$151 Find Cheap Flights from Worcester 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 Worcester to Caribbean departing on 8/27. 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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Cheap Flights from Worcester to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$355
Santo Domingo
Santo Domingo2 stops$387
Montego Bay
Montego Bay2 stops$357
Oranjestad
Oranjestad2 stops$420
Nassau
Nassau2 stops$402
Simpson Bay
Simpson Bay2 stops$362
George Town
George Town2 stops$396
St. John's
St. John's2 stops$766
Punta Cana
Punta Cana2 stops$355
Santo Domingo
Santo Domingo2 stops$387
Montego Bay
Montego Bay2 stops$357
Oranjestad
Oranjestad2 stops$420
Nassau
Nassau2 stops$402
Simpson Bay
Simpson Bay2 stops$362
George Town
George Town2 stops$396
St. John's
St. John's2 stops$766

Book Cheap Worcester to Caribbean Plane Tickets

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

Tue, Oct 13 - Wed, Oct 28
American Airlines Logo
5:17 pm - 6:05 pm
ORH
-
SJU
24h 48m
2 stops
American Airlines Logo
3:50 pm - 4:52 pm
SJU
-
ORH
25h 02m
2 stops
$302American Airlines
Fri, Aug 7 - Fri, Aug 14
American Airlines Logo
5:23 pm - 2:54 pm
ORH
-
SJU
21h 31m
2 stops
American Airlines Logo
6:51 am - 4:58 pm
SJU
-
ORH
10h 07m
1 stop
$342American Airlines
Thu, Jul 9 - Thu, Jul 16
American Airlines Logo
5:16 pm - 2:00 pm
ORH
-
PUJ
20h 44m
2 stops
American Airlines Logo
5:56 pm - 4:51 pm
PUJ
-
ORH
22h 55m
2 stops
$355American Airlines
Thu, Jul 9 - Thu, Jul 16
American Airlines Logo
5:16 pm - 2:00 pm
ORH
-
PUJ
20h 44m
2 stops
American Airlines Logo
12:01 pm - 4:51 pm
PUJ
-
ORH
28h 50m
1 stop
$356American Airlines
Tue, Sep 15 - Mon, Sep 21
Delta Logo
4:20 pm - 1:50 pm
ORH
-
SXM
21h 30m
2 stops
Delta Logo
3:20 pm - 3:37 pm
SXM
-
ORH
24h 17m
2 stops
$362Delta
Wed, Sep 2 - Tue, Sep 8
JetBlue Logo
2:35 pm - 11:06 pm
ORH
-
SJU
8h 31m
1 stop
JetBlue Logo
5:35 am - 3:50 pm
SJU
-
ORH
10h 15m
1 stop
$380JetBlue
Mon, Aug 24 - Sat, Aug 29
Delta Logo
5:40 pm - 11:51 am
ORH
-
NAS
18h 11m
2 stops
Delta Logo
6:04 pm - 5:00 pm
NAS
-
ORH
22h 56m
2 stops
$402Delta
Fri, Jul 17 - Wed, Jul 29
Delta Logo
5:40 pm - 12:16 pm
ORH
-
AUA
18h 36m
2 stops
Delta Logo
3:25 pm - 5:00 pm
AUA
-
ORH
25h 35m
2 stops
$432Delta
Tue, Sep 1 - Sat, Sep 5
JetBlue Logo
4:45 pm - 11:51 pm
ORH
-
STI
7h 06m
1 stop
JetBlue Logo
5:01 am - 3:50 pm
STI
-
ORH
10h 49m
1 stop
$488JetBlue
Tue, Sep 1 - Sat, Sep 5
JetBlue Logo
4:45 pm - 11:51 pm
ORH
-
STI
7h 06m
1 stop
JetBlue Logo
5:01 am - 3:50 pm
STI
-
ORH
10h 49m
1 stop
$498JetBlue
Booking Insights

KAYAK's insights & trends for Worcester to Caribbean flights

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

Which airlines provide the cheapest flights from Worcester to Caribbean?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 7 days.

In the past 7 days, the cheapest round-trip tickets from Worcester to Caribbean were found on American Airlines ($355) and Delta ($362).

Good to know

Cheapest flight$151
Flight from Worcester to San Juan

FAQs - booking Caribbean flights

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Worcester to Caribbean is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Worcester 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 Worcester 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 Worcester 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 Worcester 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 airline flying from Worcester to Caribbean

 
Need help choosing which airline to fly with from Worcester 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.
7.1
American AirlinesOverall score based on 11629 reviews
7.9Crew
6.9Entertainment
7.5Boarding
7.2Comfort
6.4Food
Airline reviews

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

2.0 MediocreMatthew, May 2026
ORD - PDX
Read more American Airlines reviews

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

The flight attendants were very friendly, efficient, and helpful. The plane was ahead of schedule, and it all went very smoothly. Thank you.

They lost my baggage and I am still struggling to the information and update

We got delayed getting out of DFW for broken overhead bins. Once the flight got underway the captain kept the seatbelt sign lit the entire flight despite little perceptible turbulence, preventing use of the rest rooms and any sort of refreshment service in the main cabin.

Flight delays for communication overall not a good experience uncomfortable on the plane. Person in front of me reclined his seat, putting them inches from my lap.

There were flight delays making our flight arrive at our destination after midnight didn’t seem to have enough crew or airplanes for the flights laid over in Dallas should’ve had plenty of time to make it to our next flight only made it because that flight was also delayed because our plane wasn’t even at the airport yet overall have not had a good experience on American

Flight left on time. Captain provided relevant announcements. We had to wait 45 minutes to desembark due to the ramp closed because of lightening.

It's a long flight and that is always difficult. I was comfortable and well. The movies available were great and the crew was good.

Cancelled flight. Still waiting to get home for grand daughter’s graduation .

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports