friendly and efficient.

Everything was good except the fact you charge more for a carry on bag vs a check in bag and to top it off in US$ that was not impressive

Everything went well, smooth flight, arrived on time, no lost luggage!

My flight was cancelled due to weather but Westjet got me on a new flight in a timely and efficient manor.

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.

Lots of overhead storage and a good crew and service.

On time. Friendly and efficient staff at check in and flight crew.

Very good over all , would have been nice to have entertainment on the flight

It was an awesome experience flying with Westjet. This was my first domestic flight experience in Canada.

The flight itself was fine, but two of the ladies at the gate were extremely rude to a few of us in line. Their customer service really needs some help. I’ve always had good experiences with WestJet until these two ladies. They had the worst attitudes and really left a bad taste in my mouth after a good trip

Smooth process, on time. Everything ran perfectly. It would be nice to have in flight entertainment and better food choices but these were short flights so not a big deal

Terrible 12 hours delay Terrible We lost our suitcases No medication with us nothing

I like the fact air Canada is on time The food you guys serve is not good

Upgraded to sit at the exit door so good leg room.

Very tight leg room and not a fan of the new policy on no free carry on luggage. Besides that, it was fine.

Flight delay, cancellation rescheduling and misdirected luggage which created some stress. It all worked out in the end.

The flight was delayed several times, however , they kept me well informed with enough advance warning that I had not left home yet

Sat on the tarmac with no ventilation for almost an hour, without a single word from the crew. Appalling. When Air Canada goes bankrupt, again, almost everyone in Canada will be cheering.

If you have checked the status of my booking you would have seen that it was cancelled. And the travelers insurance we purchased only covered $100 per ticket. So my overall experience with kayak and air canada is poor

The plane for my second flight was reassigned. We had to wait for them to get a different plane out of the hangar and call in a crew

Send me 20 dollars and i will do the survey. You survey people think we do things in life to do surveys.

More options for your flight to Caribbean

Complete your trip to Caribbean with a hotel stay or car rental