Find flights
Deals
When to book
Airlines
FAQs

Cheap flights from Windsor, ON to Caribbean Islands from C$ 337

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 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — SJU
28 nov. — 5 dic.1
1 adult
1 adult, Economy, 0 bags

Find 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 29 octubre 2025.

dom. 7/127:50 p.m.YQG - PUJ
2 stops17h 10mAir Canada
mié. 10/121:05 p.m.PUJ - YQG
1 stop7h 09mAir Canada
Deal found 29/10C$ 553
dom. 2/117:50 p.m.YQG - PUJ
1 stop15h 15mAir Canada
dom. 9/1110:25 p.m.PUJ - YQG
1 stop21h 49mAir Canada
Deal found 26/10C$ 567
mié. 5/117:50 p.m.YQG - PUJ
1 stop15h 15mAir Canada
mié. 12/113:35 p.m.PUJ - YQG
2 stops42h 29mAir Canada
Deal found 28/10C$ 585
vie. 31/107:50 p.m.YQG - PUJ
1 stop16h 55mAir Canada
vie. 7/113:35 p.m.PUJ - YQG
2 stops18h 29mAir Canada
Deal found 27/10C$ 598
mié. 26/119:45 a.m.YQG - PUJ
1 stop10h 50mAir Canada
dom. 30/116:15 p.m.PUJ - YQG
2 stops25h 59mAir Canada
Deal found 27/10C$ 602
jue. 27/119:45 a.m.YQG - PUJ
1 stop10h 50mAir Canada
jue. 4/123:35 p.m.PUJ - YQG
2 stops18h 29mAir Canada
Deal found 29/10C$ 613
jue. 11/129:45 a.m.YQG - PUJ
1 stop10h 50mAir Canada
jue. 18/121:00 p.m.PUJ - YQG
1 stop21h 04mAir Canada
Deal found 27/10C$ 626
vie. 12/129:45 a.m.YQG - PUJ
1 stop10h 50mAir Canada
vie. 19/1210:25 p.m.PUJ - YQG
1 stop11h 39mAir Canada
Deal found 28/10C$ 674
vie. 12/127:50 p.m.YQG - PUJ
1 stop25h 20mAir Canada
sáb. 20/123:35 p.m.PUJ - YQG
2 stops18h 29mAir Canada
Deal found 27/10C$ 675

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 29 octubre 2025.

Round-trip from

C$ 573

One-way from

C$ 337
Air Canada
  • Air Canada
  • 7/12-10/12
  • 3 total stops
  • 38h 09m total
  • Windsor to Caribbean Islands
Search Deals
Air Canada
  • Air Canada
  • 2/2
  • 1 total stop
  • 17h 10m 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 29 octubre 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

dom. 7/12

7:50 p.m.-2:00 p.m.

2 stops17h 10m

Punta Cana

mié. 10/12

3:35 p.m.-9:04 a.m.

2 stops18h 29m

C$ 553

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

mié. 14/1

9:45 a.m.-9:35 p.m.

1 stop10h 50m

Punta Cana

mié. 21/1

1:05 p.m.-9:04 a.m.

1 stop20h 59m

C$ 578

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

jue. 27/11

9:45 a.m.-9:35 p.m.

1 stop10h 50m

Punta Cana

jue. 4/12

3:35 p.m.-9:04 a.m.

2 stops18h 29m

C$ 613

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

jue. 11/12

9:45 a.m.-9:35 p.m.

1 stop10h 50m

Punta Cana

jue. 18/12

1:00 p.m.-9:04 a.m.

1 stop21h 04m

C$ 626

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

dom. 8/2

7:50 p.m.-2:00 p.m.

2 stops17h 10m

Punta Cana

mar. 17/2

7:40 p.m.-7:14 p.m.

2 stops24h 34m

C$ 632

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

mar. 10/2

9:45 a.m.-1:35 p.m.

1 stop26h 50m

Punta Cana

mar. 17/2

10:25 p.m.-9:04 a.m.

1 stop11h 39m

C$ 632

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

lun. 9/2

7:50 p.m.-9:35 p.m.

1 stop24h 45m

Punta Cana

lun. 16/2

10:25 p.m.-9:04 a.m.

1 stop11h 39m

C$ 632

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

mar. 3/2

9:45 a.m.-1:10 p.m.

1 stop27h 25m

Montego Bay Sangster Intl

mar. 17/2

2:40 p.m.-7:14 p.m.

1 stop28h 34m

C$ 829

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

dom. 8/2

7:50 p.m.-4:35 p.m.

