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Cheap flights from Caribbean to Winnipeg from C$ 812

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 5/8. 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

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Caribbean to Winnipeg

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
6:30 p.m. - 8:01 p.m.
NAS
-
YWG
26h 31m
2 stops
Air Canada Logo
7:10 p.m. - 1:35 p.m.
YWG
-
NAS
41h 25m
2 stops
C$ 1,022Air Canada
Fri, 7 Aug - Mon, 10 Aug
Air Canada Logo
6:30 p.m. - 8:01 p.m.
NAS
-
YWG
26h 31m
2 stops
Air Canada Logo
7:10 p.m. - 1:35 p.m.
YWG
-
NAS
41h 25m
2 stops
C$ 1,177Air Canada
Fri, 7 Aug - Mon, 10 Aug
Multiple Airlines Logo
12:00 p.m. - 4:25 p.m.
NAS
-
YWG
29h 25m
1 stop
Multiple Airlines Logo
9:05 p.m. - 4:15 p.m.
YWG
-
NAS
42h 10m
2 stops
C$ 1,233Multiple Airlines
Fri, 7 Aug - Mon, 10 Aug
WestJet Logo
3:30 p.m. - 3:55 p.m.
KIN
-
YWG
24h 25m
2 stops
WestJet Logo
8:00 a.m. - 2:30 p.m.
YWG
-
KIN
30h 30m
2 stops
C$ 1,388WestJet
Fri, 7 Aug - Sun, 9 Aug
WestJet Logo
3:30 p.m. - 9:40 p.m.
KIN
-
YWG
30h 10m
2 stops
WestJet Logo
7:45 a.m. - 2:30 p.m.
YWG
-
KIN
30h 45m
1 stop
C$ 1,401WestJet
Fri, 7 Aug - Sun, 9 Aug
WestJet Logo
3:30 p.m. - 8:20 p.m.
KIN
-
YWG
28h 50m
1 stop
WestJet Logo
7:45 a.m. - 2:30 p.m.
YWG
-
KIN
30h 45m
1 stop
C$ 1,482WestJet
Fri, 7 Aug - Sun, 9 Aug
Air Canada Logo
3:05 p.m. - 8:01 p.m.
KIN
-
YWG
28h 56m
2 stops
Air Canada Logo
1:30 p.m. - 1:55 p.m.
YWG
-
KIN
24h 25m
2 stops
C$ 1,502Air Canada
Fri, 7 Aug - Sun, 9 Aug
WestJet Logo
12:00 p.m. - 3:55 p.m.
NAS
-
YWG
28h 55m
2 stops
WestJet Logo
10:30 p.m. - 11:10 a.m.
YWG
-
NAS
35h 40m
2 stops
C$ 1,530WestJet
Fri, 7 Aug - Mon, 10 Aug
Air Canada Logo
6:30 p.m. - 10:00 a.m.
NAS
-
YWG
16h 30m
1 stop
Air Canada Logo
5:00 a.m. - 5:30 p.m.
YWG
-
NAS
11h 30m
1 stop
C$ 1,688Air Canada
Fri, 7 Aug - Mon, 10 Aug
Air Canada Logo
6:30 p.m. - 10:00 a.m.
NAS
-
YWG
16h 30m
1 stop
Air Canada Logo
8:15 a.m. - 5:30 p.m.
YWG
-
NAS
8h 15m
1 stop
C$ 1,808Air Canada
Fri, 7 Aug - Mon, 10 Aug

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United Airlines flights from Caribbean to Winnipeg

Our best United Airlines deals on Caribbean to Winnipeg flight tickets
United Airlines
7 Aug
NAS3:59 p.m.Nassau Intl
7h 39m
1 stop
YWG10:38 p.m.Winnipeg
10 Aug
YWG7:00 a.m.Winnipeg
6h 57m
1 stop
NAS2:57 p.m.Nassau Intl
C$ 2,455
United Airlines
7 Aug
NAS3:59 p.m.Nassau Intl
7h 39m
1 stop
YWG10:38 p.m.Winnipeg
10 Aug
YWG7:00 a.m.Winnipeg
6h 57m
1 stop
NAS2:57 p.m.Nassau Intl
C$ 2,828

