Find flights
When to book
Airlines
FAQs

Cheap flights from Windsor, ON to Caribbean from C$ 298

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 29/4. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — SJU
4 May — 11 May1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Windsor to Caribbean

Enter your travel dates to find the best prices.

Cheapest flights from Windsor to Caribbean
Explore the most affordable flight options available from Windsor to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 4 April 2026.

Mon 15/67:45 p.m.
YQG
-
MBJ
1 stop16h 35m
Air Canada
Wed 17/612:30 p.m.
MBJ
-
YQG
1 stop19h 52m
Air Canada
Deal found 1/4C$ 540
Tue 29/94:05 p.m.
YQG
-
PUJ
1 stop23h 25m
Air Canada
Sat 3/104:20 p.m.
PUJ
-
YQG
1 stop17h 02m
Air Canada
Deal found 1/4C$ 606
Sun 7/67:45 p.m.
YQG
-
PUJ
1 stop19h 40m
Air Canada
Thu 11/64:25 p.m.
PUJ
-
YQG
1 stop16h 59m
Air Canada
Deal found 3/4C$ 616
Fri 14/84:05 p.m.
YQG
-
MBJ
1 stop20h 15m
Air Canada
Sat 29/812:30 p.m.
MBJ
-
YQG
1 stop19h 52m
Air Canada
Deal found 4/4C$ 618
Tue 19/57:45 p.m.
YQG
-
PUJ
2 stops18h 10m
Air Canada
Tue 26/52:55 p.m.
PUJ
-
YQG
2 stops24h 29m
Air Canada
Deal found 3/4C$ 647
Fri 20/117:50 p.m.
YQG
-
PUJ
1 stop24h 45m
Air Canada
Thu 26/1110:35 p.m.
PUJ
-
YQG
1 stop21h 39m
Air Canada
Deal found 31/3C$ 666
Wed 25/119:45 a.m.
YQG
-
PUJ
1 stop27h 00m
Air Canada
Tue 1/121:05 p.m.
PUJ
-
YQG
1 stop21h 04m
Air Canada
Deal found 31/3C$ 668
Tue 2/64:05 p.m.
YQG
-
MBJ
1 stop20h 15m
Air Canada
Sat 6/612:30 p.m.
MBJ
-
YQG
1 stop25h 54m
Air Canada
Deal found 3/4C$ 687
Fri 14/84:00 p.m.
YQG
-
MBJ
2 stops27h 30m
Multiple Airlines
Sat 29/812:30 p.m.
MBJ
-
YQG
1 stop19h 52m
Multiple Airlines
Deal found 4/4C$ 1,032
Fri 17/47:45 p.m.
YQG
-
MBJ
1 stop16h 50m
Multiple Airlines
Thu 23/41:21 p.m.
MBJ
-
YQG
3 stops29h 12m
Multiple Airlines
Deal found 1/4C$ 1,065
Sun 12/47:45 p.m.
YQG
-
SJU
2 stops28h 05m
Air Canada
Thu 16/42:55 p.m.
SJU
-
YQG
2 stops42h 09m
Air Canada
Deal found 2/4C$ 1,066
Mon 15/64:00 p.m.
YQG
-
MBJ
2 stops20h 45m
WestJet
Wed 17/612:45 p.m.
MBJ
-
YQG
2 stops25h 25m
WestJet
Deal found 31/3C$ 1,110

Find flight deals from Windsor to Caribbean

Keep the following information in mind while searching for Windsor to Caribbean flight deals. Data was last updated 4 April 2026.

Round-trip from

C$ 540

One-way from

C$ 298
Air Canada
  • Air Canada
  • 15/6-17/6
  • 2 total stops
  • 36h 27m total
  • Windsor to Caribbean
Search Deals
Air Canada
  • Air Canada
  • 29/4
  • 1 total stop
  • 19h 45m total
  • Windsor to Caribbean
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Windsor 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 4 April 2026.
Use the filters below to find and compare flights from Windsor to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Mon 15/6

7:45 p.m.-11:20 a.m.

1 stop16h 35m

Montego Bay Sangster Intl

Wed 17/6

12:30 p.m.-9:22 a.m.

1 stop19h 52m

C$ 540

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Tue 29/9

4:05 p.m.-3:30 p.m.

1 stop23h 25m

Punta Cana

Sat 3/10

4:20 p.m.-9:22 a.m.

1 stop17h 02m

C$ 606

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sun 7/6

7:45 p.m.-3:25 p.m.

1 stop19h 40m

Punta Cana

Thu 11/6

4:25 p.m.-9:24 a.m.

1 stop16h 59m

C$ 616

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Tue 19/5

7:45 p.m.-1:55 p.m.

2 stops18h 10m

Punta Cana

Tue 26/5

2:55 p.m.-3:24 p.m.

2 stops24h 29m

C$ 647

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Tue 2/6

4:05 p.m.-11:20 a.m.

1 stop20h 15m

Montego Bay Sangster Intl

Sat 6/6

12:30 p.m.-3:24 p.m.

1 stop25h 54m

C$ 687

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Fri 14/8

4:00 p.m.-6:30 p.m.

2 stops27h 30m

Montego Bay Sangster Intl

Sat 29/8

12:30 p.m.-9:22 a.m.

1 stop19h 52m

C$ 1,032

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Fri 17/4

7:45 p.m.-11:35 a.m.

1 stop16h 50m

Montego Bay Sangster Intl

Thu 23/4

1:21 p.m.-7:33 p.m.

3 stops29h 12m

C$ 1,065

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Mon 15/6

4:00 p.m.-11:45 a.m.

2 stops20h 45m

Montego Bay Sangster Intl

Wed 17/6

12:45 p.m.-3:10 p.m.

