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Cheap flights from Windsor, ON to Caribbean Islands from C$ 300
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 15/11. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — SJU
5 Aug — 12 Aug1
Round-trip
1 adult
Economy
Cheap flight deals from Windsor to Caribbean Islands
Keep the following information in mind while searching for Windsor to Caribbean Islands flight deals. Data was last updated 31 July 2025.
Find flight deals from Windsor to Caribbean Islands
Cheapest flights from Windsor to Caribbean IslandsExplore the most affordable flight options available from Windsor to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 31 July 2025.
Explore the most affordable flight options available from Windsor to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 31 July 2025.
Sun 30/117:50 p.m.YQG - PUJ
2 stops17h 10mAir Canada
Sun 7/121:05 p.m.PUJ - YQG
1 stop7h 09mAir Canada
Deal found 30/7C$ 616
Mon 1/99:55 a.m.YQG - MBJ
1 stop26h 15mAir Canada
Mon 15/912:10 p.m.MBJ - YQG
1 stop20h 02mAir Canada
Deal found 31/7C$ 767
Wed 6/84:00 p.m.YQG - MBJ
2 stops24h 10mMultiple Airlines
Wed 13/812:52 p.m.MBJ - YQG
2 stops19h 35mMultiple Airlines
Deal found 30/7C$ 1,483
Wed 6/87:45 p.m.YQG - PUJ
2 stops42h 38mWestJet
Wed 13/83:35 p.m.PUJ - YQG
2 stops27h 20mWestJet
Deal found 29/7C$ 1,558
Wed 30/77:45 p.m.YQG - MBJ
2 stops38h 42mWestJet
Tue 12/81:40 p.m.MBJ - YQG
2 stops28h 15mWestJet
Deal found 30/7C$ 2,442
Fri 1/82:30 p.m.YQG - PUJ
3 stops21h 35mMultiple Airlines
Mon 4/83:35 p.m.PUJ - YQG
2 stops22h 15mMultiple Airlines
Deal found 31/7C$ 2,465
Cheapflights Fare Finder
Customize your flight search to find flights from Windsor 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 31 July 2025.
Use the filters below to find and compare flights from Windsor to Caribbean Islands that are best for you.
Fly from
Windsor
Fly to
Caribbean Islands
Route
Depart
Return
Price
WindsorPunta Cana
YQG - PUJ
YQGPUJ
Windsor
Sun 30/11
7:50 p.m.-2:00 p.m.
2 stops17h 10m
Punta Cana
Sun 7/12
1:05 p.m.-7:14 p.m.
1 stop7h 09m
C$ 616
WindsorMontego Bay
YQG - MBJ
YQGMBJ
Windsor
Mon 1/9
9:55 a.m.-11:10 a.m.
1 stop26h 15m
Montego Bay Sangster Intl
Mon 15/9
12:10 p.m.-9:12 a.m.
1 stop20h 02m
C$ 767
WindsorPunta Cana
YQG - PUJ
YQGPUJ
Windsor
Fri 9/1
5:35 p.m.-10:45 p.m.
Nonstop4h 10m
Punta Cana
Fri 16/1
12:40 p.m.-4:15 p.m.
Nonstop4h 35m
C$ 877
WindsorMontego Bay
YQG - MBJ
YQGMBJ
Windsor
Wed 6/8
4:00 p.m.-3:10 p.m.
2 stops24h 10m
Montego Bay Sangster Intl
Wed 13/8
12:52 p.m.-9:27 a.m.
2 stops19h 35m
C$ 1,483
WindsorPunta Cana
YQG - PUJ
YQGPUJ
Windsor
Sat 15/11
7:50 p.m.-2:00 p.m.
2 stops41h 10m
C$ 300
WindsorMontego Bay
YQG - MBJ
YQGMBJ
Windsor
Sat 13/9
3:55 p.m.-11:10 a.m.
1 stop20h 15m
C$ 327
WindsorMontego Bay
YQG - MBJ
YQGMBJ
Windsor
Sat 13/9
8:50 a.m.-11:05 a.m.
3 stops27h 15m
C$ 476
WindsorPunta Cana
YQG - PUJ
YQGPUJ
Windsor
Sat 13/9
8:50 a.m.-2:14 p.m.
3 stops29h 24m
C$ 479
Best time to book a flight from Windsor to Caribbean Islands
Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Windsor 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 Windsor to Caribbean Islands
What is the cheapest month to book a flight from Windsor, Ontario to Caribbean Islands?
Currently, April is the cheapest month in which you can book a flight from Windsor, Ontario to Caribbean Islands (average of C$ 254). Flying from Windsor, Ontario 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.
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 31 July 2025.
Check out reviews from past customers who have flown with Air Transat and Air Canada from Windsor to Caribbean Islands to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.3
Boarding
7.9
Crew
8.4
Entertainment
7.1
Overall
7.7
Food
6.7
Reviews
1 / 20
10.0
ExcellentLiam,Jun 2025
GLA - YYZ
Comfort
7.3
Boarding
7.9
Crew
8.4
Entertainment
7.1
Overall
7.7
Food
6.7
Reviews
1 / 20
10.0
ExcellentLiam,Jun 2025
GLA - YYZ
Comfort
7.3
Boarding
7.9
Crew
8.4
Entertainment
7.1
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 Windsor 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 Windsor to Caribbean Islands
See prices for flight routes from nearby airports that may be better suited for you.
Top airline flying from Windsor to Caribbean Islands
Discover the top airline that operate flights from Windsor 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 31 July 2025.
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 Windsor to Caribbean Islands?
Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Windsor to Caribbean Islands. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.
Why should you use Cheapflights to find cheap flight tickets from Windsor to Caribbean Islands?
By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Caribbean Islands from Windsor.
Can Cheapflights find flights from Windsor to Caribbean Islands with no change fees?
Certainly. Search results for flights to Caribbean Islands from Windsor shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.
Can Cheapflights notify me if prices for flights from Windsor to Caribbean Islands become cheaper?
Yes, Cheapflights offers price alerts on Windsor to Caribbean Islands flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.