Air Canada flights from Caribbean to Winnipeg

Our best Air Canada deals on Caribbean to Winnipeg flight tickets
Air Canada
7 Aug
NAS6:30 p.m.Nassau Intl
26h 31m
2 stops
YWG8:01 p.m.Winnipeg
10 Aug
YWG7:10 p.m.Winnipeg
41h 25m
2 stops
NAS1:35 p.m.Nassau Intl
C$ 1,022
Air Canada
7 Aug
NAS6:30 p.m.Nassau Intl
26h 31m
2 stops
YWG8:01 p.m.Winnipeg
10 Aug
YWG7:10 p.m.Winnipeg
41h 25m
2 stops
NAS1:35 p.m.Nassau Intl
C$ 1,177
Air Canada
7 Aug
KIN3:05 p.m.Kingston Norman Manley
28h 56m
2 stops
YWG8:01 p.m.Winnipeg
9 Aug
YWG1:30 p.m.Winnipeg
24h 25m
2 stops
KIN1:55 p.m.Kingston Norman Manley
C$ 1,502

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 27 July 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

Fri 7/8

6:30 p.m.-8:01 p.m.

2 stops26h 31m

Winnipeg

Mon 10/8

7:10 p.m.-1:35 p.m.

2 stops41h 25m

C$ 1,022

NassauWinnipeg

NAS - YWG

NASYWG

Nassau Intl

Fri 7/8

6:30 p.m.-8:01 p.m.

2 stops26h 31m

Winnipeg

Mon 10/8

7:10 p.m.-1:35 p.m.

2 stops41h 25m

C$ 1,177

NassauWinnipeg

NAS - YWG

NASYWG

Nassau Intl

Fri 7/8

12:00 p.m.-4:25 p.m.

1 stop29h 25m

Winnipeg

Mon 10/8

9:05 p.m.-4:15 p.m.

2 stops42h 10m

C$ 1,233

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Fri 7/8

3:30 p.m.-3:55 p.m.

2 stops24h 25m

Winnipeg

Sun 9/8

8:00 a.m.-2:30 p.m.

2 stops30h 30m

C$ 1,388

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Fri 7/8

3:30 p.m.-9:40 p.m.

2 stops30h 10m

Winnipeg

Sun 9/8

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

1 stop30h 45m

C$ 1,401

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Fri 7/8

3:30 p.m.-8:20 p.m.

1 stop28h 50m

Winnipeg

Sun 9/8

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

1 stop30h 45m

C$ 1,482

KingstonWinnipeg

KIN - YWG

KINYWG

Kingston Norman Manley

Fri 7/8

3:05 p.m.-8:01 p.m.

2 stops28h 56m

Winnipeg

Sun 9/8

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

2 stops24h 25m

C$ 1,502

NassauWinnipeg

NAS - YWG

NASYWG

Nassau Intl

Fri 7/8

12:00 p.m.-3:55 p.m.

2 stops28h 55m

Winnipeg

Mon 10/8

10:30 p.m.-11:10 a.m.

2 stops35h 40m

C$ 1,530

NassauWinnipeg

NAS - YWG

NASYWG

Nassau Intl

Fri 7/8

6:30 p.m.-10:00 a.m.

1 stop16h 30m

Winnipeg

Mon 10/8

5:00 a.m.-5:30 p.m.

1 stop11h 30m

C$ 1,688
Quickest round-trip

NassauWinnipeg

NAS - YWG

NASYWG

Nassau Intl

Fri 7/8

6:30 p.m.-10:00 a.m.

1 stop16h 30m

Winnipeg

Mon 10/8

8:15 a.m.-5:30 p.m.

1 stop8h 15m

C$ 1,808

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 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

7h 39m

Direct flights

None
The fastest flight from Caribbean to Winnipeg takes 7h 39m
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$ 502Free CancellationRating
7.2
3,415 reviews
Search WestJet flights
Air CanadaPriceFrom C$ 885Free CancellationRating
7.1
11,391 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 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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