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Cheap flights from Caribbean Islands to Winnipeg from C$ 431

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Caribbean Islands to Winnipeg departing on 26/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Find the cheapest flights from Caribbean Islands to Winnipeg

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
6:25 p.m. - 9:45 a.m.KIN  Kingston Norman Manley-YWG Winnipeg
15h 20m1 stop Toronto Pearson Intl
Multiple Airlines Logo
12:50 p.m. - 2:30 p.m.YWG  Winnipeg-KIN Kingston Norman Manley
25h 40m2 stops Edmonton Toronto Pearson Intl
C$ 735Multiple Airlines
Fri, 18 Sep - Fri, 25 Sep
Multiple Airlines Logo
6:25 p.m. - 9:45 a.m.KIN  Kingston Norman Manley-YWG Winnipeg
15h 20m1 stop Toronto Pearson Intl
Multiple Airlines Logo
7:45 a.m. - 2:30 p.m.YWG  Winnipeg-KIN Kingston Norman Manley
30h 45m1 stop Toronto Pearson Intl
C$ 746Multiple Airlines
Fri, 18 Sep - Fri, 25 Sep
WestJet Logo
3:30 p.m. - 5:15 p.m.KIN  Kingston Norman Manley-YWG Winnipeg
25h 45m1 stop Toronto Pearson Intl
WestJet Logo
12:50 p.m. - 2:30 p.m.YWG  Winnipeg-KIN Kingston Norman Manley
25h 40m2 stops Edmonton Toronto Pearson Intl
C$ 758WestJet
Tue, 8 Sep - Thu, 15 Oct
WestJet Logo
3:30 p.m. - 9:20 a.m.KIN  Kingston Norman Manley-YWG Winnipeg
17h 50m2 stops Toronto Pearson Intl Edmonton
WestJet Logo
7:00 a.m. - 2:30 p.m.YWG  Winnipeg-KIN Kingston Norman Manley
31h 30m2 stops Edmonton Toronto Pearson Intl
C$ 763WestJet
Tue, 8 Sep - Thu, 15 Oct
WestJet Logo
3:30 p.m. - 5:15 p.m.KIN  Kingston Norman Manley-YWG Winnipeg
25h 45m1 stop Toronto Pearson Intl
WestJet Logo
10:45 a.m. - 2:30 p.m.YWG  Winnipeg-KIN Kingston Norman Manley
27h 45m1 stop Toronto Pearson Intl
C$ 770WestJet
Tue, 8 Sep - Thu, 15 Oct
Multiple Airlines Logo
6:25 p.m. - 12:15 p.m.KIN  Kingston Norman Manley-YWG Winnipeg
17h 50m2 stops Toronto Pearson Intl Calgary
Multiple Airlines Logo
12:50 p.m. - 2:30 p.m.YWG  Winnipeg-KIN Kingston Norman Manley
25h 40m2 stops Edmonton Toronto Pearson Intl
C$ 792Multiple Airlines
Fri, 18 Sep - Fri, 25 Sep
United Airlines Logo
2:57 p.m. - 11:52 a.m.KIN  Kingston Norman Manley-YWG Winnipeg
20h 55m2 stops Panama City Tocumen Intl Chicago O'Hare Intl
United Airlines Logo
2:00 p.m. - 1:51 p.m.YWG  Winnipeg-KIN Kingston Norman Manley
23h 51m3 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl Panama City Tocumen Intl
C$ 1,404United Airlines
Fri, 18 Sep - Fri, 25 Sep
United Airlines Logo
2:57 p.m. - 11:52 a.m.KIN  Kingston Norman Manley-YWG Winnipeg
20h 55m3 stops Panama City Tocumen Intl Washington, D.C. Dulles Intl Chicago O'Hare Intl
United Airlines Logo
2:00 p.m. - 1:51 p.m.YWG  Winnipeg-KIN Kingston Norman Manley
23h 51m3 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl Panama City Tocumen Intl
C$ 1,410United Airlines
Fri, 18 Sep - Fri, 25 Sep
United Airlines Logo
2:57 p.m. - 11:52 a.m.KIN  Kingston Norman Manley-YWG Winnipeg
20h 55m2 stops Panama City Tocumen Intl Chicago O'Hare Intl
United Airlines Logo
2:00 p.m. - 1:58 p.m.YWG  Winnipeg-KIN Kingston Norman Manley
23h 58m3 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl Panama City Tocumen Intl
C$ 1,534United Airlines
Tue, 8 Sep - Thu, 15 Oct
United Airlines Logo
2:57 p.m. - 4:27 p.m.KIN  Kingston Norman Manley-YWG Winnipeg
25h 30m3 stops Panama City Tocumen Intl Chicago O'Hare Intl Toronto Pearson Intl
United Airlines Logo
2:00 p.m. - 1:58 p.m.YWG  Winnipeg-KIN Kingston Norman Manley
23h 58m3 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl Panama City Tocumen Intl
C$ 1,546United Airlines
Tue, 8 Sep - Thu, 15 Oct

