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Cheap flights from Winnipeg to Caribbean Islands from C$ 210
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 23/9. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
16 Oct — 23 Oct1
Cheap flight deals from Winnipeg to Caribbean Islands
Keep the following information in mind while searching for Winnipeg to Caribbean Islands flight deals. Data was last updated 16 September 2025.
Find flight deals from Winnipeg to Caribbean Islands
Cheapest flights from Winnipeg to Caribbean IslandsExplore the most affordable flight options available from Winnipeg to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 16 September 2025.
Explore the most affordable flight options available from Winnipeg to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 16 September 2025.
Fri 31/107:05 p.m.YWG - CUR
1 stop19h 15mAir Canada
Thu 6/115:20 p.m.CUR - YWG
1 stop18h 29mAir Canada
Deal found 15/9C$ 497
Sat 29/115:00 a.m.YWG - NAS
1 stop9h 50mWestJet
Sat 6/126:15 p.m.NAS - YWG
1 stop18h 20mWestJet
Deal found 15/9C$ 504
Wed 29/108:05 p.m.YWG - PUJ
1 stop17h 30mWestJet
Wed 5/114:30 p.m.PUJ - YWG
1 stop10h 12mWestJet
Deal found 14/9C$ 522
Fri 7/119:00 p.m.YWG - NAS
2 stops41h 50mWestJet
Thu 13/1111:30 a.m.NAS - YWG
2 stops14h 11mWestJet
Deal found 14/9C$ 533
Thu 30/104:10 p.m.YWG - MBJ
2 stops20h 44mWestJet
Tue 4/117:25 p.m.MBJ - YWG
2 stops23h 41mWestJet
Deal found 16/9C$ 551
Wed 29/108:05 p.m.YWG - MBJ
1 stop16h 49mWestJet
Sun 2/111:25 p.m.MBJ - YWG
1 stop23h 10mWestJet
Deal found 15/9C$ 555
Fri 24/109:00 a.m.YWG - MBJ
1 stop29h 46mMultiple Airlines
Fri 31/103:30 p.m.MBJ - YWG
2 stops33h 11mMultiple Airlines
Deal found 16/9C$ 565
Wed 1/105:00 a.m.YWG - PUJ
1 stop9h 20mAir Canada
Tue 7/102:25 p.m.PUJ - YWG
1 stop20h 45mAir Canada
Deal found 14/9C$ 566
Sat 15/116:45 a.m.YWG - POP
2 stops31h 48mWestJet
Mon 24/115:30 p.m.POP - YWG
2 stops44h 23mWestJet
Deal found 15/9C$ 569
Sun 26/105:00 a.m.YWG - MBJ
1 stop13h 23mWestJet
Sun 2/118:25 p.m.MBJ - YWG
1 stop16h 10mWestJet
Deal found 16/9C$ 573
Mon 22/98:10 p.m.YWG - PUJ
1 stop18h 10mAir Canada
Mon 6/104:25 p.m.PUJ - YWG
1 stop18h 14mAir Canada
Deal found 14/9C$ 575
Sat 1/116:15 a.m.YWG - MBJ
2 stops37h 08mWestJet
Sat 8/117:25 p.m.MBJ - YWG
2 stops20h 56mWestJet
Deal found 15/9C$ 580
Cheapflights 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, Cheapflights users made 629,999 searches. Data last updated 16 September 2025.
Use the filters below to find and compare flights from Winnipeg to Caribbean Islands that are best for you.
Fly from
Winnipeg
Fly to
Caribbean Islands
Route
Depart
Return
Price
WinnipegWillemstad
YWG - CUR
YWGCUR
Winnipeg
Fri 31/10
7:05 p.m.-3:20 p.m.
1 stop19h 15m
Willemstad Hato Int.
Thu 6/11
5:20 p.m.-9:49 a.m.
1 stop18h 29m
C$ 497
WinnipegNassau
YWG - NAS
YWGNAS
Winnipeg
Fri 7/11
9:00 p.m.-3:50 p.m.
2 stops41h 50m
Nassau Intl
Thu 13/11
11:30 a.m.-12:41 a.m.
2 stops14h 11m
C$ 533
WinnipegMontego Bay
YWG - MBJ
YWGMBJ
Winnipeg
Wed 29/10
9:00 p.m.-12:54 p.m.
2 stops15h 54m
Montego Bay Sangster Intl
Sun 2/11
1:25 p.m.-11:35 a.m.
1 stop23h 10m
C$ 559
WinnipegMontego Bay
YWG - MBJ
YWGMBJ
Winnipeg
Fri 24/10
9:00 a.m.-2:46 p.m.
1 stop29h 46m
Montego Bay Sangster Intl
Fri 31/10
3:30 p.m.-12:41 a.m.
2 stops33h 11m
C$ 565
WinnipegPunta Cana
YWG - PUJ
YWGPUJ
Winnipeg
Wed 1/10
5:00 a.m.-3:20 p.m.
