C$ 267 Find Cheap Flights from Hamilton 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 Hamilton to Caribbean departing on 21/3. 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 Hamilton

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stopC$ 860
Montego Bay
Montego Bay3 stopsC$ 1,021
Kingston
Kingston2 stopsC$ 1,063
Oranjestad
Oranjestad2 stopsC$ 2,381
Puerto Plata
Puerto Plata2 stopsC$ 828
Santo Domingo
Santo Domingo1 stopC$ 607
Punta Cana
Punta Cana1 stopC$ 860
Montego Bay
Montego Bay3 stopsC$ 1,021
Kingston
Kingston2 stopsC$ 1,063
Oranjestad
Oranjestad2 stopsC$ 2,381
Puerto Plata
Puerto Plata2 stopsC$ 828
Santo Domingo
Santo Domingo1 stopC$ 607

Cheap Flights from Hamilton to Caribbean

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Hamilton 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 Hamilton to Caribbean

Sat, 7 Mar - Sun, 15 Mar
Multiple Airlines Logo
3:10 p.m. - 8:37 a.m.
YHM
-
POP
16h 27m
2 stops
Multiple Airlines Logo
9:35 a.m. - 1:20 a.m.
POP
-
YHM
15h 45m
1 stop
C$ 828Multiple Airlines
Mon, 6 Apr - Sat, 11 Apr
Multiple Airlines Logo
7:25 a.m. - 3:51 p.m.
YHM
-
PUJ
8h 26m
1 stop
Multiple Airlines Logo
6:03 p.m. - 3:00 p.m.
PUJ
-
YHM
44h 57m
2 stops
C$ 860Multiple Airlines
Sun, 8 Mar - Sun, 15 Mar
Multiple Airlines Logo
7:25 a.m. - 3:36 p.m.
YHM
-
PUJ
8h 11m
1 stop
Multiple Airlines Logo
5:39 p.m. - 2:20 p.m.
PUJ
-
YHM
44h 41m
2 stops
C$ 911Multiple Airlines
Mon, 16 Feb - Mon, 23 Feb
Multiple Airlines Logo
7:25 a.m. - 4:36 p.m.
YHM
-
PUJ
8h 11m
1 stop
Multiple Airlines Logo
9:15 p.m. - 12:44 p.m.
PUJ
-
YHM
40h 29m
2 stops
C$ 913Multiple Airlines
Thu, 2 Apr - Mon, 6 Apr
Multiple Airlines Logo
6:10 p.m. - 11:35 p.m.
YHM
-
PUJ
29h 25m
3 stops
Multiple Airlines Logo
2:25 p.m. - 7:00 p.m.
PUJ
-
YHM
28h 35m
2 stops
C$ 919Multiple Airlines
Mon, 6 Apr - Sat, 11 Apr
Multiple Airlines Logo
7:25 a.m. - 3:51 p.m.
YHM
-
PUJ
8h 26m
1 stop
Multiple Airlines Logo
9:18 a.m. - 10:55 p.m.
PUJ
-
YHM
13h 37m
1 stop
C$ 929Multiple Airlines
Sun, 8 Mar - Fri, 13 Mar
Multiple Airlines Logo
7:25 a.m. - 3:36 p.m.
YHM
-
PUJ
8h 11m
1 stop
Multiple Airlines Logo
2:23 p.m. - 12:25 a.m.
PUJ
-
YHM
10h 02m
1 stop
C$ 931Multiple Airlines
Sat, 7 Feb - Sat, 14 Feb
Multiple Airlines Logo
7:25 a.m. - 1:45 p.m.
YHM
-
FPO
6h 20m
1 stop
Multiple Airlines Logo
11:00 a.m. - 2:20 p.m.
FPO
-
YHM
27h 20m
2 stops
C$ 949Multiple Airlines
Sat, 4 Apr - Sat, 11 Apr
Multiple Airlines Logo
7:00 a.m. - 11:35 p.m.
YHM
-
PUJ
16h 35m
2 stops
Multiple Airlines Logo
6:40 p.m. - 8:59 p.m.
PUJ
-
YHM
26h 19m
2 stops
C$ 956Multiple Airlines
Sun, 12 Apr - Sat, 18 Apr
WestJet Logo
6:10 p.m. - 5:24 p.m.
YHM
-
MBJ
24h 14m
1 stop
WestJet Logo
1:50 p.m. - 5:16 p.m.
MBJ
-
YHM
26h 26m
1 stop
C$ 1,120WestJet
Booking Insights

KAYAK's insights & trends for Hamilton to Caribbean flights

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

What is the cheapest Hamilton to Caribbean flight route?

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

The cheapest ticket to Caribbean from Hamilton found in the last 72 hours was to Nassau, at C$ 401 round-trip. The most popular route is from Hamilton (YHM) to Nassau (NAS), and the cheapest round-trip airline ticket found on this route in the last 72 hours was C$ 401.

Can I save money by flying with a layover from Hamilton 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$ 592 on average.

What is the cheapest month to fly from Hamilton to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Hamilton to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Hamilton to Caribbean is September, when tickets cost C$ 326 (return) on average. On the other hand, the most expensive months are August and May, when the average cost of round-trip tickets is C$ 787 and C$ 740 respectively.

Good to know

Low seasonSeptember
Cheapest flightC$ 267
Best time to beat the crowds (38% less expensive on average)
Flight from Hamilton to Montego Bay

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Hamilton 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 Hamilton to Caribbean.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Hamilton 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 Hamilton 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 Hamilton 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 Hamilton 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 Hamilton 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$ 308 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 afternoon, which is peak travel time and where the average cost of a ticket is C$ 405.

Reviews of the top airlines flying from Hamilton to Caribbean

 
Need help choosing which airline to fly with from Hamilton 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.
7.2
WestJetOverall score based on 3250 reviews
7.4Boarding
6.2Food
7.0Comfort
6.1Entertainment
7.9Crew
Airline reviews

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.

8.0 ExcellentA.K, Jan 2026
YYZ - RTB
Read more WestJet reviews

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.

Great seats, super comfortable, but no in flight entertainment which was a let down

Airplane is too small. Crew, especially the flight attendant who looked after our area, was not at all friendly and a touch authoratative. She may have been the most gruff flight attendant i've come across in 40 years of business travel

I when to Jamaica for my dad funeral and I did not get my luggage from westjet . I add to buy clothes putting me financial debt i did no want to be in Westjet did not call me to apologize are to inquire about my luggage I am still angry about it

Ground staff was not helpful, but staff at the business counter were excellent.

I selected "carry-on" for a round trip on Kayak, but my return flight on WestJet did not include a carry-on and they would not allow me to add one. My only option was to add a "checked bag" which I had to wait for on the luggage carousel after landing. Not a good experience.

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

We were happy with the service and cost of checking a bag

It's kindof ridiculous that your system is even asking me about this since my flight was canceled and I wasn't rescheduled.

3 hr delay at the gate while they were doing maintenance. Next time, do not board passengers while maintenance is being performed

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports