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Best Caribbean Islands Flight Deals from Toronto

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta CanadirectC$ 430
Montego Bay
Montego BaydirectC$ 344
Kingston
KingstondirectC$ 443
Nassau
NassaudirectC$ 357
Willemstad
Willemstad2 stopsC$ 587
Puerto Plata
Puerto PlatadirectC$ 541
Port of Spain
Port of SpaindirectC$ 628
George Town
George TowndirectC$ 363
St. George's
St. George's1 stopC$ 494
Punta Cana
Punta CanadirectC$ 430
Montego Bay
Montego BaydirectC$ 344
Kingston
KingstondirectC$ 443
Nassau
NassaudirectC$ 357
Willemstad
Willemstad2 stopsC$ 587
Puerto Plata
Puerto PlatadirectC$ 541
Port of Spain
Port of SpaindirectC$ 628
George Town
George TowndirectC$ 363
St. George's
St. George's1 stopC$ 494
Booking Insights

KAYAK's insights & trends for Toronto to Caribbean Islands flights

Get data-powered insights and trends into flights from Toronto to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Toronto to Caribbean Islands flight route?

The cheapest ticket to Caribbean Islands from Toronto found in the last 5 days was to Montego Bay, at C$ 236 round-trip. The most popular route is from Toronto Pearson Intl Airport (YYZ) to Punta Cana (PUJ), and the cheapest round-trip airline ticket found on this route in the last 5 days was C$ 391.

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

The cheapest time of day to fly to Caribbean Islands is generally in the evening, when round-trip flights cost C$ 584 on average. Morning departures are around 11% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the afternoon, which is peak travel time and where the average cost of a ticket is C$ 759.

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

No, with an average price for the route of C$ 847, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Toronto to Caribbean Islands?

The cheapest month for flights from Toronto to Caribbean Islands is November, when tickets cost C$ 602 (return) on average. On the other hand, the most expensive months are December and August, when the average cost of round-trip tickets is C$ 803 and C$ 799 respectively.

What’s the cheapest day of the week to fly from Toronto to Caribbean Islands?

Your flight ticket price will generally be cheaper if you fly to Caribbean Islands on a Friday and more expensive on a Thursday. On your return trip to Toronto, you should consider flying back on a Friday, and avoid Thursdays for better deals.

How far in advance should I book a flight from Toronto to Caribbean Islands?

To get a below-average price on a flight from Toronto to Caribbean Islands, you should book around 4 weeks before departure, which saves you about 11% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.

Good to know

Low season

September
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly (3% more expensive on average)

Flights from Toronto to Caribbean Islands: the best tips from KAYAK users

Insights shared by verified travellers who flew the route from Toronto to Caribbean Islands 
Verified travelerFlew with Air Canada-Aug 2026
Take a nap on the plane pack light so you don’t have to check luggage and enjoy the ride
Verified travelerFlew with WestJet-Nov 2025
After landing and passing through immigration, get your SIM card for Cuba before collecting your luggage!
Jadi-AnnFlew with Air Canada-Jun 2025
Air Canada, West Jet and maybe Caribbean Airlines is good. I have always flown with Air Canada. I wish I knew about the weight limit for a third bag so I didn’t pay for the extra weight for nothing. Going through the airport was so much simpler as it was mostly automated and as long as you follow airport protocols, the first part is easy. Going to Jamaica, doing that immigration form online was new to me so I had to stay back a little once I was close to customs.
Verified travelerFlew with Air Canada-Mar 2025
Air canada. Be prepared to walk of plane to arrival outside. Luggage & customs seamless
JamieFlew with WestJet-Jan 2025
Pay for your bags before going to airport. Make sure to fill in online immigration form for DR before boarding flight.
Verified travelerFlew with Air Canada-Jan 2025
Always anticipate a line in Antigua. Submit to island time as soon as the plane lands.
Verified travelerFlew with Air Canada-Jun 2024
Bring your own entertainment and make sure you eat. There was no food only food to purchase
Verified travelerFlew with Caribbean Airlines-Mar 2024
Caribbean airline is best at boarding, make sure you have extra snacks to munch during flight.
TwyaFlew with WestJet-Apr 2024
Bring bug spray! Bring a plug in adapter!
Verified travelerFlew with Caribbean Airlines-Apr 2024
Do the C-5 Immigration form before departing.
Verified travelerFlew with Air Canada-Jan 2024
Tips: book non-stop flights (avoid connecting flights at all cost); regardless of the weather when you flight out, be prepared for anything once you arrive back from your destination (i.e. there was no snow when we left yet it was a full force blizzard once we returned - glad I had a jacket).