1 stop9h 20m
Punta Cana
Tue 7/10
2:25 p.m.-10:10 a.m.
1 stop20h 45m
C$ 566
WinnipegPuerto Plata
YWG - POP
YWGPOP
Winnipeg
Sat 15/11
12:20 p.m.-4:33 p.m.
1 stop26h 13m
Puerto Plata La Union
Mon 24/11
5:30 p.m.-12:35 a.m.
1 stop9h 05m
C$ 569
WinnipegMontego Bay
YWG - MBJ
YWGMBJ
Winnipeg
Sat 1/11
6:15 a.m.-7:23 p.m.
2 stops37h 08m
Montego Bay Sangster Intl
Sat 8/11
7:25 p.m.-3:21 p.m.
2 stops20h 56m
C$ 580
WinnipegPunta Cana
YWG - PUJ
YWGPUJ
Winnipeg
Sun 26/10
8:15 a.m.-1:00 p.m.
1 stop27h 45m
Punta Cana
Sun 2/11
6:15 p.m.-10:16 a.m.
1 stop18h 01m
C$ 591
WinnipegMontego Bay
YWG - MBJ
YWGMBJ
Winnipeg
Sun 26/10
8:05 p.m.-12:53 p.m.
1 stop16h 48m
Montego Bay Sangster Intl
Sun 2/11
1:25 p.m.-11:53 a.m.
2 stops23h 28m
C$ 594
WinnipegPuerto Plata
YWG - POP
YWGPOP
Winnipeg
Sat 15/11
9:00 p.m.-4:33 p.m.
2 stops17h 33m
Puerto Plata La Union
Sun 23/11
5:30 p.m.-11:35 a.m.
1 stop20h 05m
C$ 598
Showing 1-10 of 56 results
Best time to book a flight from Winnipeg to Caribbean Islands
Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands 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 Islands
What is the cheapest month to book a flight from Winnipeg to Caribbean Islands?
Currently, April is the cheapest month in which you can book a flight from Winnipeg to Caribbean Islands (average of C$ 254). Flying from Winnipeg to Caribbean Islands in July is currently the most expensive (average of C$ 580). 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 EPX?
Find hourly flight availability from Winnipeg to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 16 September 2025.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Winnipeg to Caribbean Islands as you normally would.
Reviews of airlines servicing Caribbean Islands
Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated 16 September 2025.
Get a feel of what it's like to fly with Air Transat,United Airlines, andWestJet from Winnipeg to Caribbean Islands by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.0
Boarding
7.9
Comfort
7.3
Crew
8.4
Overall
7.7
Food
6.7
Reviews
1 / 20
10.0
ExcellentLiam,Jun 2025
GLA - YYZ
Entertainment
7.0
Boarding
7.9
Comfort
7.3
Crew
8.4
Overall
7.7
Food
6.7
Reviews
1 / 20
10.0
ExcellentLiam,Jun 2025
GLA - YYZ
Entertainment
7.0
Boarding
7.9
Comfort
7.3
Crew
8.4
Overall
7.7
Food
6.7
Reviews
1 / 20
10.0
ExcellentLiam,Jun 2025
GLA - YYZ
Entertainment
7.0
Boarding
7.9
Comfort
7.3
Crew
8.4
Overall
7.7
Food
6.7
Reviews
1 / 20
10.0
ExcellentLiam,Jun 2025
GLA - YYZ
Entertainment
7.0
Boarding
7.9
Comfort
7.3
Crew
8.4
Overall
7.7
Food
6.7
Reviews
1 / 20
10.0
ExcellentLiam,Jun 2025
GLA - YYZ
Entertainment
7.0
Boarding
7.9
Comfort
7.3
Crew
8.4
Overall
7.7
Food
6.7
Reviews
1 / 20
10.0
ExcellentLiam,Jun 2025
GLA - YYZ
Related info for your journey
Find useful and relevant information for your journey from Winnipeg to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Winnipeg to Caribbean Islands
See prices for flight routes from nearby airports that may be better suited for you.
Top 6 airlines flying from Winnipeg to Caribbean Islands
Discover the top 6 airlines that operate flights from Winnipeg to Caribbean Islands. 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 16 September 2025.
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How does Cheapflights help users find flights from Winnipeg to Caribbean Islands?
When you search for this flight from Winnipeg to Caribbean Islands, 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 Islands?
Cheapflights helps you find that perfect flight to Caribbean Islands from Winnipeg by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!
Can Cheapflights find flights from Winnipeg to Caribbean Islands with no change fees?
Need flexible booking options for your flight to Caribbean Islands from Winnipeg? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.
Can Cheapflights notify me if prices for flights from Winnipeg to Caribbean Islands become cheaper?
Yes! Start tracking prices for Winnipeg to Caribbean Islands flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.