C$ 247 Find Cheap Flights from Windsor to Caribbean – Compare and Save

1 adult
1 adult, Economy, 0 bags

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Best Caribbean Flight Deals from Windsor

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana1 stopC$ 529
Montego Bay
Montego Bay1 stopC$ 516
Punta Cana
Punta Cana1 stopC$ 529
Montego Bay
Montego Bay1 stopC$ 516
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.

What is the cheapest Windsor to Caribbean flight route?

The cheapest ticket to Caribbean from Windsor found in the last 5 days was to Punta Cana, at C$ 1,034 round-trip. The most popular route is from Windsor (YQG) to Punta Cana (PUJ), and the cheapest round-trip airline ticket found on this route in the last 5 days was C$ 1,034.

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

The cheapest time of day to fly to Caribbean is generally in the evening, when round-trip flights cost C$ 933 on average. Morning departures are around 100% 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$ 933.

Can I save money by flying with a layover from Windsor to Caribbean?

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at C$ 912 on average.

Good to know

Cheapest flight

C$ 247
Flight from Windsor to Montego Bay

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.

Reviews of the top airlines 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.
7.7
Air TransatOverall score based on 579 reviews
7.3Comfort
8.5Crew
6.8Food
8.0Boarding
7.1Entertainment
Airline reviews

On one of the flights, the situation became sufficiently frustrating that a passenger openly expressed their dissatisfaction. Despite these complaints, we did not observe any meaningful improvement or receive an adequate explanation. The fact that members of our group experienced similar conditions on two separate aircraft is particularly concerning. We recognize that cabin temperatures may vary during a flight; however, the prolonged discomfort and the apparent lack of an effective response significantly affected our travel experience. Passengers reasonably expect a long-haul international flight to provide a tolerable cabin environment. When multiple passengers raise concerns about their comfort or well-being, those concerns should be acknowledged and addressed professionally.

2.0 MediocreAnonymous, Sep 2026
Read more Air Transat reviews

On one of the flights, the situation became sufficiently frustrating that a passenger openly expressed their dissatisfaction. Despite these complaints, we did not observe any meaningful improvement or receive an adequate explanation. The fact that members of our group experienced similar conditions on two separate aircraft is particularly concerning. We recognize that cabin temperatures may vary during a flight; however, the prolonged discomfort and the apparent lack of an effective response significantly affected our travel experience. Passengers reasonably expect a long-haul international flight to provide a tolerable cabin environment. When multiple passengers raise concerns about their comfort or well-being, those concerns should be acknowledged and addressed professionally.

Flight was really good, with no middle section on an A321neo for an international flight, from Ottawa directly to London. Staff was friendly. The food was okay, and entertainment amenities could be better.

The flight was terrible based off the temperature in the plane and the air smelled so stale and gross. I have never wanted to hosed lore in my life after I got off. The food was disgusting and seemingly low quality. The staff was friendly. The bathrooms were so gross after a couple of hours. I will definitely never book with them again.

The crew was great. There was no entertainment and the internet wasn't working. We sat in the run way for a LONG time which is always so upsetting. The seats are very close together and the flights are completely full which makes for a tough flight. Flying is just an uncomfortable experience.

Very kind crew. Vegetarian food better than usual. Prompt take off. Entertainment worked well. Could always do with more room!

The dinner was bland and boring, but the economy seats were surprisingly comfortable. The flight was very packed.

Great crew and entertaining Captain. Seats were not what we had expected based on my booking but things worked out in the end. Of course, like all airlines these days not enough leg or elbow room.

The entertainment system was down; food by purchase only; several people did not receive their luggage. No one answers at the local office or online about the luggage.

This has been the worst experience I’ve ever had. Basically, I lost my round-trip tickets because one of my last names was missing, and you didn’t allow me to correct it. I had to purchase a full ticket again. Once I get home, I will start legal proceedings against you.

It’s ok just the boarding point is far too far

The usb ports to charge phones laptops did not work.

Staff never asked passengers to bring their seat backs forward during landing. Was hoping to get a little relief from the passenger in front of me (I have long legs that I cannot stow in the overhead). Otherwise the flight was very pleasant.

Everything was excellent except the breakfast was cheap yogurt and cake ????

Exorbitantly overpriced ticket. Flight was delayed as per usual with air Canada and there was zero refund or compensation.

Flight delay due to staff shortage. No snack or drinks served. Toilets had water collecting on the floor.

Flight was delayed due to crew/co-pilot change over delay and Pearson scheduling issue. Flight didn't leave until 20:05 which was 15 minutes before it was supposed to land in YYZ.

Because you didn't have the tarmac clear and then had to unboard a plane I missed my connecting flight to CLE. Cost me a day ... a 30 dollar hotel hamburger ... then the next day THAT flight was an hour late to arrive ...

My flight got Delayed due to the airline. The attending Crewe in Montreal were not super helpful and I arrived 13 1/2 hours late from my original arrival time. Air Canada lost my luggage, they stated they booked me a hotel room overnight at no fee, however when I arrive to the hotel, there was no reservation. It also took me three different attempts to get the hotel, even covered by Air Canada as they were arguing that they were not responsible for this, despite it having been delayed due to the airline. Overall, the service was very very poor and what should’ve been a short five hour trip turned into a 13 1/2 hour saga with me, spending a night in a random airport overnight due to Air Canada’s errors, and searching for my luggage until 2 o’clock in the morning. I will never fly Air Canada again.

French speaker should have an intelligible accent 4.5 hour flights with 2 hour delays should have more than a granola bar included

My only issue was the cost of the flight. I paid close to $900, and I’ve never experienced that before. Plus I had to pay for wifi on the flight. Otherwise, everything else was fine.

More options for your flight to Caribbean

Complete your trip to Caribbean with a hotel stay or car rental