C$ 442 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 18/5. 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

Wed, 8 Apr - Wed, 27 May
WestJet Logo
3:30 p.m. - 3:20 p.m.
KIN
-
YWG
23h 50m
2 stops
WestJet Logo
6:15 a.m. - 2:30 p.m.
YWG
-
KIN
8h 15m
1 stop
C$ 855WestJet
Wed, 8 Apr - Wed, 27 May
WestJet Logo
3:30 p.m. - 11:32 a.m.
KIN
-
YWG
20h 02m
1 stop
WestJet Logo
6:15 a.m. - 2:30 p.m.
YWG
-
KIN
8h 15m
1 stop
C$ 890WestJet
Wed, 19 Aug - Wed, 16 Sep
Multiple Airlines Logo
3:05 p.m. - 11:15 a.m.
KIN
-
YWG
20h 10m
1 stop
Multiple Airlines Logo
6:15 a.m. - 2:30 p.m.
YWG
-
KIN
8h 15m
1 stop
C$ 921Multiple Airlines
Wed, 19 Aug - Wed, 16 Sep
Multiple Airlines Logo
3:05 p.m. - 10:05 a.m.
KIN
-
YWG
19h 00m
2 stops
Multiple Airlines Logo
6:15 a.m. - 2:30 p.m.
YWG
-
KIN
8h 15m
1 stop
C$ 923Multiple Airlines
Wed, 19 Aug - Wed, 16 Sep
Air Canada Logo
3:05 p.m. - 10:00 a.m.
KIN
-
YWG
18h 55m
1 stop
Air Canada Logo
5:10 a.m. - 1:55 p.m.
YWG
-
KIN
8h 45m
1 stop
C$ 930Air Canada
Wed, 19 Aug - Wed, 16 Sep
Air Canada Logo
3:05 p.m. - 10:05 a.m.
KIN
-
YWG
19h 00m
2 stops
Air Canada Logo
5:10 a.m. - 1:55 p.m.
YWG
-
KIN
8h 45m
1 stop
C$ 934Air Canada
Wed, 19 Aug - Wed, 16 Sep
Air Canada Logo
3:05 p.m. - 10:05 a.m.
KIN
-
YWG
19h 00m
2 stops
Air Canada Logo
1:25 p.m. - 10:25 a.m.
YWG
-
KIN
21h 00m
2 stops
C$ 959Air Canada
Wed, 19 Aug - Wed, 16 Sep
Air Canada Logo
3:05 p.m. - 10:05 a.m.
KIN
-
YWG
19h 00m
2 stops
Air Canada Logo
1:25 p.m. - 10:25 a.m.
YWG
-
KIN
21h 00m
2 stops
C$ 960Air Canada
Wed, 19 Aug - Wed, 16 Sep
WestJet Logo
3:30 p.m. - 12:55 a.m.
KIN
-
YWG
9h 25m
1 stop
WestJet Logo
6:15 a.m. - 2:30 p.m.
YWG
-
KIN
8h 15m
1 stop
C$ 1,001WestJet
Wed, 19 Aug - Wed, 16 Sep
WestJet Logo
3:30 p.m. - 12:55 a.m.
KIN
-
YWG
9h 25m
1 stop
WestJet Logo
4:55 p.m. - 2:30 p.m.
YWG
-
KIN
45h 35m
2 stops
C$ 1,041WestJet
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Good to know

Low seasonSeptember
Cheapest flightC$ 442
Best time to beat the crowds (8% less expensive on average)
Most popular time to fly (20% 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 3300 reviews
7.0Comfort
6.1Entertainment
7.4Boarding
6.2Food
7.9Crew
Airline reviews

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.

6.0 GoodWendy, Mar 2026
YYC - YYZ
Read more WestJet reviews

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.

No pre boarding kiosk to check in, baggage claim detected luggage didn’t leave the airport, poorly managed recovery of lost luggage, and blame lost tag from conveyor to TSA/security, very poor from TSA/security check to delivery, crucial if compensation will go thru and will likely wait for months unlike United,

Waited at airport from 10 am till 4 pm and no flight due to fog. Ugh.

Flight was good, crew was excellent. No complaints at all

Delayed 3 times in a row for 4 hours total. Incrementally pushing back the flight claiming gate delays but they eventually changed the actual plane, due to technical issues. This strategy to avoid compensation to passengers is unprofessional.

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

Plane was one hour late. Hardly any space for our carry-ons. Stressful to catch connections.

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Winnipeg (YWG)