C$ 317 Find Cheap Flights from Windsor to Caribbean – Compare and Save

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 28/8. 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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Flight Deals

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$ 738
Montego Bay
Montego Bay1 stopC$ 510
Punta Cana
Punta Cana1 stopC$ 738
Montego Bay
Montego Bay1 stopC$ 510

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

Sun, 25 Oct - Thu, 29 Oct
Air Canada Logo
10:35 a.m. - 11:50 a.m.
YQG
-
MBJ
26h 15m
1 stop
Air Canada Logo
12:50 p.m. - 9:55 a.m.
MBJ
-
YQG
20h 05m
1 stop
C$ 510Air Canada
Mon, 26 Oct - Sun, 1 Nov
Air Canada Logo
10:35 a.m. - 4:20 p.m.
YQG
-
MBJ
6h 45m
1 stop
Air Canada Logo
2:20 p.m. - 9:55 a.m.
MBJ
-
YQG
19h 35m
2 stops
C$ 512Air Canada
Sat, 19 Sep - Wed, 23 Sep
Air Canada Logo
10:05 a.m. - 11:57 a.m.
YQG
-
SJU
25h 52m
2 stops
Air Canada Logo
3:00 p.m. - 3:22 p.m.
SJU
-
YQG
24h 22m
2 stops
C$ 632Air Canada
Sat, 19 Sep - Wed, 23 Sep
Air Canada Logo
10:05 a.m. - 11:57 a.m.
YQG
-
SJU
25h 52m
2 stops
Air Canada Logo
3:00 p.m. - 3:22 p.m.
SJU
-
YQG
24h 22m
2 stops
C$ 633Air Canada
Mon, 26 Oct - Sun, 1 Nov
Air Canada Logo
10:35 a.m. - 4:20 p.m.
YQG
-
MBJ
6h 45m
1 stop
Air Canada Logo
1:50 p.m. - 9:55 a.m.
MBJ
-
YQG
20h 05m
1 stop
C$ 664Air Canada
Sat, 9 Jan - Sat, 16 Jan
Air Canada Logo
10:35 a.m. - 9:40 p.m.
YQG
-
PUJ
10h 05m
1 stop
Air Canada Logo
3:35 p.m. - 9:55 a.m.
PUJ
-
YQG
19h 20m
1 stop
C$ 738Air Canada
Sat, 23 Jan - Tue, 26 Jan
Air Canada Logo
7:20 p.m. - 1:50 p.m.
YQG
-
PUJ
17h 30m
1 stop
Air Canada Logo
7:35 p.m. - 9:55 a.m.
PUJ
-
YQG
15h 20m
1 stop
C$ 741Air Canada
Sat, 9 Jan - Sat, 16 Jan
Air Canada Logo
7:20 p.m. - 1:50 p.m.
YQG
-
PUJ
17h 30m
1 stop
Air Canada Logo
7:45 p.m. - 6:45 p.m.
PUJ
-
YQG
24h 00m
2 stops
C$ 743Air Canada
Sat, 23 Jan - Tue, 26 Jan
Air Canada Logo
10:35 a.m. - 9:40 p.m.
YQG
-
PUJ
10h 05m
1 stop
Air Canada Logo
7:45 p.m. - 6:45 p.m.
PUJ
-
YQG
24h 00m
2 stops
C$ 747Air Canada
Sat, 9 Jan - Sat, 16 Jan
Air Canada Logo
10:35 a.m. - 1:45 p.m.
YQG
-
PUJ
26h 10m
2 stops
Air Canada Logo
7:45 p.m. - 6:45 p.m.
PUJ
-
YQG
24h 00m
2 stops
C$ 747Air Canada
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 5 days was to Punta Cana, at C$ 1,040 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$ 1,040.

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

The average price for all round-trip flights from Windsor to Caribbean depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Caribbean is generally in the evening, when round-trip flights cost C$ 939 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$ 939.

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$ 919 on average.

Good to know

Cheapest flight

C$ 317
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.

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.
7.8
Air TransatOverall score based on 569 reviews
8.0Boarding
7.1Entertainment
8.5Crew
6.8Food
7.3Comfort
Airline reviews

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.

2.0 MediocreMirjam, Jul 2026
YYZ - AMS
Read more Air Transat reviews

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

They are a sister company with Air Transat and the two companies do not work well together. If you have any issues the two companies will blame each other and you will miss your flights. The help line does not help

Flight delayed any hour and couple of big gate changes

Kept me waiting for hours with the excuse of aircraft needed to cool down and then cancelled.

Flight attendants had an attitude with everyone, not sure they should be working with customer service if they cannot show a pleasant attitude. Underwhelming, to say the least. The food was awful, and nothing could be purchased from Toronto to Tokyo. Do better, Air Canada.

Boarding and times were all good. Food was as expected and enough. Comfort for a 6’ tall male 200 lbs (somewhat average sized) was terrible. It was just SO much more money to upgrade to premium economy. It’s a 777 so seating is 3-4-3 and is really crammed. What are you going to do? The only real downside is not being able to sleep so your first day in Europe is a write off. I suppose if you need that first day then pay the extra $500 to get premium economy and maybe you can sleep and wake up with some energy?

No charger and no entertainment on the way back. The plane's super old-like 80s old-with zero TVs. At least the free Wi-Fi works, so definitely bring your iPad. Also, no meal on this 7-hour flight.

Horrible! Rude flight attendant, barely any service on such a long flight. I wouldn't recommend Air Canada to anyone.

The trip was very smooth; the seat was quite comfortable, and the food was excellent and tasty.

Bluetooth to use earphones with the onboard entertainment system failed. WiFi worked at least.

Pilot missed Fredericton airstrip on first go, so had to ascend again, turn around and try it again, successfully, albeit a little jittery...perhaps a new or inexperienced pilot. Not the greatest Air Canada experience. Delayed us even more.

The floor plan on the website indicated I was selecting a seat at the front of the cabin with ample leg room. In fact, I was in the row behind it. I should have wondered when the seat was free to upgrade, but it meant I traded an aisle seat three rows back for a middle seat, which was quite cramped. The Internet didn't work and the live TV didn't work until the last half hour of the trip. On a night of World Cup soccer games, not good.

Canceled my flight in March and have been waiting for 3 months now without the refund after it was promised

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports