C$ 328 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 3/4. 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$ 621
Montego Bay
Montego Bay1 stopC$ 655
Punta Cana
Punta Cana1 stopC$ 621
Montego Bay
Montego Bay1 stopC$ 655

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, 6 Mar - Fri, 13 Mar
Air Canada Logo
9:40 a.m. - 12:05 p.m.
YQG
-
PUJ
25h 25m
1 stop
Air Canada Logo
9:35 p.m. - 7:14 p.m.
PUJ
-
YQG
21h 39m
1 stop
C$ 621Air Canada
Fri, 6 Mar - Fri, 13 Mar
Air Canada Logo
9:40 a.m. - 9:45 p.m.
YQG
-
PUJ
11h 05m
1 stop
Air Canada Logo
9:35 p.m. - 9:04 a.m.
PUJ
-
YQG
11h 29m
1 stop
C$ 624Air Canada
Fri, 6 Mar - Fri, 13 Mar
Air Canada Logo
7:50 p.m. - 12:05 p.m.
YQG
-
PUJ
15h 15m
1 stop
Air Canada Logo
2:35 p.m. - 9:04 a.m.
PUJ
-
YQG
18h 29m
2 stops
C$ 627Air Canada
Mon, 2 Mar - Mon, 9 Mar
Air Canada Logo
7:50 p.m. - 12:30 p.m.
YQG
-
MBJ
16h 40m
1 stop
Air Canada Logo
12:40 p.m. - 9:04 a.m.
MBJ
-
YQG
19h 24m
1 stop
C$ 655Air Canada
Mon, 4 May - Wed, 13 May
Air Canada Logo
4:05 p.m. - 12:20 p.m.
YQG
-
PUJ
20h 15m
1 stop
Air Canada Logo
4:20 p.m. - 7:09 p.m.
PUJ
-
YQG
26h 49m
1 stop
C$ 669Air Canada
Sun, 22 Mar - Sun, 29 Mar
Air Canada Logo
9:40 a.m. - 11:05 a.m.
YQG
-
PUJ
25h 25m
1 stop
Air Canada Logo
9:40 p.m. - 7:09 p.m.
PUJ
-
YQG
21h 29m
1 stop
C$ 672Air Canada
Mon, 4 May - Tue, 12 May
Air Canada Logo
4:05 p.m. - 12:20 p.m.
YQG
-
PUJ
20h 15m
1 stop
Air Canada Logo
2:55 p.m. - 3:24 p.m.
PUJ
-
YQG
24h 29m
2 stops
C$ 673Air Canada
Sun, 22 Mar - Sun, 29 Mar
Air Canada Logo
7:50 p.m. - 1:00 p.m.
YQG
-
PUJ
17h 10m
2 stops
Air Canada Logo
9:40 p.m. - 9:04 a.m.
PUJ
-
YQG
11h 24m
1 stop
C$ 676Air Canada
Mon, 2 Mar - Mon, 9 Mar
Multiple Airlines Logo
7:50 p.m. - 12:30 p.m.
YQG
-
MBJ
16h 40m
1 stop
Multiple Airlines Logo
11:57 a.m. - 7:14 p.m.
MBJ
-
YQG
30h 17m
3 stops
C$ 1,013Multiple Airlines
Mon, 2 Mar - Mon, 9 Mar
Multiple Airlines Logo
9:40 a.m. - 12:02 p.m.
YQG
-
MBJ
26h 22m
2 stops
Multiple Airlines Logo
12:40 p.m. - 9:04 a.m.
MBJ
-
YQG
19h 24m
1 stop
C$ 1,128Multiple Airlines
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$ 851 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$ 851.

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$ 744 on average.

Good to know

Low seasonOctober
Cheapest flightC$ 328
Best time to beat the crowds (6% less expensive on average)
Most popular time to fly and prices are also 4% lower 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 evening, when round-trip flights cost C$ 867 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$ 867.

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 502 reviews
8.4Crew
7.0Entertainment
7.9Boarding
7.3Comfort
6.8Food
Airline reviews

The Turkish was good . I had a problem with air Transat terrible experience for me

2.0 MediocreAnonymous, Jan 2026
IST - YYZ
Read more Air Transat reviews

The Turkish was good . I had a problem with air Transat terrible experience for me

I did not like I have been charged for my carry on

Onward flight was okay. return from Lisbon was poor as we missed our flight due to a long line at the passport control. Air Transat made no effort to accommodate us even though we were at the passport control 40 minutes prior to the departure.

Very good. A lot better experience then I expected for an economy flight.

It was very good but no tv but the experience was great

Thank you for making my first experience very enjoyable. You made it all very pleasant

Great flight great seats will absolutely fly with you again

Porter airlines was good. I didn't have the best experience when booking through airfare assist however, as I got no final confirmation from them that the flight was booked until I called them. Even then, the confirmation code they gave me was incorrect and couldn't be used for check in. On a positive note airfare assist was actually picked up the phone relatively quickly when calling

The flight crew were very good, polite, and professional. Unfortunately, the rest of the experience left much to be desired. The food was extremely bland—almost tasteless. We chose the non vegetarian .The lasagna was just plain pasta with a tiny garnish and no seasoning. It felt like eating starch only, The bigger issue was with luggage and space. We boarded with three tickets, and while the seats in front of us were nearly empty, all the overhead compartments had already been filled by passengers boarding to the back. This left us and many others with no overhead storage for our carry-ons. Our bags couldn’t fit well under the seats either, which meant we lost the little legroom we had. The result was a horrible, cramped experience—sore knees, no space to stretch, and no way to rest or sleep comfortably. According to the crew this was a rather normal thing. It is obviously normal that people board with handbag and carry on but they should be only allowed to use their overhead compartment and under their seat not the way it is managed that all the spaces in the front of the plane being occupied by the people sitting way back in the plane.

Nice complete meal included and great services. Plus the plane was very clean.

Had to cancel the flight because there was a 14 hour layover before the flight. Unacceptable.

Terrible…. Reported missing luggage’s with injectable meds that needed refrigeration. Yet, delivery could not be expedited. Luggage’s were delivered 5 days after arrival. The meds were useless as ice pack had melted. So disappointed!!!

Terrible, luggage’s with b/p and diabetes meds including insulin and ozempic. I’ve in them had dissolved and rendered useless

It was a very small plane and was ok. No food or entertainment so there should be an option for NA.

I travelled in Business class for the first time and wish I could do that again.

The crew from Toronto Santiago (and the other way) weren't nice people. They seemed angry. Other flights with Air Canada had much nicer crews. Bathrooms always had sticky floors. Yuck!

No entertainment system. Paid extra for wider seats but not worth the cost. Flight left a little late and arrived early.

We boarded and then deboarded the plane after being told it needed something done that couldn't be fixed. Sent notice about 3h flight delay, then they clawed it back and we were 1h delayed. Very poor communication.

Was notified on a timely manner of any changes, if any, of the flight schedules.

My seat was covered in vomit and I will be reaching out to Air Canada

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports