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Cheap flights from Worcester, Massachusetts to Caribbean Islands from $111

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Worcester, Massachusetts to Caribbean Islands departing on 1/30. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Worcester, Massachusetts to Caribbean Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
1:44 pm - 10:40 pm
ORH
-
SJU
8h 56m1 stop
American Airlines Logo
11:32 am - 1:18 pm
SJU
-
ORH
25h 46m2 stops
$231American Airlines
Sun, Mar 15 - Thu, Mar 19
American Airlines Logo
1:44 pm - 10:40 pm
ORH
-
SJU
8h 56m1 stop
American Airlines Logo
5:00 am - 1:18 pm
SJU
-
ORH
8h 18m1 stop
$289American Airlines
Sun, Mar 15 - Thu, Mar 19
American Airlines Logo
2:18 pm - 11:56 pm
ORH
-
SJU
8h 38m1 stop
American Airlines Logo
7:00 am - 1:53 pm
SJU
-
ORH
7h 53m1 stop
$290American Airlines
Thu, Jan 29 - Thu, Feb 5
Delta Logo
4:16 pm - 12:26 pm
ORH
-
NAS
20h 10m2 stops
Delta Logo
6:27 pm - 3:36 pm
NAS
-
ORH
21h 09m2 stops
$329Delta
Sun, Feb 1 - Sun, Feb 8
Delta Logo
3:18 pm - 3:54 pm
ORH
-
NAS
24h 36m2 stops
Delta Logo
5:08 pm - 2:39 pm
NAS
-
ORH
21h 31m2 stops
$736Delta
Thu, Apr 16 - Thu, Apr 23
Delta Logo
3:18 pm - 1:16 pm
ORH
-
MBJ
22h 58m2 stops
Delta Logo
4:55 pm - 2:39 pm
MBJ
-
ORH
20h 44m2 stops
$799Delta
Sun, Apr 19 - Sun, Apr 26
JetBlue Logo
6:25 pm - 8:25 am
ORH
-
MBJ
14h 00m1 stop
JetBlue Logo
10:50 am - 5:27 pm
MBJ
-
ORH
6h 37m1 stop
$1,115JetBlue
Wed, Dec 31 - Fri, Jan 2
JetBlue Logo
6:25 pm - 8:25 am
ORH
-
MBJ
14h 00m1 stop
JetBlue Logo
10:50 am - 5:27 pm
MBJ
-
ORH
6h 37m1 stop
$1,170JetBlue
Tue, Dec 30 - Fri, Jan 2
JetBlue Logo
6:25 pm - 8:25 am
ORH
-
MBJ
14h 00m1 stop
JetBlue Logo
9:25 am - 5:27 pm
MBJ
-
ORH
8h 02m1 stop
$1,216JetBlue
Wed, Dec 31 - Sat, Jan 3
JetBlue Logo
6:25 pm - 8:25 am
ORH
-
MBJ
14h 00m1 stop
JetBlue Logo
10:50 am - 5:27 pm
MBJ
-
ORH
6h 37m1 stop
$1,310JetBlue
Sun, Dec 28 - Thu, Jan 1

JetBlue flights from Worcester, Massachusetts to Caribbean Islands

Our best JetBlue deals on Worcester, Massachusetts to Caribbean Islands flight tickets
JetBlue
Feb 2
ORH12:00 pmWorcester
8h 50m
1 stop
SJU9:50 pmSan Juan Luis Munoz Marin Intl
Feb 5
SJU6:01 amSan Juan Luis Munoz Marin Intl
10h 49m
1 stop
ORH3:50 pmWorcester
$344
Find similar
JetBlue
Apr 3
ORH4:54 pmWorcester
7h 57m
1 stop
SJU12:51 amSan Juan Luis Munoz Marin Intl
Apr 12
SJU7:55 amSan Juan Luis Munoz Marin Intl
8h 01m
1 stop
ORH3:56 pmWorcester
$573
Find similar
JetBlue
Dec 24
ORH6:25 pmWorcester
14h 24m
1 stop
PUJ9:49 amPunta Cana
Dec 30
PUJ10:49 amPunta Cana
7h 38m
1 stop
ORH5:27 pmWorcester
$645
Find similar

American Airlines flights from Worcester, Massachusetts to Caribbean Islands

Our best American Airlines deals on Worcester, Massachusetts to Caribbean Islands flight tickets
American Airlines
Mar 15
ORH1:44 pmWorcester
8h 56m
1 stop
SJU10:40 pmSan Juan Luis Munoz Marin Intl
Mar 19
SJU11:32 amSan Juan Luis Munoz Marin Intl
25h 46m
2 stops
ORH1:18 pmWorcester
$231
Find similar
American Airlines
Mar 15
ORH1:44 pmWorcester
8h 56m
1 stop
SJU10:40 pmSan Juan Luis Munoz Marin Intl
Mar 19
SJU5:00 amSan Juan Luis Munoz Marin Intl
8h 18m
1 stop
ORH1:18 pmWorcester
$289
Find similar
American Airlines
Mar 15
ORH1:44 pmWorcester
21h 12m
2 stops
SJU10:56 amSan Juan Luis Munoz Marin Intl
Mar 19
SJU11:32 amSan Juan Luis Munoz Marin Intl
25h 46m
2 stops
ORH1:18 pmWorcester
$293
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Worcester, Massachusetts to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated December 18, 2025.
Use the filters below to find and compare flights from Worcester, Massachusetts to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Sun 3/15

