Cheap flights from Winnipeg to Caribbean Islands from C$ 218

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 16/1. 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.
Multiple Airlines Logo
8:00 a.m. - 3:35 p.m.
YWG
-
SJU
29h 35m1 stop
Multiple Airlines Logo
4:11 p.m. - 6:05 p.m.
SJU
-
YWG
27h 54m2 stops
C$ 455Multiple Airlines
Mon, 2 Feb - Thu, 26 Feb
WestJet Logo
12:40 p.m. - 10:37 a.m.
YWG
-
NAS
20h 57m2 stops
WestJet Logo
4:50 p.m. - 11:35 a.m.
NAS
-
YWG
19h 45m1 stop
C$ 507WestJet
Wed, 14 Jan - Tue, 20 Jan
Air Canada Logo
6:00 a.m. - 8:10 p.m.
YWG
-
NAS
13h 10m2 stops
Air Canada Logo
1:15 p.m. - 10:16 a.m.
NAS
-
YWG
22h 01m1 stop
C$ 523Air Canada
Wed, 14 Jan - Tue, 20 Jan
WestJet Logo
5:00 a.m. - 4:33 p.m.
YWG
-
POP
9h 33m1 stop
WestJet Logo
5:30 p.m. - 11:32 a.m.
POP
-
YWG
20h 02m1 stop
C$ 526WestJet
Wed, 21 Jan - Wed, 4 Feb
WestJet Logo
12:55 p.m. - 6:20 a.m.
YWG
-
PUJ
15h 25m2 stops
WestJet Logo
6:20 a.m. - 10:40 p.m.
PUJ
-
YWG
17h 20m2 stops
C$ 526WestJet
Fri, 6 Mar - Mon, 9 Mar
Air Canada Logo
6:00 a.m. - 8:10 p.m.
YWG
-
NAS
13h 10m2 stops
Air Canada Logo
9:10 p.m. - 4:35 p.m.
NAS
-
YWG
20h 25m2 stops
C$ 532Air Canada
Wed, 14 Jan - Tue, 20 Jan
United Airlines Logo
2:20 p.m. - 1:33 p.m.
YWG
-
NAS
22h 13m2 stops
United Airlines Logo
2:35 p.m. - 11:57 a.m.
NAS
-
YWG
22h 22m2 stops
C$ 561United Airlines
Fri, 27 Feb - Fri, 6 Mar
United Airlines Logo
2:20 p.m. - 2:05 p.m.
YWG
-
MBJ
46h 45m2 stops
United Airlines Logo
2:20 p.m. - 11:57 a.m.
MBJ
-
YWG
21h 37m2 stops
C$ 627United Airlines
Tue, 3 Mar - Tue, 17 Mar
Air Transat Logo
12:10 p.m. - 7:00 p.m.
YWG
-
POP
28h 50m1 stop
Air Transat Logo
1:50 p.m. - 3:30 p.m.
POP
-
YWG
27h 40m1 stop
C$ 908Air Transat
Sat, 24 Jan - Wed, 28 Jan
Flair Airlines Logo
8:20 p.m. - 2:30 p.m.
YWG
-
KIN
17h 10m1 stop
Flair Airlines Logo
3:15 a.m. - 7:35 p.m.
KIN
-
YWG
17h 20m1 stop
C$ 1,185Flair Airlines
Wed, 17 Dec - Tue, 30 Dec

WestJet flights from Winnipeg to Caribbean Islands

Our best WestJet deals on Winnipeg to Caribbean Islands flight tickets
WestJet
14 Jan
YWG12:40 p.m.Winnipeg
20h 57m
2 stops
NAS10:37 a.m.Nassau Intl
20 Jan
NAS4:50 p.m.Nassau Intl
19h 45m
1 stop
YWG11:35 a.m.Winnipeg
WestJet
6 Mar
YWG12:55 p.m.Winnipeg
15h 25m
2 stops
PUJ6:20 a.m.Punta Cana
9 Mar
PUJ6:20 a.m.Punta Cana
17h 20m
2 stops
YWG10:40 p.m.Winnipeg
WestJet
11 Jan
YWG5:00 a.m.Winnipeg
23h 25m
1 stop
PUJ6:25 a.m.Punta Cana
18 Jan
PUJ4:30 p.m.Punta Cana
24h 51m
2 stops
YWG3:21 p.m.Winnipeg