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WestJet flights from Caribbean Islands to Winnipeg

Our best WestJet deals on Caribbean Islands to Winnipeg flight tickets
WestJet
8 Sep
KIN3:30 p.m.Kingston Norman Manley
25h 45m
1 stop
YWG5:15 p.m.Winnipeg
15 Oct
YWG12:50 p.m.Winnipeg
25h 40m
2 stops
KIN2:30 p.m.Kingston Norman Manley
C$ 758
WestJet
8 Sep
KIN3:30 p.m.Kingston Norman Manley
17h 50m
2 stops
YWG9:20 a.m.Winnipeg
15 Oct
YWG7:00 a.m.Winnipeg
31h 30m
2 stops
KIN2:30 p.m.Kingston Norman Manley
C$ 763
WestJet
8 Sep
KIN3:30 p.m.Kingston Norman Manley
25h 45m
1 stop
YWG5:15 p.m.Winnipeg
15 Oct
YWG10:45 a.m.Winnipeg
27h 45m
1 stop
KIN2:30 p.m.Kingston Norman Manley
C$ 770

United Airlines flights from Caribbean Islands to Winnipeg

Our best United Airlines deals on Caribbean Islands to Winnipeg flight tickets
United Airlines
18 Sep
KIN2:57 p.m.Kingston Norman Manley
20h 55m
2 stops
YWG11:52 a.m.Winnipeg
25 Sep
YWG2:00 p.m.Winnipeg
23h 51m
3 stops
KIN1:51 p.m.Kingston Norman Manley
C$ 1,404
United Airlines
18 Sep
KIN2:57 p.m.Kingston Norman Manley
20h 55m
3 stops
YWG11:52 a.m.Winnipeg
25 Sep
YWG2:00 p.m.Winnipeg
23h 51m
3 stops
KIN1:51 p.m.Kingston Norman Manley
C$ 1,410
United Airlines
8 Sep
KIN2:57 p.m.Kingston Norman Manley
20h 55m
2 stops
YWG11:52 a.m.Winnipeg
15 Oct
YWG2:00 p.m.Winnipeg
23h 58m
3 stops
KIN1:58 p.m.Kingston Norman Manley
C$ 1,534

momondo Fare Finder

 
Customize your flight search to find flights from Caribbean Islands to Winnipeg that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 96,600 searches. Data last updated 6 August 2026.
Use the filters below to find and compare flights from Caribbean Islands to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

KingstonWinnipeg

KIN Kingston Norman Manley - YWG Winnipeg

KINYWG

Kingston Norman Manley

Fri 18/9

6:25 p.m.-9:45 a.m.

1 stop15h 20m

Winnipeg

Fri 25/9

12:50 p.m.-2:30 p.m.

2 stops25h 40m

C$ 735

KingstonWinnipeg

KIN Kingston Norman Manley - YWG Winnipeg

KINYWG

Kingston Norman Manley

Fri 18/9

6:25 p.m.-9:45 a.m.

1 stop15h 20m

Winnipeg

Fri 25/9

7:45 a.m.-2:30 p.m.

1 stop30h 45m

C$ 746

KingstonWinnipeg

KIN Kingston Norman Manley - YWG Winnipeg

KINYWG

Kingston Norman Manley

Tue 8/9

3:30 p.m.-5:15 p.m.

1 stop25h 45m

Winnipeg

Thu 15/10

12:50 p.m.-2:30 p.m.

2 stops25h 40m

C$ 758

KingstonWinnipeg

KIN Kingston Norman Manley - YWG Winnipeg

KINYWG

Kingston Norman Manley

Tue 8/9

3:30 p.m.-9:20 a.m.

2 stops17h 50m

Winnipeg

Thu 15/10

7:00 a.m.-2:30 p.m.

2 stops31h 30m

C$ 763

KingstonWinnipeg

KIN Kingston Norman Manley - YWG Winnipeg

KINYWG

Kingston Norman Manley

Tue 8/9

3:30 p.m.-5:15 p.m.

1 stop25h 45m

Winnipeg

Thu 15/10

10:45 a.m.-2:30 p.m.

1 stop27h 45m

C$ 770

KingstonWinnipeg

KIN Kingston Norman Manley - YWG Winnipeg

KINYWG

Kingston Norman Manley

Fri 18/9

6:25 p.m.-12:15 p.m.

