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Cheap flights from Caribbean to Winnipeg from C$ 450

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 to Winnipeg departing on 12/7. 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

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Find the cheapest flights from Caribbean to Winnipeg

Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
12:00 p.m. - 9:45 a.m.
NAS
-
YWG
22h 45m
1 stop
WestJet Logo
4:55 p.m. - 11:10 a.m.
YWG
-
NAS
17h 15m
2 stops
C$ 753WestJet
Wed, 17 Jun - Thu, 13 Aug
WestJet Logo
12:00 p.m. - 2:25 p.m.
NAS
-
YWG
27h 25m
1 stop
WestJet Logo
4:25 p.m. - 11:10 a.m.
YWG
-
NAS
17h 45m
1 stop
C$ 765WestJet
Wed, 17 Jun - Thu, 13 Aug
WestJet Logo
12:00 p.m. - 12:00 p.m.
NAS
-
YWG
25h 00m
2 stops
WestJet Logo
7:10 p.m. - 11:10 a.m.
YWG
-
NAS
15h 00m
2 stops
C$ 775WestJet
Wed, 17 Jun - Thu, 13 Aug
Air Canada Logo
3:05 p.m. - 11:15 a.m.
KIN
-
YWG
20h 10m
1 stop
Air Canada Logo
7:10 p.m. - 1:55 p.m.
YWG
-
KIN
18h 45m
1 stop
C$ 814Air Canada
Wed, 29 Jul - Sun, 16 Aug
Air Canada Logo
3:05 p.m. - 10:05 a.m.
KIN
-
YWG
19h 00m
2 stops
Air Canada Logo
7:10 p.m. - 1:55 p.m.
YWG
-
KIN
18h 45m
1 stop
C$ 818Air Canada
Wed, 29 Jul - Sun, 16 Aug
Air Canada Logo
3:05 p.m. - 10:05 a.m.
KIN
-
YWG
19h 00m
2 stops
Air Canada Logo
1:30 p.m. - 1:55 p.m.
YWG
-
KIN
24h 25m
2 stops
C$ 873Air Canada
Wed, 29 Jul - Sun, 16 Aug
Air Canada Logo
12:25 p.m. - 10:05 a.m.
GCM
-
YWG
21h 40m
2 stops
Air Canada Logo
6:45 p.m. - 12:30 p.m.
YWG
-
GCM
17h 45m
2 stops
C$ 1,552Air Canada
Thu, 25 Jun - Thu, 2 Jul
United Airlines Logo
2:56 p.m. - 11:15 a.m.
KIN
-
YWG
20h 19m
3 stops
United Airlines Logo
3:20 p.m. - 1:54 p.m.
YWG
-
KIN
22h 34m
3 stops
C$ 2,327United Airlines
Wed, 29 Jul - Sun, 16 Aug
Multiple Airlines Logo
6:30 p.m. - 10:05 a.m.
NAS
-
YWG
16h 35m
2 stops
Multiple Airlines Logo
5:15 p.m. - 1:45 p.m.
YWG
-
NAS
19h 30m
3 stops
C$ 2,568Multiple Airlines
Wed, 17 Jun - Thu, 13 Aug
United Airlines Logo
2:56 p.m. - 11:15 a.m.
KIN
-
YWG
20h 19m
3 stops
United Airlines Logo
7:00 a.m. - 1:54 p.m.
YWG
-
KIN
30h 54m
2 stops
C$ 3,245United Airlines
Wed, 29 Jul - Sun, 16 Aug

Air Canada flights from Caribbean to Winnipeg

Our best Air Canada deals on Caribbean to Winnipeg flight tickets
Air Canada
29 Jul
KIN3:05 p.m.Kingston Norman Manley
20h 10m
1 stop
YWG11:15 a.m.Winnipeg
16 Aug
YWG7:10 p.m.Winnipeg
18h 45m
1 stop
KIN1:55 p.m.Kingston Norman Manley
C$ 814
Air Canada
29 Jul
KIN3:05 p.m.Kingston Norman Manley
19h 00m
2 stops
YWG10:05 a.m.Winnipeg
16 Aug
YWG7:10 p.m.Winnipeg
18h 45m
1 stop
KIN1:55 p.m.Kingston Norman Manley
C$ 818
Air Canada
29 Jul
KIN3:05 p.m.Kingston Norman Manley
19h 00m
2 stops
YWG10:05 a.m.Winnipeg
16 Aug
YWG1:30 p.m.Winnipeg
24h 25m
2 stops
KIN1:55 p.m.Kingston Norman Manley
C$ 873