American Airlines flights from Winnipeg to Caribbean Islands

Our best American Airlines deals on Winnipeg to Caribbean Islands flight tickets
American Airlines
2 Feb
YWG6:00 a.m.Winnipeg
15h 59m
2 stops
SJU11:59 p.m.San Juan Luis Munoz Marin Intl
26 Feb
SJU7:00 p.m.San Juan Luis Munoz Marin Intl
30h 35m
3 stops
YWG11:35 p.m.Winnipeg
C$ 1,291
Find similar
American Airlines
10 Dec
YWG12:10 p.m.Winnipeg
23h 22m
3 stops
PUJ1:32 p.m.Punta Cana
17 Dec
PUJ5:30 p.m.Punta Cana
32h 05m
3 stops
YWG11:35 p.m.Winnipeg
C$ 3,954
Find similar
American Airlines
6 Dec
YWG6:00 a.m.Winnipeg
13h 12m
2 stops
NAS8:12 p.m.Nassau Intl
8 Dec
NAS6:45 p.m.Nassau Intl
53h 50m
3 stops
YWG11:35 p.m.Winnipeg
C$ 4,372
Find similar

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 4 December 2025.
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

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Mon 2/2

8:00 a.m.-3:35 p.m.

1 stop29h 35m

San Juan Luis Munoz Marin Intl

Thu 26/2

4:11 p.m.-6:05 p.m.

2 stops27h 54m

C$ 455

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Wed 14/1

12:40 p.m.-10:37 a.m.

2 stops20h 57m

Nassau Intl

Tue 20/1

4:50 p.m.-11:35 a.m.

1 stop19h 45m

C$ 507

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Wed 14/1

6:00 a.m.-8:10 p.m.

2 stops13h 10m

Nassau Intl

Tue 20/1

1:15 p.m.-10:16 a.m.

1 stop22h 01m

C$ 523

WinnipegPuerto Plata

YWG - POP

YWGPOP

Winnipeg

Wed 21/1

5:00 a.m.-4:33 p.m.

1 stop9h 33m

Puerto Plata La Union

Wed 4/2

5:30 p.m.-11:32 a.m.

1 stop20h 02m

C$ 526

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Fri 6/3

12:55 p.m.-6:20 a.m.

2 stops15h 25m

Punta Cana

Mon 9/3

6:20 a.m.-10:40 p.m.

2 stops17h 20m

C$ 526

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Wed 14/1

6:00 a.m.-8:10 p.m.

2 stops13h 10m

Nassau Intl

Tue 20/1

9:10 p.m.-4:35 p.m.

2 stops20h 25m

C$ 532

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Fri 27/2

2:20 p.m.-1:33 p.m.

2 stops22h 13m

Nassau Intl

Fri 6/3

2:35 p.m.-11:57 a.m.

2 stops22h 22m

C$ 561

WinnipegMontego Bay

YWG - MBJ

YWGMBJ

Winnipeg

Tue 3/3

2:20 p.m.-2:05 p.m.

2 stops46h 45m

Montego Bay Sangster Intl

Tue 17/3

2:20 p.m.-11:57 a.m.

2 stops21h 37m

C$ 627

WinnipegPuerto Plata

YWG - POP

YWGPOP

Winnipeg

Sat 24/1

12:10 p.m.-7:00 p.m.

1 stop28h 50m

Puerto Plata La Union

Wed 28/1

1:50 p.m.-3:30 p.m.

1 stop27h 40m

C$ 908

WinnipegKingston

YWG - KIN

YWGKIN

Winnipeg

Wed 17/12

8:20 p.m.-2:30 p.m.

1 stop17h 10m

Kingston Norman Manley

Tue 30/12

3:15 a.m.-7:35 p.m.

1 stop17h 20m

C$ 1,185

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest 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$ 681. 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$ 737.

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 Monday when prices can be found for as low as C$ 796. 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$ 1,522.

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

According to our data, the cheapest time of day to fly to Caribbean Islands is in the afternoon. momondo users have found flights departing from Winnipeg to Caribbean Islands in the afternoon for as low as C$ 799. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Flights in the morning are often more expensive with an average ticket price of C$ 1,128.

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$ 805 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$ 728 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?

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

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 25m

Direct flights

Mon and Sun

Airports in Caribbean Islands

1 airport
The fastest flight from Winnipeg to Caribbean Islands takes 5h 25m
Direct flights go from Winnipeg to Caribbean Islands on Monday and Sunday. There are no airlines offering direct flights.
There is 1 airport near Caribbean Islands: 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
Air CanadaPriceFrom C$ 491Free CancellationRating
7.1
10,500 reviews
Search Air Canada flights
WestJetPriceFrom C$ 511Free CancellationRating
7.2
3,193 reviews
Search WestJet flights
United AirlinesPriceFrom C$ 551Free CancellationRating
7.4
9,066 reviews
Search United Airlines flights
DeltaPriceFrom C$ 707Free CancellationRating
7.9
8,011 reviews
Search Delta flights
Sunwing AirlinesPriceFrom C$ 715Free CancellationRating
6.7
36 reviews
Search Sunwing Airlines flights
Air TransatPriceFrom C$ 811Free CancellationRating
7.8
480 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
Sat 3/1
Sat 10/1

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Popular flights according to clicks in the last 7 days on momondo