1 stop20h 45m

Montego Bay Sangster Intl

mar. 17/2

2:40 p.m.-7:14 p.m.

1 stop28h 34m

C$ 854

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

jue. 5/2

9:45 a.m.-1:10 p.m.

1 stop27h 25m

Montego Bay Sangster Intl

lun. 16/2

5:45 p.m.-9:04 a.m.

1 stop15h 19m

C$ 858

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/10

Showing 1-10 of 34 results
1
2
3
4

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 29 octubre 2025.
Check out reviews from past customers who have flown with 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 Canada
7.1
Good
10,372 reviews
Check prices

Boarding

7.3

Overall

7.1

Food

6.3

Comfort

7.1

Crew

7.8

Entertainment

6.8

Reviews

1 / 20
10.0
Excellent

janet,Sep 2025

YOW - YYZ

Really appreciated the leg room despite purchasing an economy ticket. Appreciated the extra complimentary wine. Nice touch. Was given immediate support without asking at check in, at the machine!! Ottawa's boarding was very organized with distinct rows in waiting room. Allowed for the main hall to not be blocked by people waiting to board.
Air Canada
7.1
Good
10,372 reviews
Air Canada
7.1
Good
10,372 reviews
Check prices

Boarding

7.3

Overall

7.1

Food

6.3

Comfort

7.1

Crew

7.8

Entertainment

6.8

Reviews

1 / 20
10.0
Excellent

janet,Sep 2025

YOW - YYZ

Really appreciated the leg room despite purchasing an economy ticket. Appreciated the extra complimentary wine. Nice touch. Was given immediate support without asking at check in, at the machine!! Ottawa's boarding was very organized with distinct rows in waiting room. Allowed for the main hall to not be blocked by people waiting to board.

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$ 553, Air Canada can have you in Caribbean Islands from Windsor, Ontario in 17h 10m. Windsor, Ontario and Caribbean Islands are separated by a distance of 2972 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 Vancouver Intl flights
Pierre Elliott Trudeau Intl to Cancún flights
Pearson Intl to Cancún flights
Pearson Intl to John F Kennedy Intl flights
Pearson Intl to Abbotsford flights
Pierre Elliott Trudeau Intl to Vancouver Intl flights
Hamilton to Vancouver Intl flights
Pearson Intl to Newark flights
Pearson Intl to LaGuardia flights
Pierre Elliott Trudeau Intl to Fort Lauderdale flights
Toronto Island to Vancouver Intl flights
Toronto Island to Newark flights
Pearson Intl to Calgary flights
Pearson Intl to Fort Lauderdale flights
Pearson Intl to Mexico City flights
Pearson Intl to Halifax flights
Pierre Elliott Trudeau Intl to Mexico City flights
Pierre Elliott Trudeau Intl to John F Kennedy Intl flights
Pierre Elliott Trudeau Intl to Miami flights
Pierre Elliott Trudeau Intl to Calgary flights
Pierre Elliott Trudeau Intl to Puerto Vallarta flights
Pearson Intl to Miami flights
Pierre Elliott Trudeau Intl to LaGuardia flights
Pearson Intl to Los Angeles flights
Hamilton to Calgary flights
Region of Waterloo Intl to Vancouver Intl flights
Toronto Island to Cancún flights
Pearson Intl to Pierre Elliott Trudeau Intl flights
Toronto Island to Calgary flights
Pearson Intl to Dallas/Fort Worth flights
Pearson Intl to Orlando flights
Toronto Island to Halifax flights
Hamilton to Halifax flights
Pierre Elliott Trudeau Intl to Pearson Intl flights
Pierre Elliott Trudeau Intl to Newark flights
Pearson Intl to Las Vegas flights
Pearson Intl to Puerto Vallarta flights
Ottawa to Cancún flights
Pearson Intl to Cozumel flights
Toronto Island to Pierre Elliott Trudeau Intl flights
Pearson Intl to Edmonton flights
Region of Waterloo Intl to Halifax flights
Region of Waterloo Intl to Calgary flights
Pierre Elliott Trudeau Intl to Toronto Island flights
Toronto Island to Fort Lauderdale flights
Pearson Intl to San Francisco flights
Pearson Intl to Winnipeg flights
Pearson Intl to Tampa flights
Ottawa to Pearson Intl flights
Pierre Elliott Trudeau Intl to Los Angeles flights

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 29 octubre 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 564AverageC$ 772FlexibilityNo cancel feeOn-time67%
Search Air Canada 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.