2 stops25h 25m

C$ 1,110
Quickest round-trip

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Thu 23/4

7:35 a.m.-12:58 a.m.

2 stops17h 23m

San Juan Luis Munoz Marin Intl

Mon 27/4

5:01 a.m.-7:33 p.m.

2 stops14h 32m

C$ 1,380

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Fri 14/8

4:00 p.m.-6:30 p.m.

2 stops27h 30m

Montego Bay Sangster Intl

Sat 29/8

7:30 p.m.-3:10 p.m.

2 stops42h 40m

C$ 1,458

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/4

Showing 1-10 of 18 resultsSorted by cheapest first
1
2

Best time to book a flight from Windsor to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean 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
No data available for this route at this time. Please check back soon.

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 4 April 2026.
Get a feel of what it's like to fly with Air Transat and Air Canada from Windsor 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
7.7
Good
533 reviews
Check prices

Crew

8.4

Comfort

7.3

Food

6.8

Entertainment

7.0

Overall

7.7

Boarding

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Dec 2025

YOW - GCM

The flight was delayed for 3.5 hours. No compensation for a meal voucher. We were positioned at the back of the plane and the toilets were not working properly. It was a foul smell coming from the toilet.
Air Transat
7.7
Good
533 reviews
Air Transat
7.7
Good
533 reviews
Check prices

Crew

8.4

Comfort

7.3

Food

6.8

Entertainment

7.0

Overall

7.7

Boarding

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Dec 2025

YOW - GCM

The flight was delayed for 3.5 hours. No compensation for a meal voucher. We were positioned at the back of the plane and the toilets were not working properly. It was a foul smell coming from the toilet.
Air Canada
7.1
Good
10,894 reviews
Air Transat
7.7
Good
533 reviews
Check prices

Crew

8.4

Comfort

7.3

Food

6.8

Entertainment

7.0

Overall

7.7

Boarding

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Dec 2025

YOW - GCM

The flight was delayed for 3.5 hours. No compensation for a meal voucher. We were positioned at the back of the plane and the toilets were not working properly. It was a foul smell coming from the toilet.

Related info for your journey

Find useful and relevant information for your journey from Windsor 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 Windsor to Caribbean?

    For a flight from Windsor to Caribbean, you will be flying from Windsor. Windsor (YQG) is just 8.0 km from the centre of the city.

  • How long is the flight from Windsor, Ontario to Caribbean?

    Departing from Windsor, Ontario to Caribbean will take you 16h 35m. The distance between Windsor, Ontario and Caribbean is about 2683 km.

  • What are the most popular routes from Windsor, Ontario to Caribbean?

    When deciding which route to take from Windsor, Ontario to Caribbean consider Windsor - Montego Bay Sangster Intl, Windsor - Punta Cana or Windsor - San Juan Luis Munoz Marin Intl as they are the most popular.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Windsor 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Windsor to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
Pearson Intl to Cancún flights
Toronto Island to Cancún flights
Pearson Intl to Vancouver Intl flights
Pearson Intl to Cozumel flights
Hamilton to Cancún flights
Hamilton to Vancouver Intl flights
Region of Waterloo Intl to Cancún flights
Pearson Intl to Abbotsford flights
Pierre Elliott Trudeau Intl to Charles de Gaulle flights
Toronto Island to Vancouver Intl flights
Pierre Elliott Trudeau Intl to Vancouver Intl flights
Pearson Intl to Calgary flights
Pearson Intl to Victoria flights
Pierre Elliott Trudeau Intl to Cancún flights
Pearson Intl to Heathrow flights
Hamilton to Calgary flights
Pierre Elliott Trudeau Intl to Algiers flights
Pearson Intl to Narita flights
Ottawa to Vancouver Intl flights
Pearson Intl to Gatwick flights
Pearson Intl to Edmonton flights
Pearson Intl to Haneda flights
Pearson Intl to John F Kennedy Intl flights
Pierre Elliott Trudeau Intl to Casablanca flights
Toronto Island to Newark flights
Pearson Intl to Leonardo da Vinci/Fiumicino flights
Pearson Intl to New Delhi flights
Toronto Island to Calgary flights
Pierre Elliott Trudeau Intl to Leonardo da Vinci/Fiumicino flights
Pearson Intl to Newark flights
Pearson Intl to Las Vegas flights
Pearson Intl to Charles de Gaulle flights
Pierre Elliott Trudeau Intl to Miami flights
Pearson Intl to Halifax flights
Pierre Elliott Trudeau Intl to Narita flights
Toronto Island to Halifax flights
Pierre Elliott Trudeau Intl to Calgary flights
Pierre Elliott Trudeau Intl to Lisbon flights
Pierre Elliott Trudeau Intl to Fort Lauderdale flights
Pearson Intl to St. John's flights
Pearson Intl to Fort Lauderdale flights
Region of Waterloo Intl to Calgary flights
Pearson Intl to LaGuardia flights
Pearson Intl to Dublin flights
Pearson Intl to Athens flights
Pierre Elliott Trudeau Intl to Orly flights
Pearson Intl to Miami flights
Pierre Elliott Trudeau Intl to Athens flights
Pearson Intl to Lisbon flights
Pierre Elliott Trudeau Intl to Tunis flights

Top 2 airlines flying from Windsor to Caribbean

Discover the top 2 airlines that operate flights from Windsor 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 4 April 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 487AverageC$ 775FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Air TransatCheapestC$ 734AverageC$ 905FlexibilityNo 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 Windsor to Caribbean?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Windsor to Caribbean. 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?

Millions of users choose and trust Cheapflights to book the best flight deals from Windsor to Caribbean for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

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

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

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

Yes! Start tracking prices for Windsor to Caribbean 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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.