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Toronto to Caribbean Islands?

    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 Toronto to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Toronto to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Toronto to Caribbean Islands 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 Toronto to Caribbean Islands?

    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 Toronto to Caribbean Islands 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 Toronto to Caribbean Islands?

    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 Toronto to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 5 airlines flying from Toronto to Caribbean Islands

 
Need help choosing which airline to fly with from Toronto to Caribbean Islands? 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 583 reviews
7.1Entertainment
7.3Comfort
6.8Food
8.0Boarding
8.5Crew
Airline reviews

Very cold on aircraft. Everyone was wearing “Parker’s”to stay warm.

6.0 GoodGordon, Sep 2026
Read more Air Transat reviews

Very cold on aircraft. Everyone was wearing “Parker’s”to stay warm.

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.

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

I think I'd sum up my experiences on this flight (Edinburgh to Toronto) by saying that Boeing 737s are simply too small for long-haul, transatlantic flights. The crew were excellent, the food was pretty good and the in-flight Wifi was a bonus. But 7+ hours on a narrow bodied aircraft with a single aisle and no in-built entertainment system, is a tough stretch - queues for the few toilets on board were lengthy at times; plus whilst the crew were doing food/drink service the aisle is blocked. It encourages you to stay in your seat the entire time (not great for those who need to get up and move around regularly) and the legroom is tight anyway. If this was priced as uber-budget, you could perhaps argue that you're getting what you paid for......but it wasn't and the price we paid was pretty standard for such trips (around £500 pp). I'd therefore urge caution and check the aircraft that is being used if booking with Westjet for flights to Canada from smaller regional airports on the Western edge of Europe. They do operate Boeing 787s from London and other major European centres - but it seems that if travelling from Scotland/Ireland the 737 is the aircraft of choice.......

Maybe glass of wine would be nice at no charge

The flight didn’t happen because they apparently lost my check in and wouldn’t let me board.

Access to movies was rather confusing. Apart from that, I have no complaints.

As someone who never flies WestJet unless there is no other viable option I have to give this crew credit where credit is due. Extremely well done everyone.

Flight left on time. The crew was very friendly. I had to buy a proper meal. Small cookie and a drink just doesn’t cut it for a 4.5 hours flight.

Experience was good, the wifi hook up is somewhat tough

I will not be flying with westjet again. I was uncomfortable in my seat. The position made my back hurt so bad. My wife was able to fit the seatbelt around her with out an extension but was unable to put the tray table down or fit in the seat for that matter. Our bag was smashed and I spent two hours trying to fill out the application for a damaged bag before I gave up. The 80 photos I took would not work and nothing telling me the format to upload them as.. I made the mistake of unpacking the bag before taking photos so no claim for me. Next trip to Canada I will have to use air Canada.

My luggage was damaged 1 wheel was out I can't find it nowhere

Took 3 hours to check in and drop off our suitcases. Half of the passengers were still in line by boarding time. The computer systems and staff were very slow. Staff were also disorganized and kept allowing later flights to skip lines. Suitcases were piling on that several other passengers didn't get their suitcases. Then, we were sitting in the plane for 2 hours and were told that the flight was overbooked. We missed our connecting flight and had to fly the following day but with a stop over. Good thing ONE WestJet customer rep was pleasant and actually knew how to do her job when we wanted to rebook to a direct flight. Thank you to Kim at Toronto airport. Terrible experience at PUJ. Won't go back to Dominican Republic.

Signature class to Uk makes the overnight flight bearable! Duck leg dinner best food we’ve been served in the air for a long time. Well done AC!

