C$ 511 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 13/7. 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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Flight Deals

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, 1 Jul - Wed, 29 Jul
Air Canada Logo
2:35 p.m. - 10:05 a.m.
NAS
-
YWG
20h 30m
1 stop
Air Canada Logo
1:30 p.m. - 1:35 p.m.
YWG
-
NAS
23h 05m
2 stops
C$ 745Air Canada
Wed, 1 Jul - Wed, 29 Jul
Air Canada Logo
2:35 p.m. - 8:01 p.m.
NAS
-
YWG
30h 26m
2 stops
Air Canada Logo
1:30 p.m. - 1:35 p.m.
YWG
-
NAS
23h 05m
2 stops
C$ 746Air Canada
Wed, 1 Jul - Wed, 29 Jul
Air Canada Logo
2:35 p.m. - 10:05 a.m.
NAS
-
YWG
20h 30m
1 stop
Air Canada Logo
5:00 a.m. - 5:30 p.m.
YWG
-
NAS
11h 30m
1 stop
C$ 750Air Canada
Wed, 29 Jul - Sun, 16 Aug
Multiple Airlines Logo
6:25 p.m. - 5:25 p.m.
KIN
-
YWG
23h 00m
2 stops
Multiple Airlines Logo
1:10 p.m. - 2:30 p.m.
YWG
-
KIN
25h 20m
2 stops
C$ 820Multiple Airlines
Wed, 29 Jul - Sun, 16 Aug
Multiple Airlines Logo
6:25 p.m. - 9:45 a.m.
KIN
-
YWG
15h 20m
1 stop
Multiple Airlines Logo
8:00 a.m. - 2:30 p.m.
YWG
-
KIN
30h 30m
2 stops
C$ 824Multiple Airlines
Wed, 29 Jul - Sun, 16 Aug
Multiple Airlines Logo
6:25 p.m. - 9:45 a.m.
KIN
-
YWG
15h 20m
1 stop
Multiple Airlines Logo
7:45 a.m. - 2:30 p.m.
YWG
-
KIN
30h 45m
1 stop
C$ 841Multiple Airlines
Mon, 13 Jul - Fri, 28 Aug
Multiple Airlines Logo
6:25 p.m. - 9:45 a.m.
KIN
-
YWG
15h 20m
1 stop
Multiple Airlines Logo
12:50 p.m. - 2:30 p.m.
YWG
-
KIN
25h 40m
2 stops
C$ 880Multiple Airlines
Mon, 13 Jul - Fri, 28 Aug
Multiple Airlines Logo
6:25 p.m. - 10:20 a.m.
KIN
-
YWG
15h 55m
2 stops
Multiple Airlines Logo
8:00 a.m. - 2:30 p.m.
YWG
-
KIN
30h 30m
2 stops
C$ 889Multiple Airlines
Mon, 13 Jul - Fri, 28 Aug
Multiple Airlines Logo
6:25 p.m. - 9:45 a.m.
KIN
-
YWG
15h 20m
1 stop
Multiple Airlines Logo
7:45 a.m. - 2:30 p.m.
YWG
-
KIN
30h 45m
1 stop
C$ 893Multiple Airlines
Fri, 31 Jul - Sun, 16 Aug
Multiple Airlines Logo
6:25 p.m. - 11:19 a.m.
KIN
-
YWG
16h 54m
1 stop
Multiple Airlines Logo
8:00 a.m. - 2:30 p.m.
YWG
-
KIN
30h 30m
2 stops
C$ 914Multiple Airlines
Useful Info

Good to know

Low seasonMarch
Cheapest flightC$ 511
Best time to beat the crowds (4% less expensive on average)
Most popular time to fly (27% 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 3375 reviews
7.9Crew
7.4Boarding
7.0Comfort
6.1Entertainment
6.2Food
Airline reviews

Everyone was extremely friendly and nice, from the front desk to the cabin crew!

10.0 ExcellentAnonymous, Jun 2026
YYJ - YYC
Read more WestJet reviews

Everyone was extremely friendly and nice, from the front desk to the cabin crew!

The crew was excellent. The turbulence was very bad and they were unable to serve our dinner. The captain informed the passengers that we were going to get water and snack instead. They provided us ample snacks instead. Otherwise the trip was good.

Delayed but they wouldn’t tell us tell after boarding was scheduled to start. So it’s like we know it’s delayed why won’t they say anything?? How long? The. We ended up sitting on the tarmac for 2 hours before they finally cancelled the flight. Bad!

There was no food but a singular cookie for a flight that was over 5hours??? Yeah not fun I was starving and again super cramped plane and you guys need to get planes with screens too, WiFi is nice but common we need more

It wasn’t bad but I swear their planes keep getting smaller and cramped so it was uncomfortable for such a long time. Also the food is just okay they need some different options

This airline would not refund my money and I had a physician note that I could not fly. They are crooks

I like that we landed safely and that my dog was safe underneath as well. Outside of that, we were 45 mins late for a direct flight that is 1.5 hours long. And 2 of my 3 bags did not make the flight. Only my dog was onboard.

Decent entertainment although my wife was not offered any ear buds so couldn’t enjoy. Real issue was the appalling food. Presentation was unacceptable with cheap hard to open packaged bread, plastic cheese again in hard to open shrink wrap, main course in small cardboard box again hard to open, wooden utensils which lack substance making the whole experience poor. Surprised I didn’t cover myself or neighbour as the food moved all over the place. Breakfast calzone was dry and unappealing with the staff basically throwing them around. Very disappointed

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!

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