C$ 369 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 15/7. 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$ 698
Montego Bay
Montego Bay1 stopC$ 971
Punta Cana
Punta Cana1 stopC$ 698
Montego Bay
Montego Bay1 stopC$ 971

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

Sat, 26 Sep - Mon, 28 Sep
Air Canada Logo
4:05 p.m. - 1:45 p.m.
YQG
-
SJU
21h 40m
2 stops
Air Canada Logo
1:00 a.m. - 7:02 p.m.
SJU
-
YQG
18h 02m
2 stops
C$ 633Air Canada
Sat, 19 Sep - Mon, 21 Sep
Air Canada Logo
10:05 a.m. - 12:54 p.m.
YQG
-
SJU
26h 49m
2 stops
Air Canada Logo
1:00 a.m. - 7:07 p.m.
SJU
-
YQG
18h 07m
2 stops
C$ 637Air Canada
Sat, 19 Sep - Mon, 21 Sep
Air Canada Logo
10:05 a.m. - 12:54 p.m.
YQG
-
SJU
26h 49m
2 stops
Air Canada Logo
1:00 a.m. - 7:07 p.m.
SJU
-
YQG
18h 07m
2 stops
C$ 638Air Canada
Sat, 19 Sep - Mon, 21 Sep
Air Canada Logo
10:05 a.m. - 12:54 p.m.
YQG
-
SJU
26h 49m
2 stops
Air Canada Logo
1:00 a.m. - 7:07 p.m.
SJU
-
YQG
18h 07m
2 stops
C$ 640Air Canada
Mon, 3 Aug - Mon, 10 Aug
Air Canada Logo
7:45 p.m. - 3:25 p.m.
YQG
-
PUJ
19h 40m
1 stop
Air Canada Logo
4:20 p.m. - 7:02 p.m.
PUJ
-
YQG
26h 42m
1 stop
C$ 698Air Canada
Sat, 4 Jul - Mon, 13 Jul
Air Canada Logo
7:45 p.m. - 3:15 p.m.
YQG
-
PUJ
19h 30m
1 stop
Air Canada Logo
4:20 p.m. - 9:22 a.m.
PUJ
-
YQG
17h 02m
1 stop
C$ 701Air Canada
Mon, 3 Aug - Mon, 10 Aug
Air Canada Logo
7:45 p.m. - 4:05 p.m.
YQG
-
PUJ
20h 20m
2 stops
Air Canada Logo
4:20 p.m. - 9:22 a.m.
PUJ
-
YQG
17h 02m
1 stop
C$ 702Air Canada
Mon, 19 Oct - Thu, 22 Oct
Air Canada Logo
7:45 p.m. - 3:20 p.m.
YQG
-
PUJ
19h 35m
1 stop
Air Canada Logo
4:20 p.m. - 3:22 p.m.
PUJ
-
YQG
23h 02m
1 stop
C$ 703Air Canada
Fri, 14 Aug - Sat, 29 Aug
Multiple Airlines Logo
4:30 p.m. - 6:30 p.m.
YQG
-
MBJ
27h 00m
2 stops
Multiple Airlines Logo
7:30 p.m. - 3:46 p.m.
MBJ
-
YQG
19h 16m
2 stops
C$ 1,209Multiple Airlines
Sat, 1 Aug - Sat, 8 Aug
WestJet Logo
4:00 p.m. - 11:53 p.m.
YQG
-
SJU
31h 53m
2 stops
WestJet Logo
2:31 p.m. - 3:10 p.m.
SJU
-
YQG
48h 39m
2 stops
C$ 1,972WestJet
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$ 1,049 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$ 1,049.

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$ 947 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$ 947.

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$ 941 on average.

Good to know

Cheapest flightC$ 369
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 556 reviews
8.5Crew
7.9Boarding
6.8Food
7.3Comfort
7.1Entertainment
Airline reviews

My screen was broken so now movies, etc, but I didn’t really mind. They did work on it, so good effort on their part.

10.0 ExcellentWilliam, Jun 2026
LGW - YYZ
Read more Air Transat reviews

My screen was broken so now movies, etc, but I didn’t really mind. They did work on it, so good effort on their part.

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

I didn't have any problems during my flight. My main issue is with airlines in general, they keep offering less and less every year, AirTransat is no different.

Crew was good, helpful. Flight ran on time.would have liked to take airtransat home to MTL. But the price back from San Jose Costa Rica was MUCH more expensive than the flight from MTL to San Jose c.r.

i was not able to take my flight because the information i needed to book my dog correctly was not provided

We are a senior couple (70+) and chose emergency exit seats so we would have 2 seats together and neither of us had to sit in a middle seat. My husband is type 1 diabetic on an insulin pump and I monitor his blood sugar levels. I am 5'9" and 250 lbs and found the seats extremely uncomfortable. Toward the end of the flight I developed diarrhea which lasted a full 24 hours.

I was very nice to arrive earlier than scheduled. Very much appreciated. No issues with flight. All was good.

We were treated well by the staff at the airport and on board aircraft. Delay was uncontrollable due to the weather. Had to wait for another gate as we were late landing in Fort Lauderdale.

I was supose to have a carrey on incluided for each passenger and they made me paid 75$ each at the gate.

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.

Aircraft is designed with all 3 washrooms at the back of the plane, meaning that when there is service underway, there are no washrooms available and it gets very crowded at the back of the plane.

I was through check-in right away and on the plane before I knew it perfect in every way

Excellent flight crew. Very comfortable plane. Entertainment options on air Canada were great!

Flight was oversold. Seats assigned to multiple passengers. Delay 1 hour to sort out.

Good but I don’t received my bags yet is been 5days still no update

Boarding is always chaotic. Delay was over 2 hours while inside plane . Crew not very friendly

Congested seating area Toronto Poor announcements Terrible food in flight Limited entertainment options

The flight was good. My luggage didn’t land with me when I arrived in Columbus. So grateful I was able to get my luggage back within the 2 hours😍👍.

Comfortable seats with good leg room. But not screens on seat backs.

I was rescheduled when I missed my flight due to border clearance issue

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports