C$ 337 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 11/12. 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, 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 72 hours
Punta Cana
Punta Cana2 stopsC$ 564
Montego Bay
Montego Bay1 stopC$ 829
Punta Cana
Punta Cana2 stopsC$ 564
Montego Bay
Montego Bay1 stopC$ 829

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

Mon, 17 Nov - Mon, 24 Nov
Air Canada Logo
9:45 a.m. - 12:45 a.m.YQG-PUJ
14h 00m2 stops
Air Canada Logo
10:25 p.m. - 7:14 p.m.PUJ-YQG
21h 49m1 stop
C$ 564Air Canada
Find Deal
Mon, 17 Nov - Mon, 24 Nov
Air Canada Logo
9:45 a.m. - 12:45 a.m.YQG-PUJ
14h 00m2 stops
Air Canada Logo
3:35 p.m. - 7:14 p.m.PUJ-YQG
28h 39m2 stops
C$ 566Air Canada
Find Deal
Sun, 7 Dec - Wed, 10 Dec
Air Canada Logo
7:50 p.m. - 2:00 p.m.YQG-PUJ
17h 10m2 stops
Air Canada Logo
1:05 p.m. - 9:04 a.m.PUJ-YQG
20h 59m1 stop
C$ 573Air Canada
Find Deal
Wed, 14 Jan - Wed, 21 Jan
Air Canada Logo
9:45 a.m. - 9:35 p.m.YQG-PUJ
10h 50m1 stop
Air Canada Logo
7:40 p.m. - 7:14 p.m.PUJ-YQG
24h 34m2 stops
C$ 579Air Canada
Find Deal
Wed, 26 Nov - Sun, 30 Nov
Air Canada Logo
9:45 a.m. - 9:35 p.m.YQG-PUJ
10h 50m1 stop
Air Canada Logo
6:15 p.m. - 7:14 p.m.PUJ-YQG
25h 59m2 stops
C$ 603Air Canada
Find Deal
Sat, 7 Feb - Tue, 17 Feb
Air Canada Logo
9:45 a.m. - 2:00 p.m.YQG-PUJ
51h 15m2 stops
Air Canada Logo
7:40 p.m. - 7:14 p.m.PUJ-YQG
24h 34m2 stops
C$ 608Air Canada
Find Deal
Fri, 9 Jan - Fri, 23 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$ 759Air Transat
Find Deal
Fri, 6 Feb - Fri, 13 Feb
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$ 864Air Transat
Find Deal
Fri, 6 Feb - Tue, 17 Feb
Multiple Airlines Logo
5:35 p.m. - 10:45 p.m.YQG-PUJ
4h 10mdirect
Multiple Airlines Logo
8:05 p.m. - 7:33 p.m.PUJ-YQG
24h 28m1 stop
C$ 911Multiple Airlines
Find Deal
Fri, 20 Feb - Fri, 27 Feb
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$ 915Air Transat
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.

What is the cheapest Windsor to Caribbean flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean from Windsor found in the last 72 hours was to Punta Cana, at C$ 737 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 72 hours was C$ 737.

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

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

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$ 803 on average.

Good to know

Low seasonOctober
Cheapest flightC$ 350
Best time to beat the crowds (5% less expensive on average)
Most popular time to fly and prices are also 11% lower on average.
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.

  • 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$ 738 on average. Morning departures are around 19% 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$ 908.

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 10370 reviews
6.8Entertainment
7.8Crew
7.1Comfort
6.3Food
7.3Boarding
Airline reviews

Snacks were just placed and many people were hungry and unaware they were available. Ran out of water bottles. Attendants not available. Missed entire meal.

2.0 MediocreR, Oct 2025YYZ - HND
Read more Air Canada reviews

Snacks were just placed and many people were hungry and unaware they were available. Ran out of water bottles. Attendants not available. Missed entire meal.

Very Bad experience with Swiss, they robbed me for additional baggage and misguided. The flight was delayed for 2hr 55 minutes, screens were not functional and food was also bad.

The free Wi-fi for Aeroplan members was a great touch. The time passed quickly. I found the seats seemed a little closer together than I remember. Not Air Canada's fault, but we were about 20 minutes late landing because the airport was too busy. We had to circle around for a while. The boarding and disembarking went very smoothly.

Too many delays. Seats too small. A budget airline. Will never fly Air Canada again.

On board wifi or other entertainment. Landlines option was good but ran late to Pearson

Extremely turbulent landing. Crew was friendly and plane comfortable. Airport and US pre clearance was understaffed

More space on a sold out fight and food trays were dirty

The airplane is way too tight, you can hardly enter into your row to sit.. more like kids seats than adults.

My original flight was cancelled -- but I have to mention the excellent service I was given by the agent working at check-in who found me an earlier flight -- and helped me navigate security, ensured my baggage kept up with the quick check-in and boarding process -- and just generally made the re-booking process a breeze. Thank you! On flight was fine, but we unfortunately meant no in-flight service -- no water, or coffee (it was an early morning flight...), but the crew was pleasant and accommodating throughout.

No in flight entertainment on a 750 mile flight. Made you join their "program" to get it. It was free on my first leg of the flight from Cincinnati to Toronto. In addition, there was brief period of turbulence that prohibited the crew from serving refreshments. They used that short interruption as an excuse to never serve drinks at all. They had ample time to do so and chose not to. They went around serving half cups of water instead rather than have their carts in the aisle with drinks.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

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