Find flights
When to book
Airlines
FAQs

Cheap flights from Windsor, ON to Caribbean Islands from C$ 310

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 13/7. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — SJU
1 Jul — 8 Jul1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Windsor to Caribbean Islands

Enter your travel dates to find the best prices.

Cheapest flights from Windsor to Caribbean Islands
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 1 June 2026.

Sat 6/67:45 p.m.
YQG
-
PUJ
1 stop19h 40m
Air Canada
Sat 13/65:25 p.m.
PUJ
-
YQG
2 stops21h 59m
Air Canada
Deal found 30/5C$ 585
Mon 15/67:45 p.m.
YQG
-
MBJ
1 stop16h 35m
Air Canada
Fri 19/612:30 p.m.
MBJ
-
YQG
1 stop25h 52m
Air Canada
Deal found 28/5C$ 586
Sat 31/107:50 p.m.
YQG
-
PUJ
1 stop18h 00m
Air Canada
Sat 7/117:35 p.m.
PUJ
-
YQG
1 stop14h 34m
Air Canada
Deal found 28/5C$ 615
Sat 21/117:50 p.m.
YQG
-
PUJ
1 stop24h 50m
Air Canada
Sat 28/117:35 p.m.
PUJ
-
YQG
1 stop24h 39m
Air Canada
Deal found 29/5C$ 618
Tue 22/97:45 p.m.
YQG
-
SJU
2 stops18h 08m
Air Canada
Fri 25/91:00 a.m.
SJU
-
YQG
2 stops18h 07m
Air Canada
Deal found 29/5C$ 633
Mon 1/67:45 p.m.
YQG
-
PUJ
1 stop19h 40m
Air Canada
Thu 4/64:25 p.m.
PUJ
-
YQG
1 stop22h 59m
Air Canada
Deal found 27/5C$ 641
Sun 12/77:45 p.m.
YQG
-
PUJ
1 stop19h 30m
Air Canada
Sun 19/74:20 p.m.
PUJ
-
YQG
1 stop17h 02m
Air Canada
Deal found 30/5C$ 647
Tue 27/109:45 a.m.
YQG
-
SJU
2 stops27h 55m
Air Canada
Thu 29/101:05 a.m.
SJU
-
YQG
2 stops18h 09m
Air Canada
Deal found 28/5C$ 751

Find 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 1 June 2026.

Round-trip from

C$ 586

One-way from

C$ 310
Air Canada
  • Air Canada
  • 15/6-19/6
  • 2 total stops
  • 42h 27m total
  • Windsor to Caribbean Islands
Search Deals
Air Canada
  • Air Canada
  • 13/7
  • 1 total stop
  • 16h 35m total
  • Windsor to Caribbean Islands
Search Deals

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 1 June 2026.
Use the filters below to find and compare flights from Windsor to Caribbean Islands 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

Fri 19/6

12:30 p.m.-3:22 p.m.

1 stop25h 52m

C$ 586
Quickest round-trip

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sat 31/10

9:45 a.m.-8:40 p.m.

1 stop10h 55m

Punta Cana

Sat 7/11

3:30 p.m.-9:09 a.m.

1 stop18h 39m

C$ 615

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sat 21/11

7:50 p.m.-9:40 p.m.

1 stop24h 50m

Punta Cana

Sat 28/11

7:35 p.m.-7:14 p.m.

1 stop24h 39m

C$ 618

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Thu 26/11

7:50 p.m.-9:40 p.m.

1 stop24h 50m

Punta Cana

Mon 30/11

9:35 p.m.-7:14 p.m.

1 stop22h 39m

C$ 618

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Tue 22/9

7:45 p.m.-1:53 p.m.

2 stops18h 08m

San Juan Luis Munoz Marin Intl

Fri 25/9

1:00 a.m.-7:07 p.m.

2 stops18h 07m

C$ 633

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sun 12/7

7:45 p.m.-3:15 p.m.

1 stop19h 30m

Punta Cana

Sun 19/7

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

1 stop17h 02m

C$ 647

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Mon 13/7

7:45 p.m.-4:05 p.m.

2 stops20h 20m

Punta Cana

Thu 16/7

5:05 p.m.-7:02 p.m.

2 stops25h 57m

C$ 657

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sat 12/9

4:05 p.m.-3:25 p.m.

