Find flights
When to book
Airlines
FAQs

Cheap flights from Windsor, ON to Caribbean from C$ 355

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 20/8. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — SJU
5 Aug — 12 Aug1
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 6 July 2026.

Mon 21/97:45 p.m.
YQG
-
SJU
2 stops18h 08m
Air Canada
Fri 25/96:45 p.m.
SJU
-
YQG
2 stops24h 17m
Air Canada
Deal found 1/7C$ 632
Fri 28/84:05 p.m.
YQG
-
PUJ
1 stop23h 20m
Air Canada
Tue 1/94:20 p.m.
PUJ
-
YQG
1 stop26h 42m
Air Canada
Deal found 2/7C$ 647
Mon 3/87:45 p.m.
YQG
-
PUJ
1 stop19h 40m
Air Canada
Sun 9/84:20 p.m.
PUJ
-
YQG
1 stop17h 02m
Air Canada
Deal found 3/7C$ 697
Tue 4/87:45 p.m.
YQG
-
PUJ
2 stops44h 20m
Air Canada
Sun 9/85:05 p.m.
PUJ
-
YQG
2 stops22h 17m
Air Canada
Deal found 3/7C$ 708
Tue 1/1210:35 a.m.
YQG
-
PUJ
1 stop7h 00m
Air Canada
Mon 1/23:35 p.m.
PUJ
-
YQG
1 stop19h 20m
Air Canada
Deal found 4/7C$ 755
Tue 10/1110:35 a.m.
YQG
-
PUJ
1 stop26h 15m
Air Canada
Sat 14/1110:40 p.m.
PUJ
-
YQG
1 stop12h 15m
Air Canada
Deal found 5/7C$ 757
Sun 16/87:45 p.m.
YQG
-
MBJ
1 stop16h 35m
Air Canada
Sun 23/812:30 p.m.
MBJ
-
YQG
1 stop25h 52m
Air Canada
Deal found 2/7C$ 1,130
Sun 16/84:30 p.m.
YQG
-
MBJ
2 stops20h 15m
Multiple Airlines
Sun 23/87:30 p.m.
MBJ
-
YQG
2 stops19h 16m
Multiple Airlines
Deal found 2/7C$ 1,415
Wed 19/84:00 p.m.
YQG
-
SJU
2 stops30h 29m
WestJet
Wed 26/87:00 a.m.
SJU
-
YQG
2 stops32h 10m
WestJet
Deal found 5/7C$ 1,747

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 6 July 2026.

Round-trip from

C$ 632

One-way from

C$ 362
Air Canada
  • Air Canada
  • 21/9-25/9
  • 4 total stops
  • 42h 25m total
  • Windsor to Caribbean
Search Deals
Air Canada
  • Air Canada
  • 1/8
  • 1 total stop
  • 29h 20m 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 6 July 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

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Mon 21/9

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

2 stops18h 08m

San Juan Luis Munoz Marin Intl

Fri 25/9

6:45 p.m.-7:02 p.m.

2 stops24h 17m

C$ 632

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Fri 28/8

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

1 stop23h 20m

Punta Cana

Tue 1/9

4:20 p.m.-7:02 p.m.

1 stop26h 42m

C$ 647

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Tue 4/8

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

2 stops44h 20m

Punta Cana

Sun 9/8

5:05 p.m.-3:22 p.m.

2 stops22h 17m

C$ 708

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Sun 16/8

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

1 stop16h 35m

Montego Bay Sangster Intl

Sun 23/8

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

1 stop25h 52m

C$ 1,130
Quickest round-trip

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Sun 16/8

4:30 p.m.-11:45 a.m.

2 stops20h 15m

Montego Bay Sangster Intl

Sun 23/8

7:30 p.m.-3:46 p.m.

2 stops19h 16m

C$ 1,415

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Wed 19/8

4:00 p.m.-10:29 p.m.

2 stops30h 29m

San Juan Luis Munoz Marin Intl

Wed 26/8

7:00 a.m.-3:10 p.m.

2 stops32h 10m

C$ 1,747
Cheapest one-way

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Thu 20/8

7:45 p.m.-11:50 p.m.