United Airlines flights from Caribbean to Winnipeg

Our best United Airlines deals on Caribbean to Winnipeg flight tickets
United Airlines
29 Jul
KIN2:56 p.m.Kingston Norman Manley
20h 19m
3 stops
YWG11:15 a.m.Winnipeg
16 Aug
YWG3:20 p.m.Winnipeg
22h 34m
3 stops
KIN1:54 p.m.Kingston Norman Manley
C$ 2,327
United Airlines
29 Jul
KIN2:56 p.m.Kingston Norman Manley
20h 19m
3 stops
YWG11:15 a.m.Winnipeg
16 Aug
YWG7:00 a.m.Winnipeg
30h 54m
2 stops
KIN1:54 p.m.Kingston Norman Manley
C$ 3,245
United Airlines
25 Jun
GCM1:35 p.m.George Town Owen Roberts Intl
20h 25m
3 stops
YWG10:00 a.m.Winnipeg
2 Jul
YWG12:56 p.m.Winnipeg
23h 34m
2 stops
GCM12:30 p.m.George Town Owen Roberts Intl
C$ 6,485

momondo Fare Finder

 
Customize your flight search to find flights from Caribbean 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 31 May 2026.
Use the filters below to find and compare flights from Caribbean to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

NassauWinnipeg

NAS - YWG

NASYWG

Nassau Intl

Wed 17/6

12:00 p.m.-9:45 a.m.

1 stop22h 45m

Winnipeg

Thu 13/8

4:55 p.m.-11:10 a.m.

2 stops17h 15m

C$ 753

NassauWinnipeg

NAS - YWG

NASYWG

Nassau Intl

Wed 17/6

12:00 p.m.-2:25 p.m.

1 stop27h 25m

Winnipeg

Thu 13/8

4:25 p.m.-11:10 a.m.

1 stop17h 45m

C$ 765

NassauWinnipeg

NAS - YWG

NASYWG

Nassau Intl

Wed 17/6

12:00 p.m.-12:00 p.m.

2 stops25h 00m

Winnipeg

Thu 13/8

7:10 p.m.-11:10 a.m.

2 stops15h 00m

C$ 775

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Wed 29/7

3:05 p.m.-11:15 a.m.

1 stop20h 10m

Winnipeg

Sun 16/8

7:10 p.m.-1:55 p.m.

1 stop18h 45m

C$ 814

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Wed 29/7

3:05 p.m.-10:05 a.m.

2 stops19h 00m

Winnipeg

Sun 16/8

7:10 p.m.-1:55 p.m.

1 stop18h 45m

C$ 818

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Wed 29/7

3:05 p.m.-10:05 a.m.

2 stops19h 00m

Winnipeg

Sun 16/8

1:30 p.m.-1:55 p.m.

2 stops24h 25m

C$ 873

George TownWinnipeg

GCM - YWG

GCMYWG

George Town Owen Roberts Intl

Thu 25/6

12:25 p.m.-10:05 a.m.

2 stops21h 40m

Winnipeg

Thu 2/7

6:45 p.m.-12:30 p.m.

2 stops17h 45m

C$ 1,552

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Wed 29/7

2:56 p.m.-11:15 a.m.

3 stops20h 19m

Winnipeg

Sun 16/8

3:20 p.m.-1:54 p.m.

3 stops22h 34m

C$ 2,327
Quickest round-trip

NassauWinnipeg

NAS - YWG

NASYWG

Nassau Intl

Wed 17/6

6:30 p.m.-10:05 a.m.

2 stops16h 35m

Winnipeg

Thu 13/8

5:15 p.m.-1:45 p.m.

3 stops19h 30m

C$ 2,568

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Wed 29/7

2:56 p.m.-11:15 a.m.

3 stops20h 19m

Winnipeg

Sun 16/8

7:00 a.m.-1:54 p.m.

2 stops30h 54m

C$ 3,245

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 15 resultsSorted by cheapest first
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See travel insights to Winnipeg from

How to get the cheapest flight ticket from Caribbean 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 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 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 to Winnipeg flight route?

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

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

There is only 1 cabin class available to choose from on Caribbean 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 to Winnipeg flights?

You could potentially save up to 45% on your flight if you consider stops on a Caribbean to Winnipeg flight.

Cheap Caribbean to Winnipeg flight deals and tips

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

Fastest flight time

11h 10m

Direct flights

None
The fastest flight from Caribbean to Winnipeg takes 11h 10m
There are no direct flights from Caribbean to Winnipeg. There are no popular flight routes from Caribbean to Winnipeg.
Search flight deals

Frequently asked questions about flying from Caribbean to Winnipeg

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

    Prices for flights from Caribbean to Winnipeg Airport refresh daily.

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Caribbean to Winnipeg Airport.

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

    The travel and health documents required for your trip to Winnipeg Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Winnipeg Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

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

Best airlines flying from Caribbean to Winnipeg

Compare and see reviews for airlines that fly from Caribbean to Winnipeg with momondo
Airline
Rating
Free Cancellation
Price
WestJetPriceFrom C$ 615Free CancellationRating
7.2
3,350 reviews
Search WestJet flights

Travelling to a place near Winnipeg?

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

Why use momondo?

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

Finding the right flight to Winnipeg from Caribbean is quick and easy when you have a range of options in front of you, from reputable agents and recognizable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Winnipeg quick and easy, saving you time and money.

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

Yes. momondo allows you to filter the results for Caribbean to Winnipeg flights to just show those with flexible booking policies.

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

momondo provides multiple filters to help you find the best flight to Winnipeg from Caribbean. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

If you are not ready to book a flight from Caribbean 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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