1 stop23h 20m

Punta Cana

Tue 15/9

4:20 p.m.-7:07 p.m.

1 stop26h 47m

C$ 683

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Tue 27/10

9:45 a.m.-1:40 p.m.

2 stops27h 55m

San Juan Luis Munoz Marin Intl

Thu 29/10

1:05 a.m.-7:14 p.m.

2 stops18h 09m

C$ 751
Cheapest one-way
Quickest one-way

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Mon 13/7

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

1 stop16h 35m

C$ 310

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/5

Showing 1-10 of 13 resultsSorted by cheapest first
1
2

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
No data available for this route at this time. Please check back soon.

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 1 June 2026.
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.
Air Transat
7.8
Good
554 reviews
Check prices

Boarding

7.9

Food

6.8

Entertainment

7.1

Comfort

7.3

Crew

8.5

Overall

7.8

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
7.8
Good
554 reviews
Air Transat
7.8
Good
554 reviews
Check prices

Boarding

7.9

Food

6.8

Entertainment

7.1

Comfort

7.3

Crew

8.5

Overall

7.8

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
11,111 reviews
Air Transat
7.8
Good
554 reviews
Check prices

Boarding

7.9

Food

6.8

Entertainment

7.1

Comfort

7.3

Crew

8.5

Overall

7.8

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 Islands. 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 Islands?

    Windsor (YQG), located 8.0 km from the city centre, is the airport you fly out of when you book flights from Windsor to Caribbean Islands.

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

    For as low as C$ 586, Air Canada can have you in Caribbean Islands from Windsor, Ontario in 16h 35m. Windsor, Ontario and Caribbean Islands are separated by a distance of 2683 km.

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

    The most popular flight routes from Windsor, Ontario to Caribbean Islands are Windsor - Punta Cana, Windsor - Montego Bay Sangster Intl and Windsor - San Juan Luis Munoz Marin Intl.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Windsor to Caribbean Islands 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 Islands

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
Region of Waterloo Intl to Cancún flights
Hamilton to Vancouver Intl flights
Pearson Intl to Calgary flights
Pearson Intl to Abbotsford flights
Toronto Island to Vancouver Intl flights
Hamilton to Calgary flights
Toronto Island to Newark flights
Pearson Intl to Newark flights
Pierre Elliott Trudeau Intl to Calgary flights
Toronto Island to Calgary flights
Pierre Elliott Trudeau Intl to Vancouver Intl flights
Pierre Elliott Trudeau Intl to Cancún flights
Pearson Intl to Pierre Elliott Trudeau Intl flights
Hamilton to Edmonton flights
Hamilton to Halifax flights
Pearson Intl to LaGuardia flights
Toronto Island to Halifax flights
Region of Waterloo Intl to Calgary flights
Pearson Intl to John F Kennedy Intl flights
Pearson Intl to Halifax flights
Pearson Intl to Edmonton flights
Region of Waterloo Intl to Vancouver Intl flights
Ottawa to Vancouver Intl flights
Pearson Intl to Las Vegas flights
Pearson Intl to St. John's flights
Pierre Elliott Trudeau Intl to LaGuardia flights
Pierre Elliott Trudeau Intl to Pearson Intl flights
Toronto Island to Pierre Elliott Trudeau Intl flights
Pearson Intl to Dallas/Fort Worth flights
Pierre Elliott Trudeau Intl to Miami flights
Pearson Intl to Los Angeles flights
Pearson Intl to Orlando flights
Pearson Intl to Mexico City flights
Pearson Intl to Seattle flights
Pearson Intl to O'Hare Intl flights
Pearson Intl to Fort Lauderdale flights
Pearson Intl to Miami flights
Ottawa to Calgary flights
Pierre Elliott Trudeau Intl to Toronto Island flights
Pierre Elliott Trudeau Intl to Mexico City flights
Pierre Elliott Trudeau Intl to Newark flights
Region of Waterloo Intl to Halifax flights
Pearson Intl to Kelowna flights
Pearson Intl to Winnipeg flights
Toronto Island to Edmonton flights

Top 2 airlines flying from Windsor to Caribbean Islands

Discover the top 2 airlines 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 1 June 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 584AverageC$ 994FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Air TransatCheapestC$ 728AverageC$ 925FlexibilityNo 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 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.

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.