2 stops28h 05m

C$ 355

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sat 1/8

10:05 a.m.-3:25 p.m.

1 stop29h 20m

C$ 362

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Wed 19/8

10:05 a.m.-11:20 a.m.

1 stop26h 15m

C$ 393

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Thu 20/8

4:30 p.m.-4:20 p.m.

3 stops23h 50m

C$ 538

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/7

Showing 1-10 of 12 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 6 July 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
7.8
Good
562 reviews
Check prices

Entertainment

7.1

Food

6.8

Overall

7.8

Comfort

7.3

Crew

8.5

Boarding

8.0

Reviews

1 / 20
8.0
Excellent

Paul,Jul 2026

YUL - LGW

Had to bus to the plane which made priority boarding at the back of the bus
Air Transat
7.8
Good
562 reviews
Air Transat
7.8
Good
562 reviews
Check prices

Entertainment

7.1

Food

6.8

Overall

7.8

Comfort

7.3

Crew

8.5

Boarding

8.0

Reviews

1 / 20
8.0
Excellent

Paul,Jul 2026

YUL - LGW

Had to bus to the plane which made priority boarding at the back of the bus
Air Canada
7.1
Good
11,305 reviews
Air Transat
7.8
Good
562 reviews
Check prices

Entertainment

7.1

Food

6.8

Overall

7.8

Comfort

7.3

Crew

8.5

Boarding

8.0

Reviews

1 / 20
8.0
Excellent

Paul,Jul 2026

YUL - LGW

Had to bus to the plane which made priority boarding at the back of the bus

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 18h 08m. The distance between Windsor, Ontario and Caribbean is about 3095 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 - Punta Cana, Windsor - Montego Bay Sangster Intl 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
Hamilton to Cancún flights
Hamilton to Vancouver Intl flights
Region of Waterloo Intl to Cancún flights
Pearson Intl to Cozumel flights
Pearson Intl to Abbotsford flights
Toronto Island to Vancouver Intl flights
Pearson Intl to Calgary flights
Region of Waterloo Intl to Vancouver Intl flights
Hamilton to Calgary flights
Pearson Intl to New Delhi flights
Toronto Island to Newark flights
Pearson Intl to Newark flights
Pierre Elliott Trudeau Intl to Cancún flights
Pierre Elliott Trudeau Intl to Charles de Gaulle flights
Pearson Intl to Heathrow flights
Pearson Intl to John F Kennedy Intl flights
Toronto Island to Calgary flights
Pierre Elliott Trudeau Intl to Vancouver Intl flights
Region of Waterloo Intl to Calgary flights
Hamilton to Halifax flights
Pearson Intl to Istanbul flights
Pearson Intl to LaGuardia flights
Pearson Intl to Halifax flights
Pierre Elliott Trudeau Intl to Calgary flights
Toronto Island to Halifax flights
Region of Waterloo Intl to Abbotsford flights
Pearson Intl to Gatwick flights
Ottawa to Vancouver Intl flights
Pearson Intl to Edmonton flights
Hamilton to Edmonton flights
Pearson Intl to Pierre Elliott Trudeau Intl flights
Pearson Intl to Fort Lauderdale flights
Pearson Intl to Leonardo da Vinci/Fiumicino flights
Pearson Intl to Mexico City flights
Pierre Elliott Trudeau Intl to Newark flights
Pierre Elliott Trudeau Intl to Narita flights
Pearson Intl to Narita flights
Toronto Island to John F Kennedy Intl flights
Pearson Intl to Charles de Gaulle flights
Toronto Island to LaGuardia flights
Pearson Intl to Haneda flights
Pearson Intl to Lisbon flights
Toronto Island to New Delhi flights
Pearson Intl to Suvarnabhumi flights
Pierre Elliott Trudeau Intl to Leonardo da Vinci/Fiumicino flights
Pearson Intl to Las Vegas flights
Pierre Elliott Trudeau Intl to Abbotsford flights

Top airline flying from Windsor to Caribbean

Discover the top airline 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 6 July 2026.
AirlineCheapestAverageFlexibilityOn-time
Air TransatCheapestC$ 748AverageC$ 949FlexibilityNo 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.