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Cheap flights from Hamilton, ON to Caribbean Islands from C$ 223

YHM — SJU
6 Oct — 13 Oct1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Hamilton to Caribbean Islands

Enter your travel dates to find the best prices.

Cheapest flights from Hamilton to Caribbean Islands

Tue 22/123:50 p.m. -
Nonstop4h 07m
Sun 27/128:10 p.m. -
Nonstop4h 11m
Deal found 1/9C$ 458
Tue 22/123:50 p.m. -
Nonstop4h 07m
Tue 5/12:05 p.m. -
Nonstop4h 11m
Deal found 4/9C$ 461
Wed 16/1212:10 p.m. -
1 stop6h 45m
Tue 22/128:55 p.m. -
Nonstop4h 11m
Deal found 3/9C$ 470
Wed 16/1212:10 p.m. -
1 stop6h 45m
Tue 29/128:55 p.m. -
Nonstop4h 11m
Deal found 4/9C$ 484
Sun 20/123:05 p.m. -
Nonstop4h 07m
Sun 10/18:10 p.m. -
Nonstop4h 11m
Deal found 5/9C$ 497
Sun 27/123:05 p.m. -
Nonstop4h 07m
Tue 5/12:05 p.m. -
Nonstop4h 11m
Deal found 4/9C$ 504
Sun 13/1212:10 p.m. -
1 stop6h 45m
Sun 27/128:10 p.m. -
Nonstop4h 11m
Deal found 4/9C$ 505
Sun 20/123:05 p.m. -
Nonstop4h 07m
Tue 5/12:05 p.m. -
Nonstop4h 11m
Deal found 5/9C$ 571
Fri 27/1112:10 p.m. -
2 stops34h 25m
Fri 4/127:45 p.m. -
2 stops20h 40m
Deal found 5/9C$ 725
Thu 19/116:05 a.m. -
2 stops10h 35m
Tue 24/1112:35 p.m. -
3 stops34h 35m
Deal found 2/9C$ 822
Sun 20/123:25 p.m. -
2 stops25h 20m
Mon 28/126:45 p.m. -
2 stops20h 40m
Deal found 5/9C$ 854
Tue 29/123:25 p.m. -
2 stops26h 10m
Sat 16/18:45 p.m. -
2 stops18h 40m
Deal found 1/9C$ 956

Find flight deals from Hamilton to Caribbean Islands

Round-trip from

C$ 430

One-way from

C$ 228

Popular in

August

Cheapest in

June

Average price

C$ 646
Porter Airlines
  • Porter Airlines
  • 2/3-9/3
  • Nonstop
  • 8h 18m total
  • Hamilton to Caribbean Islands
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Porter Airlines
  • Porter Airlines
  • 2/12-31/12
  • 1 total stop
  • 6h 45m total
  • Hamilton to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 69 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2026
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Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Hamilton to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

HamiltonMontego Bay

YHM Hamilton - MBJ Montego Bay Sangster Intl

YHMMBJ

Hamilton

Sun 13/12

12:10 p.m.-6:55 p.m.

1 stop6h 45m

Montego Bay Sangster Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 223
Quickest round-trip

HamiltonMontego Bay

YHM Hamilton - MBJ Montego Bay Sangster Intl

YHMMBJ

Hamilton

Sun 20/12

3:05 p.m.-7:12 p.m.

Nonstop4h 07m

Montego Bay Sangster Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 239

HamiltonMontego Bay

YHM Hamilton - MBJ Montego Bay Sangster Intl

YHMMBJ

Hamilton

Tue 22/12

3:50 p.m.-7:57 p.m.

Nonstop4h 07m

Montego Bay Sangster Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 241

HamiltonMontego Bay

YHM Hamilton - MBJ Montego Bay Sangster Intl

YHMMBJ

Hamilton

Tue 15/12

4:05 p.m.-6:55 p.m.

1 stop26h 50m

Montego Bay Sangster Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 347

HamiltonFreeport

YHM Hamilton - FPO Freeport Grand Bahama Intl

YHMFPO

Hamilton

Sun 1/11

6:25 a.m.-1:30 p.m.

1 stop7h 05m

Freeport Grand Bahama Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 349

HamiltonPunta Cana

YHM Hamilton - PUJ Punta Cana

YHMPUJ

Hamilton

Thu 1/10

3:45 p.m.-11:40 a.m.