Better this time, the pilot communicated to passengers of delay

Delays after delays only to announce we don't know how long it will take

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.

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.

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 ...

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.

I got to the airport and the airline told me i did not have a flight. I never got a confirmation email yet I did get charged. Please refund my money asap

Was charged for ticket, unable to check in online, made the line to speak to someone at the counter but was told I did not show up in the system as having a ticket to fly - even though I have the email with confirmation and credit card was charged. I could not purchase another ticket at the counter, only online which was not working. Ended up buying a flight on another airline at the airport. Called customer service to claim the cost of the original ticket, was told I showed up in their system as having a ticket but did not check-in or show up to board the flight. Currently pending review for refund via their customer service team, they were very nice and helpful over the phone despite the many glitches.

Do not book with this airline. Flights delayed over 3 hours and no explanation. They keep changing your itinerary every hour.

Awful. Not water, or chargers or space under the seats, the plane was very old and poor maintenance, seats really dirty, sticky, seats pockets with wires pinching your knees. Connection with no announcements, plane departed 1.30 hour earlier for an extra stop to refueling in Trinidad & Tobago. Even that we had a 3 hrs delay, seated in the plane in the runway.

Staff were unfriendly and rude. Was stuck on runway for 2 hours after arrival in Boston.

We waited in an overcrowded bus for over a half hour. It was uncomfortable. It would have been better to have waited in the terminal in a line

The food for sale on board has opportunity for improvement.

I paid extra for a comfortable seat in the second flight, but the plane didn't have those seats, the first one did

The Arajet person who greeted us initially was unhelpful & rude about the mandatory migration form which has to be completed digitally but the systems don’t work properly. The boarding gate was changed twice and initial boarding was delayed. Once on board we we had to wait an hour and a half before take off. It was hot and there was very little room for tall-ish people to fit their knees in. The crew were pleasant but working in a poor situation. The plane was delayed because we were waiting for people from a delayed interconnecting flight. Arajet must have known that before we were asked to board. Better information, decisions & communication were needed.

My seat was broken and the crew had to find me somewhere else to sit. The crew was extremely courteous about this

The experience was awful. I didn’t expect to pay $100 for my luggage both ways. Then we start boarding late, they then make us go back out of the line and go back into the airport for maintenance. The delay was 45 mins and I also hated the fact that I paid so much and still had to pay for a seat when I checked in. I will not be rebooking with this airline

Very bead I am going to Vancouver to toronto. Not boarding receive. Before flight ✈️ time I have to take boarding. Boarding manager asking me pay $89 . Just flight ✈️ time before I pay .after provided the Boarding pass. Flair Airlines management not good. But kayak is best application.

Leg room was terrible and seats very narrow. Flight was also delayed.

The crew of this flight, specially the flight attendant in the front were the sweetest I’ve had in all my life, I genuinely hope they get a race or sum cuz of their efforts. It was just quite unsettling that the flight took so long to departure. It was supposed to leave at 10:35pm and we ended up taking off at 11:22pm…👎🏻👎🏻👎🏻

It’s bare bones but was on time so can’t complain.

TThe first time I have ever flown with flare and both ways sucked

I try to buy water the cabin crews told me I had to wait for them to come around with the trolley I waited over 2 hours !!!!! Literally 2 hours I was so thirsty .

Lots of leg room in the front rows. Wish water was free.

The worst airlines I have seen in my life they don’t respect anyone they don’t care about anyone they lost our luggage and no one is responding. We waited for five hours to get our luggage back.🤬🤬🤬👎🏻👎🏻👎🏻👎🏻

Great staff. Cramped seating for someone 5 feet, 2 inches and average weight. So if you're tall or heavy -- good luck. Even if you wait until the 24 hour checkin time, you still charge for seating. Really? So either it is a less-than-pleasant experience or pay the price of a "big name" airline. And if I'm going to pay their prices, why would I fly in your cramped seat? So, in the end, you want to give less comfort for the same prices as Air Canada. Go figure.

More options for your flight to Caribbean Islands

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