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Cheap flights from Winnipeg to Caribbean from C$ 229

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 25/1. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
11 Jan — 18 Jan1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to Caribbean

Enter your travel dates to find the best prices.

Cheapest flights from Winnipeg to Caribbean
Explore the most affordable flight options available from Winnipeg to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 12 December 2025.

Tue 23/126:00 a.m.YWG - NAS
1 stop7h 15mPorter Airlines
Mon 29/123:15 p.m.NAS - YWG
1 stop9h 20mPorter Airlines
Deal found 11/12C$ 785
Tue 23/127:05 a.m.YWG - NAS
1 stop28h 50mAir Canada
Mon 29/129:10 p.m.NAS - YWG
2 stops24h 18mAir Canada
Deal found 11/12C$ 852
Sat 27/128:00 a.m.YWG - MBJ
Nonstop5h 30mWestJet
Sun 4/16:25 p.m.MBJ - YWG
Nonstop5h 49mWestJet
Deal found 11/12C$ 909
Tue 23/128:40 a.m.YWG - NAS
2 stops51h 53mUnited Airlines
Mon 29/124:25 p.m.NAS - YWG
2 stops30h 19mUnited Airlines
Deal found 11/12C$ 960
Wed 31/128:40 a.m.YWG - POP
2 stops26h 28mUnited Airlines
Sat 28/22:15 p.m.POP - YWG
2 stops21h 34mUnited Airlines
Deal found 11/12C$ 1,285
Sat 20/128:00 a.m.YWG - MBJ
Nonstop5h 30mWestJet
Sun 4/16:25 p.m.MBJ - YWG
Nonstop5h 49mWestJet
Deal found 11/12C$ 1,353
Wed 31/126:00 a.m.YWG - SJU
3 stops26h 33mMultiple Airlines
Sun 4/13:15 p.m.SJU - YWG
2 stops32h 29mMultiple Airlines
Deal found 10/12C$ 1,425
Tue 30/128:00 a.m.YWG - PUJ
2 stops30h 50mMultiple Airlines
Sun 4/14:35 p.m.PUJ - YWG
1 stop21h 00mMultiple Airlines
Deal found 8/12C$ 1,524
Fri 19/127:30 a.m.YWG - MBJ
1 stop25h 27mMultiple Airlines
Fri 2/13:05 p.m.MBJ - YWG
1 stop11h 21mMultiple Airlines
Deal found 9/12C$ 1,561
Mon 22/126:00 a.m.YWG - MBJ
1 stop28h 15mMultiple Airlines
Wed 31/128:25 p.m.MBJ - YWG
1 stop16h 10mMultiple Airlines
Deal found 11/12C$ 1,601
Wed 31/128:05 p.m.YWG - POP
1 stop18h 28mWestJet
Sat 28/25:30 p.m.POP - YWG
1 stop27h 54mWestJet
Deal found 10/12C$ 1,682
Thu 18/128:15 a.m.YWG - CUR
1 stop28h 55mAir Canada
Thu 1/13:25 p.m.CUR - YWG
2 stops32h 19mAir Canada
Deal found 11/12C$ 1,830

Find flight deals from Winnipeg to Caribbean

Keep the following information in mind while searching for Winnipeg to Caribbean flight deals. Data was last updated 12 December 2025.

Round-trip from

C$ 519

One-way from

C$ 229

Popular in

December

Cheapest in

April

Average price

C$ 1,052

Good round-trip deal

C$ 590 or less

Good one-way deal

C$ 335 or less
WestJet
  • WestJet
  • 13/1-19/1
  • 3 total stops
  • 24h 40m total
  • Winnipeg to Caribbean
Search Deals
25/1
  • 25/1
  • 1 total stop
  • 8h 15m total
  • Winnipeg to Caribbean
Search Deals
Highest demand for flights based on searches. 12% potential increase in price (C$ 171 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 28 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Winnipeg to Caribbean.
Search Deals
Price to beat on a one-way flight from Winnipeg to Caribbean.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg to Caribbean 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, Cheapflights users made 629,999 searches. Data last updated 12 December 2025.
Use the filters below to find and compare flights from Winnipeg to Caribbean that are best for you.

Fly from

Winnipeg

Fly to

Caribbean

Route

Depart

Return

Price

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Sat 17/1

8:20 p.m.-3:35 p.m.

1 stop17h 15m

Punta Cana

Thu 22/1

4:35 p.m.-7:35 p.m.

1 stop29h 00m

C$ 517

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Tue 13/1

9:00 p.m.-1:35 p.m.

2 stops14h 35m

Punta Cana

Mon 19/1

4:30 p.m.-12:35 a.m.

1 stop10h 05m

C$ 519

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Sat 17/1

8:20 p.m.-3:35 p.m.

1 stop17h 15m

Punta Cana

Thu 22/1

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

2 stops20h 38m

C$ 523

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Wed 14/1

4:10 p.m.-3:35 p.m.

2 stops21h 25m

Punta Cana

Wed 21/1

4:30 p.m.-3:21 p.m.

2 stops24h 51m

C$ 525

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Mon 19/1

12:20 p.m.-3:50 p.m.

1 stop26h 30m

Nassau Intl

Mon 26/1

4:50 p.m.-12:42 a.m.

1 stop8h 52m

C$ 531

WinnipegNassau

YWG - NAS

YWGNAS

Winnipeg

Mon 19/1

5:30 p.m.-12:25 p.m.

1 stop17h 55m

Nassau Intl

Mon 26/1

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

1 stop22h 01m

C$ 532

WinnipegGeorge Town

YWG - GCM

YWGGCM

Winnipeg

Sat 17/1

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

1 stop20h 35m

George Town Owen Roberts Intl

Sat 24/1

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

1 stop23h 05m

C$ 541

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Mon 12/1

8:05 p.m.-1:35 p.m.

1 stop15h 30m

Punta Cana

Sun 18/1

2:30 p.m.-12:35 a.m.

1 stop12h 05m

C$ 570

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Sun 1/2

7:30 a.m.-4:36 p.m.

2 stops31h 06m

Punta Cana

Sat 7/2

4:11 p.m.-3:09 p.m.

1 stop24h 58m

C$ 575

WinnipegPunta Cana

YWG - PUJ

YWGPUJ

Winnipeg

Mon 12/1

10:55 a.m.-1:35 p.m.

2 stops24h 40m

Punta Cana

Thu 15/1

4:30 p.m.-11:53 a.m.

2 stops21h 23m

C$ 589

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

Showing 1-10 of 60 results
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Best time to book a flight from Winnipeg to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Winnipeg with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Winnipeg to Caribbean

What is the cheapest month to book a flight from Winnipeg to Caribbean?

Currently, September is the cheapest month in which you can book a flight from Winnipeg to Caribbean (average of C$ 367). Flying from Winnipeg to Caribbean in August is currently the most expensive (average of C$ 603). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from YWG to CB?

Find hourly flight availability from Winnipeg to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 12 December 2025.

When flying from Winnipeg to Caribbean, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 18% versus a flight in the afternoon.

What is the cheapest day to fly from Winnipeg to Caribbean?

Use this chart to determine the cheapest time to fly round-trip from Winnipeg to Caribbean. Price data was last updated on 16 December 2024.

Travelers seeking maximum savings on their Winnipeg to Caribbean flight should consider departing on Thursday evenings when fares are most often at their lowest. Friday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated 12 December 2025.
Get a feel of what it's like to fly with Air Transat,United Airlines, andWestJet from Winnipeg to Caribbean by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Air Transat
7.8
Good
480 reviews
Check prices

Crew

8.4

Food

6.8

Comfort

7.3

Entertainment

7.1

Boarding

7.9

Overall

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

YYZ - YUL

Easy, fast onboarding, very friendly staff. Seats were very narrow, OK for me but we were elbow to elbow with both neighbours of small size. The seat width should be indicated at the time of booking to prevent an uncomfortable situation with oversized travellers.
Air Transat
7.8
Good
480 reviews
Air Transat
7.8
Good
480 reviews
Check prices

Crew

8.4

Food

6.8

Comfort

7.3

Entertainment

7.1

Boarding

7.9

Overall

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

YYZ - YUL

Easy, fast onboarding, very friendly staff. Seats were very narrow, OK for me but we were elbow to elbow with both neighbours of small size. The seat width should be indicated at the time of booking to prevent an uncomfortable situation with oversized travellers.
United Airlines
7.4
Good
9,095 reviews
Air Transat
7.8
Good
480 reviews
Check prices

