C$ 390 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 9/10. 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

Mon, 25 Aug - Thu, 28 Aug
Air Canada Logo
12:50 p.m. - 6:59 p.m.GCM-YWG
30h 09m2 stops
Air Canada Logo
8:10 p.m. - 12:30 p.m.YWG-GCM
40h 20m2 stops
C$ 772Air Canada
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Mon, 25 Aug - Thu, 28 Aug
Air Canada Logo
12:50 p.m. - 10:14 a.m.GCM-YWG
21h 24m2 stops
Air Canada Logo
8:10 p.m. - 12:30 p.m.YWG-GCM
40h 20m2 stops
C$ 786Air Canada
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Wed, 8 Oct - Wed, 5 Nov
 Logo
6:25 p.m. - 9:41 a.m.KIN-YWG
15h 16m1 stop
 Logo
5:00 a.m. - 7:00 p.m.YWG-KIN
13h 00m1 stop
C$ 830
Find Deal
Wed, 8 Oct - Wed, 5 Nov
 Logo
6:25 p.m. - 9:41 a.m.KIN-YWG
15h 16m1 stop
 Logo
5:00 a.m. - 7:00 p.m.YWG-KIN
13h 00m1 stop
C$ 844
Find Deal
Sat, 13 Sep - Sat, 20 Sep
 Logo
12:08 p.m. - 5:40 p.m.KIN-YWG
29h 32m3 stops
 Logo
6:30 a.m. - 6:52 p.m.YWG-KIN
12h 22m2 stops
C$ 855
Find Deal
Fri, 15 Aug - Wed, 1 Oct
 Logo
12:32 p.m. - 7:24 p.m.KIN-YWG
30h 52m3 stops
 Logo
5:00 a.m. - 5:10 p.m.YWG-KIN
12h 10m1 stop
C$ 863
Find Deal
Fri, 15 Aug - Wed, 1 Oct
 Logo
9:47 a.m. - 7:24 p.m.KIN-YWG
33h 37m3 stops
 Logo
11:20 a.m. - 11:02 a.m.YWG-KIN
23h 42m3 stops
C$ 879
Find Deal
Fri, 15 Aug - Wed, 1 Oct
 Logo
12:32 p.m. - 10:46 p.m.KIN-YWG
34h 14m2 stops
 Logo
6:30 a.m. - 5:10 p.m.YWG-KIN
10h 40m1 stop
C$ 884
Find Deal
Sat, 13 Sep - Sat, 20 Sep
WestJet Logo
3:30 p.m. - 12:13 a.m.KIN-YWG
8h 43m1 stop
WestJet Logo
6:30 a.m. - 2:28 p.m.YWG-KIN
7h 58m1 stop
C$ 886WestJet
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Wed, 8 Oct - Wed, 5 Nov
Delta Logo
9:00 a.m. - 11:27 p.m.KIN-YWG
14h 27m2 stops
Delta Logo
5:00 a.m. - 9:00 p.m.YWG-KIN
15h 00m2 stops
C$ 1,248Delta
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Good to know

Low seasonJanuary
Cheapest flightC$ 390
Best time to beat the crowds but there is an average 30% increase in price.
Most popular time to fly and prices are also 6% lower on average.
Flight from George Town 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 2978 reviews
7.0Comfort
7.4Boarding
6.2Food
7.9Crew
6.1Entertainment
Airline reviews

7 hour layover was a drag. Free internet on the long leg was great.

6.0 GoodAnonymous, Jul 2025YYC - YLW
Read more WestJet reviews

7 hour layover was a drag. Free internet on the long leg was great.

They cancelled and moved my flight with no email or text or any other notice. I discovered this only when I attempted to check in for my flight. Actual flying experience was above average.

They were on time and everything went as expected. The only thing that could be better was they didn't wait for us to get through customs to pick up our luggage off the carousel. An employee picked it up and was shoving it together with others onto a cart. Later we found one of our luggage was slightly bent.

From vancouver go calgary nd vice vetsa fligjt was delayed

Delayed boarding. Delayed taking off. Delayed landing. Missed our connecting flight. Our seats on this plane were not assigned until last minute, splitting up our family with kids. I sat in the last row next to the bathroom with so many people rubbing up against me to get to the bathroom the entire flight.

It was good! Short flight and it was on time!

Another delayed flight. Then got bumped to a later connecting flight, over two hours later! Plane was hot and uncomfortable.

Asked to cancel flight 6 days in advance of flight back to St. Louis, MO. Would not allow. No credit either.

My flight was delayed three times then eventually cancelled the next flight was the following day scheduled for 1030 it was delayed I had to cancel reservations I had to put people up in hotels on the other end as they came out of town to pick me up all at my expense because WestJet couldn’t get it together I’m very disappointed in WestJet’s performance and how they handled the situation Get your customers to where they need to be in a timely fashion, even if that means putting them on your competitors jets Customer service should be number one I will think twice now with booking with WestJet

Arrival at Comox from, London,ON 6 hours later... No bueano

Staff was not frankly. I asked about what beverages you have and air hostess told me like before so very rude answer.

On-time boarding, departure, and flight. Electronic notifications about bags for the whole of their own journey too - from when they got accepted into the system through to being loaded onto the plane and then finally being disgorged onto the right carousel. That was an excellent feature.

I liked that the plane landed safely. I didn't like that the food and leg room is horrible.

Liked getting into Milan at 10 AM. Also ok to get into LAX at 9:35 pm. - less traffic driving home. Layover a bit long - say 3-4 hours each way. Montreal airport kind of grim these days. Would lose the duty free area. Think art versus advertising. Maybe local shops and food spots. And keep layover short - like 1 hour on Finnair in Helsinki.

Flying in the Dreamliner is always comfortable. Though the food options for Air Canada aren't great.

Everything could have been better from the planes not being delayed to the rudeness of staff to it was just horrible will not use kayak again or Air Canada I can't see what would ever change my mind now

I wish someone would wake me up so I could eat the free food :( slept for 90mins on a 10hr flight and I missed breakfast. I’m sad about that lol.

Business class was not worth the extra charge. Overpriced for slightly larger seat. Nothing special. Small older plane.

Both flights are delayed so I rate the whole experience as mediocre.

Bad experience flying with air Canada . Seats not comfortable . Checked bag was delayed and was bought home next day by airport employee. Had to buy toiletries since bag was delayed . No compensation was even suggested . Will not fly air canada again

Travelling to a place near Winnipeg?

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