1 stop19h 55m

Punta Cana

Wed 31/12

12:00 a.m.-11:30 p.m.

Nonstop0h 00m

C$ 350

HamiltonMontego Bay

YHM Hamilton - MBJ Montego Bay Sangster Intl

YHMMBJ

Hamilton

Wed 2/12

8:10 a.m.-6:55 p.m.

2 stops10h 45m

Montego Bay Sangster Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 394

HamiltonMontego Bay

YHM Hamilton - MBJ Montego Bay Sangster Intl

YHMMBJ

Hamilton

Wed 27/1

12:10 p.m.-6:55 p.m.

1 stop6h 45m

Montego Bay Sangster Intl

Sun 31/1

8:10 p.m.-12:21 a.m.

Nonstop4h 11m

C$ 454

HamiltonMontego Bay

YHM Hamilton - MBJ Montego Bay Sangster Intl

YHMMBJ

Hamilton

Tue 9/2

9:00 a.m.-1:07 p.m.

Nonstop4h 07m

Montego Bay Sangster Intl

Tue 16/2

8:55 p.m.-1:06 a.m.

Nonstop4h 11m

C$ 455

HamiltonMontego Bay

YHM Hamilton - MBJ Montego Bay Sangster Intl

YHMMBJ

Hamilton

Tue 22/12

3:50 p.m.-7:57 p.m.

Nonstop4h 07m

Montego Bay Sangster Intl

Sun 27/12

8:10 p.m.-12:21 a.m.

Nonstop4h 11m

C$ 458

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/9

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Hamilton to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Hamilton with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Hamilton to Caribbean Islands

No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Caribbean Islands

See what other customers who have flown with Air Canada from Hamilton to Caribbean Islands have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Air Canada
7.1
Good
11,592 reviews
Check prices

Food

6.3

Boarding

7.3

Crew

7.8

Comfort

7.1

Entertainment

6.8

Overall

7.1

Reviews

1 / 20
2.0
Mediocre

Sylvia,Aug 2026

YYZ - PHL

Our flight from Kelowna was 5 hours delayed. We missed our connection. We were able to get to a hotel by 3:00 a.m. but the breakfast cost us $40. The hotel was good. We were rescheduled for the flight the next night when it was canceled. There were no hotel vouchers available which didn't matter because there were no hotel rooms available. We decided to just drive which was not easy doing a one-way rental to the United States. Worst possible trip I've ever had
Air Canada
7.1
Good
11,592 reviews
Air Canada
7.1
Good
11,592 reviews
Check prices

Food

6.3

Boarding

7.3

Crew

7.8

Comfort

7.1

Entertainment

6.8

Overall

7.1

Reviews

1 / 20
2.0
Mediocre

Sylvia,Aug 2026

YYZ - PHL

Our flight from Kelowna was 5 hours delayed. We missed our connection. We were able to get to a hotel by 3:00 a.m. but the breakfast cost us $40. The hotel was good. We were rescheduled for the flight the next night when it was canceled. There were no hotel vouchers available which didn't matter because there were no hotel rooms available. We decided to just drive which was not easy doing a one-way rental to the United States. Worst possible trip I've ever had

Related info for your journey

  • What airport do you fly from for flights from Hamilton to Caribbean Islands?

    Located just 10.9 km from the city centre, Hamilton (YHM) is the airport most travellers will use when flying to Caribbean Islands from Hamilton.

  • How long is the flight from Hamilton, Ontario to Caribbean Islands?

    Porter Airlines and WestJet can get you from Hamilton, Ontario to Caribbean Islands in just under 4h 07m. Your travel time can differ by up to 21h 13m. The distance from Hamilton, Ontario to Caribbean Islands is about 2747 km. This flight may include one or multiple stops.

  • What are the most popular routes from Hamilton, Ontario to Caribbean Islands?

    Most travellers choose Hamilton - Punta Cana, Hamilton - Montego Bay Sangster Intl or Hamilton - Santo Domingo Las Americas when deciding on the best route from Hamilton, Ontario to Caribbean Islands.

  • Can I find deals for flights from Hamilton to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Hamilton to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Hamilton to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Hamilton to Caribbean Islands.

  • Can I find deals for business class flights from Hamilton to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Hamilton to Caribbean Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Hamilton to Caribbean Islands

AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 257AverageC$ 568FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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