C$ 377 Find Cheap Flights from Caribbean to Winnipeg

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Winnipeg departing on 31/10. 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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Cheap Flights from Caribbean to Winnipeg

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean to Winnipeg 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 Caribbean to Winnipeg

Fri, 6 Mar - Mon, 9 Mar
WestJet Logo
4:30 p.m. - 10:47 p.m.KIN-YWG
55h 17m2 stops
WestJet Logo
12:20 p.m. - 2:30 p.m.YWG-KIN
26h 10m1 stop
C$ 960WestJet
Find Deal
Fri, 6 Mar - Mon, 9 Mar
WestJet Logo
4:30 p.m. - 11:32 a.m.KIN-YWG
20h 02m1 stop
WestJet Logo
5:00 a.m. - 2:30 p.m.YWG-KIN
9h 30m1 stop
C$ 964WestJet
Find Deal

Everything you should know

Cheapest round-trip
C$ 960
WestJet
Fri 6/3Mon 9/3
KIN - YWG • 2 stops
Cheapest one-way flights
C$ 377
Multiple Airlines
Fri 31/10
KIN - YWG • 3 stops
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KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Winnipeg!
Useful Info

Good to know

Low seasonJanuary
Cheapest flightC$ 377
Best time to beat the crowds but there is an average 48% increase in price.
Most popular time to fly and prices are also 11% lower on average.
Flight from Kingston to Winnipeg

FAQs for booking flights from Caribbean to Winnipeg

  • How does KAYAK find such low prices on flights from Caribbean to Winnipeg?

    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 Caribbean to Winnipeg.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Caribbean to Winnipeg?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Winnipeg from Caribbean 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 Caribbean to Winnipeg?

    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 Winnipeg with an airline and back to Caribbean with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean to Winnipeg?

    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 Winnipeg from Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Caribbean to Winnipeg

 
Need help choosing which airline to fly with from Caribbean to Winnipeg? 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.
7.2
WestJetOverall score based on 3093 reviews
7.1Comfort
6.2Food
7.9Crew
6.1Entertainment
7.4Boarding
Airline reviews

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

2.0 MediocreScott, Sep 2025YVR - YXS
Read more WestJet reviews

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.

I like the web site, prompt notifications, website checks in process, and airport check in. The flight attendants are attentive and polite. The return flight was 2 hours late and reason vine doesn't sound like an unplanned and unexpected issue (scheduled plane maintenance).

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

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

The keg from Edmonton to Toronto My wife found it very cold. Other than that great flight.

It was generally pretty good, but the check-in and boarding process were a little difficult. Check in was in terminal 2F, but there was a shuttle required to get to the gate, which added significant time. The gate was changed 30 minutes before boarding, which took us by surprise - we did not get the notice until boarding had started. The check in line moved very slowly - the agent was friendly, but did not seem very efficient/urgent given the growing line.

Delays and missed connections were very hard the crew were wonderful but 1 1/2 hours late from Abbotsford to a 4 hour wait in Calgary was too much. I am 79 years old and I didn’t get to my destination until after 1 in the morning. They could have offered a seat in the lounge or a meal. I was very disappointed in the treatment

No dogs! Can we have no dogs in the cabin? Why was there a yappy little dog behind me? Lucky I had ear plugs. Sorry for others without

Flying with Air Canada is still better than the discount airlines like Flair. The seats are more comfortable and the on-board entertainment is better, with each seat having a built in screen and lots of content to watch. Onboard WIFI is also great to have, as well as plugs for charging. I think passengers in general are getting better at not bringing too much luggage onboard, and Air Canada is better at managing this without customers feeling like they are being taken advantage of with extra fees. I have travelled on different airlines and all seem to be loading faster, with fewer people bringing both a carry on and a personal item. Now I just bring one item and it fits under the seat so I don't need to worry about finding a place in the overhead bins. Overall, across the industry, asking customers to pay for carry on baggage is fair because it allows customers to only pay for what they need, and it helps to keep the planes on time. Kudos to Air Canada for its approach - the desired result is achieved without customers feeling that they are being surprised and caught with unexpected extra fees.

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!

For the price, it was a really good experience. There was no entertainment on board, so I couldn't really rate this, and I didn't order a meal. I appreciated that there was a free glass of wine.

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.

Short flight. Everything was fine except the flight was delayed twice for a total of an hour.

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

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

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