C$ 318 Find Cheap Flights from Windsor to Caribbean

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Windsor to Caribbean departing on 13/9. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

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Best Caribbean Flight Deals from Windsor

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stopC$ 609
Montego Bay
Montego Bay1 stopC$ 2,711
Oranjestad
Oranjestad2 stopsC$ 630
Bridgetown
Bridgetown1 stopC$ 583
Punta Cana
Punta Cana1 stopC$ 609
Montego Bay
Montego Bay1 stopC$ 2,711
Oranjestad
Oranjestad2 stopsC$ 630
Bridgetown
Bridgetown1 stopC$ 583

Cheap Flights from Windsor to Caribbean

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Windsor to Caribbean that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Windsor to Caribbean

Fri, 26 Sep - Mon, 29 Sep
Air Canada Logo
3:55 p.m. - 3:20 p.m.YQG-PUJ
23h 25m1 stop
Air Canada Logo
2:25 p.m. - 9:12 a.m.PUJ-YQG
18h 47m2 stops
C$ 609Air Canada
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Fri, 26 Sep - Mon, 29 Sep
Air Canada Logo
3:55 p.m. - 1:25 p.m.YQG-PUJ
45h 30m2 stops
Air Canada Logo
2:25 p.m. - 3:17 p.m.PUJ-YQG
24h 52m2 stops
C$ 612Air Canada
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Sat, 29 Nov - Sun, 7 Dec
Air Canada Logo
7:50 p.m. - 2:00 p.m.YQG-PUJ
41h 10m2 stops
Air Canada Logo
1:05 p.m. - 7:14 p.m.PUJ-YQG
7h 09m1 stop
C$ 637Air Canada
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Sat, 29 Nov - Sun, 7 Dec
Air Canada Logo
9:45 a.m. - 1:45 p.m.YQG-PUJ
27h 00m1 stop
Air Canada Logo
1:05 p.m. - 9:04 a.m.PUJ-YQG
20h 59m1 stop
C$ 664Air Canada
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Tue, 13 Jan - Tue, 20 Jan
Air Canada Logo
9:45 a.m. - 12:45 a.m.YQG-PUJ
14h 00m2 stops
Air Canada Logo
10:25 p.m. - 9:04 a.m.PUJ-YQG
11h 39m1 stop
C$ 669Air Canada
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Sun, 25 Jan - Sat, 31 Jan
Air Canada Logo
7:50 p.m. - 2:00 p.m.YQG-PUJ
17h 10m2 stops
Air Canada Logo
7:40 p.m. - 7:14 p.m.PUJ-YQG
24h 34m2 stops
C$ 699Air Canada
Find Deal
Fri, 26 Sep - Mon, 29 Sep
Air Canada Logo
3:55 p.m. - 3:20 p.m.YQG-PUJ
23h 25m1 stop
Air Canada Logo
4:25 p.m. - 3:17 p.m.PUJ-YQG
22h 52m1 stop
C$ 772Air Canada
Find Deal
Sun, 25 Jan - Sat, 31 Jan
Air Canada Logo
9:45 a.m. - 1:45 p.m.YQG-PUJ
27h 00m1 stop
Air Canada Logo
10:50 p.m. - 9:04 a.m.PUJ-YQG
11h 14m1 stop
C$ 922Air Canada
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Fri, 26 Dec - Fri, 2 Jan
Air Transat Logo
5:35 p.m. - 10:45 p.m.YQG-PUJ
4h 10mdirect
Air Transat Logo
12:40 p.m. - 4:15 p.m.PUJ-YQG
4h 35mdirect
C$ 1,347Air Transat
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Fri, 26 Dec - Fri, 2 Jan
Logo
5:35 p.m. - 10:45 p.m.YQG-PUJ
4h 10mdirect
Logo
3:35 p.m. - 7:14 p.m.PUJ-YQG
28h 39m2 stops
C$ 1,744
Find Deal
Booking Insights

KAYAK's insights & trends for Windsor to Caribbean flights

Get data-powered insights and trends into flights from Windsor to Caribbean to help you find the cheapest flights, the best time to fly and much more.

Which airlines provide the cheapest flights from Windsor to Caribbean?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Windsor to Caribbean were found on Air Canada (C$ 609) and Air Transat (C$ 1,347).

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Good to know

Low seasonMay
Cheapest flightC$ 318
Best time to beat the crowds but there is an average 6% increase in price.
Most popular time to fly (27% more expensive on average)
Flight from Windsor to Punta Cana

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Windsor to Caribbean?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Windsor to Caribbean.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Windsor to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Windsor to Caribbean is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Windsor to Caribbean?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Windsor to Caribbean with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Windsor to Caribbean?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Windsor to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Caribbean?

    The cheapest time of day to fly to Caribbean is generally in the morning, when round-trip flights cost C$ 528 on average. Morning departures are around 16% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the evening, which is peak travel time and where the average cost of a ticket is C$ 626.

Reviews of the top airline flying from Windsor to Caribbean

 
Need help choosing which airline to fly with from Windsor to Caribbean? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
Air CanadaOverall score based on 9837 reviews
6.3Food
7.1Comfort
7.3Boarding
6.8Entertainment
7.8Crew
Airline reviews

Flight got delayed for no reason. And Air Canada was doing 3 boardings via the same gate. It was chaotic!

2.0 MediocreAnonymous, Jul 2025YYZ - LGA
Read more Air Canada reviews

Flight got delayed for no reason. And Air Canada was doing 3 boardings via the same gate. It was chaotic!

I n the Toronto airport I had trouble finding my zone. It was 47. I went from Zone 1 to the end of the line.didn't find it. Then saw my zone somewhat by accident over by where you first come in. Signs could be more helpful or more personnel directing people like me.

Wonderful airline. All staff were pleasant and helpful. What is sad is that it wasn’t grand gestures just everyday pleasantness and friendliness that are missing from the other airlines I have flown recently.

Friendly efficient crew, but plane had no way to charge phone. That is a near necessity with today’s travel where we carry out travel documents on our phones.

Orderly boarding. The flight to Montreal was difficult to get to on time, but had help from staffer.

Orlando to Canada, despite being close and an international flight, the plane was not at all comfortable. It felt like the chair was being pushed forward, in addition to not having a TV and having to choose from a tiny glass of drink, for example, water or soda. I couldn't have both. When I asked the flight attendant for an extra glass of water, she looked at me with an ugly face. This is ridiculous. They don't want to give water to passengers. I will never fly with this airline again in my life.

The checking of my carry-on was not the greatest idea. It was selected for a security check in Toronto and didn't make it to my connecting flight. Fortunately Air Canada delivers late luggage to Whistler so I got it at 2 A M.

The seating and lack of leg room. I paid extra for more leg room. The space for under seat storage was a joke.

Well managed flight comfortable. Wish they had back of seat screens

Because of a change in aircraft, I was unable to experience the business class I paid for and was disappointed.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

Windsor (YQG)

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