C$ 261 Find Cheap Flights from Caribbean to Winnipeg – Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 25% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Useful Info
Flight Deals

Cheap Flights from Caribbean to Winnipeg

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Caribbean to Winnipeg

Wed, 18 Nov - Sun, 22 Nov
Multiple Airlines Logo
1:10 p.m. - 9:29 p.m.GCM  George Town Owen Roberts Intl-YWG Winnipeg
8h 19m1 stop Toronto Pearson Intl
Multiple Airlines Logo
6:00 a.m. - 2:35 p.m.YWG  Winnipeg-GCM George Town Owen Roberts Intl
8h 35m1 stop Toronto Pearson Intl
C$ 660Multiple Airlines
Thu, 3 Dec - Sun, 6 Dec
Multiple Airlines Logo
3:35 p.m. - 10:15 a.m.GCM  George Town Owen Roberts Intl-YWG Winnipeg
18h 40m1 stop Toronto Pearson Intl
Multiple Airlines Logo
7:55 p.m. - 2:35 p.m.YWG  Winnipeg-GCM George Town Owen Roberts Intl
18h 40m1 stop Toronto Pearson Intl
C$ 689Multiple Airlines
Wed, 2 Dec - Sun, 6 Dec
Air Canada Logo
1:10 p.m. - 12:44 a.m.GCM  George Town Owen Roberts Intl-YWG Winnipeg
11h 34m1 stop Toronto Pearson Intl
Air Canada Logo
8:20 p.m. - 12:10 p.m.YWG  Winnipeg-GCM George Town Owen Roberts Intl
15h 50m1 stop Toronto Pearson Intl
C$ 697Air Canada
Thu, 3 Dec - Tue, 8 Dec
Air Canada Logo
1:10 p.m. - 12:49 p.m.GCM  George Town Owen Roberts Intl-YWG Winnipeg
23h 39m1 stop Toronto Pearson Intl
Air Canada Logo
7:00 a.m. - 12:10 p.m.YWG  Winnipeg-GCM George Town Owen Roberts Intl
29h 10m2 stops Ottawa Toronto Pearson Intl
C$ 697Air Canada
Thu, 3 Dec - Mon, 7 Dec
Air Canada Logo
1:10 p.m. - 12:49 p.m.GCM  George Town Owen Roberts Intl-YWG Winnipeg
23h 39m1 stop Toronto Pearson Intl
Air Canada Logo
7:00 a.m. - 12:10 p.m.YWG  Winnipeg-GCM George Town Owen Roberts Intl
29h 10m2 stops Ottawa Toronto Pearson Intl
C$ 697Air Canada
Wed, 2 Dec - Mon, 7 Dec
Air Canada Logo
1:10 p.m. - 12:44 a.m.GCM  George Town Owen Roberts Intl-YWG Winnipeg
11h 34m1 stop Toronto Pearson Intl
Air Canada Logo
7:00 a.m. - 12:10 p.m.YWG  Winnipeg-GCM George Town Owen Roberts Intl
29h 10m2 stops Ottawa Toronto Pearson Intl
C$ 697Air Canada
Wed, 2 Dec - Sun, 6 Dec
Air Canada Logo
1:10 p.m. - 7:25 p.m.GCM  George Town Owen Roberts Intl-YWG Winnipeg
54h 15m2 stops Toronto Pearson Intl Ottawa
Air Canada Logo
8:20 p.m. - 12:10 p.m.YWG  Winnipeg-GCM George Town Owen Roberts Intl
15h 50m1 stop Toronto Pearson Intl
C$ 697Air Canada
Wed, 2 Dec - Mon, 7 Dec
Air Canada Logo
1:10 p.m. - 12:44 a.m.GCM  George Town Owen Roberts Intl-YWG Winnipeg
11h 34m1 stop Toronto Pearson Intl
Air Canada Logo
4:05 p.m. - 12:10 p.m.YWG  Winnipeg-GCM George Town Owen Roberts Intl
20h 05m1 stop Toronto Pearson Intl
C$ 697Air Canada
Thu, 3 Dec - Mon, 7 Dec
Air Canada Logo
1:10 p.m. - 12:49 p.m.GCM  George Town Owen Roberts Intl-YWG Winnipeg
23h 39m1 stop Toronto Pearson Intl
Air Canada Logo
4:05 p.m. - 12:10 p.m.YWG  Winnipeg-GCM George Town Owen Roberts Intl
20h 05m1 stop Toronto Pearson Intl
C$ 697Air Canada
Thu, 3 Dec - Mon, 7 Dec
Air Canada Logo
1:10 p.m. - 7:25 p.m.GCM  George Town Owen Roberts Intl-YWG Winnipeg
30h 15m2 stops Toronto Pearson Intl Ottawa
Air Canada Logo
7:00 a.m. - 12:10 p.m.YWG  Winnipeg-GCM George Town Owen Roberts Intl
29h 10m2 stops Ottawa Toronto Pearson Intl
C$ 697Air Canada
Useful Info

Good to know

Cheapest flight

C$ 261
Flight from Montego Bay 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.
7.1
Air CanadaOverall score based on 11845 reviews
6.8Entertainment
7.3Boarding
7.8Crew
6.3Food
7.1Comfort
Airline reviews

They put us on stand by even though we booked it on the air Canada website and had seats picked so that sucked. Flight was awesome nice having a free beer and a movie

10.0 ExcellentRyan, Oct 2026
Read more Air Canada reviews

They put us on stand by even though we booked it on the air Canada website and had seats picked so that sucked. Flight was awesome nice having a free beer and a movie

Packed very carefully and did a 4 day trip with a 'personal item' only. Much less trouble than a carry on. Only 'entertainment' i need is the flight map. Did not work.

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.

Travelling to a place near Winnipeg?

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

More options for your flight to Winnipeg