C$ 453 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 20/5. 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, 10 Jul - Fri, 31 Jul
Multiple Airlines Logo
6:25 p.m. - 9:45 a.m.
KIN
-
YWG
15h 20m
1 stop
Multiple Airlines Logo
7:00 a.m. - 2:30 p.m.
YWG
-
KIN
31h 30m
2 stops
C$ 781Multiple Airlines
Fri, 10 Jul - Fri, 31 Jul
WestJet Logo
3:30 p.m. - 12:55 a.m.
KIN
-
YWG
9h 25m
1 stop
WestJet Logo
6:05 p.m. - 2:30 p.m.
YWG
-
KIN
20h 25m
1 stop
C$ 798WestJet
Fri, 10 Jul - Fri, 31 Jul
WestJet Logo
3:30 p.m. - 9:20 a.m.
KIN
-
YWG
17h 50m
2 stops
WestJet Logo
12:00 p.m. - 2:30 p.m.
YWG
-
KIN
26h 30m
2 stops
C$ 806WestJet
Fri, 10 Jul - Fri, 31 Jul
United Airlines Logo
2:56 p.m. - 4:20 p.m.
KIN
-
YWG
25h 24m
3 stops
United Airlines Logo
2:00 p.m. - 1:54 p.m.
YWG
-
KIN
23h 54m
3 stops
C$ 2,710United Airlines
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Good to know

Low seasonMarch
Cheapest flightC$ 453
Best time to beat the crowds (4% less expensive on average)
Most popular time to fly (30% 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 airline 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 3331 reviews
6.2Food
7.4Boarding
7.0Comfort
7.9Crew
6.1Entertainment
Airline reviews

Westjet never disappoint always terrible small plane ,crowded cheap snack if you can call it snack

4.0 OkayMiguel, Apr 2026
MBJ - YYZ
Read more WestJet reviews

Westjet never disappoint always terrible small plane ,crowded cheap snack if you can call it snack

Westjet was late and we missed our connecting flight with Cathay. Had to wait 8 hours. Westjet only allows 1 checked in baggage for international flights- it’s always been 2. Canada allows only 1 sandwhich bag size full off small liquids. Everything else will be tossed. Awful trip. Will never fly west jet or go to Toronto to connect flights!

I didn’t have any food but my Prosecco hit the spot. We left on time and the crew was friendly.

Flight didn’t happen because both my connections were lost and Toronto wouldn’t let me board. I was checked in to all 3 flights at the check-in fest in Dublin.

The flight didn’t happen because they apparently lost my check in and wouldn’t let me board.

I thought the coffee was excellent! The wait for the luggage was acceptable.. It left and arrived on time. My son found that his device worked very well and he really enjoyed his flight! The stewardess moved him up to the emergency exit and he very much appreciated that!

I wasn’t able to book or pay for a seat and they forgot to check me in for my third flight so I spent 24 hours in Toronto waiting for another one.

I wasn’t checked in for the third leg of my flight, my bag was checked through to Dublin but when I went to the gate in Toronto they said I wasn’t on the flight and had given my seat away. I had to wait 24 hours for another flight and instead on the one I had booked it was now 2 flights.

Flight was delayed by 3/4 of an hour. Overall flight was good.

No kiosk to help pre boarding unlike other airlines, still lost the luggage despite its own crew/TSA or security tagging it, poor handling of lost luggage and possibly compensation is likely poor too.

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)