Crew

8.4

Food

6.8

Comfort

7.3

Entertainment

7.1

Boarding

7.9

Overall

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

YYZ - YUL

Easy, fast onboarding, very friendly staff. Seats were very narrow, OK for me but we were elbow to elbow with both neighbours of small size. The seat width should be indicated at the time of booking to prevent an uncomfortable situation with oversized travellers.
WestJet
7.2
Good
3,195 reviews
Air Transat
7.8
Good
480 reviews
Check prices

Crew

8.4

Food

6.8

Comfort

7.3

Entertainment

7.1

Boarding

7.9

Overall

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

YYZ - YUL

Easy, fast onboarding, very friendly staff. Seats were very narrow, OK for me but we were elbow to elbow with both neighbours of small size. The seat width should be indicated at the time of booking to prevent an uncomfortable situation with oversized travellers.
Air Canada
7.1
Good
10,516 reviews
Air Transat
7.8
Good
480 reviews
Check prices

Crew

8.4

Food

6.8

Comfort

7.3

Entertainment

7.1

Boarding

7.9

Overall

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

YYZ - YUL

Easy, fast onboarding, very friendly staff. Seats were very narrow, OK for me but we were elbow to elbow with both neighbours of small size. The seat width should be indicated at the time of booking to prevent an uncomfortable situation with oversized travellers.
Sunwing Airlines
6.7
Okay
36 reviews
Air Transat
7.8
Good
480 reviews
Check prices

Crew

8.4

Food

6.8

Comfort

7.3

Entertainment

7.1

Boarding

7.9

Overall

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

YYZ - YUL

Easy, fast onboarding, very friendly staff. Seats were very narrow, OK for me but we were elbow to elbow with both neighbours of small size. The seat width should be indicated at the time of booking to prevent an uncomfortable situation with oversized travellers.

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Winnipeg to Caribbean?

    Winnipeg (YWG), located 7.3 km from the city centre, is the airport you fly out of when you book flights from Winnipeg to Caribbean.

  • How long is the flight from Winnipeg to Caribbean?

    Airlines like Flair Airlines, WestJet, and Air Canada fly from Winnipeg to Caribbean in about 14h 35m. The time it takes to get you to your destination can typically vary by up to 3h 20m. Winnipeg and Caribbean are separated by a distance of 4323 km. Both multi-stop and direct flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Winnipeg to Caribbean one-way?

    The cheapest airlines for a one-way flight from Winnipeg to Caribbean are WestJet (C$ 253), Air Canada (C$ 276), and Air Transat (C$ 361).

  • What are the most popular routes from Winnipeg to Caribbean?

    The most popular route from Winnipeg to Caribbean is Winnipeg - Punta Cana. You may also consider Winnipeg - Montego Bay Sangster Intl or Winnipeg - San Juan Luis Munoz Marin Intl.

  • Can I find deals for flights from Winnipeg to Caribbean that include hotel bookings?

    Yes. In addition to deals on Winnipeg to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Winnipeg to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to Caribbean.

  • Can I find deals for business class flights from Winnipeg to Caribbean?

    Yes. Cheapflights offers flight deals from Winnipeg to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Winnipeg to Caribbean?

    Currently, September is the cheapest month in which you can book a flight from Winnipeg to Caribbean (average of C$ 367). Flying from Winnipeg to Caribbean in August is currently the most expensive (average of C$ 603). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Top 6 airlines flying from Winnipeg to Caribbean

Discover the top 6 airlines that operate flights from Winnipeg to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 12 December 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 485AverageC$ 773FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 503AverageC$ 863FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 544AverageC$ 725FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
DeltaCheapestC$ 699AverageC$ 1,086FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
Sunwing AirlinesCheapestC$ 734AverageC$ 1,188FlexibilityNo cancel feeOn-timeN/A
Search Sunwing Airlines flights
Air TransatCheapestC$ 802AverageC$ 919FlexibilityNo cancel feeOn-time50%
Search Air Transat flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Winnipeg to Caribbean?

When you search for this flight from Winnipeg to Caribbean, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

Why should you use Cheapflights to find cheap flight tickets from Winnipeg to Caribbean?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Winnipeg to Caribbean for you. Better yet — we are completely free to use.

Can Cheapflights find flights from Winnipeg to Caribbean with no change fees?

Yes! Cheapflights helps users easily find flights from Winnipeg to Caribbean with no change fees.

Can Cheapflights notify me if prices for flights from Winnipeg to Caribbean become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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