1:44 pm-10:40 pm

1 stop8h 56m

San Juan Luis Munoz Marin Intl

Thu 3/19

11:32 am-1:18 pm

2 stops25h 46m

$231

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Sun 3/15

1:44 pm-10:40 pm

1 stop8h 56m

San Juan Luis Munoz Marin Intl

Thu 3/19

5:00 am-1:18 pm

1 stop8h 18m

$289

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Thu 1/29

2:18 pm-11:56 pm

1 stop8h 38m

San Juan Luis Munoz Marin Intl

Thu 2/5

7:00 am-1:53 pm

1 stop7h 53m

$290

WorcesterNassau

ORH - NAS

ORHNAS

Worcester

Sun 2/1

4:16 pm-12:26 pm

2 stops20h 10m

Nassau Intl

Sun 2/8

6:27 pm-3:36 pm

2 stops21h 09m

$329

WorcesterNassau

ORH - NAS

ORHNAS

Worcester

Thu 4/16

3:18 pm-3:54 pm

2 stops24h 36m

Nassau Intl

Thu 4/23

5:08 pm-2:39 pm

2 stops21h 31m

$736

WorcesterMontego Bay

ORH - MBJ

ORHMBJ

Worcester

Sun 4/19

3:18 pm-1:16 pm

2 stops22h 58m

Montego Bay Sangster Intl

Sun 4/26

4:55 pm-2:39 pm

2 stops20h 44m

$799

WorcesterMontego Bay

ORH - MBJ

ORHMBJ

Worcester

Wed 12/31

6:25 pm-8:25 am

1 stop14h 00m

Montego Bay Sangster Intl

Fri 1/2

10:50 am-5:27 pm

1 stop6h 37m

$1,115

WorcesterMontego Bay

ORH - MBJ

ORHMBJ

Worcester

Tue 12/30

6:25 pm-8:25 am

1 stop14h 00m

Montego Bay Sangster Intl

Fri 1/2

10:50 am-5:27 pm

1 stop6h 37m

$1,170

WorcesterMontego Bay

ORH - MBJ

ORHMBJ

Worcester

Wed 12/31

6:25 pm-8:25 am

1 stop14h 00m

Montego Bay Sangster Intl

Sat 1/3

9:25 am-5:27 pm

1 stop8h 02m

$1,216

WorcesterMontego Bay

ORH - MBJ

ORHMBJ

Worcester

Sun 12/28

6:25 pm-8:25 am

1 stop14h 00m

Montego Bay Sangster Intl

Thu 1/1

10:50 am-5:27 pm

1 stop6h 37m

$1,310

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Caribbean Islands from

How to get the cheapest flight ticket from Worcester, Massachusetts to Caribbean Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Caribbean Islands?

The cheapest day to depart from Worcester, Massachusetts to Caribbean Islands is on a Wednesday. Travelers who choose to depart for Caribbean Islands on a Wednesday will often find tickets for as low as $210. If your travel schedule is flexible, try to avoid departing on a Saturday because tickets tend to average around $975. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.

What is the cheapest time of day to depart on your flight to Caribbean Islands?

According to our data, the cheapest time of day to fly to Caribbean Islands is in the morning. momondo users have found flights departing from Worcester, Massachusetts to Caribbean Islands in the morning for as low as $233. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets in the afternoon because they tend to be around $1,005. Of course, these prices can vary depending on the time of year and what airport you fly to.

Can stopping save me money on Worcester, Massachusetts to Caribbean Islands flights?

No. A direct flight is the cheapest option for a flight between Worcester, Massachusetts to Caribbean Islands.

Cheap Worcester, Massachusetts to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Worcester, Massachusetts to Caribbean Islands

Fastest flight time

6h 56m

Direct flights

None
The fastest flight from Worcester, Massachusetts to Caribbean Islands takes 6h 56m
There are no direct flights from Worcester, Massachusetts to Caribbean Islands. There are no popular flight routes from Worcester, Massachusetts to Caribbean Islands.
Search flight deals

  • When did momondo last update prices for flights from Worcester Airport to Caribbean Islands?

    Prices for flights from Worcester Airport to Caribbean Islands were last updated today.

  • How many operators does momondo search for flights from Worcester Airport to Caribbean Islands?

  • How old do you have to be to fly from Worcester Airport to Caribbean Islands?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Worcester Airport to Caribbean Islands.

  • What documentation or ID do you need to fly to Caribbean Islands?

    The required travel and health documents for your Caribbean Islands trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Caribbean Islands. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Worcester, Massachusetts to Caribbean Islands?

Best airlines flying from Worcester, Massachusetts to Caribbean Islands

Compare and see reviews for airlines that fly from Worcester, Massachusetts to Caribbean Islands with momondo
Airline
Rating
Free Cancellation
Price
JetBluePriceFrom $99Free CancellationRating
7.2
2,897 reviews
Search JetBlue flights

Why use momondo?

Why should I use momondo to find a flight deal from Worcester to Caribbean Islands?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Worcester to Caribbean Islands. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Worcester to Caribbean Islands with flexible booking policies on momondo?

Flights from Worcester to Caribbean Islands with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Worcester to Caribbean Islands?

momondo provides multiple filters to help you find the best flight to Caribbean Islands from Worcester. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Worcester to Caribbean Islands right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Caribbean Islands, momondo offers a useful price alert feature which will track prices for flights to Caribbean Islands from Worcester and alert you when they change.

An easier way to manage your Caribbean Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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