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Cheap flights from Windsor, ON to Caribbean from C$ 321

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 27/7. Fares are subject to change and may not be available on all flights or dates of travel.
YQG — SJU
17 Jun — 24 Jun1
1 adult

Cheap flight deals from Windsor to Caribbean

Keep the following information in mind while searching for Windsor to Caribbean flight deals. Data was last updated 12 June 2025.

Round-trip from

C$ 763

One-way from

C$ 321
Air Canada
  • Air Canada
  • 24/6-27/6
  • 2 total stops
  • 52h 12m total
  • Windsor to Caribbean
Search Deals
Air Canada
  • Air Canada
  • 27/7
  • 1 total stop
  • 26h 00m total
  • Windsor to Caribbean
Search Deals

Find flight deals from Windsor to Caribbean

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 12 June 2025.

Tue 24/610:15 a.m.YQG - MBJ
1 stop25h 55mAir Canada
Fri 27/612:05 p.m.MBJ - YQG
1 stop26h 17mAir Canada
Deal found 10/6C$ 763
Wed 18/61:50 p.m.YQG - PUJ
2 stops23h 55mMultiple Airlines
Wed 25/68:15 p.m.PUJ - YQG
2 stops41h 35mMultiple Airlines
Deal found 11/6C$ 775
Sun 3/84:00 p.m.YQG - PUJ
1 stop23h 20mAir Canada
Wed 6/82:25 p.m.PUJ - YQG
2 stops19h 02mAir Canada
Deal found 12/6C$ 801
Fri 27/62:30 p.m.YQG - PUJ
2 stops23h 15mAir Transat
Thu 3/73:05 p.m.PUJ - YQG
2 stops22h 45mAir Transat
Deal found 12/6C$ 965
Wed 30/77:45 p.m.YQG - MBJ
2 stops38h 42mWestJet
Tue 12/81:40 p.m.MBJ - YQG
2 stops52h 15mWestJet
Deal found 9/6C$ 1,259
Wed 30/77:45 p.m.YQG - SJU
2 stops24h 54mWestJet
Mon 4/87:30 a.m.SJU - YQG
2 stops35h 25mWestJet
Deal found 11/6C$ 1,460
Wed 30/710:05 a.m.YQG - SJU
2 stops13h 49mAir Canada
Sun 3/81:05 a.m.SJU - YQG
2 stops14h 17mAir Canada
Deal found 11/6C$ 1,999

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 12 June 2025.
Use the filters below to find and compare flights from Windsor to Caribbean that are best for you.

Fly from

Windsor

Fly to

Caribbean

Route

Depart

Return

Price

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Tue 24/6

10:15 a.m.-11:10 a.m.

1 stop25h 55m

Montego Bay Sangster Intl

Fri 27/6

12:05 p.m.-3:22 p.m.

1 stop26h 17m

C$ 763

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Wed 30/7

7:45 p.m.-9:27 a.m.

2 stops38h 42m

Montego Bay Sangster Intl

Tue 12/8

1:40 p.m.-6:55 p.m.

2 stops52h 15m

C$ 1,259

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Wed 30/7

7:45 p.m.-8:39 p.m.

2 stops24h 54m

San Juan Luis Munoz Marin Intl

Mon 4/8

7:30 a.m.-6:55 p.m.

2 stops35h 25m

C$ 1,460

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Wed 30/7

10:05 a.m.-11:54 p.m.

2 stops13h 49m

San Juan Luis Munoz Marin Intl

Sun 3/8

1:05 a.m.-3:22 p.m.

2 stops14h 17m

C$ 1,999

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Sun 27/7

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

1 stop26h 00m

C$ 321

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sat 26/7

4:00 p.m.-1:25 p.m.

2 stops45h 25m

C$ 353

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sat 26/7

2:30 p.m.-11:45 a.m.

3 stops21h 15m

C$ 491

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Sun 27/7

4:00 p.m.-11:05 a.m.

3 stops20h 05m

C$ 524

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/6

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

What is the cheapest month to book a flight from Windsor, Ontario to Caribbean?

Currently, April is the cheapest month in which you can book a flight from Windsor, Ontario to Caribbean (average of C$ 254). Flying from Windsor, Ontario to Caribbean 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.

Rainfall in Caribbean by month

Plan your trip to Caribbean by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean ranges from 40.0 - 180.0 mm per month. October is typically the wettest month, when rainfall can reach 180.0 mm. February is typically the driest time to visit Caribbean when rainfall is around 40.0 mm.

Temperature in Caribbean by month

Plan your trip to Caribbean by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 28.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 25.0 C).

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 12 June 2025.
Air Transat
7.8
Good
396 reviews
Check prices

Boarding

7.9

Food

6.8

Crew

8.5

Comfort

7.4

Overall

7.8

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Janice,Mar 2025

OPO - YYZ

I upgraded to Club Pass Business, and it made my trip a pleasant flight. The service was excellent and the food and drink options were good. The seats were comfy.
Air Transat
7.8
Good
396 reviews
Air Transat
7.8
Good
396 reviews
Check prices

Boarding

7.9

Food

6.8

Crew

8.5

Comfort

7.4

Overall

7.8

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Janice,Mar 2025

OPO - YYZ

I upgraded to Club Pass Business, and it made my trip a pleasant flight. The service was excellent and the food and drink options were good. The seats were comfy.
WestJet
7.2
Good
2,868 reviews
Air Transat
7.8
Good
396 reviews
Check prices

Boarding

7.9

Food

6.8

Crew

8.5

Comfort

7.4

Overall

7.8

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Janice,Mar 2025

OPO - YYZ

I upgraded to Club Pass Business, and it made my trip a pleasant flight. The service was excellent and the food and drink options were good. The seats were comfy.
Air Canada
7.1
Good
9,531 reviews
Air Transat
7.8
Good
396 reviews
Check prices

Boarding

7.9

Food

6.8

Crew

8.5

Comfort

7.4

Overall

7.8

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Janice,Mar 2025

OPO - YYZ

I upgraded to Club Pass Business, and it made my trip a pleasant flight. The service was excellent and the food and drink options were good. The seats were comfy.

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.

  • 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.

  • What is the cheapest month to book a flight from Windsor, Ontario to Caribbean?

    Currently, April is the cheapest month in which you can book a flight from Windsor, Ontario to Caribbean (average of C$ 254). Flying from Windsor, Ontario to Caribbean 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Windsor to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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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 12 June 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 481AverageC$ 755FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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How does Cheapflights help users find flights from Windsor to Caribbean?

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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.

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