Cheap flights from Winnipeg to Caribbean Islands from C$ 204

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Winnipeg to Caribbean Islands departing on 25/4. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
6:45 a.m. - 3:40 p.m.
YWG
-
NAS
55h 55m
2 stops
WestJet Logo
11:25 a.m. - 12:07 p.m.
NAS
-
YWG
25h 42m
2 stops
C$ 504WestJet
jue., 2 abr. - dom., 12 abr.
WestJet Logo
5:00 a.m. - 3:40 p.m.
YWG
-
NAS
9h 40m
1 stop
WestJet Logo
4:50 p.m. - 11:32 a.m.
NAS
-
YWG
19h 42m
1 stop
C$ 508WestJet
sáb., 4 abr. - lun., 13 abr.
Multiple Airlines Logo
8:20 p.m. - 12:25 p.m.
YWG
-
PUJ
14h 05m
1 stop
Multiple Airlines Logo
7:05 p.m. - 7:35 p.m.
PUJ
-
YWG
25h 30m
1 stop
C$ 571Multiple Airlines
mar., 3 mar. - mar., 10 mar.
Multiple Airlines Logo
8:20 p.m. - 4:36 p.m.
YWG
-
PUJ
18h 16m
2 stops
Multiple Airlines Logo
4:35 p.m. - 11:13 a.m.
PUJ
-
YWG
20h 38m
2 stops
C$ 598Multiple Airlines
dom., 1 feb. - mar., 3 feb.
Air Canada Logo
6:00 a.m. - 12:25 p.m.
YWG
-
GCM
29h 25m
2 stops
Air Canada Logo
11:30 a.m. - 8:28 p.m.
GCM
-
YWG
32h 58m
2 stops
C$ 601Air Canada
lun., 2 mar. - lun., 9 mar.
Air Canada Logo
6:00 a.m. - 2:00 p.m.
YWG
-
AUA
31h 00m
2 stops
Air Canada Logo
4:05 p.m. - 9:53 a.m.
AUA
-
YWG
18h 48m
1 stop
C$ 601Air Canada
sáb., 25 abr. - mar., 28 abr.
United Airlines Logo
2:00 p.m. - 12:40 p.m.
YWG
-
PUJ
21h 40m
2 stops
United Airlines Logo
4:40 p.m. - 11:52 a.m.
PUJ
-
YWG
20h 12m
2 stops
C$ 614United Airlines
jue., 7 may. - mié., 13 may.
United Airlines Logo
2:20 p.m. - 3:14 p.m.
YWG
-
PUJ
23h 54m
2 stops
United Airlines Logo
2:28 p.m. - 11:57 a.m.
PUJ
-
YWG
22h 29m
2 stops
C$ 619United Airlines
mié., 18 mar. - mar., 24 mar.
Porter Airlines Logo
4:25 p.m. - 2:00 p.m.
YWG
-
GCM
20h 35m
1 stop
Porter Airlines Logo
5:25 p.m. - 3:30 p.m.
GCM
-
YWG
23h 05m
1 stop
C$ 955Porter Airlines
sáb., 31 ene. - sáb., 14 feb.
Porter Airlines Logo
4:25 p.m. - 2:00 p.m.
YWG
-
GCM
20h 35m
1 stop
Porter Airlines Logo
5:25 p.m. - 11:13 a.m.
GCM
-
YWG
18h 48m
2 stops
C$ 966Porter Airlines
sáb., 31 ene. - sáb., 14 feb.

Delta flights from Winnipeg to Caribbean Islands

Our best Delta deals on Winnipeg to Caribbean Islands flight tickets
Delta
12 Feb
YWG5:19 p.m.Winnipeg
19h 59m
1 stop
SJU3:18 p.m.San Juan Luis Munoz Marin Intl
15 Feb
SJU6:15 a.m.San Juan Luis Munoz Marin Intl
10h 54m
1 stop
YWG3:09 p.m.Winnipeg
C$ 1,442
Delta
29 Jan
YWG5:21 p.m.Winnipeg
20h 32m
2 stops
POP3:53 p.m.Puerto Plata La Union
26 Feb
POP4:55 p.m.Puerto Plata La Union
25h 32m
2 stops
YWG4:27 p.m.Winnipeg
C$ 2,135
Delta
22 Jan
YWG5:21 p.m.Winnipeg
18h 19m
2 stops
GCM12:40 p.m.George Town Owen Roberts Intl
1 Feb
GCM2:05 p.m.George Town Owen Roberts Intl
21h 58m
2 stops
YWG11:03 a.m.Winnipeg
C$ 5,803

WestJet flights from Winnipeg to Caribbean Islands

Our best WestJet deals on Winnipeg to Caribbean Islands flight tickets
WestJet
2 Apr
YWG6:45 a.m.Winnipeg
55h 55m
2 stops
NAS3:40 p.m.Nassau Intl
12 Apr
NAS11:25 a.m.Nassau Intl
25h 42m
2 stops
YWG12:07 p.m.Winnipeg
C$ 504
WestJet
4 Apr
YWG5:00 a.m.Winnipeg
9h 40m
1 stop
NAS3:40 p.m.Nassau Intl
13 Apr
NAS4:50 p.m.Nassau Intl
19h 42m
1 stop
YWG11:32 a.m.Winnipeg
C$ 508
WestJet
2 Apr
YWG4:10 p.m.Winnipeg
22h 30m
2 stops
NAS3:40 p.m.Nassau Intl
12 Apr
NAS11:25 a.m.Nassau Intl
14h 14m
1 stop
YWG12:39 a.m.Winnipeg
C$ 512

momondo Fare Finder

 
Customize your flight search to find flights from Winnipeg to Caribbean Islands 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 20 enero 2026.
Use the filters below to find and compare flights from Winnipeg to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

jue. 2/4

6:45 a.m.-3:40 p.m.

