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Cheap flights from Winnipeg to Caribbean Islands from C$ 305
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 3/12. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
7 Aug — 14 Aug1
Round-trip
1 adult
Economy
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 2 August 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 2 August 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 2 August 2025.
Mon 17/115:00 a.m.YWG - PUJ
1 stop30h 35mWestJet
Mon 24/114:30 p.m.PUJ - YWG
1 stop21h 05mWestJet
Deal found 1/8C$ 550
Thu 13/112:20 p.m.YWG - PUJ
1 stop23h 42mUnited Airlines
Sat 22/112:55 p.m.PUJ - YWG
1 stop23h 02mUnited Airlines
Deal found 1/8C$ 556
Tue 2/911:40 a.m.YWG - PUJ
1 stop24h 45mAir Canada
Tue 9/94:25 p.m.PUJ - YWG
2 stops19h 15mAir Canada
Deal found 2/8C$ 607
Fri 19/95:45 p.m.YWG - PUJ
1 stop19h 40mMultiple Airlines
Thu 25/98:00 p.m.PUJ - YWG
1 stop14h 41mMultiple Airlines
Deal found 1/8C$ 625
Wed 29/107:30 a.m.YWG - MBJ
1 stop24h 23mMultiple Airlines
Sun 2/118:25 p.m.MBJ - YWG
1 stop16h 10mMultiple Airlines
Deal found 1/8C$ 711
Wed 17/92:35 p.m.YWG - MBJ
1 stop21h 06mWestJet
Fri 19/912:45 p.m.MBJ - YWG
1 stop11h 28mWestJet
Deal found 2/8C$ 733
Fri 12/95:00 a.m.YWG - KIN
1 stop7h 35mAir Canada
Tue 16/91:45 p.m.KIN - YWG
2 stops20h 55mAir Canada
Deal found 1/8C$ 735
Wed 17/97:00 p.m.YWG - MBJ
1 stop16h 10mAir Canada
Fri 19/912:10 p.m.MBJ - YWG
2 stops29h 40mAir Canada
Deal found 2/8C$ 738
Mon 15/94:25 p.m.YWG - MBJ
2 stops19h 18mUnited Airlines
Fri 17/1012:52 p.m.MBJ - YWG
2 stops33h 41mUnited Airlines
Deal found 2/8C$ 776
Fri 12/98:30 a.m.YWG - KIN
2 stops29h 58mMultiple Airlines
Tue 16/91:45 p.m.KIN - YWG
2 stops20h 55mMultiple Airlines
Deal found 1/8C$ 823
Sun 14/96:30 a.m.YWG - AUA
2 stops27h 52mWestJet
Tue 30/92:50 p.m.AUA - YWG
2 stops21h 51mWestJet
Deal found 31/7C$ 869
Wed 31/126:45 a.m.YWG - POP
2 stops55h 48mWestJet
Sat 28/25:30 p.m.POP - YWG
2 stops31h 10mWestJet
Deal found 1/8C$ 969
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 2 August 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
WinnipegPunta Cana
YWG - PUJ
YWGPUJ
Winnipeg
Mon 17/11
5:00 a.m.-1:35 p.m.
1 stop30h 35m
Punta Cana
Mon 24/11
4:30 p.m.-11:35 a.m.
1 stop21h 05m
C$ 550
WinnipegPunta Cana
YWG - PUJ
YWGPUJ
Winnipeg
Thu 13/11
2:20 p.m.-4:02 p.m.
1 stop23h 42m
Punta Cana
Sat 22/11
2:55 p.m.-11:57 a.m.
1 stop23h 02m
C$ 556
WinnipegPunta Cana
YWG - PUJ
YWGPUJ
Winnipeg
Tue 2/9
11:40 a.m.-1:25 p.m.
1 stop24h 45m
Punta Cana
Tue 9/9
4:25 p.m.-10:40 a.m.
2 stops19h 15m
C$ 607
WinnipegPunta Cana
YWG - PUJ
YWGPUJ
Winnipeg
Fri 19/9
5:45 p.m.-2:25 p.m.
1 stop19h 40m
Punta Cana
Thu 25/9
8:00 p.m.-9:41 a.m.
1 stop14h 41m
C$ 625
WinnipegMontego Bay
YWG - MBJ
YWGMBJ
Winnipeg
Wed 29/10
7:30 a.m.-7:53 a.m.
1 stop24h 23m
Montego Bay Sangster Intl
Sun 2/11
8:25 p.m.-11:35 a.m.
1 stop16h 10m
C$ 711
WinnipegKingston
YWG - KIN
YWGKIN
Winnipeg
Fri 12/9
5:00 a.m.-12:35 p.m.
1 stop7h 35m
Kingston Norman Manley
Tue 16/9
1:45 p.m.-10:40 a.m.
2 stops20h 55m
C$ 735
WinnipegKingston
YWG - KIN
YWGKIN
Winnipeg
Fri 29/8
9:00 a.m.-11:27 a.m.
2 stops26h 27m
Kingston Norman Manley
Wed 3/9
6:25 p.m.-9:41 a.m.
1 stop15h 16m
C$ 749
WinnipegMontego Bay
YWG - MBJ
YWGMBJ
Winnipeg
Fri 26/9
4:25 p.m.-3:45 p.m.
1 stop23h 20m
Montego Bay Sangster Intl
Fri 3/10
12:52 p.m.-10:33 p.m.
2 stops33h 41m
C$ 776
WinnipegMontego Bay
YWG - MBJ
YWGMBJ
Winnipeg
Fri 29/8
6:30 a.m.-9:27 a.m.
2 stops26h 57m
Montego Bay Sangster Intl
Wed 3/9
10:30 a.m.-11:26 a.m.
2 stops24h 56m
C$ 786
WinnipegOranjestad
YWG - AUA
YWGAUA
Winnipeg
Sun 14/9
6:30 a.m.-11:22 a.m.
2 stops27h 52m
Oranjestad Reina Beatrix
Tue 30/9
2:50 p.m.-11:41 a.m.
2 stops21h 51m
C$ 869
Showing 1-10 of 34 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 2 August 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 2 August 2025.
Get a feel of what it's like to fly with Delta,Air Transat, andUnited Airlines 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.
Comfort
7.9
Food
7.3
Boarding
8.2
Overall
8.0
Crew
8.5
Entertainment
7.9
Reviews
1 / 20
10.0
ExcellentAaron,Oct 2024
LAX - LHR
Comfort
7.9
Food
7.3
Boarding
8.2
Overall
8.0
Crew
8.5
Entertainment
7.9
Reviews
1 / 20
10.0
ExcellentAaron,Oct 2024
LAX - LHR
Comfort
7.9
Food
7.3
Boarding
8.2
Overall
8.0
Crew
8.5
Entertainment
7.9
Reviews
1 / 20
10.0
ExcellentAaron,Oct 2024
LAX - LHR
Comfort
7.9
Food
7.3
Boarding
8.2
Overall
8.0
Crew
8.5
Entertainment
7.9
Reviews
1 / 20
10.0
ExcellentAaron,Oct 2024
LAX - LHR
Comfort
7.9
Food
7.3
Boarding
8.2
Overall
8.0
Crew
8.5
Entertainment
7.9
Reviews
1 / 20
10.0
ExcellentAaron,Oct 2024
LAX - LHR
Comfort
7.9
Food
7.3
Boarding
8.2
Overall
8.0
Crew
8.5
Entertainment
7.9
Reviews
1 / 20
10.0
ExcellentAaron,Oct 2024
LAX - LHR
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 5 airlines flying from Winnipeg to Caribbean Islands
Discover the top 5 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 2 August 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.