2 stops17h 50m

Winnipeg

Fri 25/9

12:50 p.m.-2:30 p.m.

2 stops25h 40m

C$ 792

KingstonWinnipeg

KIN Kingston Norman Manley - YWG Winnipeg

KINYWG

Kingston Norman Manley

Fri 18/9

2:57 p.m.-11:52 a.m.

2 stops20h 55m

Winnipeg

Fri 25/9

2:00 p.m.-1:51 p.m.

3 stops23h 51m

C$ 1,404

KingstonWinnipeg

KIN Kingston Norman Manley - YWG Winnipeg

KINYWG

Kingston Norman Manley

Fri 18/9

2:57 p.m.-11:52 a.m.

3 stops20h 55m

Winnipeg

Fri 25/9

2:00 p.m.-1:51 p.m.

3 stops23h 51m

C$ 1,410

KingstonWinnipeg

KIN Kingston Norman Manley - YWG Winnipeg

KINYWG

Kingston Norman Manley

Tue 8/9

2:57 p.m.-11:52 a.m.

2 stops20h 55m

Winnipeg

Thu 15/10

2:00 p.m.-1:58 p.m.

3 stops23h 58m

C$ 1,534

KingstonWinnipeg

KIN Kingston Norman Manley - YWG Winnipeg

KINYWG

Kingston Norman Manley

Tue 8/9

2:57 p.m.-4:27 p.m.

3 stops25h 30m

Winnipeg

Thu 15/10

2:00 p.m.-1:58 p.m.

3 stops23h 58m

C$ 1,546

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 19 resultsSorted by cheapest first
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See travel insights to Winnipeg from

How to get the cheapest flight ticket from Caribbean Islands to Winnipeg

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Winnipeg?

The cheapest month to fly to Winnipeg from Caribbean Islands is in May. Flight prices, which tend to average around C$ 0, are often lower during this time because this is during the off-season. If you are unable to visit Winnipeg during the month of May, then departing from Caribbean Islands during the month April is also very affordable. Most momondo users find prices during this month for around C$ 0.

What is the cheapest Caribbean Islands to Winnipeg flight route?

Fly from Montego Bay Sangster Intl to Winnipeg for the best Caribbean Islands - Winnipeg flight prices

What cabin class options are available on Caribbean Islands to Winnipeg flights?

There is only 1 cabin class available to choose from on Caribbean Islands to Winnipeg flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Caribbean Islands to Winnipeg flights?

No. A direct flight is the cheapest option for a flight between Caribbean Islands to Winnipeg.

Cheap Caribbean Islands to Winnipeg flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Caribbean Islands to Winnipeg

Fastest flight time

13h 55m

Direct flights

None
The fastest flight from Caribbean Islands to Winnipeg takes 13h 55m
There are no direct flights from Caribbean Islands to Winnipeg. There are no popular flight routes from Caribbean Islands to Winnipeg.
Search flight deals

Frequently asked questions about flying from Caribbean Islands to Winnipeg

  • When did momondo last update prices for flights from Caribbean Islands to Winnipeg Airport?

    Prices for flights from Caribbean Islands to Winnipeg Airport were last updated today.

  • How old do you have to be to fly from Caribbean Islands to Winnipeg Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Caribbean Islands to Winnipeg Airport.

  • What documentation or ID do you need to fly to Winnipeg Airport?

    The necessary travel and health documents for your Winnipeg Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Caribbean Islands to Winnipeg?

Best airlines flying from Caribbean Islands to Winnipeg

Compare and see reviews for airlines that fly from Caribbean Islands to Winnipeg with momondo
Airline
Rating
Free Cancellation
Price
WestJetPriceFrom C$ 500Free CancellationRating
7.2
3,426 reviews
Search WestJet flights
Air CanadaPriceFrom C$ 882Free CancellationRating
7.1
11,431 reviews
Search Air Canada flights

Travelling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Portage la Prairie
Morden
Selkirk

Why use momondo?

Why should I use momondo to find a flight deal from Caribbean Islands to Winnipeg?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Caribbean Islands to Winnipeg. momondo saves you time and could save you money on your trip.

Can I find flights from Caribbean Islands to Winnipeg with flexible booking policies on momondo?

momondo does allow users to show only those flights to Winnipeg from Caribbean Islands which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Caribbean Islands to Winnipeg?

Once you have performed a search for Caribbean Islands to Winnipeg flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Caribbean Islands to Winnipeg right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Caribbean Islands to Winnipeg now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Winnipeg and let you know when they change.

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