2 stops55h 55m

Nassau Intl

dom. 12/4

11:25 a.m.-12:07 p.m.

2 stops25h 42m

C$ 504

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

sáb. 4/4

5:00 a.m.-3:40 p.m.

1 stop9h 40m

Nassau Intl

lun. 13/4

4:50 p.m.-11:32 a.m.

1 stop19h 42m

C$ 508

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

mar. 3/3

8:20 p.m.-12:25 p.m.

1 stop14h 05m

Punta Cana

mar. 10/3

7:05 p.m.-7:35 p.m.

1 stop25h 30m

C$ 571

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

dom. 1/2

8:20 p.m.-4:36 p.m.

2 stops18h 16m

Punta Cana

mar. 3/2

4:35 p.m.-11:13 a.m.

2 stops20h 38m

C$ 598

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

lun. 2/3

6:00 a.m.-12:25 p.m.

2 stops29h 25m

George Town Owen Roberts Intl

lun. 9/3

11:30 a.m.-8:28 p.m.

2 stops32h 58m

C$ 601

WinnipegOranjestad

YWG - AUA

YWGAUA

Winnipeg

sáb. 25/4

6:00 a.m.-2:00 p.m.

2 stops31h 00m

Oranjestad Reina Beatrix

mar. 28/4

4:05 p.m.-9:53 a.m.

1 stop18h 48m

C$ 601

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

jue. 7/5

2:00 p.m.-12:40 p.m.

2 stops21h 40m

Punta Cana

mié. 13/5

4:40 p.m.-11:52 a.m.

2 stops20h 12m

C$ 614

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

mié. 18/3

2:20 p.m.-3:14 p.m.

2 stops23h 54m

Punta Cana

mar. 24/3

2:28 p.m.-11:57 a.m.

2 stops22h 29m

C$ 619

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

sáb. 31/1

4:25 p.m.-2:00 p.m.

1 stop20h 35m

George Town Owen Roberts Intl

sáb. 14/2

5:25 p.m.-3:30 p.m.

1 stop23h 05m

C$ 955

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

sáb. 31/1

4:25 p.m.-2:00 p.m.

1 stop20h 35m

George Town Owen Roberts Intl

sáb. 14/2

5:25 p.m.-11:13 a.m.

2 stops18h 48m

C$ 966

Flights are sorted by cheapest round-trip flights first.

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See travel insights to Caribbean Islands from

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

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 Caribbean Islands?

In general, June is the cheapest month to fly from Winnipeg to Caribbean Islands. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 677. If you aren’t able to travel to Caribbean Islands during the month of June, then flying in July is also cheap. Prices for this month can be found on momondo for an average of C$ 732.

What is the cheapest day to depart on your flight to Caribbean Islands?

The cheapest day to depart from Winnipeg to Caribbean Islands is on a Wednesday when prices can be found for as low as C$ 959. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Caribbean Islands on Sunday is C$ 2,106.

What is the cheapest Winnipeg to Caribbean Islands flight route?

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

How far in advance should I book a flight to Caribbean Islands?

You are more likely to see cheaper flights to Caribbean Islands from Winnipeg when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around C$ 794 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Winnipeg for as low as C$ 562 on momondo.

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

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

You could potentially save up to 3% on your flight if you consider stops on a Winnipeg to Caribbean Islands flight.

Cheap Winnipeg to Caribbean Islands flight deals and tips

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

Fastest flight time

5h 30m

Direct flights

Sun

Airports in Caribbean Islands

99 airports
The fastest flight from Winnipeg to Caribbean Islands takes 5h 30m
Direct flights go from Winnipeg to Caribbean Islands on Sunday. There are no airlines offering direct flights.
There are 99 airports in Caribbean Islands. From Winnipeg there are direct flights to Montego Bay Sangster Intl (MBJ).
  • When did momondo last update prices for flights from Winnipeg Airport to Caribbean Islands?

    Prices for flights from Winnipeg Airport to Caribbean Islands refresh daily.

  • How many operators does momondo search for flights from Winnipeg Airport to Caribbean Islands?

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Winnipeg Airport to Caribbean Islands.

  • What documentation or ID do you need to fly to Caribbean Islands?

    The necessary travel and health documents for your Caribbean Islands 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 Winnipeg to Caribbean Islands?

Best airlines flying from Winnipeg to Caribbean Islands

Compare and see reviews for airlines that fly from Winnipeg to Caribbean Islands with momondo
Airline
Rating
Free Cancellation
Price
WestJetPriceFrom C$ 480Free CancellationRating
7.2
3,247 reviews
Search WestJet flights
Air CanadaPriceFrom C$ 489Free CancellationRating
7.1
10,641 reviews
Search Air Canada flights
United AirlinesPriceFrom C$ 557Free CancellationRating
7.4
9,186 reviews
Search United Airlines flights
Porter AirlinesPriceFrom C$ 607Free CancellationRating
8.0
411 reviews
Search Porter Airlines flights
DeltaPriceFrom C$ 703Free CancellationRating
7.9
8,079 reviews
Search Delta flights
Air TransatPriceFrom C$ 807Free CancellationRating
7.7
499 reviews
Search Air Transat flights

Why use momondo?

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

Finding the right flight to Caribbean Islands from Winnipeg 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 Caribbean Islands quick and easy, saving you time and money.

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

Flights from Winnipeg to Caribbean Islands with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once you have performed a search for Winnipeg to Caribbean Islands 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 Winnipeg to Caribbean Islands right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Caribbean Islands from Winnipeg. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Caribbean Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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1 adult
jue. 19/2
jue. 26/2

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