C$ 441 Find Cheap Flights from Caribbean to Winnipeg – Compare and Save

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 17/9. 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, 0 bags

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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, 18 Sep - Fri, 25 Sep
Multiple Airlines Logo
6:25 p.m. - 9:45 a.m.-
15h 20m
Multiple Airlines Logo
12:50 p.m. - 2:30 p.m.-
25h 40m
C$ 735Multiple Airlines
Fri, 18 Sep - Fri, 25 Sep
Multiple Airlines Logo
6:25 p.m. - 9:45 a.m.-
15h 20m
Multiple Airlines Logo
7:45 a.m. - 2:30 p.m.-
30h 45m
C$ 746Multiple Airlines
Fri, 18 Sep - Fri, 25 Sep
Multiple Airlines Logo
6:25 p.m. - 12:15 p.m.-
17h 50m
Multiple Airlines Logo
12:50 p.m. - 2:30 p.m.-
25h 40m
C$ 793Multiple Airlines
Fri, 18 Sep - Fri, 25 Sep
United Airlines Logo
2:57 p.m. - 11:52 a.m.-
20h 55m
United Airlines Logo
2:00 p.m. - 1:51 p.m.-
23h 51m
C$ 1,406United Airlines
Fri, 18 Sep - Fri, 25 Sep
United Airlines Logo
2:57 p.m. - 11:52 a.m.-
20h 55m
United Airlines Logo
2:00 p.m. - 1:51 p.m.-
23h 51m
C$ 1,411United Airlines
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Good to know

Low season

March

Cheapest flight

C$ 441
Best time to beat the crowds (5% less expensive on average)
Most popular time to fly (38% more expensive 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 3426 reviews
7.4Boarding
7.9Crew
6.2Food
7.0Comfort
6.1Entertainment
Airline reviews

The flight was full and good as could be expected. We arrived early which is always a good thing.

8.0 ExcellentReg, Jan 2026
Read more WestJet reviews

The flight was full and good as could be expected. We arrived early which is always a good thing.

When flying premium on a two our flight a light lunch would have been nice considering the price you pay. A Kit Kat bar and bag of chips is rather cheap service.

What do you expect from a Dash 8 plane? No seats really comfortable.

We got delayed to the point of having a 20 hour layover. That is absurd. I couldn’t believe it. I’m furious.

everything was fine expect massive delays - not the airline’s fault

The checked luggage still hasn't arrived yet. 42 h later. We saw it being unloaded in the stopover location. It was. 5 hour layover so it wasn't a rushed transfer. One positive aspect, it was close to being on time and the crew that came on the clean the plane was very efficient.

The small prop plane was crowded and the overhead luggage storage is a smaller than on the jets. Other than that, the crew was good, the flight was on time and the landing was smooth.

Was on a Swoop plane. No wifi and no Westjet connect

Plane should have entertainment, instead of people paying to use wifi

no staff available to help, no systems available to coordinate

I was rescheduled when I missed my flight due to border clearance issue

Delays. Poor support booking a hotel after a diverted flight.

Because of a change in aircraft, I was unable to experience the business class I paid for and was disappointed.

Very clean plane, staff were courteous, complimentary wifi and beverages are nice, and it was nice to have a whole row to myself! I do miss having seatback entertainment, though. And the prices are getting ridiculous, especially with the different teared tickets. But the flight overall was great.

Nuts would be better than pretzels as the non sweet snack

Kind and accommodating staff. Comfy seats. Plenty of leg and luggage room.

Flight was great, no plug in for charging and no inflight entertainment.

Seat cushion had lost much of its give and the entertainment monitors on the old A320 fleet are small.

The flight was good, the inflight tv's are too old and hard to work

The aircraft was very spacious and comfortable. Loved that the rows were more spread out.

Travelling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Morden
Scanterbury

Everything you need to know for your flight to Winnipeg

Information on the airport you'll fly into in Winnipeg

Winnipeg (YWG)